CHEM2522 cheatsheet
May 28, 2026
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我拿到了一份我在上的课的考前宝典！你帮我拆解一下这节课，告诉我复习重点，我快final了
越详细越好，公式，定义，核心考点我都需要，救救孩子
- 好的，我按你这份 CHEM2522《Sustainable Chemical Manufacture》考前宝典（你当前文件）把整门课拆开，做一份“Final 冲刺复习总纲”。我会尽量把公式、定义、最爱考点、做题流程、常见陷阱都写清楚；你照着这份过一遍，再去刷题会快很多。
- 说明：我下面所有内容都只来自你这份 cheatsheet 的摘录部分，所以某些小节如果你课堂还讲了更多细节，我不会乱补；我会把“已覆盖/未覆盖”说清楚。
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一、这门课到底考什么（先建立总地图）
- 课程分两大半，但思维方式是同一个：
- 做出来（合成 + 聚合物）
- 证明你做出来了什么（光谱解析：IR / MS / $^1H$ & $^{13}C$ NMR）
- 同时必须用绿色化学/可持续指标评价“做得绿不绿”[2]Source: asksia-cheatsheet-chem2522.pdfSIDE 1/2 ANALYSE . Green chemistry . Sustainability metrics . Feedstocks . Catalysis . Structure elucidation . IR . MS . 1H & 13C NMR 0 . Revision Blueprint READ FIRST * This unit has two halves that share one mindset: make the molecule (synthesis + polymers) and prove what you made (spectroscopy) - both judged against the green-chemistry yardstick of doing it with the least waste, energy and hazard. Side 1 = analysis & sustainability metrics. Side 2 = reactions & polymers. The exam reflex you need: read a structure, predict its spectra; read spectra, deduce the structure; and for any route, judge its atom economy. Most-tested skills: calculate atom economy / E-factor; assign an IR + MS + NMR set to one structure; pick Sn1 vs Sn2; classify a polymerisation; name a greener alternative (solvent, catalyst, feedstock). -- SIA > Two-line discipline: always state degrees of unsaturation first in any structure problem, and always quote the metric (a number) when asked "is this green?" - markers reward the calculation, not the adjective. 1 . Green Chemistry . ANASTAS & 12 Principles WARNER 1998 The design framework for the whole unit. Memorise the mnemonic "PRODUCTIVELY" idea - but really know the high-yield five (*). 1. * Prevent waste - better than treating/cleaning it up 2. * Atom economy - maximise atoms of reactant in product 3. Less hazardous synthesis (low toxicity to people/environment) 4. Design safer chemicals (function with minimal toxicity) 5. * Safer solvents/auxiliaries - avoid where possible 6. Design for energy efficiency - ambient T & P 7. Renewable feedstocks not depleting ones 8. Reduce derivatives (protecting groups add waste steps) 9. * Catalysis > stoichiometric reagents 10. * Design for degradation - break down after use, no persistence 11. Real-time analysis to prevent pollution 12. Inherently safer chemistry (accident prevention) Prevention > remediation is the spine: principles 1, 2, 9 do most of the exam work. 1b . Worked . Atom Economy[3]Source: asksia-cheatsheet-chem2522.pdfCHEM2522 Sustainable Chemical Manufacture UNIVERSITY OF SYDNEY . SCHOOL OF CHEMISTRY EXAM REVISION Sem 1 2026 · SIDE 1 OF 2 Whole-unit revision . all topics SIDE 1/2 ANALYSE . Green chemistry . Sustainability metrics . Feedstocks . Catalysis . Structure elucidation . IR . MS . 1H & 13C NMR 0 . Revision Blueprint READ FIRST * This unit has two halves that share one mindset: make the molecule (synthesis + polymers) and prove what you made (spectroscopy) - both judged against the green-chemistry yardstick of doing it with the least waste, energy and hazard. Side 1 = analysis & sustainability metrics. Side 2 = reactions & polymers. The exam reflex you need: read a structure, predict its spectra; read spectra, deduce the structure; and for any route, judge its atom economy. Most-tested skills: calculate atom economy / E-factor; assign an IR + MS + NMR set to one structure; pick Sn1 vs Sn2; classify a polymerisation; name a greener alternative (solvent, catalyst, feedstock). -- SIA > Two-line discipline: always state degrees of unsaturation first in any structure problem, and always quote the metric (a number) when asked "is this green?" - markers reward the calculation, not the adjective. 1 . Green Chemistry . ANASTAS & 12 Principles WARNER 1998 The design framework for the whole unit. Memorise the mnemonic "PRODUCTIVELY" idea - but really know the high-yield five (*). 1. * Prevent waste - better than treating/cleaning it up 2. * Atom economy - maximise atoms of reactant in product 3. Less hazardous synthesis (low toxicity to people/environment) 4. Design safer chemicals (function with minimal toxicity) 5. * Safer solvents/auxiliaries - avoid where possible 6. Design for energy efficiency - ambient T & P 7. Renewable feedstocks not depleting ones 8. Reduce derivatives (protecting groups add waste steps) 9. * Catalysis > stoichiometric reagents 10. * Design for degradation - break down after use, no persistence 11. Real-time analysis to prevent pollution
- 最常考的技能清单（cheatsheet 直接点名）：[2]Source: asksia-cheatsheet-chem2522.pdfSIDE 1/2
ANALYSE . Green chemistry . Sustainability metrics . Feedstocks . Catalysis . Structure elucidation . IR . MS . 1H & 13C
NMR
0 . Revision Blueprint READ FIRST * This unit has two halves that share one mindset: make the molecule (synthesis + polymers) and prove what you made (spectroscopy) - both judged against the green-chemistry yardstick of doing it with the least waste, energy and hazard. Side 1 = analysis & sustainability metrics. Side 2 = reactions & polymers. The exam reflex you need: read a structure, predict its spectra; read spectra, deduce the structure; and for any route, judge its atom economy. Most-tested skills: calculate atom economy / E-factor; assign an IR + MS + NMR set to one structure; pick Sn1 vs Sn2; classify a polymerisation; name a greener alternative (solvent, catalyst, feedstock). --
SIA > Two-line discipline: always state degrees of unsaturation first in any structure problem, and always quote the metric (a number) when asked "is this green?" - markers reward the calculation, not the adjective.
1 . Green Chemistry . ANASTAS & 12 Principles WARNER 1998
The design framework for the whole unit. Memorise the mnemonic "PRODUCTIVELY" idea - but really know the high-yield five (*).
1. * Prevent waste - better than treating/cleaning it up
2. * Atom economy - maximise atoms of reactant in product
3. Less hazardous synthesis (low toxicity to people/environment)
4. Design safer chemicals (function with minimal toxicity)
5. * Safer solvents/auxiliaries - avoid where possible
6. Design for energy efficiency - ambient T & P
7. Renewable feedstocks not depleting ones
8. Reduce derivatives (protecting groups add waste steps)
9. * Catalysis > stoichiometric reagents 10. * Design for degradation - break down after use, no persistence
11. Real-time analysis to prevent pollution
12. Inherently safer chemistry (accident prevention)
Prevention > remediation is the spine: principles 1, 2, 9 do most of the exam work.
1b . Worked . Atom Economy[3]Source: asksia-cheatsheet-chem2522.pdfCHEM2522
Sustainable Chemical Manufacture UNIVERSITY OF SYDNEY . SCHOOL OF CHEMISTRY
EXAM REVISION Sem 1 2026 · SIDE 1 OF 2 Whole-unit revision . all topics
SIDE 1/2
ANALYSE . Green chemistry . Sustainability metrics . Feedstocks . Catalysis . Structure elucidation . IR . MS . 1H & 13C
NMR
0 . Revision Blueprint READ FIRST * This unit has two halves that share one mindset: make the molecule (synthesis + polymers) and prove what you made (spectroscopy) - both judged against the green-chemistry yardstick of doing it with the least waste, energy and hazard. Side 1 = analysis & sustainability metrics. Side 2 = reactions & polymers. The exam reflex you need: read a structure, predict its spectra; read spectra, deduce the structure; and for any route, judge its atom economy. Most-tested skills: calculate atom economy / E-factor; assign an IR + MS + NMR set to one structure; pick Sn1 vs Sn2; classify a polymerisation; name a greener alternative (solvent, catalyst, feedstock). --
SIA > Two-line discipline: always state degrees of unsaturation first in any structure problem, and always quote the metric (a number) when asked "is this green?" - markers reward the calculation, not the adjective.
1 . Green Chemistry . ANASTAS & 12 Principles WARNER 1998
The design framework for the whole unit. Memorise the mnemonic "PRODUCTIVELY" idea - but really know the high-yield five (*).
1. * Prevent waste - better than treating/cleaning it up
2. * Atom economy - maximise atoms of reactant in product
3. Less hazardous synthesis (low toxicity to people/environment)
4. Design safer chemicals (function with minimal toxicity)
5. * Safer solvents/auxiliaries - avoid where possible
6. Design for energy efficiency - ambient T & P
7. Renewable feedstocks not depleting ones
8. Reduce derivatives (protecting groups add waste steps)
9. * Catalysis > stoichiometric reagents 10. * Design for degradation - break down after use, no persistence
11. Real-time analysis to prevent pollution
- 算 Atom economy / E-factor（以及 PMI）
- 把 IR + MS + NMR 一套数据“归到同一个结构”
- 选 SN1 vs SN2；（以及 E1/E2 的分叉判断）
- 聚合反应分类（尤其 step-growth 相关）
- 给出更绿色替代（溶剂 / 催化剂 / 原料 feedstock）
- 课程分两大半，但思维方式是同一个：
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二、考试“保命纪律”（能直接多拿分）
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1) “不要丢方法分”的规则
- 机制题：一定要画卷曲箭头，从 Nu（亲核体）→ E（亲电中心），并且把电荷、孤对电子画出来[1]Source: asksia-cheatsheet-chem2522.pdf24 . Exam Discipline DON'T LOSE MARKS Assign every spectral peak - reconcile to one structure "Is it green?" = give a number + name the waste · Mechanisms: curly arrows from Nu->E, charges & lone pairs shown QUICK SIA > Half the marks here are "show the calculation / show the arrow. " Method marks survive even when the final number slips - always write the working. 25 . Green Metrics Recap NAME THE TRADE- OFF METRIC CAPTURES MISSES Atom by-products yield, solvent economy (theory) Yield conversion achieved waste atoms E-factor real total waste[4]Source: asksia-cheatsheet-chem2522.pdf· Mechanisms: curly arrows from Nu->E, charges & lone pairs shown QUICK SIA > Half the marks here are "show the calculation / show the arrow. " Method marks survive even when the final number slips - always write the working. 25 . Green Metrics Recap NAME THE TRADE- OFF METRIC CAPTURES MISSES Atom by-products yield, solvent economy (theory) Yield conversion achieved waste atoms E-factor real total waste toxicity PMI + solvent & water hazard
- 计算题：写清楚计算过程；哪怕结果错一点，方法分会留住[1]Source: asksia-cheatsheet-chem2522.pdf24 . Exam Discipline DON'T LOSE MARKS Assign every spectral peak - reconcile to one structure "Is it green?" = give a number + name the waste · Mechanisms: curly arrows from Nu->E, charges & lone pairs shown QUICK SIA > Half the marks here are "show the calculation / show the arrow. " Method marks survive even when the final number slips - always write the working. 25 . Green Metrics Recap NAME THE TRADE- OFF METRIC CAPTURES MISSES Atom by-products yield, solvent economy (theory) Yield conversion achieved waste atoms E-factor real total waste[4]Source: asksia-cheatsheet-chem2522.pdf· Mechanisms: curly arrows from Nu->E, charges & lone pairs shown QUICK SIA > Half the marks here are "show the calculation / show the arrow. " Method marks survive even when the final number slips - always write the working. 25 . Green Metrics Recap NAME THE TRADE- OFF METRIC CAPTURES MISSES Atom by-products yield, solvent economy (theory) Yield conversion achieved waste atoms E-factor real total waste toxicity PMI + solvent & water hazard
- 结构解析题：每一个谱峰都要解释，最后要“所有数据只支持一个结构”[1]Source: asksia-cheatsheet-chem2522.pdf24 . Exam Discipline DON'T LOSE MARKS Assign every spectral peak - reconcile to one structure "Is it green?" = give a number + name the waste · Mechanisms: curly arrows from Nu->E, charges & lone pairs shown QUICK SIA > Half the marks here are "show the calculation / show the arrow. " Method marks survive even when the final number slips - always write the working. 25 . Green Metrics Recap NAME THE TRADE- OFF METRIC CAPTURES MISSES Atom by-products yield, solvent economy (theory) Yield conversion achieved waste atoms E-factor real total waste[8]Source: asksia-cheatsheet-chem2522.pdf21b · Structure -> Property RULES Branching \ = packs tighter = denser & . stronger (HDPE > LDPE) · Chain length / M 1 = higher Tm, strength, viscosity Polar groups / H-bonds (nylon) = stronger, higher Tm · Plasticiser = lowers Ta (rigid PVC > flexible) 21c . Measuring Molar METHODS Mass GPC / SEC - size-exclusion; gives the full distribution > Mn, Mw, Đ · End-group analysis (NMR/titration) > Mn (low MW only) 22 . Greener Process PRINCIPLES 5,6,9 Toolkit · Green solvents - water, scCO2, ionic liquids, bio-solvents (2-MeTHF, ethanol); avoid chlorinated & VOCs · Biocatalysis - enzymes; mild, aqueous, enantioselective 23 . Worked . Atom Economy SHOW THE NUMBER Q. Wittig vs substitution to make an alkene - which is greener by AE? Wittig expels Ph3P=O (M, 278) - a large by- product = low atom economy despite high yield. An elimination or a catalytic metathesis keeps more atoms in product. LESSON high yield # green. Quote AE/E-factor, then name the by-product driving waste. 24 . Exam Discipline DON'T LOSE MARKS Assign every spectral peak - reconcile to one structure "Is it green?" = give a number + name the waste[17]Source: asksia-cheatsheet-chem2522.pdfEdits by # attached H: CH & CH3 up, CH2 down, quaternary C absent (the give-away for C=O & substituted aromatic). COUNTING SIGNALS = SYMMETRY # of signals = # of chemically distinct environments. Benzene = 1 13C; para- disubstituted ring = 4 (two pairs equivalent). Fewer signals than carbons = symmetry - a fast structural clue. 11 . Worked . C4H8O PUT IT TOGETHER MS M+ = 72. DBE = (2. 4+2-8)/2 = 1 = one C=O or C=C/ring. IR 1715 cm-1 strong = ketone C=O (no broad O-H, no ~2720 aldehyde C-H, no 1735 ester). 1H NMR triplet 1. 0 (3H), quartet 2. 4 (2H), singlet 2. 1 (3H) = ethyl + isolated methyl on C=O. butan-2-one, CH3COCH2CH3. MS loss of 15 (>57) and 29 (>43, CH3CO+) confirm a- cleavage either side of C=O. ---- SIA - Reconcile every piece of data to one structure - if a single peak doesn't fit, the structure is wrong. Examiners build the trap on the one ignored signal. 11b . Worked . C8H8O SPOT THE RING DBE = (2. 8+2-8)/2 = 5 = benzene ring (4) + one more (a C=O). IR 1685 (conjugated C=O). 1H: 5H multiplet 7. 4-8. 0 (mono-substituted ring) + singlet 2. 6 (3H, CH3CO). = acetophenone, C&H;COCH3. 13C ~198 (C=O); m/z 105 (PhCO+) & 77 (C6H5*) confirm. Which Technique? RECAP QUESTION USE Mass / formula MS (M+1, isotopes) Functional groups? IR (C=0, O-H, N-H) # unique C; C type 13C + DEPT H count & connectivity 1H (6, integ, J)
- “Is it green?” 这类问法：不能只写 green/not green，必须：
- 给一个指标数字（AE/E-factor/PMI 等）
- 再点名 waste/trade-off（比如副产物、溶剂、水、毒性等）[1]Source: asksia-cheatsheet-chem2522.pdf24 . Exam Discipline DON'T LOSE MARKS Assign every spectral peak - reconcile to one structure "Is it green?" = give a number + name the waste · Mechanisms: curly arrows from Nu->E, charges & lone pairs shown QUICK SIA > Half the marks here are "show the calculation / show the arrow. " Method marks survive even when the final number slips - always write the working. 25 . Green Metrics Recap NAME THE TRADE- OFF METRIC CAPTURES MISSES Atom by-products yield, solvent economy (theory) Yield conversion achieved waste atoms E-factor real total waste[8]Source: asksia-cheatsheet-chem2522.pdf21b · Structure -> Property RULES Branching \ = packs tighter = denser & . stronger (HDPE > LDPE) · Chain length / M 1 = higher Tm, strength, viscosity Polar groups / H-bonds (nylon) = stronger, higher Tm · Plasticiser = lowers Ta (rigid PVC > flexible) 21c . Measuring Molar METHODS Mass GPC / SEC - size-exclusion; gives the full distribution > Mn, Mw, Đ · End-group analysis (NMR/titration) > Mn (low MW only) 22 . Greener Process PRINCIPLES 5,6,9 Toolkit · Green solvents - water, scCO2, ionic liquids, bio-solvents (2-MeTHF, ethanol); avoid chlorinated & VOCs · Biocatalysis - enzymes; mild, aqueous, enantioselective 23 . Worked . Atom Economy SHOW THE NUMBER Q. Wittig vs substitution to make an alkene - which is greener by AE? Wittig expels Ph3P=O (M, 278) - a large by- product = low atom economy despite high yield. An elimination or a catalytic metathesis keeps more atoms in product. LESSON high yield # green. Quote AE/E-factor, then name the by-product driving waste. 24 . Exam Discipline DON'T LOSE MARKS Assign every spectral peak - reconcile to one structure "Is it green?" = give a number + name the waste[18]Source: asksia-cheatsheet-chem2522.pdfNo single number means "green" - name which trade-off the question tests. Formula Belt SIDE 2 Xn = 1/(1-p) . Đ = Mw/Mn ≥1 splitting n+1 . reactivity: RCOCl>ester>amide Sn2 inversion . E2 anti-periplanar green: catalysis . renewable . degrade asksia. ai/cheatsheet/ usyd-chem2522 . side 2/2 AskSia CHEATSHEET SERIES 20 . Polymer Properties MOLAR MASS AVERAGES & DISPERSITY ΜΠ = Ση;Μ;/ Ση; (number avg) Mw = Ση;Μ12/Ση;Μ; (weight avg) Đ = M/Mn ≥ 1 (dispersity) Đ = 1 = perfectly uniform; step-growth ~2; controlled radical > low Đ. THERMAL & ORDER · Tg glass transition (amorphous softens); Tm melts (crystalline) · Tacticity - iso / syndio / atactic; regular = crystalline, higher Tm 21 · Sustainable Polymers · Polyamide (nylon) - diacid + diamine > amide links + H2O. · Polycarbonate - bisphenol + carbonate source. Need exact stoichiometry & high purity (Carothers) for high MW. The ester/amide links are also the handle for chemical recycling (hydrolysis/solvolysis back to monomer). 19b . Nature's Step- Growth BIOPOLYMERS The largest condensation polymers are biological: proteins (amino acids - peptide/amide bonds + H2O), polysaccharides (sugars >> glycosidic bonds + H2O), nucleic acids (phosphodiester). All are hydrolysable = inherently degradable - the design template for sustainable polymers. 19c . Worked . Carothers WHY PURITY MATTERS Degree of polymerisation vs conversion p: P
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三、绿色化学核心：12 Principles（定义 + 最高频的那几个）
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1) 12 原则（Anastas & Warner 1998）
- 这是全课的“设计框架”，cheatsheet 强调：记 mnemonic 可以，但更重要的是掌握高频原则[2]Source: asksia-cheatsheet-chem2522.pdfSIDE 1/2 ANALYSE . Green chemistry . Sustainability metrics . Feedstocks . Catalysis . Structure elucidation . IR . MS . 1H & 13C NMR 0 . Revision Blueprint READ FIRST * This unit has two halves that share one mindset: make the molecule (synthesis + polymers) and prove what you made (spectroscopy) - both judged against the green-chemistry yardstick of doing it with the least waste, energy and hazard. Side 1 = analysis & sustainability metrics. Side 2 = reactions & polymers. The exam reflex you need: read a structure, predict its spectra; read spectra, deduce the structure; and for any route, judge its atom economy. Most-tested skills: calculate atom economy / E-factor; assign an IR + MS + NMR set to one structure; pick Sn1 vs Sn2; classify a polymerisation; name a greener alternative (solvent, catalyst, feedstock). -- SIA > Two-line discipline: always state degrees of unsaturation first in any structure problem, and always quote the metric (a number) when asked "is this green?" - markers reward the calculation, not the adjective. 1 . Green Chemistry . ANASTAS & 12 Principles WARNER 1998 The design framework for the whole unit. Memorise the mnemonic "PRODUCTIVELY" idea - but really know the high-yield five (*). 1. * Prevent waste - better than treating/cleaning it up 2. * Atom economy - maximise atoms of reactant in product 3. Less hazardous synthesis (low toxicity to people/environment) 4. Design safer chemicals (function with minimal toxicity) 5. * Safer solvents/auxiliaries - avoid where possible 6. Design for energy efficiency - ambient T & P 7. Renewable feedstocks not depleting ones 8. Reduce derivatives (protecting groups add waste steps) 9. * Catalysis > stoichiometric reagents 10. * Design for degradation - break down after use, no persistence 11. Real-time analysis to prevent pollution 12. Inherently safer chemistry (accident prevention) Prevention > remediation is the spine: principles 1, 2, 9 do most of the exam work. 1b . Worked . Atom Economy[3]Source: asksia-cheatsheet-chem2522.pdfCHEM2522 Sustainable Chemical Manufacture UNIVERSITY OF SYDNEY . SCHOOL OF CHEMISTRY EXAM REVISION Sem 1 2026 · SIDE 1 OF 2 Whole-unit revision . all topics SIDE 1/2 ANALYSE . Green chemistry . Sustainability metrics . Feedstocks . Catalysis . Structure elucidation . IR . MS . 1H & 13C NMR 0 . Revision Blueprint READ FIRST * This unit has two halves that share one mindset: make the molecule (synthesis + polymers) and prove what you made (spectroscopy) - both judged against the green-chemistry yardstick of doing it with the least waste, energy and hazard. Side 1 = analysis & sustainability metrics. Side 2 = reactions & polymers. The exam reflex you need: read a structure, predict its spectra; read spectra, deduce the structure; and for any route, judge its atom economy. Most-tested skills: calculate atom economy / E-factor; assign an IR + MS + NMR set to one structure; pick Sn1 vs Sn2; classify a polymerisation; name a greener alternative (solvent, catalyst, feedstock). -- SIA > Two-line discipline: always state degrees of unsaturation first in any structure problem, and always quote the metric (a number) when asked "is this green?" - markers reward the calculation, not the adjective. 1 . Green Chemistry . ANASTAS & 12 Principles WARNER 1998 The design framework for the whole unit. Memorise the mnemonic "PRODUCTIVELY" idea - but really know the high-yield five (*). 1. * Prevent waste - better than treating/cleaning it up 2. * Atom economy - maximise atoms of reactant in product 3. Less hazardous synthesis (low toxicity to people/environment) 4. Design safer chemicals (function with minimal toxicity) 5. * Safer solvents/auxiliaries - avoid where possible 6. Design for energy efficiency - ambient T & P 7. Renewable feedstocks not depleting ones 8. Reduce derivatives (protecting groups add waste steps) 9. * Catalysis > stoichiometric reagents 10. * Design for degradation - break down after use, no persistence 11. Real-time analysis to prevent pollution
- 12 条（按你材料列的表述）[2]Source: asksia-cheatsheet-chem2522.pdfSIDE 1/2
ANALYSE . Green chemistry . Sustainability metrics . Feedstocks . Catalysis . Structure elucidation . IR . MS . 1H & 13C
NMR
0 . Revision Blueprint READ FIRST * This unit has two halves that share one mindset: make the molecule (synthesis + polymers) and prove what you made (spectroscopy) - both judged against the green-chemistry yardstick of doing it with the least waste, energy and hazard. Side 1 = analysis & sustainability metrics. Side 2 = reactions & polymers. The exam reflex you need: read a structure, predict its spectra; read spectra, deduce the structure; and for any route, judge its atom economy. Most-tested skills: calculate atom economy / E-factor; assign an IR + MS + NMR set to one structure; pick Sn1 vs Sn2; classify a polymerisation; name a greener alternative (solvent, catalyst, feedstock). --
SIA > Two-line discipline: always state degrees of unsaturation first in any structure problem, and always quote the metric (a number) when asked "is this green?" - markers reward the calculation, not the adjective.
1 . Green Chemistry . ANASTAS & 12 Principles WARNER 1998
The design framework for the whole unit. Memorise the mnemonic "PRODUCTIVELY" idea - but really know the high-yield five (*).
1. * Prevent waste - better than treating/cleaning it up
2. * Atom economy - maximise atoms of reactant in product
3. Less hazardous synthesis (low toxicity to people/environment)
4. Design safer chemicals (function with minimal toxicity)
5. * Safer solvents/auxiliaries - avoid where possible
6. Design for energy efficiency - ambient T & P
7. Renewable feedstocks not depleting ones
8. Reduce derivatives (protecting groups add waste steps)
9. * Catalysis > stoichiometric reagents 10. * Design for degradation - break down after use, no persistence
11. Real-time analysis to prevent pollution
12. Inherently safer chemistry (accident prevention)
Prevention > remediation is the spine: principles 1, 2, 9 do most of the exam work.
1b . Worked . Atom Economy[3]Source: asksia-cheatsheet-chem2522.pdfCHEM2522
Sustainable Chemical Manufacture UNIVERSITY OF SYDNEY . SCHOOL OF CHEMISTRY
EXAM REVISION Sem 1 2026 · SIDE 1 OF 2 Whole-unit revision . all topics
SIDE 1/2
ANALYSE . Green chemistry . Sustainability metrics . Feedstocks . Catalysis . Structure elucidation . IR . MS . 1H & 13C
NMR
0 . Revision Blueprint READ FIRST * This unit has two halves that share one mindset: make the molecule (synthesis + polymers) and prove what you made (spectroscopy) - both judged against the green-chemistry yardstick of doing it with the least waste, energy and hazard. Side 1 = analysis & sustainability metrics. Side 2 = reactions & polymers. The exam reflex you need: read a structure, predict its spectra; read spectra, deduce the structure; and for any route, judge its atom economy. Most-tested skills: calculate atom economy / E-factor; assign an IR + MS + NMR set to one structure; pick Sn1 vs Sn2; classify a polymerisation; name a greener alternative (solvent, catalyst, feedstock). --
SIA > Two-line discipline: always state degrees of unsaturation first in any structure problem, and always quote the metric (a number) when asked "is this green?" - markers reward the calculation, not the adjective.
1 . Green Chemistry . ANASTAS & 12 Principles WARNER 1998
The design framework for the whole unit. Memorise the mnemonic "PRODUCTIVELY" idea - but really know the high-yield five (*).
1. * Prevent waste - better than treating/cleaning it up
2. * Atom economy - maximise atoms of reactant in product
3. Less hazardous synthesis (low toxicity to people/environment)
4. Design safer chemicals (function with minimal toxicity)
5. * Safer solvents/auxiliaries - avoid where possible
6. Design for energy efficiency - ambient T & P
7. Renewable feedstocks not depleting ones
8. Reduce derivatives (protecting groups add waste steps)
9. * Catalysis > stoichiometric reagents 10. * Design for degradation - break down after use, no persistence
11. Real-time analysis to prevent pollution
- 1 Prevent waste：预防废物 > 事后处理
- 2 Atom economy：最大化反应物原子进入产物
- 3 Less hazardous synthesis：更低毒/更少环境危害
- 4 Design safer chemicals：功能满足同时最小毒性
- 5 Safer solvents/auxiliaries：尽量不用或用更安全溶剂/助剂
- 6 Energy efficiency：常温常压更好
- 7 Renewable feedstocks：可再生原料
- 8 Reduce derivatives：少用保护基/衍生化（因为增加步骤与废物）
- 9 Catalysis > stoichiometric：催化优于化学计量试剂
- 10 Design for degradation：可降解/不持久
- 11 Real-time analysis：实时监测减少污染
- 12 Inherently safer chemistry：过程本质更安全（事故预防）
- 考点提示（材料里的“脊梁”）：原则 1、2、9 是最能“撑起考试题”的三条：预防废物、原子经济性、催化[10]Source: asksia-cheatsheet-chem2522.pdf12. Inherently safer chemistry (accident prevention) Prevention > remediation is the spine: principles 1, 2, 9 do most of the exam work. 1b . Worked . Atom Economy TWO ROUTES Target = ethanol (C2HBO, M, 46): Hydration CH2=CH2 + H2O -> C2H5OH AE = 46/(28+18) = 100% (addition, no by- product). Fermentation C 6H1206 -> 2 C2H5OH + 2 CO2 AE = (2-46)/180 = 51% - CO2 is lost mass, but the feedstock is renewable. = greenness trades AE vs feedstock vs energy. Quote all three, don't crown a winner on AE alone. 2 . Sustainability Metrics CALCULATE THESE Yield tells you nothing about waste. A 100% yield reaction can still be wasteful if half the reactant mass ends up as by- product. That's why we measure atoms and mass. ATOM ECONOMY TROST 1991 % ATOM ECONOMY AE = (M, desired product / E Mr all products) x 100 = Mr product / E Mr reactants x 100 Theoretical (uses the balanced equation, ignores yield). Addition & rearrangement > 100% AE ; substitution & especially elimination/condensation lose atoms. E-FACTOR SHELDON ENVIRONMENTAL FACTOR E = mass of waste / mass of product ideal E = 0 (zero waste) INDUSTRY TONNAGE E-FACTOR Bulk chems 104-106 <1-5 Fine chems 102-104
-
四、可持续/绿色指标：定义、公式、怎么被考
-
1) Yield（产率）— 常见误区
-
2) Atom Economy（AE，原子经济性）
- 定义（Trost 1991）：理论指标，用配平方程算，忽略产率[10]Source: asksia-cheatsheet-chem2522.pdf12. Inherently safer chemistry (accident prevention) Prevention > remediation is the spine: principles 1, 2, 9 do most of the exam work. 1b . Worked . Atom Economy TWO ROUTES Target = ethanol (C2HBO, M, 46): Hydration CH2=CH2 + H2O -> C2H5OH AE = 46/(28+18) = 100% (addition, no by- product). Fermentation C 6H1206 -> 2 C2H5OH + 2 CO2 AE = (2-46)/180 = 51% - CO2 is lost mass, but the feedstock is renewable. = greenness trades AE vs feedstock vs energy. Quote all three, don't crown a winner on AE alone. 2 . Sustainability Metrics CALCULATE THESE Yield tells you nothing about waste. A 100% yield reaction can still be wasteful if half the reactant mass ends up as by- product. That's why we measure atoms and mass. ATOM ECONOMY TROST 1991 % ATOM ECONOMY AE = (M, desired product / E Mr all products) x 100 = Mr product / E Mr reactants x 100 Theoretical (uses the balanced equation, ignores yield). Addition & rearrangement > 100% AE ; substitution & especially elimination/condensation lose atoms. E-FACTOR SHELDON ENVIRONMENTAL FACTOR E = mass of waste / mass of product ideal E = 0 (zero waste) INDUSTRY TONNAGE E-FACTOR Bulk chems 104-106 <1-5 Fine chems 102-104
- 公式（cheatsheet 两种等价写法）：[10]Source: asksia-cheatsheet-chem2522.pdf12. Inherently safer chemistry (accident prevention)
Prevention > remediation is the spine: principles 1, 2, 9 do most of the exam work.
1b . Worked . Atom Economy
TWO ROUTES
Target = ethanol (C2HBO, M, 46): Hydration CH2=CH2 + H2O -> C2H5OH AE = 46/(28+18) = 100% (addition, no by- product). Fermentation C 6H1206 -> 2 C2H5OH + 2 CO2 AE = (2-46)/180 = 51% - CO2 is lost mass, but the feedstock is renewable. = greenness trades AE vs feedstock vs energy. Quote all three, don't crown a winner on AE alone.
2 . Sustainability Metrics
CALCULATE THESE
Yield tells you nothing about waste. A 100% yield reaction can still be wasteful if half the reactant mass ends up as by- product. That's why we measure atoms and mass.
ATOM ECONOMY TROST 1991
% ATOM ECONOMY AE = (M, desired product / E Mr all products) x 100 = Mr product / E Mr reactants x 100 Theoretical (uses the balanced equation, ignores yield). Addition & rearrangement > 100% AE ; substitution & especially elimination/condensation lose atoms.
E-FACTOR SHELDON
ENVIRONMENTAL FACTOR E = mass of waste / mass of product ideal E = 0 (zero waste)
INDUSTRY
TONNAGE
E-FACTOR
Bulk chems
104-106
<1-5
Fine chems
102-104[12]Source: asksia-cheatsheet-chem2522.pdf13C + DEPT
H count & connectivity
1H (6, integ, J)
Rings / Tt count
DBE from formula
Formula Belt SIDE 1 | ΑΕ = Mc (prod)/ ΣΜ, (react) x100 E = waste / product . PMI = E+1 DBE = (2C+2+N-H-X)/2 splitting = n+1 . M+1 = 1. 1% . nC Cl 3:1 . Br 1:1 (M:M+2)
asksia. ai/cheatsheet/ usyd-chem2522 . side 1/2
AskSia CHEATSHEET SERIES
THE 6 . Structure Elucidation WORKFLOW
Combine the techniques - each answers a different question:
· 1H/13C NMR > carbon-hydrogen skeleton (how connected?)
STEP 1 ALWAYS: DBE
DEGREES OF UNSATURATION (IHD/DBE) DBE = (2C + 2 + N - H - X) / 2 (0 is ignored). Ring or n-bond = 1 each.
DBE ≥ 4 = suspect a benzene ring (3 C=C + 1 ring). C=O = 1, C=N = 2, C=C = 2.
7 . IR Spectroscopy CM-1
Bond stretching frequency . /(k/u): stronger bond & lighter atoms = higher cm-1. Read the diagnostic 4000-1500 region; 1500-500 is the "fingerprint".
BOND / GROUP
CM-1
NOTE
O-H alcohol
- $$%AE=\frac{M_r(\text{desired product})}{\sum M_r(\text{all products})}\times100$$
- 等价地（基于反应物）： $$%AE=\frac{M_r(\text{product})}{\sum M_r(\text{reactants})}\times100$$
- 判断题套路（材料给的结论）[10]Source: asksia-cheatsheet-chem2522.pdf12. Inherently safer chemistry (accident prevention)
Prevention > remediation is the spine: principles 1, 2, 9 do most of the exam work.
1b . Worked . Atom Economy
TWO ROUTES
Target = ethanol (C2HBO, M, 46): Hydration CH2=CH2 + H2O -> C2H5OH AE = 46/(28+18) = 100% (addition, no by- product). Fermentation C 6H1206 -> 2 C2H5OH + 2 CO2 AE = (2-46)/180 = 51% - CO2 is lost mass, but the feedstock is renewable. = greenness trades AE vs feedstock vs energy. Quote all three, don't crown a winner on AE alone.
2 . Sustainability Metrics
CALCULATE THESE
Yield tells you nothing about waste. A 100% yield reaction can still be wasteful if half the reactant mass ends up as by- product. That's why we measure atoms and mass.
ATOM ECONOMY TROST 1991
% ATOM ECONOMY AE = (M, desired product / E Mr all products) x 100 = Mr product / E Mr reactants x 100 Theoretical (uses the balanced equation, ignores yield). Addition & rearrangement > 100% AE ; substitution & especially elimination/condensation lose atoms.
E-FACTOR SHELDON
ENVIRONMENTAL FACTOR E = mass of waste / mass of product ideal E = 0 (zero waste)
INDUSTRY
TONNAGE
E-FACTOR
Bulk chems
104-106
<1-5
Fine chems
102-104
- addition / rearrangement 往往 AE 高（几乎不丢原子）
- substitution、尤其 elimination / condensation 往往会“丢掉小分子”→ AE 低
- 经典对比题（cheatsheet 明示）：Wittig 制烯烃 vs 消除/催化复分解
- Wittig 会排出 Ph$_3$P=O（Mr 278） 这种大副产物 → AE 低（即使 yield 高）[8]Source: asksia-cheatsheet-chem2522.pdf21b · Structure -> Property RULES Branching \ = packs tighter = denser & . stronger (HDPE > LDPE) · Chain length / M 1 = higher Tm, strength, viscosity Polar groups / H-bonds (nylon) = stronger, higher Tm · Plasticiser = lowers Ta (rigid PVC > flexible) 21c . Measuring Molar METHODS Mass GPC / SEC - size-exclusion; gives the full distribution > Mn, Mw, Đ · End-group analysis (NMR/titration) > Mn (low MW only) 22 . Greener Process PRINCIPLES 5,6,9 Toolkit · Green solvents - water, scCO2, ionic liquids, bio-solvents (2-MeTHF, ethanol); avoid chlorinated & VOCs · Biocatalysis - enzymes; mild, aqueous, enantioselective 23 . Worked . Atom Economy SHOW THE NUMBER Q. Wittig vs substitution to make an alkene - which is greener by AE? Wittig expels Ph3P=O (M, 278) - a large by- product = low atom economy despite high yield. An elimination or a catalytic metathesis keeps more atoms in product. LESSON high yield # green. Quote AE/E-factor, then name the by-product driving waste. 24 . Exam Discipline DON'T LOSE MARKS Assign every spectral peak - reconcile to one structure "Is it green?" = give a number + name the waste
- 结论句：high yield ≠ green；答题要“报 AE / E-factor 数字 + 点名副产物”[8]Source: asksia-cheatsheet-chem2522.pdf21b · Structure -> Property RULES Branching \ = packs tighter = denser & . stronger (HDPE > LDPE) · Chain length / M 1 = higher Tm, strength, viscosity Polar groups / H-bonds (nylon) = stronger, higher Tm · Plasticiser = lowers Ta (rigid PVC > flexible) 21c . Measuring Molar METHODS Mass GPC / SEC - size-exclusion; gives the full distribution > Mn, Mw, Đ · End-group analysis (NMR/titration) > Mn (low MW only) 22 . Greener Process PRINCIPLES 5,6,9 Toolkit · Green solvents - water, scCO2, ionic liquids, bio-solvents (2-MeTHF, ethanol); avoid chlorinated & VOCs · Biocatalysis - enzymes; mild, aqueous, enantioselective 23 . Worked . Atom Economy SHOW THE NUMBER Q. Wittig vs substitution to make an alkene - which is greener by AE? Wittig expels Ph3P=O (M, 278) - a large by- product = low atom economy despite high yield. An elimination or a catalytic metathesis keeps more atoms in product. LESSON high yield # green. Quote AE/E-factor, then name the by-product driving waste. 24 . Exam Discipline DON'T LOSE MARKS Assign every spectral peak - reconcile to one structure "Is it green?" = give a number + name the waste
-
3) E-factor（E，环境因子）
- 定义（Sheldon）：[10]Source: asksia-cheatsheet-chem2522.pdf12. Inherently safer chemistry (accident prevention)
Prevention > remediation is the spine: principles 1, 2, 9 do most of the exam work.
1b . Worked . Atom Economy
TWO ROUTES
Target = ethanol (C2HBO, M, 46): Hydration CH2=CH2 + H2O -> C2H5OH AE = 46/(28+18) = 100% (addition, no by- product). Fermentation C 6H1206 -> 2 C2H5OH + 2 CO2 AE = (2-46)/180 = 51% - CO2 is lost mass, but the feedstock is renewable. = greenness trades AE vs feedstock vs energy. Quote all three, don't crown a winner on AE alone.
2 . Sustainability Metrics
CALCULATE THESE
Yield tells you nothing about waste. A 100% yield reaction can still be wasteful if half the reactant mass ends up as by- product. That's why we measure atoms and mass.
ATOM ECONOMY TROST 1991
% ATOM ECONOMY AE = (M, desired product / E Mr all products) x 100 = Mr product / E Mr reactants x 100 Theoretical (uses the balanced equation, ignores yield). Addition & rearrangement > 100% AE ; substitution & especially elimination/condensation lose atoms.
E-FACTOR SHELDON
ENVIRONMENTAL FACTOR E = mass of waste / mass of product ideal E = 0 (zero waste)
INDUSTRY
TONNAGE
E-FACTOR
Bulk chems
104-106
<1-5
Fine chems
102-104
- $$E=\frac{\text{mass of waste}}{\text{mass of product}}$$
- 理想：$E=0$（零废物）
- 考试怎么用：常用来比较“真实总废物”，比 AE 更“落地”[1]Source: asksia-cheatsheet-chem2522.pdf24 . Exam Discipline DON'T LOSE MARKS Assign every spectral peak - reconcile to one structure "Is it green?" = give a number + name the waste · Mechanisms: curly arrows from Nu->E, charges & lone pairs shown QUICK SIA > Half the marks here are "show the calculation / show the arrow. " Method marks survive even when the final number slips - always write the working. 25 . Green Metrics Recap NAME THE TRADE- OFF METRIC CAPTURES MISSES Atom by-products yield, solvent economy (theory) Yield conversion achieved waste atoms E-factor real total waste[4]Source: asksia-cheatsheet-chem2522.pdf· Mechanisms: curly arrows from Nu->E, charges & lone pairs shown QUICK SIA > Half the marks here are "show the calculation / show the arrow. " Method marks survive even when the final number slips - always write the working. 25 . Green Metrics Recap NAME THE TRADE- OFF METRIC CAPTURES MISSES Atom by-products yield, solvent economy (theory) Yield conversion achieved waste atoms E-factor real total waste toxicity PMI + solvent & water hazard
- 定义（Sheldon）：[10]Source: asksia-cheatsheet-chem2522.pdf12. Inherently safer chemistry (accident prevention)
Prevention > remediation is the spine: principles 1, 2, 9 do most of the exam work.
1b . Worked . Atom Economy
TWO ROUTES
Target = ethanol (C2HBO, M, 46): Hydration CH2=CH2 + H2O -> C2H5OH AE = 46/(28+18) = 100% (addition, no by- product). Fermentation C 6H1206 -> 2 C2H5OH + 2 CO2 AE = (2-46)/180 = 51% - CO2 is lost mass, but the feedstock is renewable. = greenness trades AE vs feedstock vs energy. Quote all three, don't crown a winner on AE alone.
2 . Sustainability Metrics
CALCULATE THESE
Yield tells you nothing about waste. A 100% yield reaction can still be wasteful if half the reactant mass ends up as by- product. That's why we measure atoms and mass.
ATOM ECONOMY TROST 1991
% ATOM ECONOMY AE = (M, desired product / E Mr all products) x 100 = Mr product / E Mr reactants x 100 Theoretical (uses the balanced equation, ignores yield). Addition & rearrangement > 100% AE ; substitution & especially elimination/condensation lose atoms.
E-FACTOR SHELDON
ENVIRONMENTAL FACTOR E = mass of waste / mass of product ideal E = 0 (zero waste)
INDUSTRY
TONNAGE
E-FACTOR
Bulk chems
104-106
<1-5
Fine chems
102-104
-
4) PMI（Process Mass Intensity）
-
5) “没有一个数字能直接等于 green”
- cheatsheet 明确提醒：没有单一数字能定义绿色，你必须说明题目在考哪个 trade-off（比如 AE vs 可再生原料 vs 能耗等）[18]Source: asksia-cheatsheet-chem2522.pdfNo single number means "green" - name which trade-off the question tests. Formula Belt SIDE 2 Xn = 1/(1-p) . Đ = Mw/Mn ≥1 splitting n+1 . reactivity: RCOCl>ester>amide Sn2 inversion . E2 anti-periplanar green: catalysis . renewable . degrade asksia. ai/cheatsheet/ usyd-chem2522 . side 2/2 AskSia CHEATSHEET SERIES 20 . Polymer Properties MOLAR MASS AVERAGES & DISPERSITY ΜΠ = Ση;Μ;/ Ση; (number avg) Mw = Ση;Μ12/Ση;Μ; (weight avg) Đ = M/Mn ≥ 1 (dispersity) Đ = 1 = perfectly uniform; step-growth ~2; controlled radical > low Đ. THERMAL & ORDER · Tg glass transition (amorphous softens); Tm melts (crystalline) · Tacticity - iso / syndio / atactic; regular = crystalline, higher Tm 21 · Sustainable Polymers · Polyamide (nylon) - diacid + diamine > amide links + H2O. · Polycarbonate - bisphenol + carbonate source. Need exact stoichiometry & high purity (Carothers) for high MW. The ester/amide links are also the handle for chemical recycling (hydrolysis/solvolysis back to monomer). 19b . Nature's Step- Growth BIOPOLYMERS The largest condensation polymers are biological: proteins (amino acids - peptide/amide bonds + H2O), polysaccharides (sugars >> glycosidic bonds + H2O), nucleic acids (phosphodiester). All are hydrolysable = inherently degradable - the design template for sustainable polymers. 19c . Worked . Carothers WHY PURITY MATTERS Degree of polymerisation vs conversion p: P
- 例子（材料给了 AE vs 可再生的冲突）：乙醇两条路线[10]Source: asksia-cheatsheet-chem2522.pdf12. Inherently safer chemistry (accident prevention)
Prevention > remediation is the spine: principles 1, 2, 9 do most of the exam work.
1b . Worked . Atom Economy
TWO ROUTES
Target = ethanol (C2HBO, M, 46): Hydration CH2=CH2 + H2O -> C2H5OH AE = 46/(28+18) = 100% (addition, no by- product). Fermentation C 6H1206 -> 2 C2H5OH + 2 CO2 AE = (2-46)/180 = 51% - CO2 is lost mass, but the feedstock is renewable. = greenness trades AE vs feedstock vs energy. Quote all three, don't crown a winner on AE alone.
2 . Sustainability Metrics
CALCULATE THESE
Yield tells you nothing about waste. A 100% yield reaction can still be wasteful if half the reactant mass ends up as by- product. That's why we measure atoms and mass.
ATOM ECONOMY TROST 1991
% ATOM ECONOMY AE = (M, desired product / E Mr all products) x 100 = Mr product / E Mr reactants x 100 Theoretical (uses the balanced equation, ignores yield). Addition & rearrangement > 100% AE ; substitution & especially elimination/condensation lose atoms.
E-FACTOR SHELDON
ENVIRONMENTAL FACTOR E = mass of waste / mass of product ideal E = 0 (zero waste)
INDUSTRY
TONNAGE
E-FACTOR
Bulk chems
104-106
<1-5
Fine chems
102-104
- 水合：CH$_2$=CH$_2$ + H$_2$O → C$_2$H$_5$OH
$$AE=\frac{46}{28+18}=100%$$ - 发酵：C$6$H${12}$O$_6$ → 2 C$_2$H$_5$OH + 2 CO$_2$
$$AE=\frac{2\times46}{180}=51%$$ - 但发酵 feedstock 可再生；所以不能只凭 AE 盖章，答题要把 trade-off 说全[10]Source: asksia-cheatsheet-chem2522.pdf12. Inherently safer chemistry (accident prevention) Prevention > remediation is the spine: principles 1, 2, 9 do most of the exam work. 1b . Worked . Atom Economy TWO ROUTES Target = ethanol (C2HBO, M, 46): Hydration CH2=CH2 + H2O -> C2H5OH AE = 46/(28+18) = 100% (addition, no by- product). Fermentation C 6H1206 -> 2 C2H5OH + 2 CO2 AE = (2-46)/180 = 51% - CO2 is lost mass, but the feedstock is renewable. = greenness trades AE vs feedstock vs energy. Quote all three, don't crown a winner on AE alone. 2 . Sustainability Metrics CALCULATE THESE Yield tells you nothing about waste. A 100% yield reaction can still be wasteful if half the reactant mass ends up as by- product. That's why we measure atoms and mass. ATOM ECONOMY TROST 1991 % ATOM ECONOMY AE = (M, desired product / E Mr all products) x 100 = Mr product / E Mr reactants x 100 Theoretical (uses the balanced equation, ignores yield). Addition & rearrangement > 100% AE ; substitution & especially elimination/condensation lose atoms. E-FACTOR SHELDON ENVIRONMENTAL FACTOR E = mass of waste / mass of product ideal E = 0 (zero waste) INDUSTRY TONNAGE E-FACTOR Bulk chems 104-106 <1-5 Fine chems 102-104
- 水合：CH$_2$=CH$_2$ + H$_2$O → C$_2$H$_5$OH
-
五、结构解析（IR / MS / NMR）—— 最稳的“流水线做题法”
-
总原则：综合判断，“任何一个不匹配都推翻结构”
- cheatsheet 的核心要求：把每条信息都对到同一个结构；只要有一个峰你解释不了，结构就很可能错[17]Source: asksia-cheatsheet-chem2522.pdfEdits by # attached H: CH & CH3 up, CH2 down, quaternary C absent (the give-away for C=O & substituted aromatic). COUNTING SIGNALS = SYMMETRY # of signals = # of chemically distinct environments. Benzene = 1 13C; para- disubstituted ring = 4 (two pairs equivalent). Fewer signals than carbons = symmetry - a fast structural clue. 11 . Worked . C4H8O PUT IT TOGETHER MS M+ = 72. DBE = (2. 4+2-8)/2 = 1 = one C=O or C=C/ring. IR 1715 cm-1 strong = ketone C=O (no broad O-H, no ~2720 aldehyde C-H, no 1735 ester). 1H NMR triplet 1. 0 (3H), quartet 2. 4 (2H), singlet 2. 1 (3H) = ethyl + isolated methyl on C=O. butan-2-one, CH3COCH2CH3. MS loss of 15 (>57) and 29 (>43, CH3CO+) confirm a- cleavage either side of C=O. ---- SIA - Reconcile every piece of data to one structure - if a single peak doesn't fit, the structure is wrong. Examiners build the trap on the one ignored signal. 11b . Worked . C8H8O SPOT THE RING DBE = (2. 8+2-8)/2 = 5 = benzene ring (4) + one more (a C=O). IR 1685 (conjugated C=O). 1H: 5H multiplet 7. 4-8. 0 (mono-substituted ring) + singlet 2. 6 (3H, CH3CO). = acetophenone, C&H;COCH3. 13C ~198 (C=O); m/z 105 (PhCO+) & 77 (C6H5*) confirm. Which Technique? RECAP QUESTION USE Mass / formula MS (M+1, isotopes) Functional groups? IR (C=0, O-H, N-H) # unique C; C type 13C + DEPT H count & connectivity 1H (6, integ, J)[20]Source: asksia-cheatsheet-chem2522.pdfC=O ketone/aldehyde 190-220 DEPT Edits by # attached H: CH & CH3 up, CH2 down, quaternary C absent (the give-away for C=O & substituted aromatic). COUNTING SIGNALS = SYMMETRY # of signals = # of chemically distinct environments. Benzene = 1 13C; para- disubstituted ring = 4 (two pairs equivalent). Fewer signals than carbons = symmetry - a fast structural clue. 11 . Worked . C4H8O PUT IT TOGETHER MS M+ = 72. DBE = (2. 4+2-8)/2 = 1 = one C=O or C=C/ring. IR 1715 cm-1 strong = ketone C=O (no broad O-H, no ~2720 aldehyde C-H, no 1735 ester). 1H NMR triplet 1. 0 (3H), quartet 2. 4 (2H), singlet 2. 1 (3H) = ethyl + isolated methyl on C=O. butan-2-one, CH3COCH2CH3. MS loss of 15 (>57) and 29 (>43, CH3CO+) confirm a- cleavage either side of C=O. ---- SIA - Reconcile every piece of data to one structure - if a single peak doesn't fit, the structure is wrong. Examiners build the trap on the one ignored signal. 11b . Worked . C8H8O SPOT THE RING DBE = (2. 8+2-8)/2 = 5 = benzene ring (4) + one more (a C=O). IR 1685 (conjugated C=O). 1H: 5H multiplet 7. 4-8. 0 (mono-substituted ring) + singlet 2. 6 (3H, CH3CO). = acetophenone, C&H;COCH3. 13C ~198 (C=O); m/z 105 (PhCO+) & 77 (C6H5*) confirm. Which Technique? RECAP QUESTION USE Mass / formula MS (M+1, isotopes) Functional groups? IR (C=0, O-H, N-H) # unique C; C type
-
Step 1（永远第一步）：DBE / IHD（不饱和度）
- 公式（cheatsheet 给的）：[12]Source: asksia-cheatsheet-chem2522.pdf13C + DEPT
H count & connectivity
1H (6, integ, J)
Rings / Tt count
DBE from formula
Formula Belt SIDE 1 | ΑΕ = Mc (prod)/ ΣΜ, (react) x100 E = waste / product . PMI = E+1 DBE = (2C+2+N-H-X)/2 splitting = n+1 . M+1 = 1. 1% . nC Cl 3:1 . Br 1:1 (M:M+2)
asksia. ai/cheatsheet/ usyd-chem2522 . side 1/2
AskSia CHEATSHEET SERIES
THE 6 . Structure Elucidation WORKFLOW
Combine the techniques - each answers a different question:
· 1H/13C NMR > carbon-hydrogen skeleton (how connected?)
STEP 1 ALWAYS: DBE
DEGREES OF UNSATURATION (IHD/DBE) DBE = (2C + 2 + N - H - X) / 2 (0 is ignored). Ring or n-bond = 1 each.
DBE ≥ 4 = suspect a benzene ring (3 C=C + 1 ring). C=O = 1, C=N = 2, C=C = 2.
7 . IR Spectroscopy CM-1
Bond stretching frequency . /(k/u): stronger bond & lighter atoms = higher cm-1. Read the diagnostic 4000-1500 region; 1500-500 is the "fingerprint".
BOND / GROUP
CM-1
NOTE
O-H alcohol[16]Source: asksia-cheatsheet-chem2522.pdfRings / Tt count
DBE from formula
Formula Belt SIDE 1 | ΑΕ = Mc (prod)/ ΣΜ, (react) x100 E = waste / product . PMI = E+1 DBE = (2C+2+N-H-X)/2 splitting = n+1 . M+1 = 1. 1% . nC Cl 3:1 . Br 1:1 (M:M+2)
asksia. ai/cheatsheet/ usyd-chem2522 . side 1/2
AskSia CHEATSHEET SERIES
THE 6 . Structure Elucidation WORKFLOW
Combine the techniques - each answers a different question:
· 1H/13C NMR > carbon-hydrogen skeleton (how connected?)
STEP 1 ALWAYS: DBE
DEGREES OF UNSATURATION (IHD/DBE) DBE = (2C + 2 + N - H - X) / 2 (0 is ignored). Ring or n-bond = 1 each.
DBE ≥ 4 = suspect a benzene ring (3 C=C + 1 ring). C=O = 1, C=N = 2, C=C = 2.
7 . IR Spectroscopy CM-1
Bond stretching frequency . /(k/u): stronger bond & lighter atoms = higher cm-1. Read the diagnostic 4000-1500 region; 1500-500 is the "fingerprint".
BOND / GROUP
CM-1
NOTE
O-H alcohol
3200-3550
broad
O-H carb. acid
- $$DBE=\frac{2C+2+N-H-X}{2}$$
- 其中 $X$ 是卤素数（按氢来扣）
- 0 忽略（即算出来是 0 就说明无不饱和/无环）
- 解释规则：[12]Source: asksia-cheatsheet-chem2522.pdf13C + DEPT
H count & connectivity
1H (6, integ, J)
Rings / Tt count
DBE from formula
Formula Belt SIDE 1 | ΑΕ = Mc (prod)/ ΣΜ, (react) x100 E = waste / product . PMI = E+1 DBE = (2C+2+N-H-X)/2 splitting = n+1 . M+1 = 1. 1% . nC Cl 3:1 . Br 1:1 (M:M+2)
asksia. ai/cheatsheet/ usyd-chem2522 . side 1/2
AskSia CHEATSHEET SERIES
THE 6 . Structure Elucidation WORKFLOW
Combine the techniques - each answers a different question:
· 1H/13C NMR > carbon-hydrogen skeleton (how connected?)
STEP 1 ALWAYS: DBE
DEGREES OF UNSATURATION (IHD/DBE) DBE = (2C + 2 + N - H - X) / 2 (0 is ignored). Ring or n-bond = 1 each.
DBE ≥ 4 = suspect a benzene ring (3 C=C + 1 ring). C=O = 1, C=N = 2, C=C = 2.
7 . IR Spectroscopy CM-1
Bond stretching frequency . /(k/u): stronger bond & lighter atoms = higher cm-1. Read the diagnostic 4000-1500 region; 1500-500 is the "fingerprint".
BOND / GROUP
CM-1
NOTE
O-H alcohol[16]Source: asksia-cheatsheet-chem2522.pdfRings / Tt count
DBE from formula
Formula Belt SIDE 1 | ΑΕ = Mc (prod)/ ΣΜ, (react) x100 E = waste / product . PMI = E+1 DBE = (2C+2+N-H-X)/2 splitting = n+1 . M+1 = 1. 1% . nC Cl 3:1 . Br 1:1 (M:M+2)
asksia. ai/cheatsheet/ usyd-chem2522 . side 1/2
AskSia CHEATSHEET SERIES
THE 6 . Structure Elucidation WORKFLOW
Combine the techniques - each answers a different question:
· 1H/13C NMR > carbon-hydrogen skeleton (how connected?)
STEP 1 ALWAYS: DBE
DEGREES OF UNSATURATION (IHD/DBE) DBE = (2C + 2 + N - H - X) / 2 (0 is ignored). Ring or n-bond = 1 each.
DBE ≥ 4 = suspect a benzene ring (3 C=C + 1 ring). C=O = 1, C=N = 2, C=C = 2.
7 . IR Spectroscopy CM-1
Bond stretching frequency . /(k/u): stronger bond & lighter atoms = higher cm-1. Read the diagnostic 4000-1500 region; 1500-500 is the "fingerprint".
BOND / GROUP
CM-1
NOTE
O-H alcohol
3200-3550
broad
O-H carb. acid
- 1 个环或 1 个 $\pi$ 键 → DBE 加 1
- DBE $\ge 4$：高度怀疑苯环（3 个 C=C + 1 个环 = 4）
- C=O 计 1；C=N 计 2（按你材料写法）；C=C 也会贡献不饱和度[12]Source: asksia-cheatsheet-chem2522.pdf13C + DEPT H count & connectivity 1H (6, integ, J) Rings / Tt count DBE from formula Formula Belt SIDE 1 | ΑΕ = Mc (prod)/ ΣΜ, (react) x100 E = waste / product . PMI = E+1 DBE = (2C+2+N-H-X)/2 splitting = n+1 . M+1 = 1. 1% . nC Cl 3:1 . Br 1:1 (M:M+2) asksia. ai/cheatsheet/ usyd-chem2522 . side 1/2 AskSia CHEATSHEET SERIES THE 6 . Structure Elucidation WORKFLOW Combine the techniques - each answers a different question: · 1H/13C NMR > carbon-hydrogen skeleton (how connected?) STEP 1 ALWAYS: DBE DEGREES OF UNSATURATION (IHD/DBE) DBE = (2C + 2 + N - H - X) / 2 (0 is ignored). Ring or n-bond = 1 each. DBE ≥ 4 = suspect a benzene ring (3 C=C + 1 ring). C=O = 1, C=N = 2, C=C = 2. 7 . IR Spectroscopy CM-1 Bond stretching frequency . /(k/u): stronger bond & lighter atoms = higher cm-1. Read the diagnostic 4000-1500 region; 1500-500 is the "fingerprint". BOND / GROUP CM-1 NOTE O-H alcohol[16]Source: asksia-cheatsheet-chem2522.pdfRings / Tt count DBE from formula Formula Belt SIDE 1 | ΑΕ = Mc (prod)/ ΣΜ, (react) x100 E = waste / product . PMI = E+1 DBE = (2C+2+N-H-X)/2 splitting = n+1 . M+1 = 1. 1% . nC Cl 3:1 . Br 1:1 (M:M+2) asksia. ai/cheatsheet/ usyd-chem2522 . side 1/2 AskSia CHEATSHEET SERIES THE 6 . Structure Elucidation WORKFLOW Combine the techniques - each answers a different question: · 1H/13C NMR > carbon-hydrogen skeleton (how connected?) STEP 1 ALWAYS: DBE DEGREES OF UNSATURATION (IHD/DBE) DBE = (2C + 2 + N - H - X) / 2 (0 is ignored). Ring or n-bond = 1 each. DBE ≥ 4 = suspect a benzene ring (3 C=C + 1 ring). C=O = 1, C=N = 2, C=C = 2. 7 . IR Spectroscopy CM-1 Bond stretching frequency . /(k/u): stronger bond & lighter atoms = higher cm-1. Read the diagnostic 4000-1500 region; 1500-500 is the "fingerprint". BOND / GROUP CM-1 NOTE O-H alcohol 3200-3550 broad O-H carb. acid
- 公式（cheatsheet 给的）：[12]Source: asksia-cheatsheet-chem2522.pdf13C + DEPT
H count & connectivity
1H (6, integ, J)
Rings / Tt count
DBE from formula
Formula Belt SIDE 1 | ΑΕ = Mc (prod)/ ΣΜ, (react) x100 E = waste / product . PMI = E+1 DBE = (2C+2+N-H-X)/2 splitting = n+1 . M+1 = 1. 1% . nC Cl 3:1 . Br 1:1 (M:M+2)
asksia. ai/cheatsheet/ usyd-chem2522 . side 1/2
AskSia CHEATSHEET SERIES
THE 6 . Structure Elucidation WORKFLOW
Combine the techniques - each answers a different question:
· 1H/13C NMR > carbon-hydrogen skeleton (how connected?)
STEP 1 ALWAYS: DBE
DEGREES OF UNSATURATION (IHD/DBE) DBE = (2C + 2 + N - H - X) / 2 (0 is ignored). Ring or n-bond = 1 each.
DBE ≥ 4 = suspect a benzene ring (3 C=C + 1 ring). C=O = 1, C=N = 2, C=C = 2.
7 . IR Spectroscopy CM-1
Bond stretching frequency . /(k/u): stronger bond & lighter atoms = higher cm-1. Read the diagnostic 4000-1500 region; 1500-500 is the "fingerprint".
BOND / GROUP
CM-1
NOTE
O-H alcohol[16]Source: asksia-cheatsheet-chem2522.pdfRings / Tt count
DBE from formula
Formula Belt SIDE 1 | ΑΕ = Mc (prod)/ ΣΜ, (react) x100 E = waste / product . PMI = E+1 DBE = (2C+2+N-H-X)/2 splitting = n+1 . M+1 = 1. 1% . nC Cl 3:1 . Br 1:1 (M:M+2)
asksia. ai/cheatsheet/ usyd-chem2522 . side 1/2
AskSia CHEATSHEET SERIES
THE 6 . Structure Elucidation WORKFLOW
Combine the techniques - each answers a different question:
· 1H/13C NMR > carbon-hydrogen skeleton (how connected?)
STEP 1 ALWAYS: DBE
DEGREES OF UNSATURATION (IHD/DBE) DBE = (2C + 2 + N - H - X) / 2 (0 is ignored). Ring or n-bond = 1 each.
DBE ≥ 4 = suspect a benzene ring (3 C=C + 1 ring). C=O = 1, C=N = 2, C=C = 2.
7 . IR Spectroscopy CM-1
Bond stretching frequency . /(k/u): stronger bond & lighter atoms = higher cm-1. Read the diagnostic 4000-1500 region; 1500-500 is the "fingerprint".
BOND / GROUP
CM-1
NOTE
O-H alcohol
3200-3550
broad
O-H carb. acid
-
Step 2：IR（先锁定官能团）
- 读谱三问（材料直接给的“问题清单”）：[13]Source: asksia-cheatsheet-chem2522.pdfweak
aromatic C=C c-0
1450-1600
1000-1300
strong
C=O fine print: amide ~1650 < acid ~1710 = ketone 1715 < aldehyde 1725 < ester 1735 < acyl chloride 1800. Conjugation lowers C=O by ~30.
3 7b · Reading an IR Spectrum QUESTIONS
1. C=O? strong, sharp 1650-1750 = carbonyl present
2. Broad O-H / N-H? 2500-3550 = acid/alcohol/amine
3. C-H above or below 3000? = sp2/aromatic vs sp3
Tell-tales: aldehyde = C=O + twin C-H (Fermi) ~2720/2820; nitrile = sharp 2250; anhydride = two C=O bands.
7c . Distinguish by IR
ISOMER TRAP
TON = 0. 8 / 0. 001 = 800 TOF = 800 / 2 = 400 h-1
Industrial/enzyme catalysts reach TON 106- 109. Real TON is capped by deactivation (poisoning, leaching, sintering) - recyclability is the green prize.
REVISION SHEET . ALL TOPICS
Compiled by AskSia . mapped to the CHEM2522 syllabus . asksia. ai/cheatsheet/usyd- chem2522
Revision aid . check the official unit outline for assessment . 0 2026 flip - for side 2 . synthesis, mechanisms & polymers
CHEM2522
Sustainable Chemical Manufacture UNIVERSITY OF SYDNEY . SCHOOL OF CHEMISTRY[15]Source: asksia-cheatsheet-chem2522.pdfstrong *
C=C alkene
1620-1680
weak
aromatic C=C c-0
1450-1600
1000-1300
strong
C=O fine print: amide ~1650 < acid ~1710 = ketone 1715 < aldehyde 1725 < ester 1735 < acyl chloride 1800. Conjugation lowers C=O by ~30.
3 7b · Reading an IR Spectrum QUESTIONS
1. C=O? strong, sharp 1650-1750 = carbonyl present
2. Broad O-H / N-H? 2500-3550 = acid/alcohol/amine
3. C-H above or below 3000? = sp2/aromatic vs sp3
Tell-tales: aldehyde = C=O + twin C-H (Fermi) ~2720/2820; nitrile = sharp 2250; anhydride = two C=O bands.
7c . Distinguish by IR
ISOMER TRAP
TON = 0. 8 / 0. 001 = 800 TOF = 800 / 2 = 400 h-1
Industrial/enzyme catalysts reach TON 106- 109. Real TON is capped by deactivation (poisoning, leaching, sintering) - recyclability is the green prize.
REVISION SHEET . ALL TOPICS
Compiled by AskSia . mapped to the CHEM2522 syllabus . asksia. ai/cheatsheet/usyd- chem2522
- 1）有没有 C=O：1650–1750 cm$^{-1}$ 强而尖 → 有羰基
- 2）有没有 宽峰 O–H / N–H：2500–3550 cm$^{-1}$（区分酸/醇/胺）
- 3）C–H 在 3000 上下：>3000 偏 sp$^2$/芳香；<3000 偏 sp$^3$
- 常见“tell-tales / 陷阱峰”：[13]Source: asksia-cheatsheet-chem2522.pdfweak
aromatic C=C c-0
1450-1600
1000-1300
strong
C=O fine print: amide ~1650 < acid ~1710 = ketone 1715 < aldehyde 1725 < ester 1735 < acyl chloride 1800. Conjugation lowers C=O by ~30.
3 7b · Reading an IR Spectrum QUESTIONS
1. C=O? strong, sharp 1650-1750 = carbonyl present
2. Broad O-H / N-H? 2500-3550 = acid/alcohol/amine
3. C-H above or below 3000? = sp2/aromatic vs sp3
Tell-tales: aldehyde = C=O + twin C-H (Fermi) ~2720/2820; nitrile = sharp 2250; anhydride = two C=O bands.
7c . Distinguish by IR
ISOMER TRAP
TON = 0. 8 / 0. 001 = 800 TOF = 800 / 2 = 400 h-1
Industrial/enzyme catalysts reach TON 106- 109. Real TON is capped by deactivation (poisoning, leaching, sintering) - recyclability is the green prize.
REVISION SHEET . ALL TOPICS
Compiled by AskSia . mapped to the CHEM2522 syllabus . asksia. ai/cheatsheet/usyd- chem2522
Revision aid . check the official unit outline for assessment . 0 2026 flip - for side 2 . synthesis, mechanisms & polymers
CHEM2522
Sustainable Chemical Manufacture UNIVERSITY OF SYDNEY . SCHOOL OF CHEMISTRY[15]Source: asksia-cheatsheet-chem2522.pdfstrong *
C=C alkene
1620-1680
weak
aromatic C=C c-0
1450-1600
1000-1300
strong
C=O fine print: amide ~1650 < acid ~1710 = ketone 1715 < aldehyde 1725 < ester 1735 < acyl chloride 1800. Conjugation lowers C=O by ~30.
3 7b · Reading an IR Spectrum QUESTIONS
1. C=O? strong, sharp 1650-1750 = carbonyl present
2. Broad O-H / N-H? 2500-3550 = acid/alcohol/amine
3. C-H above or below 3000? = sp2/aromatic vs sp3
Tell-tales: aldehyde = C=O + twin C-H (Fermi) ~2720/2820; nitrile = sharp 2250; anhydride = two C=O bands.
7c . Distinguish by IR
ISOMER TRAP
TON = 0. 8 / 0. 001 = 800 TOF = 800 / 2 = 400 h-1
Industrial/enzyme catalysts reach TON 106- 109. Real TON is capped by deactivation (poisoning, leaching, sintering) - recyclability is the green prize.
REVISION SHEET . ALL TOPICS
Compiled by AskSia . mapped to the CHEM2522 syllabus . asksia. ai/cheatsheet/usyd- chem2522
- 醛：C=O + 2720/2820 cm$^{-1}$ 两个弱峰（Fermi 双峰）
- 腈：2250 cm$^{-1}$ 尖峰
- 酸酐：两个 C=O 峰
- 羰基“细分区间”（很爱考）：[13]Source: asksia-cheatsheet-chem2522.pdfweak
aromatic C=C c-0
1450-1600
1000-1300
strong
C=O fine print: amide ~1650 < acid ~1710 = ketone 1715 < aldehyde 1725 < ester 1735 < acyl chloride 1800. Conjugation lowers C=O by ~30.
3 7b · Reading an IR Spectrum QUESTIONS
1. C=O? strong, sharp 1650-1750 = carbonyl present
2. Broad O-H / N-H? 2500-3550 = acid/alcohol/amine
3. C-H above or below 3000? = sp2/aromatic vs sp3
Tell-tales: aldehyde = C=O + twin C-H (Fermi) ~2720/2820; nitrile = sharp 2250; anhydride = two C=O bands.
7c . Distinguish by IR
ISOMER TRAP
TON = 0. 8 / 0. 001 = 800 TOF = 800 / 2 = 400 h-1
Industrial/enzyme catalysts reach TON 106- 109. Real TON is capped by deactivation (poisoning, leaching, sintering) - recyclability is the green prize.
REVISION SHEET . ALL TOPICS
Compiled by AskSia . mapped to the CHEM2522 syllabus . asksia. ai/cheatsheet/usyd- chem2522
Revision aid . check the official unit outline for assessment . 0 2026 flip - for side 2 . synthesis, mechanisms & polymers
CHEM2522
Sustainable Chemical Manufacture UNIVERSITY OF SYDNEY . SCHOOL OF CHEMISTRY[15]Source: asksia-cheatsheet-chem2522.pdfstrong *
C=C alkene
1620-1680
weak
aromatic C=C c-0
1450-1600
1000-1300
strong
C=O fine print: amide ~1650 < acid ~1710 = ketone 1715 < aldehyde 1725 < ester 1735 < acyl chloride 1800. Conjugation lowers C=O by ~30.
3 7b · Reading an IR Spectrum QUESTIONS
1. C=O? strong, sharp 1650-1750 = carbonyl present
2. Broad O-H / N-H? 2500-3550 = acid/alcohol/amine
3. C-H above or below 3000? = sp2/aromatic vs sp3
Tell-tales: aldehyde = C=O + twin C-H (Fermi) ~2720/2820; nitrile = sharp 2250; anhydride = two C=O bands.
7c . Distinguish by IR
ISOMER TRAP
TON = 0. 8 / 0. 001 = 800 TOF = 800 / 2 = 400 h-1
Industrial/enzyme catalysts reach TON 106- 109. Real TON is capped by deactivation (poisoning, leaching, sintering) - recyclability is the green prize.
REVISION SHEET . ALL TOPICS
Compiled by AskSia . mapped to the CHEM2522 syllabus . asksia. ai/cheatsheet/usyd- chem2522
- 酰氯 $\sim 1800$
- 酯 $\sim 1735$
- 醛 $\sim 1725$
- 酮 $\sim 1715$
- 羧酸 $\sim 1710$
- 酰胺 $\sim 1650$
- 共轭会让 C=O 降低约 30 cm$^{-1}$（数值题/判断题常见）[13]Source: asksia-cheatsheet-chem2522.pdfweak aromatic C=C c-0 1450-1600 1000-1300 strong C=O fine print: amide ~1650 < acid ~1710 = ketone 1715 < aldehyde 1725 < ester 1735 < acyl chloride 1800. Conjugation lowers C=O by ~30. 3 7b · Reading an IR Spectrum QUESTIONS 1. C=O? strong, sharp 1650-1750 = carbonyl present 2. Broad O-H / N-H? 2500-3550 = acid/alcohol/amine 3. C-H above or below 3000? = sp2/aromatic vs sp3 Tell-tales: aldehyde = C=O + twin C-H (Fermi) ~2720/2820; nitrile = sharp 2250; anhydride = two C=O bands. 7c . Distinguish by IR ISOMER TRAP TON = 0. 8 / 0. 001 = 800 TOF = 800 / 2 = 400 h-1 Industrial/enzyme catalysts reach TON 106- 109. Real TON is capped by deactivation (poisoning, leaching, sintering) - recyclability is the green prize. REVISION SHEET . ALL TOPICS Compiled by AskSia . mapped to the CHEM2522 syllabus . asksia. ai/cheatsheet/usyd- chem2522 Revision aid . check the official unit outline for assessment . 0 2026 flip - for side 2 . synthesis, mechanisms & polymers CHEM2522 Sustainable Chemical Manufacture UNIVERSITY OF SYDNEY . SCHOOL OF CHEMISTRY[15]Source: asksia-cheatsheet-chem2522.pdfstrong * C=C alkene 1620-1680 weak aromatic C=C c-0 1450-1600 1000-1300 strong C=O fine print: amide ~1650 < acid ~1710 = ketone 1715 < aldehyde 1725 < ester 1735 < acyl chloride 1800. Conjugation lowers C=O by ~30. 3 7b · Reading an IR Spectrum QUESTIONS 1. C=O? strong, sharp 1650-1750 = carbonyl present 2. Broad O-H / N-H? 2500-3550 = acid/alcohol/amine 3. C-H above or below 3000? = sp2/aromatic vs sp3 Tell-tales: aldehyde = C=O + twin C-H (Fermi) ~2720/2820; nitrile = sharp 2250; anhydride = two C=O bands. 7c . Distinguish by IR ISOMER TRAP TON = 0. 8 / 0. 001 = 800 TOF = 800 / 2 = 400 h-1 Industrial/enzyme catalysts reach TON 106- 109. Real TON is capped by deactivation (poisoning, leaching, sintering) - recyclability is the green prize. REVISION SHEET . ALL TOPICS Compiled by AskSia . mapped to the CHEM2522 syllabus . asksia. ai/cheatsheet/usyd- chem2522
- 读谱三问（材料直接给的“问题清单”）：[13]Source: asksia-cheatsheet-chem2522.pdfweak
aromatic C=C c-0
1450-1600
1000-1300
strong
C=O fine print: amide ~1650 < acid ~1710 = ketone 1715 < aldehyde 1725 < ester 1735 < acyl chloride 1800. Conjugation lowers C=O by ~30.
3 7b · Reading an IR Spectrum QUESTIONS
1. C=O? strong, sharp 1650-1750 = carbonyl present
2. Broad O-H / N-H? 2500-3550 = acid/alcohol/amine
3. C-H above or below 3000? = sp2/aromatic vs sp3
Tell-tales: aldehyde = C=O + twin C-H (Fermi) ~2720/2820; nitrile = sharp 2250; anhydride = two C=O bands.
7c . Distinguish by IR
ISOMER TRAP
TON = 0. 8 / 0. 001 = 800 TOF = 800 / 2 = 400 h-1
Industrial/enzyme catalysts reach TON 106- 109. Real TON is capped by deactivation (poisoning, leaching, sintering) - recyclability is the green prize.
REVISION SHEET . ALL TOPICS
Compiled by AskSia . mapped to the CHEM2522 syllabus . asksia. ai/cheatsheet/usyd- chem2522
Revision aid . check the official unit outline for assessment . 0 2026 flip - for side 2 . synthesis, mechanisms & polymers
CHEM2522
Sustainable Chemical Manufacture UNIVERSITY OF SYDNEY . SCHOOL OF CHEMISTRY[15]Source: asksia-cheatsheet-chem2522.pdfstrong *
C=C alkene
1620-1680
weak
aromatic C=C c-0
1450-1600
1000-1300
strong
C=O fine print: amide ~1650 < acid ~1710 = ketone 1715 < aldehyde 1725 < ester 1735 < acyl chloride 1800. Conjugation lowers C=O by ~30.
3 7b · Reading an IR Spectrum QUESTIONS
1. C=O? strong, sharp 1650-1750 = carbonyl present
2. Broad O-H / N-H? 2500-3550 = acid/alcohol/amine
3. C-H above or below 3000? = sp2/aromatic vs sp3
Tell-tales: aldehyde = C=O + twin C-H (Fermi) ~2720/2820; nitrile = sharp 2250; anhydride = two C=O bands.
7c . Distinguish by IR
ISOMER TRAP
TON = 0. 8 / 0. 001 = 800 TOF = 800 / 2 = 400 h-1
Industrial/enzyme catalysts reach TON 106- 109. Real TON is capped by deactivation (poisoning, leaching, sintering) - recyclability is the green prize.
REVISION SHEET . ALL TOPICS
Compiled by AskSia . mapped to the CHEM2522 syllabus . asksia. ai/cheatsheet/usyd- chem2522
-
Step 3：MS（分子量、同位素与碎片）
- cheatsheet 在 workflow 里强调 MS 用来回答：mass / formula，包括 M+1、同位素模式[17]Source: asksia-cheatsheet-chem2522.pdfEdits by # attached H: CH & CH3 up, CH2 down, quaternary C absent (the give-away for C=O & substituted aromatic). COUNTING SIGNALS = SYMMETRY # of signals = # of chemically distinct environments. Benzene = 1 13C; para- disubstituted ring = 4 (two pairs equivalent). Fewer signals than carbons = symmetry - a fast structural clue. 11 . Worked . C4H8O PUT IT TOGETHER MS M+ = 72. DBE = (2. 4+2-8)/2 = 1 = one C=O or C=C/ring. IR 1715 cm-1 strong = ketone C=O (no broad O-H, no ~2720 aldehyde C-H, no 1735 ester). 1H NMR triplet 1. 0 (3H), quartet 2. 4 (2H), singlet 2. 1 (3H) = ethyl + isolated methyl on C=O. butan-2-one, CH3COCH2CH3. MS loss of 15 (>57) and 29 (>43, CH3CO+) confirm a- cleavage either side of C=O. ---- SIA - Reconcile every piece of data to one structure - if a single peak doesn't fit, the structure is wrong. Examiners build the trap on the one ignored signal. 11b . Worked . C8H8O SPOT THE RING DBE = (2. 8+2-8)/2 = 5 = benzene ring (4) + one more (a C=O). IR 1685 (conjugated C=O). 1H: 5H multiplet 7. 4-8. 0 (mono-substituted ring) + singlet 2. 6 (3H, CH3CO). = acetophenone, C&H;COCH3. 13C ~198 (C=O); m/z 105 (PhCO+) & 77 (C6H5*) confirm. Which Technique? RECAP QUESTION USE Mass / formula MS (M+1, isotopes) Functional groups? IR (C=0, O-H, N-H) # unique C; C type 13C + DEPT H count & connectivity 1H (6, integ, J)[20]Source: asksia-cheatsheet-chem2522.pdfC=O ketone/aldehyde 190-220 DEPT Edits by # attached H: CH & CH3 up, CH2 down, quaternary C absent (the give-away for C=O & substituted aromatic). COUNTING SIGNALS = SYMMETRY # of signals = # of chemically distinct environments. Benzene = 1 13C; para- disubstituted ring = 4 (two pairs equivalent). Fewer signals than carbons = symmetry - a fast structural clue. 11 . Worked . C4H8O PUT IT TOGETHER MS M+ = 72. DBE = (2. 4+2-8)/2 = 1 = one C=O or C=C/ring. IR 1715 cm-1 strong = ketone C=O (no broad O-H, no ~2720 aldehyde C-H, no 1735 ester). 1H NMR triplet 1. 0 (3H), quartet 2. 4 (2H), singlet 2. 1 (3H) = ethyl + isolated methyl on C=O. butan-2-one, CH3COCH2CH3. MS loss of 15 (>57) and 29 (>43, CH3CO+) confirm a- cleavage either side of C=O. ---- SIA - Reconcile every piece of data to one structure - if a single peak doesn't fit, the structure is wrong. Examiners build the trap on the one ignored signal. 11b . Worked . C8H8O SPOT THE RING DBE = (2. 8+2-8)/2 = 5 = benzene ring (4) + one more (a C=O). IR 1685 (conjugated C=O). 1H: 5H multiplet 7. 4-8. 0 (mono-substituted ring) + singlet 2. 6 (3H, CH3CO). = acetophenone, C&H;COCH3. 13C ~198 (C=O); m/z 105 (PhCO+) & 77 (C6H5*) confirm. Which Technique? RECAP QUESTION USE Mass / formula MS (M+1, isotopes) Functional groups? IR (C=0, O-H, N-H) # unique C; C type
- 同位素速记（材料给的“公式腰带”）：[12]Source: asksia-cheatsheet-chem2522.pdf13C + DEPT
H count & connectivity
1H (6, integ, J)
Rings / Tt count
DBE from formula
Formula Belt SIDE 1 | ΑΕ = Mc (prod)/ ΣΜ, (react) x100 E = waste / product . PMI = E+1 DBE = (2C+2+N-H-X)/2 splitting = n+1 . M+1 = 1. 1% . nC Cl 3:1 . Br 1:1 (M:M+2)
asksia. ai/cheatsheet/ usyd-chem2522 . side 1/2
AskSia CHEATSHEET SERIES
THE 6 . Structure Elucidation WORKFLOW
Combine the techniques - each answers a different question:
· 1H/13C NMR > carbon-hydrogen skeleton (how connected?)
STEP 1 ALWAYS: DBE
DEGREES OF UNSATURATION (IHD/DBE) DBE = (2C + 2 + N - H - X) / 2 (0 is ignored). Ring or n-bond = 1 each.
DBE ≥ 4 = suspect a benzene ring (3 C=C + 1 ring). C=O = 1, C=N = 2, C=C = 2.
7 . IR Spectroscopy CM-1
Bond stretching frequency . /(k/u): stronger bond & lighter atoms = higher cm-1. Read the diagnostic 4000-1500 region; 1500-500 is the "fingerprint".
BOND / GROUP
CM-1
NOTE
O-H alcohol[16]Source: asksia-cheatsheet-chem2522.pdfRings / Tt count
DBE from formula
Formula Belt SIDE 1 | ΑΕ = Mc (prod)/ ΣΜ, (react) x100 E = waste / product . PMI = E+1 DBE = (2C+2+N-H-X)/2 splitting = n+1 . M+1 = 1. 1% . nC Cl 3:1 . Br 1:1 (M:M+2)
asksia. ai/cheatsheet/ usyd-chem2522 . side 1/2
AskSia CHEATSHEET SERIES
THE 6 . Structure Elucidation WORKFLOW
Combine the techniques - each answers a different question:
· 1H/13C NMR > carbon-hydrogen skeleton (how connected?)
STEP 1 ALWAYS: DBE
DEGREES OF UNSATURATION (IHD/DBE) DBE = (2C + 2 + N - H - X) / 2 (0 is ignored). Ring or n-bond = 1 each.
DBE ≥ 4 = suspect a benzene ring (3 C=C + 1 ring). C=O = 1, C=N = 2, C=C = 2.
7 . IR Spectroscopy CM-1
Bond stretching frequency . /(k/u): stronger bond & lighter atoms = higher cm-1. Read the diagnostic 4000-1500 region; 1500-500 is the "fingerprint".
BOND / GROUP
CM-1
NOTE
O-H alcohol
3200-3550
broad
O-H carb. acid
- M+1 约等于 $1.1% \times n_C$
- Cl：M : M+2 约 3:1
- Br：M : M+2 约 1:1
-
Step 4：$^1$H NMR（化学位移、积分、裂分）
- cheatsheet 提示它回答：H 的数量与连接方式（integration + J splitting）[17]Source: asksia-cheatsheet-chem2522.pdfEdits by # attached H: CH & CH3 up, CH2 down, quaternary C absent (the give-away for C=O & substituted aromatic). COUNTING SIGNALS = SYMMETRY # of signals = # of chemically distinct environments. Benzene = 1 13C; para- disubstituted ring = 4 (two pairs equivalent). Fewer signals than carbons = symmetry - a fast structural clue. 11 . Worked . C4H8O PUT IT TOGETHER MS M+ = 72. DBE = (2. 4+2-8)/2 = 1 = one C=O or C=C/ring. IR 1715 cm-1 strong = ketone C=O (no broad O-H, no ~2720 aldehyde C-H, no 1735 ester). 1H NMR triplet 1. 0 (3H), quartet 2. 4 (2H), singlet 2. 1 (3H) = ethyl + isolated methyl on C=O. butan-2-one, CH3COCH2CH3. MS loss of 15 (>57) and 29 (>43, CH3CO+) confirm a- cleavage either side of C=O. ---- SIA - Reconcile every piece of data to one structure - if a single peak doesn't fit, the structure is wrong. Examiners build the trap on the one ignored signal. 11b . Worked . C8H8O SPOT THE RING DBE = (2. 8+2-8)/2 = 5 = benzene ring (4) + one more (a C=O). IR 1685 (conjugated C=O). 1H: 5H multiplet 7. 4-8. 0 (mono-substituted ring) + singlet 2. 6 (3H, CH3CO). = acetophenone, C&H;COCH3. 13C ~198 (C=O); m/z 105 (PhCO+) & 77 (C6H5*) confirm. Which Technique? RECAP QUESTION USE Mass / formula MS (M+1, isotopes) Functional groups? IR (C=0, O-H, N-H) # unique C; C type 13C + DEPT H count & connectivity 1H (6, integ, J)[20]Source: asksia-cheatsheet-chem2522.pdfC=O ketone/aldehyde 190-220 DEPT Edits by # attached H: CH & CH3 up, CH2 down, quaternary C absent (the give-away for C=O & substituted aromatic). COUNTING SIGNALS = SYMMETRY # of signals = # of chemically distinct environments. Benzene = 1 13C; para- disubstituted ring = 4 (two pairs equivalent). Fewer signals than carbons = symmetry - a fast structural clue. 11 . Worked . C4H8O PUT IT TOGETHER MS M+ = 72. DBE = (2. 4+2-8)/2 = 1 = one C=O or C=C/ring. IR 1715 cm-1 strong = ketone C=O (no broad O-H, no ~2720 aldehyde C-H, no 1735 ester). 1H NMR triplet 1. 0 (3H), quartet 2. 4 (2H), singlet 2. 1 (3H) = ethyl + isolated methyl on C=O. butan-2-one, CH3COCH2CH3. MS loss of 15 (>57) and 29 (>43, CH3CO+) confirm a- cleavage either side of C=O. ---- SIA - Reconcile every piece of data to one structure - if a single peak doesn't fit, the structure is wrong. Examiners build the trap on the one ignored signal. 11b . Worked . C8H8O SPOT THE RING DBE = (2. 8+2-8)/2 = 5 = benzene ring (4) + one more (a C=O). IR 1685 (conjugated C=O). 1H: 5H multiplet 7. 4-8. 0 (mono-substituted ring) + singlet 2. 6 (3H, CH3CO). = acetophenone, C&H;COCH3. 13C ~198 (C=O); m/z 105 (PhCO+) & 77 (C6H5*) confirm. Which Technique? RECAP QUESTION USE Mass / formula MS (M+1, isotopes) Functional groups? IR (C=0, O-H, N-H) # unique C; C type
- 裂分规则（n+1）：[12]Source: asksia-cheatsheet-chem2522.pdf13C + DEPT
H count & connectivity
1H (6, integ, J)
Rings / Tt count
DBE from formula
Formula Belt SIDE 1 | ΑΕ = Mc (prod)/ ΣΜ, (react) x100 E = waste / product . PMI = E+1 DBE = (2C+2+N-H-X)/2 splitting = n+1 . M+1 = 1. 1% . nC Cl 3:1 . Br 1:1 (M:M+2)
asksia. ai/cheatsheet/ usyd-chem2522 . side 1/2
AskSia CHEATSHEET SERIES
THE 6 . Structure Elucidation WORKFLOW
Combine the techniques - each answers a different question:
· 1H/13C NMR > carbon-hydrogen skeleton (how connected?)
STEP 1 ALWAYS: DBE
DEGREES OF UNSATURATION (IHD/DBE) DBE = (2C + 2 + N - H - X) / 2 (0 is ignored). Ring or n-bond = 1 each.
DBE ≥ 4 = suspect a benzene ring (3 C=C + 1 ring). C=O = 1, C=N = 2, C=C = 2.
7 . IR Spectroscopy CM-1
Bond stretching frequency . /(k/u): stronger bond & lighter atoms = higher cm-1. Read the diagnostic 4000-1500 region; 1500-500 is the "fingerprint".
BOND / GROUP
CM-1
NOTE
O-H alcohol[16]Source: asksia-cheatsheet-chem2522.pdfRings / Tt count
DBE from formula
Formula Belt SIDE 1 | ΑΕ = Mc (prod)/ ΣΜ, (react) x100 E = waste / product . PMI = E+1 DBE = (2C+2+N-H-X)/2 splitting = n+1 . M+1 = 1. 1% . nC Cl 3:1 . Br 1:1 (M:M+2)
asksia. ai/cheatsheet/ usyd-chem2522 . side 1/2
AskSia CHEATSHEET SERIES
THE 6 . Structure Elucidation WORKFLOW
Combine the techniques - each answers a different question:
· 1H/13C NMR > carbon-hydrogen skeleton (how connected?)
STEP 1 ALWAYS: DBE
DEGREES OF UNSATURATION (IHD/DBE) DBE = (2C + 2 + N - H - X) / 2 (0 is ignored). Ring or n-bond = 1 each.
DBE ≥ 4 = suspect a benzene ring (3 C=C + 1 ring). C=O = 1, C=N = 2, C=C = 2.
7 . IR Spectroscopy CM-1
Bond stretching frequency . /(k/u): stronger bond & lighter atoms = higher cm-1. Read the diagnostic 4000-1500 region; 1500-500 is the "fingerprint".
BOND / GROUP
CM-1
NOTE
O-H alcohol
3200-3550
broad
O-H carb. acid[18]Source: asksia-cheatsheet-chem2522.pdfNo single number means "green" - name which trade-off the question tests.
Formula Belt SIDE 2
Xn = 1/(1-p) . Đ = Mw/Mn ≥1 splitting n+1 . reactivity: RCOCl>ester>amide Sn2 inversion . E2 anti-periplanar green: catalysis . renewable . degrade
asksia. ai/cheatsheet/ usyd-chem2522 . side 2/2
AskSia CHEATSHEET SERIES
20 . Polymer Properties MOLAR MASS
AVERAGES & DISPERSITY ΜΠ = Ση;Μ;/ Ση; (number avg) Mw = Ση;Μ12/Ση;Μ; (weight avg) Đ = M/Mn ≥ 1 (dispersity) Đ = 1 = perfectly uniform; step-growth ~2; controlled radical > low Đ.
THERMAL & ORDER
· Tg glass transition (amorphous softens); Tm melts (crystalline)
· Tacticity - iso / syndio / atactic; regular = crystalline, higher Tm
21 · Sustainable Polymers
· Polyamide (nylon) - diacid + diamine > amide links + H2O.
· Polycarbonate - bisphenol + carbonate source.
Need exact stoichiometry & high purity (Carothers) for high MW. The ester/amide links are also the handle for chemical recycling (hydrolysis/solvolysis back to monomer).
19b . Nature's Step- Growth BIOPOLYMERS
The largest condensation polymers are biological: proteins (amino acids - peptide/amide bonds + H2O), polysaccharides (sugars >> glycosidic bonds + H2O), nucleic acids (phosphodiester). All are hydrolysable = inherently degradable - the design template for sustainable polymers.
19c . Worked . Carothers
WHY PURITY MATTERS
Degree of polymerisation vs conversion p:
P
- 相邻等效氢数为 $n$ → 裂成 $n+1$ 重峰
- （注意：你给我的摘录里没有系统列化学位移表，所以我不补“具体 ppm 区间”；如果你把那一页截图/补充，我可以继续扩展。）
-
Step 5：$^{13}$C NMR + DEPT（碳类型与信号数）
- cheatsheet：$^{13}$C/DEPT 用于 “数有多少种碳环境 + 判断 CH/CH$_2$/CH$_3$/季碳”[12]Source: asksia-cheatsheet-chem2522.pdf13C + DEPT H count & connectivity 1H (6, integ, J) Rings / Tt count DBE from formula Formula Belt SIDE 1 | ΑΕ = Mc (prod)/ ΣΜ, (react) x100 E = waste / product . PMI = E+1 DBE = (2C+2+N-H-X)/2 splitting = n+1 . M+1 = 1. 1% . nC Cl 3:1 . Br 1:1 (M:M+2) asksia. ai/cheatsheet/ usyd-chem2522 . side 1/2 AskSia CHEATSHEET SERIES THE 6 . Structure Elucidation WORKFLOW Combine the techniques - each answers a different question: · 1H/13C NMR > carbon-hydrogen skeleton (how connected?) STEP 1 ALWAYS: DBE DEGREES OF UNSATURATION (IHD/DBE) DBE = (2C + 2 + N - H - X) / 2 (0 is ignored). Ring or n-bond = 1 each. DBE ≥ 4 = suspect a benzene ring (3 C=C + 1 ring). C=O = 1, C=N = 2, C=C = 2. 7 . IR Spectroscopy CM-1 Bond stretching frequency . /(k/u): stronger bond & lighter atoms = higher cm-1. Read the diagnostic 4000-1500 region; 1500-500 is the "fingerprint". BOND / GROUP CM-1 NOTE O-H alcohol[17]Source: asksia-cheatsheet-chem2522.pdfEdits by # attached H: CH & CH3 up, CH2 down, quaternary C absent (the give-away for C=O & substituted aromatic). COUNTING SIGNALS = SYMMETRY # of signals = # of chemically distinct environments. Benzene = 1 13C; para- disubstituted ring = 4 (two pairs equivalent). Fewer signals than carbons = symmetry - a fast structural clue. 11 . Worked . C4H8O PUT IT TOGETHER MS M+ = 72. DBE = (2. 4+2-8)/2 = 1 = one C=O or C=C/ring. IR 1715 cm-1 strong = ketone C=O (no broad O-H, no ~2720 aldehyde C-H, no 1735 ester). 1H NMR triplet 1. 0 (3H), quartet 2. 4 (2H), singlet 2. 1 (3H) = ethyl + isolated methyl on C=O. butan-2-one, CH3COCH2CH3. MS loss of 15 (>57) and 29 (>43, CH3CO+) confirm a- cleavage either side of C=O. ---- SIA - Reconcile every piece of data to one structure - if a single peak doesn't fit, the structure is wrong. Examiners build the trap on the one ignored signal. 11b . Worked . C8H8O SPOT THE RING DBE = (2. 8+2-8)/2 = 5 = benzene ring (4) + one more (a C=O). IR 1685 (conjugated C=O). 1H: 5H multiplet 7. 4-8. 0 (mono-substituted ring) + singlet 2. 6 (3H, CH3CO). = acetophenone, C&H;COCH3. 13C ~198 (C=O); m/z 105 (PhCO+) & 77 (C6H5*) confirm. Which Technique? RECAP QUESTION USE Mass / formula MS (M+1, isotopes) Functional groups? IR (C=0, O-H, N-H) # unique C; C type 13C + DEPT H count & connectivity 1H (6, integ, J)[20]Source: asksia-cheatsheet-chem2522.pdfC=O ketone/aldehyde 190-220 DEPT Edits by # attached H: CH & CH3 up, CH2 down, quaternary C absent (the give-away for C=O & substituted aromatic). COUNTING SIGNALS = SYMMETRY # of signals = # of chemically distinct environments. Benzene = 1 13C; para- disubstituted ring = 4 (two pairs equivalent). Fewer signals than carbons = symmetry - a fast structural clue. 11 . Worked . C4H8O PUT IT TOGETHER MS M+ = 72. DBE = (2. 4+2-8)/2 = 1 = one C=O or C=C/ring. IR 1715 cm-1 strong = ketone C=O (no broad O-H, no ~2720 aldehyde C-H, no 1735 ester). 1H NMR triplet 1. 0 (3H), quartet 2. 4 (2H), singlet 2. 1 (3H) = ethyl + isolated methyl on C=O. butan-2-one, CH3COCH2CH3. MS loss of 15 (>57) and 29 (>43, CH3CO+) confirm a- cleavage either side of C=O. ---- SIA - Reconcile every piece of data to one structure - if a single peak doesn't fit, the structure is wrong. Examiners build the trap on the one ignored signal. 11b . Worked . C8H8O SPOT THE RING DBE = (2. 8+2-8)/2 = 5 = benzene ring (4) + one more (a C=O). IR 1685 (conjugated C=O). 1H: 5H multiplet 7. 4-8. 0 (mono-substituted ring) + singlet 2. 6 (3H, CH3CO). = acetophenone, C&H;COCH3. 13C ~198 (C=O); m/z 105 (PhCO+) & 77 (C6H5*) confirm. Which Technique? RECAP QUESTION USE Mass / formula MS (M+1, isotopes) Functional groups? IR (C=0, O-H, N-H) # unique C; C type
- DEPT 规则（材料给的）：[17]Source: asksia-cheatsheet-chem2522.pdfEdits by # attached H: CH & CH3 up, CH2 down, quaternary C absent (the give-away for C=O & substituted aromatic).
COUNTING SIGNALS = SYMMETRY
# of signals = # of chemically distinct environments. Benzene = 1 13C; para- disubstituted ring = 4 (two pairs equivalent). Fewer signals than carbons = symmetry - a fast structural clue.
11 . Worked . C4H8O PUT IT TOGETHER MS M+ = 72. DBE = (2. 4+2-8)/2 = 1 = one C=O or C=C/ring. IR 1715 cm-1 strong = ketone C=O (no broad O-H, no ~2720 aldehyde C-H, no 1735 ester). 1H NMR triplet 1. 0 (3H), quartet 2. 4 (2H), singlet 2. 1 (3H) = ethyl + isolated methyl on C=O.
butan-2-one, CH3COCH2CH3. MS loss of 15 (>57) and 29 (>43, CH3CO+) confirm a- cleavage either side of C=O. ----
SIA - Reconcile every piece of data to one structure - if a single peak doesn't fit, the structure is wrong. Examiners build the trap on the one ignored signal.
11b . Worked . C8H8O SPOT THE RING DBE = (2. 8+2-8)/2 = 5 = benzene ring (4) + one more (a C=O). IR 1685 (conjugated C=O). 1H: 5H multiplet 7. 4-8. 0 (mono-substituted ring) + singlet 2. 6 (3H, CH3CO).
= acetophenone, C&H;COCH3. 13C ~198 (C=O); m/z 105 (PhCO+) & 77 (C6H5*) confirm.
Which Technique?
RECAP
QUESTION
USE
Mass / formula
MS (M+1, isotopes)
Functional groups?
IR (C=0, O-H, N-H)
# unique C; C type
13C + DEPT
H count & connectivity
1H (6, integ, J)[20]Source: asksia-cheatsheet-chem2522.pdfC=O ketone/aldehyde
190-220
DEPT
Edits by # attached H: CH & CH3 up, CH2 down, quaternary C absent (the give-away for C=O & substituted aromatic).
COUNTING SIGNALS = SYMMETRY
# of signals = # of chemically distinct environments. Benzene = 1 13C; para- disubstituted ring = 4 (two pairs equivalent). Fewer signals than carbons = symmetry - a fast structural clue.
11 . Worked . C4H8O PUT IT TOGETHER MS M+ = 72. DBE = (2. 4+2-8)/2 = 1 = one C=O or C=C/ring. IR 1715 cm-1 strong = ketone C=O (no broad O-H, no ~2720 aldehyde C-H, no 1735 ester). 1H NMR triplet 1. 0 (3H), quartet 2. 4 (2H), singlet 2. 1 (3H) = ethyl + isolated methyl on C=O.
butan-2-one, CH3COCH2CH3. MS loss of 15 (>57) and 29 (>43, CH3CO+) confirm a- cleavage either side of C=O. ----
SIA - Reconcile every piece of data to one structure - if a single peak doesn't fit, the structure is wrong. Examiners build the trap on the one ignored signal.
11b . Worked . C8H8O SPOT THE RING DBE = (2. 8+2-8)/2 = 5 = benzene ring (4) + one more (a C=O). IR 1685 (conjugated C=O). 1H: 5H multiplet 7. 4-8. 0 (mono-substituted ring) + singlet 2. 6 (3H, CH3CO).
= acetophenone, C&H;COCH3. 13C ~198 (C=O); m/z 105 (PhCO+) & 77 (C6H5*) confirm.
Which Technique?
RECAP
QUESTION
USE
Mass / formula
MS (M+1, isotopes)
Functional groups?
IR (C=0, O-H, N-H)
# unique C; C type
- CH 和 CH$_3$ “向上”
- CH$_2$ “向下”
- 季碳不出现（常用来锁定羰基碳、取代芳环的季碳）
- 信号数 = 对称性（非常高频）[17]Source: asksia-cheatsheet-chem2522.pdfEdits by # attached H: CH & CH3 up, CH2 down, quaternary C absent (the give-away for C=O & substituted aromatic).
COUNTING SIGNALS = SYMMETRY
# of signals = # of chemically distinct environments. Benzene = 1 13C; para- disubstituted ring = 4 (two pairs equivalent). Fewer signals than carbons = symmetry - a fast structural clue.
11 . Worked . C4H8O PUT IT TOGETHER MS M+ = 72. DBE = (2. 4+2-8)/2 = 1 = one C=O or C=C/ring. IR 1715 cm-1 strong = ketone C=O (no broad O-H, no ~2720 aldehyde C-H, no 1735 ester). 1H NMR triplet 1. 0 (3H), quartet 2. 4 (2H), singlet 2. 1 (3H) = ethyl + isolated methyl on C=O.
butan-2-one, CH3COCH2CH3. MS loss of 15 (>57) and 29 (>43, CH3CO+) confirm a- cleavage either side of C=O. ----
SIA - Reconcile every piece of data to one structure - if a single peak doesn't fit, the structure is wrong. Examiners build the trap on the one ignored signal.
11b . Worked . C8H8O SPOT THE RING DBE = (2. 8+2-8)/2 = 5 = benzene ring (4) + one more (a C=O). IR 1685 (conjugated C=O). 1H: 5H multiplet 7. 4-8. 0 (mono-substituted ring) + singlet 2. 6 (3H, CH3CO).
= acetophenone, C&H;COCH3. 13C ~198 (C=O); m/z 105 (PhCO+) & 77 (C6H5*) confirm.
Which Technique?
RECAP
QUESTION
USE
Mass / formula
MS (M+1, isotopes)
Functional groups?
IR (C=0, O-H, N-H)
# unique C; C type
13C + DEPT
H count & connectivity
1H (6, integ, J)[20]Source: asksia-cheatsheet-chem2522.pdfC=O ketone/aldehyde
190-220
DEPT
Edits by # attached H: CH & CH3 up, CH2 down, quaternary C absent (the give-away for C=O & substituted aromatic).
COUNTING SIGNALS = SYMMETRY
# of signals = # of chemically distinct environments. Benzene = 1 13C; para- disubstituted ring = 4 (two pairs equivalent). Fewer signals than carbons = symmetry - a fast structural clue.
11 . Worked . C4H8O PUT IT TOGETHER MS M+ = 72. DBE = (2. 4+2-8)/2 = 1 = one C=O or C=C/ring. IR 1715 cm-1 strong = ketone C=O (no broad O-H, no ~2720 aldehyde C-H, no 1735 ester). 1H NMR triplet 1. 0 (3H), quartet 2. 4 (2H), singlet 2. 1 (3H) = ethyl + isolated methyl on C=O.
butan-2-one, CH3COCH2CH3. MS loss of 15 (>57) and 29 (>43, CH3CO+) confirm a- cleavage either side of C=O. ----
SIA - Reconcile every piece of data to one structure - if a single peak doesn't fit, the structure is wrong. Examiners build the trap on the one ignored signal.
11b . Worked . C8H8O SPOT THE RING DBE = (2. 8+2-8)/2 = 5 = benzene ring (4) + one more (a C=O). IR 1685 (conjugated C=O). 1H: 5H multiplet 7. 4-8. 0 (mono-substituted ring) + singlet 2. 6 (3H, CH3CO).
= acetophenone, C&H;COCH3. 13C ~198 (C=O); m/z 105 (PhCO+) & 77 (C6H5*) confirm.
Which Technique?
RECAP
QUESTION
USE
Mass / formula
MS (M+1, isotopes)
Functional groups?
IR (C=0, O-H, N-H)
# unique C; C type
- 信号数 = 化学不等价环境数
- “信号数少于碳数” → 说明有对称性（快速结构线索）
- 例子：苯环（全部等价）$^{13}$C 只有 1 个信号；对位二取代苯环有 4 个信号（两对等价）[17]Source: asksia-cheatsheet-chem2522.pdfEdits by # attached H: CH & CH3 up, CH2 down, quaternary C absent (the give-away for C=O & substituted aromatic). COUNTING SIGNALS = SYMMETRY # of signals = # of chemically distinct environments. Benzene = 1 13C; para- disubstituted ring = 4 (two pairs equivalent). Fewer signals than carbons = symmetry - a fast structural clue. 11 . Worked . C4H8O PUT IT TOGETHER MS M+ = 72. DBE = (2. 4+2-8)/2 = 1 = one C=O or C=C/ring. IR 1715 cm-1 strong = ketone C=O (no broad O-H, no ~2720 aldehyde C-H, no 1735 ester). 1H NMR triplet 1. 0 (3H), quartet 2. 4 (2H), singlet 2. 1 (3H) = ethyl + isolated methyl on C=O. butan-2-one, CH3COCH2CH3. MS loss of 15 (>57) and 29 (>43, CH3CO+) confirm a- cleavage either side of C=O. ---- SIA - Reconcile every piece of data to one structure - if a single peak doesn't fit, the structure is wrong. Examiners build the trap on the one ignored signal. 11b . Worked . C8H8O SPOT THE RING DBE = (2. 8+2-8)/2 = 5 = benzene ring (4) + one more (a C=O). IR 1685 (conjugated C=O). 1H: 5H multiplet 7. 4-8. 0 (mono-substituted ring) + singlet 2. 6 (3H, CH3CO). = acetophenone, C&H;COCH3. 13C ~198 (C=O); m/z 105 (PhCO+) & 77 (C6H5*) confirm. Which Technique? RECAP QUESTION USE Mass / formula MS (M+1, isotopes) Functional groups? IR (C=0, O-H, N-H) # unique C; C type 13C + DEPT H count & connectivity 1H (6, integ, J)[20]Source: asksia-cheatsheet-chem2522.pdfC=O ketone/aldehyde 190-220 DEPT Edits by # attached H: CH & CH3 up, CH2 down, quaternary C absent (the give-away for C=O & substituted aromatic). COUNTING SIGNALS = SYMMETRY # of signals = # of chemically distinct environments. Benzene = 1 13C; para- disubstituted ring = 4 (two pairs equivalent). Fewer signals than carbons = symmetry - a fast structural clue. 11 . Worked . C4H8O PUT IT TOGETHER MS M+ = 72. DBE = (2. 4+2-8)/2 = 1 = one C=O or C=C/ring. IR 1715 cm-1 strong = ketone C=O (no broad O-H, no ~2720 aldehyde C-H, no 1735 ester). 1H NMR triplet 1. 0 (3H), quartet 2. 4 (2H), singlet 2. 1 (3H) = ethyl + isolated methyl on C=O. butan-2-one, CH3COCH2CH3. MS loss of 15 (>57) and 29 (>43, CH3CO+) confirm a- cleavage either side of C=O. ---- SIA - Reconcile every piece of data to one structure - if a single peak doesn't fit, the structure is wrong. Examiners build the trap on the one ignored signal. 11b . Worked . C8H8O SPOT THE RING DBE = (2. 8+2-8)/2 = 5 = benzene ring (4) + one more (a C=O). IR 1685 (conjugated C=O). 1H: 5H multiplet 7. 4-8. 0 (mono-substituted ring) + singlet 2. 6 (3H, CH3CO). = acetophenone, C&H;COCH3. 13C ~198 (C=O); m/z 105 (PhCO+) & 77 (C6H5*) confirm. Which Technique? RECAP QUESTION USE Mass / formula MS (M+1, isotopes) Functional groups? IR (C=0, O-H, N-H) # unique C; C type
-
Worked example（你材料里给了两套完整示范）
- 例 1：C$_4$H$_8$O → butan-2-one（你可以拿它当模板）[17]Source: asksia-cheatsheet-chem2522.pdfEdits by # attached H: CH & CH3 up, CH2 down, quaternary C absent (the give-away for C=O & substituted aromatic).
COUNTING SIGNALS = SYMMETRY
# of signals = # of chemically distinct environments. Benzene = 1 13C; para- disubstituted ring = 4 (two pairs equivalent). Fewer signals than carbons = symmetry - a fast structural clue.
11 . Worked . C4H8O PUT IT TOGETHER MS M+ = 72. DBE = (2. 4+2-8)/2 = 1 = one C=O or C=C/ring. IR 1715 cm-1 strong = ketone C=O (no broad O-H, no ~2720 aldehyde C-H, no 1735 ester). 1H NMR triplet 1. 0 (3H), quartet 2. 4 (2H), singlet 2. 1 (3H) = ethyl + isolated methyl on C=O.
butan-2-one, CH3COCH2CH3. MS loss of 15 (>57) and 29 (>43, CH3CO+) confirm a- cleavage either side of C=O. ----
SIA - Reconcile every piece of data to one structure - if a single peak doesn't fit, the structure is wrong. Examiners build the trap on the one ignored signal.
11b . Worked . C8H8O SPOT THE RING DBE = (2. 8+2-8)/2 = 5 = benzene ring (4) + one more (a C=O). IR 1685 (conjugated C=O). 1H: 5H multiplet 7. 4-8. 0 (mono-substituted ring) + singlet 2. 6 (3H, CH3CO).
= acetophenone, C&H;COCH3. 13C ~198 (C=O); m/z 105 (PhCO+) & 77 (C6H5*) confirm.
Which Technique?
RECAP
QUESTION
USE
Mass / formula
MS (M+1, isotopes)
Functional groups?
IR (C=0, O-H, N-H)
# unique C; C type
13C + DEPT
H count & connectivity
1H (6, integ, J)[20]Source: asksia-cheatsheet-chem2522.pdfC=O ketone/aldehyde
190-220
DEPT
Edits by # attached H: CH & CH3 up, CH2 down, quaternary C absent (the give-away for C=O & substituted aromatic).
COUNTING SIGNALS = SYMMETRY
# of signals = # of chemically distinct environments. Benzene = 1 13C; para- disubstituted ring = 4 (two pairs equivalent). Fewer signals than carbons = symmetry - a fast structural clue.
11 . Worked . C4H8O PUT IT TOGETHER MS M+ = 72. DBE = (2. 4+2-8)/2 = 1 = one C=O or C=C/ring. IR 1715 cm-1 strong = ketone C=O (no broad O-H, no ~2720 aldehyde C-H, no 1735 ester). 1H NMR triplet 1. 0 (3H), quartet 2. 4 (2H), singlet 2. 1 (3H) = ethyl + isolated methyl on C=O.
butan-2-one, CH3COCH2CH3. MS loss of 15 (>57) and 29 (>43, CH3CO+) confirm a- cleavage either side of C=O. ----
SIA - Reconcile every piece of data to one structure - if a single peak doesn't fit, the structure is wrong. Examiners build the trap on the one ignored signal.
11b . Worked . C8H8O SPOT THE RING DBE = (2. 8+2-8)/2 = 5 = benzene ring (4) + one more (a C=O). IR 1685 (conjugated C=O). 1H: 5H multiplet 7. 4-8. 0 (mono-substituted ring) + singlet 2. 6 (3H, CH3CO).
= acetophenone, C&H;COCH3. 13C ~198 (C=O); m/z 105 (PhCO+) & 77 (C6H5*) confirm.
Which Technique?
RECAP
QUESTION
USE
Mass / formula
MS (M+1, isotopes)
Functional groups?
IR (C=0, O-H, N-H)
# unique C; C type
- MS：$M^+=72$
- DBE：1
- IR：1715 强 → 酮羰基
- $^1$H：t 1.0 (3H), q 2.4 (2H), s 2.1 (3H) → 乙基 + 羰基旁甲基
- 例 2：C$_8$H$_8$O → acetophenone（“先看 DBE 抓芳环”）[17]Source: asksia-cheatsheet-chem2522.pdfEdits by # attached H: CH & CH3 up, CH2 down, quaternary C absent (the give-away for C=O & substituted aromatic).
COUNTING SIGNALS = SYMMETRY
# of signals = # of chemically distinct environments. Benzene = 1 13C; para- disubstituted ring = 4 (two pairs equivalent). Fewer signals than carbons = symmetry - a fast structural clue.
11 . Worked . C4H8O PUT IT TOGETHER MS M+ = 72. DBE = (2. 4+2-8)/2 = 1 = one C=O or C=C/ring. IR 1715 cm-1 strong = ketone C=O (no broad O-H, no ~2720 aldehyde C-H, no 1735 ester). 1H NMR triplet 1. 0 (3H), quartet 2. 4 (2H), singlet 2. 1 (3H) = ethyl + isolated methyl on C=O.
butan-2-one, CH3COCH2CH3. MS loss of 15 (>57) and 29 (>43, CH3CO+) confirm a- cleavage either side of C=O. ----
SIA - Reconcile every piece of data to one structure - if a single peak doesn't fit, the structure is wrong. Examiners build the trap on the one ignored signal.
11b . Worked . C8H8O SPOT THE RING DBE = (2. 8+2-8)/2 = 5 = benzene ring (4) + one more (a C=O). IR 1685 (conjugated C=O). 1H: 5H multiplet 7. 4-8. 0 (mono-substituted ring) + singlet 2. 6 (3H, CH3CO).
= acetophenone, C&H;COCH3. 13C ~198 (C=O); m/z 105 (PhCO+) & 77 (C6H5*) confirm.
Which Technique?
RECAP
QUESTION
USE
Mass / formula
MS (M+1, isotopes)
Functional groups?
IR (C=0, O-H, N-H)
# unique C; C type
13C + DEPT
H count & connectivity
1H (6, integ, J)[20]Source: asksia-cheatsheet-chem2522.pdfC=O ketone/aldehyde
190-220
DEPT
Edits by # attached H: CH & CH3 up, CH2 down, quaternary C absent (the give-away for C=O & substituted aromatic).
COUNTING SIGNALS = SYMMETRY
# of signals = # of chemically distinct environments. Benzene = 1 13C; para- disubstituted ring = 4 (two pairs equivalent). Fewer signals than carbons = symmetry - a fast structural clue.
11 . Worked . C4H8O PUT IT TOGETHER MS M+ = 72. DBE = (2. 4+2-8)/2 = 1 = one C=O or C=C/ring. IR 1715 cm-1 strong = ketone C=O (no broad O-H, no ~2720 aldehyde C-H, no 1735 ester). 1H NMR triplet 1. 0 (3H), quartet 2. 4 (2H), singlet 2. 1 (3H) = ethyl + isolated methyl on C=O.
butan-2-one, CH3COCH2CH3. MS loss of 15 (>57) and 29 (>43, CH3CO+) confirm a- cleavage either side of C=O. ----
SIA - Reconcile every piece of data to one structure - if a single peak doesn't fit, the structure is wrong. Examiners build the trap on the one ignored signal.
11b . Worked . C8H8O SPOT THE RING DBE = (2. 8+2-8)/2 = 5 = benzene ring (4) + one more (a C=O). IR 1685 (conjugated C=O). 1H: 5H multiplet 7. 4-8. 0 (mono-substituted ring) + singlet 2. 6 (3H, CH3CO).
= acetophenone, C&H;COCH3. 13C ~198 (C=O); m/z 105 (PhCO+) & 77 (C6H5*) confirm.
Which Technique?
RECAP
QUESTION
USE
Mass / formula
MS (M+1, isotopes)
Functional groups?
IR (C=0, O-H, N-H)
# unique C; C type
- DBE = 5 → 苯环 4 + 额外 1（羰基）
- IR 1685（共轭羰基）
- $^1$H：5H 芳香多重峰 + 3H singlet（乙酰基甲基）
- 例 1：C$_4$H$_8$O → butan-2-one（你可以拿它当模板）[17]Source: asksia-cheatsheet-chem2522.pdfEdits by # attached H: CH & CH3 up, CH2 down, quaternary C absent (the give-away for C=O & substituted aromatic).
COUNTING SIGNALS = SYMMETRY
# of signals = # of chemically distinct environments. Benzene = 1 13C; para- disubstituted ring = 4 (two pairs equivalent). Fewer signals than carbons = symmetry - a fast structural clue.
11 . Worked . C4H8O PUT IT TOGETHER MS M+ = 72. DBE = (2. 4+2-8)/2 = 1 = one C=O or C=C/ring. IR 1715 cm-1 strong = ketone C=O (no broad O-H, no ~2720 aldehyde C-H, no 1735 ester). 1H NMR triplet 1. 0 (3H), quartet 2. 4 (2H), singlet 2. 1 (3H) = ethyl + isolated methyl on C=O.
butan-2-one, CH3COCH2CH3. MS loss of 15 (>57) and 29 (>43, CH3CO+) confirm a- cleavage either side of C=O. ----
SIA - Reconcile every piece of data to one structure - if a single peak doesn't fit, the structure is wrong. Examiners build the trap on the one ignored signal.
11b . Worked . C8H8O SPOT THE RING DBE = (2. 8+2-8)/2 = 5 = benzene ring (4) + one more (a C=O). IR 1685 (conjugated C=O). 1H: 5H multiplet 7. 4-8. 0 (mono-substituted ring) + singlet 2. 6 (3H, CH3CO).
= acetophenone, C&H;COCH3. 13C ~198 (C=O); m/z 105 (PhCO+) & 77 (C6H5*) confirm.
Which Technique?
RECAP
QUESTION
USE
Mass / formula
MS (M+1, isotopes)
Functional groups?
IR (C=0, O-H, N-H)
# unique C; C type
13C + DEPT
H count & connectivity
1H (6, integ, J)[20]Source: asksia-cheatsheet-chem2522.pdfC=O ketone/aldehyde
190-220
DEPT
Edits by # attached H: CH & CH3 up, CH2 down, quaternary C absent (the give-away for C=O & substituted aromatic).
COUNTING SIGNALS = SYMMETRY
# of signals = # of chemically distinct environments. Benzene = 1 13C; para- disubstituted ring = 4 (two pairs equivalent). Fewer signals than carbons = symmetry - a fast structural clue.
11 . Worked . C4H8O PUT IT TOGETHER MS M+ = 72. DBE = (2. 4+2-8)/2 = 1 = one C=O or C=C/ring. IR 1715 cm-1 strong = ketone C=O (no broad O-H, no ~2720 aldehyde C-H, no 1735 ester). 1H NMR triplet 1. 0 (3H), quartet 2. 4 (2H), singlet 2. 1 (3H) = ethyl + isolated methyl on C=O.
butan-2-one, CH3COCH2CH3. MS loss of 15 (>57) and 29 (>43, CH3CO+) confirm a- cleavage either side of C=O. ----
SIA - Reconcile every piece of data to one structure - if a single peak doesn't fit, the structure is wrong. Examiners build the trap on the one ignored signal.
11b . Worked . C8H8O SPOT THE RING DBE = (2. 8+2-8)/2 = 5 = benzene ring (4) + one more (a C=O). IR 1685 (conjugated C=O). 1H: 5H multiplet 7. 4-8. 0 (mono-substituted ring) + singlet 2. 6 (3H, CH3CO).
= acetophenone, C&H;COCH3. 13C ~198 (C=O); m/z 105 (PhCO+) & 77 (C6H5*) confirm.
Which Technique?
RECAP
QUESTION
USE
Mass / formula
MS (M+1, isotopes)
Functional groups?
IR (C=0, O-H, N-H)
# unique C; C type
-
六、反应机理与反应选择：SN1 / SN2 / E1 / E2（考点极密）
-
1) 两个“总模式”
- 极性/离子型：亲核体进攻亲电中心；卷曲箭头 Nu→E[6]Source: asksia-cheatsheet-chem2522.pdfRevision aid . check the official unit outline for assessment . 0 2026 flip - for side 2 . synthesis, mechanisms & polymers CHEM2522 Sustainable Chemical Manufacture UNIVERSITY OF SYDNEY . SCHOOL OF CHEMISTRY EXAM REVISION Sem 1 2026 . SIDE 2 OF 2 Synthesis . mechanisms . polymers SIDE 2/2 polymers 12 · Functional Groups REACTIVITY MAP Reactivity lives at the functional group; the carbon skeleton is mostly inert. Two master patterns: · Polar / ionic - a nucleophile (electron- rich, 8-) attacks an electrophile (electron- poor, 8+). Curly arrows go from Nu to E. . Radical - homolysis, single-electron (fish-hook) arrows; chain initiation/propagation/termination. Electrophilic carbons: C-X (halide), C=O (carbonyl). Nucleophiles: OH", RO", CN", NH3, enolates, RMgX (carbanion equiv. ). 13 . Substitution & Elimination En1/2 Sn2 Sn1 Steps 1 (concerted) 2 (carbocation) Rate k[RX][Nu] k[RX][11]Source: asksia-cheatsheet-chem2522.pdfEXAM REVISION Sem 1 2026 . SIDE 2 OF 2 Synthesis . mechanisms . polymers SIDE 2/2 polymers 12 · Functional Groups REACTIVITY MAP Reactivity lives at the functional group; the carbon skeleton is mostly inert. Two master patterns: · Polar / ionic - a nucleophile (electron- rich, 8-) attacks an electrophile (electron- poor, 8+). Curly arrows go from Nu to E. . Radical - homolysis, single-electron (fish-hook) arrows; chain initiation/propagation/termination. Electrophilic carbons: C-X (halide), C=O (carbonyl). Nucleophiles: OH", RO", CN", NH3, enolates, RMgX (carbanion equiv. ). 13 . Substitution & Elimination En1/2 Sn2 Sn1 Steps 1 (concerted) 2 (carbocation) Rate k[RX][Nu] k[RX] Substrate 1° > 2° 3° > 2°
- 自由基型：均裂、鱼钩箭头，链式：引发/传播/终止[6]Source: asksia-cheatsheet-chem2522.pdfRevision aid . check the official unit outline for assessment . 0 2026 flip - for side 2 . synthesis, mechanisms & polymers CHEM2522 Sustainable Chemical Manufacture UNIVERSITY OF SYDNEY . SCHOOL OF CHEMISTRY EXAM REVISION Sem 1 2026 . SIDE 2 OF 2 Synthesis . mechanisms . polymers SIDE 2/2 polymers 12 · Functional Groups REACTIVITY MAP Reactivity lives at the functional group; the carbon skeleton is mostly inert. Two master patterns: · Polar / ionic - a nucleophile (electron- rich, 8-) attacks an electrophile (electron- poor, 8+). Curly arrows go from Nu to E. . Radical - homolysis, single-electron (fish-hook) arrows; chain initiation/propagation/termination. Electrophilic carbons: C-X (halide), C=O (carbonyl). Nucleophiles: OH", RO", CN", NH3, enolates, RMgX (carbanion equiv. ). 13 . Substitution & Elimination En1/2 Sn2 Sn1 Steps 1 (concerted) 2 (carbocation) Rate k[RX][Nu] k[RX][11]Source: asksia-cheatsheet-chem2522.pdfEXAM REVISION Sem 1 2026 . SIDE 2 OF 2 Synthesis . mechanisms . polymers SIDE 2/2 polymers 12 · Functional Groups REACTIVITY MAP Reactivity lives at the functional group; the carbon skeleton is mostly inert. Two master patterns: · Polar / ionic - a nucleophile (electron- rich, 8-) attacks an electrophile (electron- poor, 8+). Curly arrows go from Nu to E. . Radical - homolysis, single-electron (fish-hook) arrows; chain initiation/propagation/termination. Electrophilic carbons: C-X (halide), C=O (carbonyl). Nucleophiles: OH", RO", CN", NH3, enolates, RMgX (carbanion equiv. ). 13 . Substitution & Elimination En1/2 Sn2 Sn1 Steps 1 (concerted) 2 (carbocation) Rate k[RX][Nu] k[RX] Substrate 1° > 2° 3° > 2°
-
2) 亲电/亲核“常见成员表”（你材料列出的）
- 亲电碳：C–X（卤代烃）、C=O（羰基）[6]Source: asksia-cheatsheet-chem2522.pdfRevision aid . check the official unit outline for assessment . 0 2026 flip - for side 2 . synthesis, mechanisms & polymers CHEM2522 Sustainable Chemical Manufacture UNIVERSITY OF SYDNEY . SCHOOL OF CHEMISTRY EXAM REVISION Sem 1 2026 . SIDE 2 OF 2 Synthesis . mechanisms . polymers SIDE 2/2 polymers 12 · Functional Groups REACTIVITY MAP Reactivity lives at the functional group; the carbon skeleton is mostly inert. Two master patterns: · Polar / ionic - a nucleophile (electron- rich, 8-) attacks an electrophile (electron- poor, 8+). Curly arrows go from Nu to E. . Radical - homolysis, single-electron (fish-hook) arrows; chain initiation/propagation/termination. Electrophilic carbons: C-X (halide), C=O (carbonyl). Nucleophiles: OH", RO", CN", NH3, enolates, RMgX (carbanion equiv. ). 13 . Substitution & Elimination En1/2 Sn2 Sn1 Steps 1 (concerted) 2 (carbocation) Rate k[RX][Nu] k[RX][11]Source: asksia-cheatsheet-chem2522.pdfEXAM REVISION Sem 1 2026 . SIDE 2 OF 2 Synthesis . mechanisms . polymers SIDE 2/2 polymers 12 · Functional Groups REACTIVITY MAP Reactivity lives at the functional group; the carbon skeleton is mostly inert. Two master patterns: · Polar / ionic - a nucleophile (electron- rich, 8-) attacks an electrophile (electron- poor, 8+). Curly arrows go from Nu to E. . Radical - homolysis, single-electron (fish-hook) arrows; chain initiation/propagation/termination. Electrophilic carbons: C-X (halide), C=O (carbonyl). Nucleophiles: OH", RO", CN", NH3, enolates, RMgX (carbanion equiv. ). 13 . Substitution & Elimination En1/2 Sn2 Sn1 Steps 1 (concerted) 2 (carbocation) Rate k[RX][Nu] k[RX] Substrate 1° > 2° 3° > 2°
- 常见亲核体：OH$^-$, RO$^-$, CN$^-$, NH$_3$, enolates, RMgX（类碳负离子）[6]Source: asksia-cheatsheet-chem2522.pdfRevision aid . check the official unit outline for assessment . 0 2026 flip - for side 2 . synthesis, mechanisms & polymers CHEM2522 Sustainable Chemical Manufacture UNIVERSITY OF SYDNEY . SCHOOL OF CHEMISTRY EXAM REVISION Sem 1 2026 . SIDE 2 OF 2 Synthesis . mechanisms . polymers SIDE 2/2 polymers 12 · Functional Groups REACTIVITY MAP Reactivity lives at the functional group; the carbon skeleton is mostly inert. Two master patterns: · Polar / ionic - a nucleophile (electron- rich, 8-) attacks an electrophile (electron- poor, 8+). Curly arrows go from Nu to E. . Radical - homolysis, single-electron (fish-hook) arrows; chain initiation/propagation/termination. Electrophilic carbons: C-X (halide), C=O (carbonyl). Nucleophiles: OH", RO", CN", NH3, enolates, RMgX (carbanion equiv. ). 13 . Substitution & Elimination En1/2 Sn2 Sn1 Steps 1 (concerted) 2 (carbocation) Rate k[RX][Nu] k[RX][11]Source: asksia-cheatsheet-chem2522.pdfEXAM REVISION Sem 1 2026 . SIDE 2 OF 2 Synthesis . mechanisms . polymers SIDE 2/2 polymers 12 · Functional Groups REACTIVITY MAP Reactivity lives at the functional group; the carbon skeleton is mostly inert. Two master patterns: · Polar / ionic - a nucleophile (electron- rich, 8-) attacks an electrophile (electron- poor, 8+). Curly arrows go from Nu to E. . Radical - homolysis, single-electron (fish-hook) arrows; chain initiation/propagation/termination. Electrophilic carbons: C-X (halide), C=O (carbonyl). Nucleophiles: OH", RO", CN", NH3, enolates, RMgX (carbanion equiv. ). 13 . Substitution & Elimination En1/2 Sn2 Sn1 Steps 1 (concerted) 2 (carbocation) Rate k[RX][Nu] k[RX] Substrate 1° > 2° 3° > 2°
-
3) SN2 vs SN1（最常考：看底物/溶剂/速率式/立体化学）
- SN2（材料表格）[6]Source: asksia-cheatsheet-chem2522.pdfRevision aid . check the official unit outline for assessment . 0 2026 flip - for side 2 . synthesis, mechanisms & polymers
CHEM2522
Sustainable Chemical Manufacture UNIVERSITY OF SYDNEY . SCHOOL OF CHEMISTRY
EXAM REVISION Sem 1 2026 . SIDE 2 OF 2 Synthesis . mechanisms . polymers
SIDE 2/2 polymers
12 · Functional Groups
REACTIVITY MAP
Reactivity lives at the functional group; the carbon skeleton is mostly inert. Two master patterns:
· Polar / ionic - a nucleophile (electron- rich, 8-) attacks an electrophile (electron- poor, 8+). Curly arrows go from Nu to E. . Radical - homolysis, single-electron (fish-hook) arrows; chain initiation/propagation/termination.
Electrophilic carbons: C-X (halide), C=O (carbonyl). Nucleophiles: OH", RO", CN", NH3, enolates, RMgX (carbanion equiv. ).
13 . Substitution & Elimination
En1/2
Sn2
Sn1
Steps
1 (concerted)
2 (carbocation)
Rate
k[RX][Nu]
k[RX][11]Source: asksia-cheatsheet-chem2522.pdfEXAM REVISION Sem 1 2026 . SIDE 2 OF 2 Synthesis . mechanisms . polymers
SIDE 2/2 polymers
12 · Functional Groups
REACTIVITY MAP
Reactivity lives at the functional group; the carbon skeleton is mostly inert. Two master patterns:
· Polar / ionic - a nucleophile (electron- rich, 8-) attacks an electrophile (electron- poor, 8+). Curly arrows go from Nu to E. . Radical - homolysis, single-electron (fish-hook) arrows; chain initiation/propagation/termination.
Electrophilic carbons: C-X (halide), C=O (carbonyl). Nucleophiles: OH", RO", CN", NH3, enolates, RMgX (carbanion equiv. ).
13 . Substitution & Elimination
En1/2
Sn2
Sn1
Steps
1 (concerted)
2 (carbocation)
Rate
k[RX][Nu]
k[RX]
Substrate
1° > 2°
3° > 2°
- 一步协同（concerted）
- 速率：$k[\text{RX}][\text{Nu}]$
- 底物趋势（材料写法）：$1^\circ > 2^\circ$（位阻越小越好）
- 立体：反转（inversion）[19]Source: asksia-cheatsheet-chem2522.pdfStereo inversion racemisation Solvent Nu polar aprotic strong weak ok E2: concerted, anti-periplanar H & LG, strong base, rate k[RX] [base]; E1: via carbocation, rate k[RX]. Both follow Zaitsev (more-substituted alkene) - except a bulky base (t-BuO-) gives Hofmann (less- substituted). The fork: strong bulky base + heat = elimination; good Nu, weaker base = substitution. 3º + weak Nu/protic = Sn1/E1 mix. 13b . Nucleophiles & Leaving Groups RANK THEM Leaving group best->worst: I" > Br" > CI- >> F -; TsO- & H2O good. A weak base is a good LG (stable once it leaves); OH-, RO", NH2- are poor LGs. Nucleophilicity 1 with negative charge & less steric bulk. Basicity # nucleophilicity: in polar aprotic they track; in polar protic the bigger, more-polarisable ion wins (I" > F-). 13c · Carbocation Stability DRIVES Sn1/E1 Order 3° > 2° > 1º > methyl (hyperconjugation + induction); benzylic/allylic are extra-stable (resonance). An unstable cation rearranges (1,2-hydride or alkyl shift) to a more stable one - the classic Sn1/E1 "wrong product" trap. 13d . Mechanism Arrows METHOD MARKS Arrow starts at a lone pair or bond, points where electrons go · Never start an arrow at H+ or a + charge Conserve charge & atoms each step Double-head = 2e- (polar); fish-hook = 1e- (radical)
- 溶剂：极性非质子（polar aprotic）更利于强亲核体（材料也强调 aprotic/protic 对亲核性的影响）[19]Source: asksia-cheatsheet-chem2522.pdfStereo inversion racemisation Solvent Nu polar aprotic strong weak ok E2: concerted, anti-periplanar H & LG, strong base, rate k[RX] [base]; E1: via carbocation, rate k[RX]. Both follow Zaitsev (more-substituted alkene) - except a bulky base (t-BuO-) gives Hofmann (less- substituted). The fork: strong bulky base + heat = elimination; good Nu, weaker base = substitution. 3º + weak Nu/protic = Sn1/E1 mix. 13b . Nucleophiles & Leaving Groups RANK THEM Leaving group best->worst: I" > Br" > CI- >> F -; TsO- & H2O good. A weak base is a good LG (stable once it leaves); OH-, RO", NH2- are poor LGs. Nucleophilicity 1 with negative charge & less steric bulk. Basicity # nucleophilicity: in polar aprotic they track; in polar protic the bigger, more-polarisable ion wins (I" > F-). 13c · Carbocation Stability DRIVES Sn1/E1 Order 3° > 2° > 1º > methyl (hyperconjugation + induction); benzylic/allylic are extra-stable (resonance). An unstable cation rearranges (1,2-hydride or alkyl shift) to a more stable one - the classic Sn1/E1 "wrong product" trap. 13d . Mechanism Arrows METHOD MARKS Arrow starts at a lone pair or bond, points where electrons go · Never start an arrow at H+ or a + charge Conserve charge & atoms each step Double-head = 2e- (polar); fish-hook = 1e- (radical)
- SN1（材料表格 + 补充点）[6]Source: asksia-cheatsheet-chem2522.pdfRevision aid . check the official unit outline for assessment . 0 2026 flip - for side 2 . synthesis, mechanisms & polymers
CHEM2522
Sustainable Chemical Manufacture UNIVERSITY OF SYDNEY . SCHOOL OF CHEMISTRY
EXAM REVISION Sem 1 2026 . SIDE 2 OF 2 Synthesis . mechanisms . polymers
SIDE 2/2 polymers
12 · Functional Groups
REACTIVITY MAP
Reactivity lives at the functional group; the carbon skeleton is mostly inert. Two master patterns:
· Polar / ionic - a nucleophile (electron- rich, 8-) attacks an electrophile (electron- poor, 8+). Curly arrows go from Nu to E. . Radical - homolysis, single-electron (fish-hook) arrows; chain initiation/propagation/termination.
Electrophilic carbons: C-X (halide), C=O (carbonyl). Nucleophiles: OH", RO", CN", NH3, enolates, RMgX (carbanion equiv. ).
13 . Substitution & Elimination
En1/2
Sn2
Sn1
Steps
1 (concerted)
2 (carbocation)
Rate
k[RX][Nu]
k[RX][11]Source: asksia-cheatsheet-chem2522.pdfEXAM REVISION Sem 1 2026 . SIDE 2 OF 2 Synthesis . mechanisms . polymers
SIDE 2/2 polymers
12 · Functional Groups
REACTIVITY MAP
Reactivity lives at the functional group; the carbon skeleton is mostly inert. Two master patterns:
· Polar / ionic - a nucleophile (electron- rich, 8-) attacks an electrophile (electron- poor, 8+). Curly arrows go from Nu to E. . Radical - homolysis, single-electron (fish-hook) arrows; chain initiation/propagation/termination.
Electrophilic carbons: C-X (halide), C=O (carbonyl). Nucleophiles: OH", RO", CN", NH3, enolates, RMgX (carbanion equiv. ).
13 . Substitution & Elimination
En1/2
Sn2
Sn1
Steps
1 (concerted)
2 (carbocation)
Rate
k[RX][Nu]
k[RX]
Substrate
1° > 2°
3° > 2°[19]Source: asksia-cheatsheet-chem2522.pdfStereo
inversion
racemisation
Solvent Nu
polar aprotic strong
weak ok
E2: concerted, anti-periplanar H & LG, strong base, rate k[RX] [base]; E1: via carbocation, rate k[RX]. Both follow Zaitsev (more-substituted alkene) - except a bulky base (t-BuO-) gives Hofmann (less- substituted).
The fork: strong bulky base + heat = elimination; good Nu, weaker base = substitution. 3º + weak Nu/protic = Sn1/E1 mix.
13b . Nucleophiles & Leaving Groups
RANK THEM
Leaving group best->worst: I" > Br" > CI- >> F -; TsO- & H2O good. A weak base is a good LG (stable once it leaves); OH-, RO", NH2- are poor LGs.
Nucleophilicity 1 with negative charge & less steric bulk. Basicity # nucleophilicity: in polar aprotic they track; in polar protic the bigger, more-polarisable ion wins (I" > F-).
13c · Carbocation Stability
DRIVES Sn1/E1
Order 3° > 2° > 1º > methyl (hyperconjugation + induction); benzylic/allylic are extra-stable (resonance). An unstable cation rearranges (1,2-hydride or alkyl shift) to a more stable one - the classic Sn1/E1 "wrong product" trap.
13d . Mechanism Arrows
METHOD MARKS
Arrow starts at a lone pair or bond, points where electrons go
· Never start an arrow at H+ or a + charge Conserve charge & atoms each step
Double-head = 2e- (polar); fish-hook = 1e- (radical)
- 两步，经碳正离子（carbocation）
- 速率：$k[\text{RX}]$
- 底物趋势：$3^\circ > 2^\circ$（因为碳正离子稳定）
- 立体：外消旋（racemisation）倾向[19]Source: asksia-cheatsheet-chem2522.pdfStereo inversion racemisation Solvent Nu polar aprotic strong weak ok E2: concerted, anti-periplanar H & LG, strong base, rate k[RX] [base]; E1: via carbocation, rate k[RX]. Both follow Zaitsev (more-substituted alkene) - except a bulky base (t-BuO-) gives Hofmann (less- substituted). The fork: strong bulky base + heat = elimination; good Nu, weaker base = substitution. 3º + weak Nu/protic = Sn1/E1 mix. 13b . Nucleophiles & Leaving Groups RANK THEM Leaving group best->worst: I" > Br" > CI- >> F -; TsO- & H2O good. A weak base is a good LG (stable once it leaves); OH-, RO", NH2- are poor LGs. Nucleophilicity 1 with negative charge & less steric bulk. Basicity # nucleophilicity: in polar aprotic they track; in polar protic the bigger, more-polarisable ion wins (I" > F-). 13c · Carbocation Stability DRIVES Sn1/E1 Order 3° > 2° > 1º > methyl (hyperconjugation + induction); benzylic/allylic are extra-stable (resonance). An unstable cation rearranges (1,2-hydride or alkyl shift) to a more stable one - the classic Sn1/E1 "wrong product" trap. 13d . Mechanism Arrows METHOD MARKS Arrow starts at a lone pair or bond, points where electrons go · Never start an arrow at H+ or a + charge Conserve charge & atoms each step Double-head = 2e- (polar); fish-hook = 1e- (radical)
- 重排：不稳定碳正离子会 1,2-氢/烷基迁移 → “产物不对”陷阱[19]Source: asksia-cheatsheet-chem2522.pdfStereo inversion racemisation Solvent Nu polar aprotic strong weak ok E2: concerted, anti-periplanar H & LG, strong base, rate k[RX] [base]; E1: via carbocation, rate k[RX]. Both follow Zaitsev (more-substituted alkene) - except a bulky base (t-BuO-) gives Hofmann (less- substituted). The fork: strong bulky base + heat = elimination; good Nu, weaker base = substitution. 3º + weak Nu/protic = Sn1/E1 mix. 13b . Nucleophiles & Leaving Groups RANK THEM Leaving group best->worst: I" > Br" > CI- >> F -; TsO- & H2O good. A weak base is a good LG (stable once it leaves); OH-, RO", NH2- are poor LGs. Nucleophilicity 1 with negative charge & less steric bulk. Basicity # nucleophilicity: in polar aprotic they track; in polar protic the bigger, more-polarisable ion wins (I" > F-). 13c · Carbocation Stability DRIVES Sn1/E1 Order 3° > 2° > 1º > methyl (hyperconjugation + induction); benzylic/allylic are extra-stable (resonance). An unstable cation rearranges (1,2-hydride or alkyl shift) to a more stable one - the classic Sn1/E1 "wrong product" trap. 13d . Mechanism Arrows METHOD MARKS Arrow starts at a lone pair or bond, points where electrons go · Never start an arrow at H+ or a + charge Conserve charge & atoms each step Double-head = 2e- (polar); fish-hook = 1e- (radical)
- 碳正离子稳定性顺序（必背）：[19]Source: asksia-cheatsheet-chem2522.pdfStereo
inversion
racemisation
Solvent Nu
polar aprotic strong
weak ok
E2: concerted, anti-periplanar H & LG, strong base, rate k[RX] [base]; E1: via carbocation, rate k[RX]. Both follow Zaitsev (more-substituted alkene) - except a bulky base (t-BuO-) gives Hofmann (less- substituted).
The fork: strong bulky base + heat = elimination; good Nu, weaker base = substitution. 3º + weak Nu/protic = Sn1/E1 mix.
13b . Nucleophiles & Leaving Groups
RANK THEM
Leaving group best->worst: I" > Br" > CI- >> F -; TsO- & H2O good. A weak base is a good LG (stable once it leaves); OH-, RO", NH2- are poor LGs.
Nucleophilicity 1 with negative charge & less steric bulk. Basicity # nucleophilicity: in polar aprotic they track; in polar protic the bigger, more-polarisable ion wins (I" > F-).
13c · Carbocation Stability
DRIVES Sn1/E1
Order 3° > 2° > 1º > methyl (hyperconjugation + induction); benzylic/allylic are extra-stable (resonance). An unstable cation rearranges (1,2-hydride or alkyl shift) to a more stable one - the classic Sn1/E1 "wrong product" trap.
13d . Mechanism Arrows
METHOD MARKS
Arrow starts at a lone pair or bond, points where electrons go
· Never start an arrow at H+ or a + charge Conserve charge & atoms each step
Double-head = 2e- (polar); fish-hook = 1e- (radical)
- $3^\circ > 2^\circ > 1^\circ > \text{methyl}$
- benzylic / allylic 额外稳定（共振）
- SN2（材料表格）[6]Source: asksia-cheatsheet-chem2522.pdfRevision aid . check the official unit outline for assessment . 0 2026 flip - for side 2 . synthesis, mechanisms & polymers
CHEM2522
Sustainable Chemical Manufacture UNIVERSITY OF SYDNEY . SCHOOL OF CHEMISTRY
EXAM REVISION Sem 1 2026 . SIDE 2 OF 2 Synthesis . mechanisms . polymers
SIDE 2/2 polymers
12 · Functional Groups
REACTIVITY MAP
Reactivity lives at the functional group; the carbon skeleton is mostly inert. Two master patterns:
· Polar / ionic - a nucleophile (electron- rich, 8-) attacks an electrophile (electron- poor, 8+). Curly arrows go from Nu to E. . Radical - homolysis, single-electron (fish-hook) arrows; chain initiation/propagation/termination.
Electrophilic carbons: C-X (halide), C=O (carbonyl). Nucleophiles: OH", RO", CN", NH3, enolates, RMgX (carbanion equiv. ).
13 . Substitution & Elimination
En1/2
Sn2
Sn1
Steps
1 (concerted)
2 (carbocation)
Rate
k[RX][Nu]
k[RX][11]Source: asksia-cheatsheet-chem2522.pdfEXAM REVISION Sem 1 2026 . SIDE 2 OF 2 Synthesis . mechanisms . polymers
SIDE 2/2 polymers
12 · Functional Groups
REACTIVITY MAP
Reactivity lives at the functional group; the carbon skeleton is mostly inert. Two master patterns:
· Polar / ionic - a nucleophile (electron- rich, 8-) attacks an electrophile (electron- poor, 8+). Curly arrows go from Nu to E. . Radical - homolysis, single-electron (fish-hook) arrows; chain initiation/propagation/termination.
Electrophilic carbons: C-X (halide), C=O (carbonyl). Nucleophiles: OH", RO", CN", NH3, enolates, RMgX (carbanion equiv. ).
13 . Substitution & Elimination
En1/2
Sn2
Sn1
Steps
1 (concerted)
2 (carbocation)
Rate
k[RX][Nu]
k[RX]
Substrate
1° > 2°
3° > 2°
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4) E2 vs E1（消除反应）
- E2：协同；要求 H 和离去基团反式共平面（anti-periplanar）；强碱；速率 $k[\text{RX}][\text{base}]$[19]Source: asksia-cheatsheet-chem2522.pdfStereo inversion racemisation Solvent Nu polar aprotic strong weak ok E2: concerted, anti-periplanar H & LG, strong base, rate k[RX] [base]; E1: via carbocation, rate k[RX]. Both follow Zaitsev (more-substituted alkene) - except a bulky base (t-BuO-) gives Hofmann (less- substituted). The fork: strong bulky base + heat = elimination; good Nu, weaker base = substitution. 3º + weak Nu/protic = Sn1/E1 mix. 13b . Nucleophiles & Leaving Groups RANK THEM Leaving group best->worst: I" > Br" > CI- >> F -; TsO- & H2O good. A weak base is a good LG (stable once it leaves); OH-, RO", NH2- are poor LGs. Nucleophilicity 1 with negative charge & less steric bulk. Basicity # nucleophilicity: in polar aprotic they track; in polar protic the bigger, more-polarisable ion wins (I" > F-). 13c · Carbocation Stability DRIVES Sn1/E1 Order 3° > 2° > 1º > methyl (hyperconjugation + induction); benzylic/allylic are extra-stable (resonance). An unstable cation rearranges (1,2-hydride or alkyl shift) to a more stable one - the classic Sn1/E1 "wrong product" trap. 13d . Mechanism Arrows METHOD MARKS Arrow starts at a lone pair or bond, points where electrons go · Never start an arrow at H+ or a + charge Conserve charge & atoms each step Double-head = 2e- (polar); fish-hook = 1e- (radical)
- E1：经碳正离子；速率 $k[\text{RX}]$[19]Source: asksia-cheatsheet-chem2522.pdfStereo inversion racemisation Solvent Nu polar aprotic strong weak ok E2: concerted, anti-periplanar H & LG, strong base, rate k[RX] [base]; E1: via carbocation, rate k[RX]. Both follow Zaitsev (more-substituted alkene) - except a bulky base (t-BuO-) gives Hofmann (less- substituted). The fork: strong bulky base + heat = elimination; good Nu, weaker base = substitution. 3º + weak Nu/protic = Sn1/E1 mix. 13b . Nucleophiles & Leaving Groups RANK THEM Leaving group best->worst: I" > Br" > CI- >> F -; TsO- & H2O good. A weak base is a good LG (stable once it leaves); OH-, RO", NH2- are poor LGs. Nucleophilicity 1 with negative charge & less steric bulk. Basicity # nucleophilicity: in polar aprotic they track; in polar protic the bigger, more-polarisable ion wins (I" > F-). 13c · Carbocation Stability DRIVES Sn1/E1 Order 3° > 2° > 1º > methyl (hyperconjugation + induction); benzylic/allylic are extra-stable (resonance). An unstable cation rearranges (1,2-hydride or alkyl shift) to a more stable one - the classic Sn1/E1 "wrong product" trap. 13d . Mechanism Arrows METHOD MARKS Arrow starts at a lone pair or bond, points where electrons go · Never start an arrow at H+ or a + charge Conserve charge & atoms each step Double-head = 2e- (polar); fish-hook = 1e- (radical)
- Zaitsev vs Hofmann：一般 Zaitsev（更取代烯烃）为主；但大位阻碱（如 t-BuO$^-$）会给 Hofmann（较少取代烯烃）[19]Source: asksia-cheatsheet-chem2522.pdfStereo inversion racemisation Solvent Nu polar aprotic strong weak ok E2: concerted, anti-periplanar H & LG, strong base, rate k[RX] [base]; E1: via carbocation, rate k[RX]. Both follow Zaitsev (more-substituted alkene) - except a bulky base (t-BuO-) gives Hofmann (less- substituted). The fork: strong bulky base + heat = elimination; good Nu, weaker base = substitution. 3º + weak Nu/protic = Sn1/E1 mix. 13b . Nucleophiles & Leaving Groups RANK THEM Leaving group best->worst: I" > Br" > CI- >> F -; TsO- & H2O good. A weak base is a good LG (stable once it leaves); OH-, RO", NH2- are poor LGs. Nucleophilicity 1 with negative charge & less steric bulk. Basicity # nucleophilicity: in polar aprotic they track; in polar protic the bigger, more-polarisable ion wins (I" > F-). 13c · Carbocation Stability DRIVES Sn1/E1 Order 3° > 2° > 1º > methyl (hyperconjugation + induction); benzylic/allylic are extra-stable (resonance). An unstable cation rearranges (1,2-hydride or alkyl shift) to a more stable one - the classic Sn1/E1 "wrong product" trap. 13d . Mechanism Arrows METHOD MARKS Arrow starts at a lone pair or bond, points where electrons go · Never start an arrow at H+ or a + charge Conserve charge & atoms each step Double-head = 2e- (polar); fish-hook = 1e- (radical)
-
5) “分叉判断题”速记（题目会给条件让你选）
- 强、笨重碱 + 加热 → 倾向消除（E2）[19]Source: asksia-cheatsheet-chem2522.pdfStereo inversion racemisation Solvent Nu polar aprotic strong weak ok E2: concerted, anti-periplanar H & LG, strong base, rate k[RX] [base]; E1: via carbocation, rate k[RX]. Both follow Zaitsev (more-substituted alkene) - except a bulky base (t-BuO-) gives Hofmann (less- substituted). The fork: strong bulky base + heat = elimination; good Nu, weaker base = substitution. 3º + weak Nu/protic = Sn1/E1 mix. 13b . Nucleophiles & Leaving Groups RANK THEM Leaving group best->worst: I" > Br" > CI- >> F -; TsO- & H2O good. A weak base is a good LG (stable once it leaves); OH-, RO", NH2- are poor LGs. Nucleophilicity 1 with negative charge & less steric bulk. Basicity # nucleophilicity: in polar aprotic they track; in polar protic the bigger, more-polarisable ion wins (I" > F-). 13c · Carbocation Stability DRIVES Sn1/E1 Order 3° > 2° > 1º > methyl (hyperconjugation + induction); benzylic/allylic are extra-stable (resonance). An unstable cation rearranges (1,2-hydride or alkyl shift) to a more stable one - the classic Sn1/E1 "wrong product" trap. 13d . Mechanism Arrows METHOD MARKS Arrow starts at a lone pair or bond, points where electrons go · Never start an arrow at H+ or a + charge Conserve charge & atoms each step Double-head = 2e- (polar); fish-hook = 1e- (radical)
- 好亲核体、较弱碱 → 倾向取代（SN2）[19]Source: asksia-cheatsheet-chem2522.pdfStereo inversion racemisation Solvent Nu polar aprotic strong weak ok E2: concerted, anti-periplanar H & LG, strong base, rate k[RX] [base]; E1: via carbocation, rate k[RX]. Both follow Zaitsev (more-substituted alkene) - except a bulky base (t-BuO-) gives Hofmann (less- substituted). The fork: strong bulky base + heat = elimination; good Nu, weaker base = substitution. 3º + weak Nu/protic = Sn1/E1 mix. 13b . Nucleophiles & Leaving Groups RANK THEM Leaving group best->worst: I" > Br" > CI- >> F -; TsO- & H2O good. A weak base is a good LG (stable once it leaves); OH-, RO", NH2- are poor LGs. Nucleophilicity 1 with negative charge & less steric bulk. Basicity # nucleophilicity: in polar aprotic they track; in polar protic the bigger, more-polarisable ion wins (I" > F-). 13c · Carbocation Stability DRIVES Sn1/E1 Order 3° > 2° > 1º > methyl (hyperconjugation + induction); benzylic/allylic are extra-stable (resonance). An unstable cation rearranges (1,2-hydride or alkyl shift) to a more stable one - the classic Sn1/E1 "wrong product" trap. 13d . Mechanism Arrows METHOD MARKS Arrow starts at a lone pair or bond, points where electrons go · Never start an arrow at H+ or a + charge Conserve charge & atoms each step Double-head = 2e- (polar); fish-hook = 1e- (radical)
- $3^\circ$ + 弱亲核体/质子溶剂 → SN1/E1 混合[19]Source: asksia-cheatsheet-chem2522.pdfStereo inversion racemisation Solvent Nu polar aprotic strong weak ok E2: concerted, anti-periplanar H & LG, strong base, rate k[RX] [base]; E1: via carbocation, rate k[RX]. Both follow Zaitsev (more-substituted alkene) - except a bulky base (t-BuO-) gives Hofmann (less- substituted). The fork: strong bulky base + heat = elimination; good Nu, weaker base = substitution. 3º + weak Nu/protic = Sn1/E1 mix. 13b . Nucleophiles & Leaving Groups RANK THEM Leaving group best->worst: I" > Br" > CI- >> F -; TsO- & H2O good. A weak base is a good LG (stable once it leaves); OH-, RO", NH2- are poor LGs. Nucleophilicity 1 with negative charge & less steric bulk. Basicity # nucleophilicity: in polar aprotic they track; in polar protic the bigger, more-polarisable ion wins (I" > F-). 13c · Carbocation Stability DRIVES Sn1/E1 Order 3° > 2° > 1º > methyl (hyperconjugation + induction); benzylic/allylic are extra-stable (resonance). An unstable cation rearranges (1,2-hydride or alkyl shift) to a more stable one - the classic Sn1/E1 "wrong product" trap. 13d . Mechanism Arrows METHOD MARKS Arrow starts at a lone pair or bond, points where electrons go · Never start an arrow at H+ or a + charge Conserve charge & atoms each step Double-head = 2e- (polar); fish-hook = 1e- (radical)
-
6) Leaving group 与 nucleophilicity（排序题常考）
- 离去基团（best → worst）：I$^-$ > Br$^-$ > Cl$^-$ >> F$^-$；TsO$^-$ 与 H$_2$O 也可以是好离去基团[19]Source: asksia-cheatsheet-chem2522.pdfStereo inversion racemisation Solvent Nu polar aprotic strong weak ok E2: concerted, anti-periplanar H & LG, strong base, rate k[RX] [base]; E1: via carbocation, rate k[RX]. Both follow Zaitsev (more-substituted alkene) - except a bulky base (t-BuO-) gives Hofmann (less- substituted). The fork: strong bulky base + heat = elimination; good Nu, weaker base = substitution. 3º + weak Nu/protic = Sn1/E1 mix. 13b . Nucleophiles & Leaving Groups RANK THEM Leaving group best->worst: I" > Br" > CI- >> F -; TsO- & H2O good. A weak base is a good LG (stable once it leaves); OH-, RO", NH2- are poor LGs. Nucleophilicity 1 with negative charge & less steric bulk. Basicity # nucleophilicity: in polar aprotic they track; in polar protic the bigger, more-polarisable ion wins (I" > F-). 13c · Carbocation Stability DRIVES Sn1/E1 Order 3° > 2° > 1º > methyl (hyperconjugation + induction); benzylic/allylic are extra-stable (resonance). An unstable cation rearranges (1,2-hydride or alkyl shift) to a more stable one - the classic Sn1/E1 "wrong product" trap. 13d . Mechanism Arrows METHOD MARKS Arrow starts at a lone pair or bond, points where electrons go · Never start an arrow at H+ or a + charge Conserve charge & atoms each step Double-head = 2e- (polar); fish-hook = 1e- (radical)
- 核心理由：弱碱是好离去基团（离去后更稳定）[19]Source: asksia-cheatsheet-chem2522.pdfStereo inversion racemisation Solvent Nu polar aprotic strong weak ok E2: concerted, anti-periplanar H & LG, strong base, rate k[RX] [base]; E1: via carbocation, rate k[RX]. Both follow Zaitsev (more-substituted alkene) - except a bulky base (t-BuO-) gives Hofmann (less- substituted). The fork: strong bulky base + heat = elimination; good Nu, weaker base = substitution. 3º + weak Nu/protic = Sn1/E1 mix. 13b . Nucleophiles & Leaving Groups RANK THEM Leaving group best->worst: I" > Br" > CI- >> F -; TsO- & H2O good. A weak base is a good LG (stable once it leaves); OH-, RO", NH2- are poor LGs. Nucleophilicity 1 with negative charge & less steric bulk. Basicity # nucleophilicity: in polar aprotic they track; in polar protic the bigger, more-polarisable ion wins (I" > F-). 13c · Carbocation Stability DRIVES Sn1/E1 Order 3° > 2° > 1º > methyl (hyperconjugation + induction); benzylic/allylic are extra-stable (resonance). An unstable cation rearranges (1,2-hydride or alkyl shift) to a more stable one - the classic Sn1/E1 "wrong product" trap. 13d . Mechanism Arrows METHOD MARKS Arrow starts at a lone pair or bond, points where electrons go · Never start an arrow at H+ or a + charge Conserve charge & atoms each step Double-head = 2e- (polar); fish-hook = 1e- (radical)
- 亲核性与溶剂效应：[19]Source: asksia-cheatsheet-chem2522.pdfStereo
inversion
racemisation
Solvent Nu
polar aprotic strong
weak ok
E2: concerted, anti-periplanar H & LG, strong base, rate k[RX] [base]; E1: via carbocation, rate k[RX]. Both follow Zaitsev (more-substituted alkene) - except a bulky base (t-BuO-) gives Hofmann (less- substituted).
The fork: strong bulky base + heat = elimination; good Nu, weaker base = substitution. 3º + weak Nu/protic = Sn1/E1 mix.
13b . Nucleophiles & Leaving Groups
RANK THEM
Leaving group best->worst: I" > Br" > CI- >> F -; TsO- & H2O good. A weak base is a good LG (stable once it leaves); OH-, RO", NH2- are poor LGs.
Nucleophilicity 1 with negative charge & less steric bulk. Basicity # nucleophilicity: in polar aprotic they track; in polar protic the bigger, more-polarisable ion wins (I" > F-).
13c · Carbocation Stability
DRIVES Sn1/E1
Order 3° > 2° > 1º > methyl (hyperconjugation + induction); benzylic/allylic are extra-stable (resonance). An unstable cation rearranges (1,2-hydride or alkyl shift) to a more stable one - the classic Sn1/E1 "wrong product" trap.
13d . Mechanism Arrows
METHOD MARKS
Arrow starts at a lone pair or bond, points where electrons go
· Never start an arrow at H+ or a + charge Conserve charge & atoms each step
Double-head = 2e- (polar); fish-hook = 1e- (radical)
- 极性非质子溶剂中：亲核性与碱性更“同步”
- 极性质子溶剂中：更大、更易极化的阴离子亲核性更强（材料举例：I$^-$ > F$^-$）
-
7) 箭头画法（非常容易扣分）
- 箭头从孤对电子或键出发，指向电子要去的地方[19]Source: asksia-cheatsheet-chem2522.pdfStereo inversion racemisation Solvent Nu polar aprotic strong weak ok E2: concerted, anti-periplanar H & LG, strong base, rate k[RX] [base]; E1: via carbocation, rate k[RX]. Both follow Zaitsev (more-substituted alkene) - except a bulky base (t-BuO-) gives Hofmann (less- substituted). The fork: strong bulky base + heat = elimination; good Nu, weaker base = substitution. 3º + weak Nu/protic = Sn1/E1 mix. 13b . Nucleophiles & Leaving Groups RANK THEM Leaving group best->worst: I" > Br" > CI- >> F -; TsO- & H2O good. A weak base is a good LG (stable once it leaves); OH-, RO", NH2- are poor LGs. Nucleophilicity 1 with negative charge & less steric bulk. Basicity # nucleophilicity: in polar aprotic they track; in polar protic the bigger, more-polarisable ion wins (I" > F-). 13c · Carbocation Stability DRIVES Sn1/E1 Order 3° > 2° > 1º > methyl (hyperconjugation + induction); benzylic/allylic are extra-stable (resonance). An unstable cation rearranges (1,2-hydride or alkyl shift) to a more stable one - the classic Sn1/E1 "wrong product" trap. 13d . Mechanism Arrows METHOD MARKS Arrow starts at a lone pair or bond, points where electrons go · Never start an arrow at H+ or a + charge Conserve charge & atoms each step Double-head = 2e- (polar); fish-hook = 1e- (radical)
- 不要从 H$^+$ 或 “+” 号出发画箭头；每步要守恒电荷与原子[19]Source: asksia-cheatsheet-chem2522.pdfStereo inversion racemisation Solvent Nu polar aprotic strong weak ok E2: concerted, anti-periplanar H & LG, strong base, rate k[RX] [base]; E1: via carbocation, rate k[RX]. Both follow Zaitsev (more-substituted alkene) - except a bulky base (t-BuO-) gives Hofmann (less- substituted). The fork: strong bulky base + heat = elimination; good Nu, weaker base = substitution. 3º + weak Nu/protic = Sn1/E1 mix. 13b . Nucleophiles & Leaving Groups RANK THEM Leaving group best->worst: I" > Br" > CI- >> F -; TsO- & H2O good. A weak base is a good LG (stable once it leaves); OH-, RO", NH2- are poor LGs. Nucleophilicity 1 with negative charge & less steric bulk. Basicity # nucleophilicity: in polar aprotic they track; in polar protic the bigger, more-polarisable ion wins (I" > F-). 13c · Carbocation Stability DRIVES Sn1/E1 Order 3° > 2° > 1º > methyl (hyperconjugation + induction); benzylic/allylic are extra-stable (resonance). An unstable cation rearranges (1,2-hydride or alkyl shift) to a more stable one - the classic Sn1/E1 "wrong product" trap. 13d . Mechanism Arrows METHOD MARKS Arrow starts at a lone pair or bond, points where electrons go · Never start an arrow at H+ or a + charge Conserve charge & atoms each step Double-head = 2e- (polar); fish-hook = 1e- (radical)
- 双头箭头 = 2e$^-$（极性）；鱼钩 = 1e$^-$（自由基）[19]Source: asksia-cheatsheet-chem2522.pdfStereo inversion racemisation Solvent Nu polar aprotic strong weak ok E2: concerted, anti-periplanar H & LG, strong base, rate k[RX] [base]; E1: via carbocation, rate k[RX]. Both follow Zaitsev (more-substituted alkene) - except a bulky base (t-BuO-) gives Hofmann (less- substituted). The fork: strong bulky base + heat = elimination; good Nu, weaker base = substitution. 3º + weak Nu/protic = Sn1/E1 mix. 13b . Nucleophiles & Leaving Groups RANK THEM Leaving group best->worst: I" > Br" > CI- >> F -; TsO- & H2O good. A weak base is a good LG (stable once it leaves); OH-, RO", NH2- are poor LGs. Nucleophilicity 1 with negative charge & less steric bulk. Basicity # nucleophilicity: in polar aprotic they track; in polar protic the bigger, more-polarisable ion wins (I" > F-). 13c · Carbocation Stability DRIVES Sn1/E1 Order 3° > 2° > 1º > methyl (hyperconjugation + induction); benzylic/allylic are extra-stable (resonance). An unstable cation rearranges (1,2-hydride or alkyl shift) to a more stable one - the classic Sn1/E1 "wrong product" trap. 13d . Mechanism Arrows METHOD MARKS Arrow starts at a lone pair or bond, points where electrons go · Never start an arrow at H+ or a + charge Conserve charge & atoms each step Double-head = 2e- (polar); fish-hook = 1e- (radical)
-
七、官能团与反应（你材料里出现的高频点）
-
1) 保护基 vs 绿色（原则 8：Reduce derivatives）
- 碳yl + 2 ROH → acetal，可作为 C=O 保护基（耐碱/耐亲核，水酸可脱保护）[7]Source: asksia-cheatsheet-chem2522.pdfR-X + terminal alkyne Cycle: oxidative addition > transmetalation > reductive elimination . Catalytic in Pd, mild, tolerant of functional groups = green & widely used in pharma. 15b . Imines, Acetals & Protecting Groups + N/O Carbonyl + 1° amine > imine (C=N); + 2° amine > enamine. Acid-catalysed, water removed to drive the equilibrium. Carbonyl + 2 ROH > acetal = a protecting group for C=O (stable to base & nucleophiles, removed by aqueous acid). But every protecting group adds steps = poor atom economy (principle 8 - reduce derivatives). 15c . Enols & Conjugate A & B Addition REACTIVITY Keto-enol tautomerism: the keto form dominates, but the enol is the nucleophile in a-substitution (halogenation, the aldol). a, ß-unsaturated carbonyl is electrophilic at the carbonyl C (1,2-addition) and at the B-C: 1,4 / Michael / conjugate addition . Soft nucleophiles & stabilised enolates favour 1,4. C=O MAKE . Functional groups . Substitution/elimination . Carbonyl . Named C-C coupling . Redox . Polymers . Sustainable REVISION SHEET . ALL TOPICS STRUCTURE-PROPERTY H2 / Pd catalytic CLASSIFY FIRST Sonogashira polar protic CARBONYL Revision aid . check the official unit outline for assessment . 0 2026 good luck. revise smart. CHEM2522 Sustainable Chemical Manufacture UNIVERSITY OF SYDNEY . SCHOOL OF CHEMISTRY EXAM REVISION Sem 1 2026 · SIDE 1 OF 2 Whole-unit revision . all topics[14]Source: asksia-cheatsheet-chem2522.pdfCarbonyl + 1° amine > imine (C=N); + 2° amine > enamine. Acid-catalysed, water removed to drive the equilibrium. Carbonyl + 2 ROH > acetal = a protecting group for C=O (stable to base & nucleophiles, removed by aqueous acid). But every protecting group adds steps = poor atom economy (principle 8 - reduce derivatives). 15c . Enols & Conjugate A & B Addition REACTIVITY Keto-enol tautomerism: the keto form dominates, but the enol is the nucleophile in a-substitution (halogenation, the aldol). a, ß-unsaturated carbonyl is electrophilic at the carbonyl C (1,2-addition) and at the B-C: 1,4 / Michael / conjugate addition . Soft nucleophiles & stabilised enolates favour 1,4. C=O MAKE . Functional groups . Substitution/elimination . Carbonyl . Named C-C coupling . Redox . Polymers . Sustainable REVISION SHEET . ALL TOPICS STRUCTURE-PROPERTY H2 / Pd catalytic CLASSIFY FIRST Sonogashira polar protic CARBONYL Revision aid . check the official unit outline for assessment . 0 2026 good luck. revise smart.
- 但结论要会写：保护基会增加步骤与废物 → 原子经济性变差（principle 8）[7]Source: asksia-cheatsheet-chem2522.pdfR-X + terminal alkyne Cycle: oxidative addition > transmetalation > reductive elimination . Catalytic in Pd, mild, tolerant of functional groups = green & widely used in pharma. 15b . Imines, Acetals & Protecting Groups + N/O Carbonyl + 1° amine > imine (C=N); + 2° amine > enamine. Acid-catalysed, water removed to drive the equilibrium. Carbonyl + 2 ROH > acetal = a protecting group for C=O (stable to base & nucleophiles, removed by aqueous acid). But every protecting group adds steps = poor atom economy (principle 8 - reduce derivatives). 15c . Enols & Conjugate A & B Addition REACTIVITY Keto-enol tautomerism: the keto form dominates, but the enol is the nucleophile in a-substitution (halogenation, the aldol). a, ß-unsaturated carbonyl is electrophilic at the carbonyl C (1,2-addition) and at the B-C: 1,4 / Michael / conjugate addition . Soft nucleophiles & stabilised enolates favour 1,4. C=O MAKE . Functional groups . Substitution/elimination . Carbonyl . Named C-C coupling . Redox . Polymers . Sustainable REVISION SHEET . ALL TOPICS STRUCTURE-PROPERTY H2 / Pd catalytic CLASSIFY FIRST Sonogashira polar protic CARBONYL Revision aid . check the official unit outline for assessment . 0 2026 good luck. revise smart. CHEM2522 Sustainable Chemical Manufacture UNIVERSITY OF SYDNEY . SCHOOL OF CHEMISTRY EXAM REVISION Sem 1 2026 · SIDE 1 OF 2 Whole-unit revision . all topics[14]Source: asksia-cheatsheet-chem2522.pdfCarbonyl + 1° amine > imine (C=N); + 2° amine > enamine. Acid-catalysed, water removed to drive the equilibrium. Carbonyl + 2 ROH > acetal = a protecting group for C=O (stable to base & nucleophiles, removed by aqueous acid). But every protecting group adds steps = poor atom economy (principle 8 - reduce derivatives). 15c . Enols & Conjugate A & B Addition REACTIVITY Keto-enol tautomerism: the keto form dominates, but the enol is the nucleophile in a-substitution (halogenation, the aldol). a, ß-unsaturated carbonyl is electrophilic at the carbonyl C (1,2-addition) and at the B-C: 1,4 / Michael / conjugate addition . Soft nucleophiles & stabilised enolates favour 1,4. C=O MAKE . Functional groups . Substitution/elimination . Carbonyl . Named C-C coupling . Redox . Polymers . Sustainable REVISION SHEET . ALL TOPICS STRUCTURE-PROPERTY H2 / Pd catalytic CLASSIFY FIRST Sonogashira polar protic CARBONYL Revision aid . check the official unit outline for assessment . 0 2026 good luck. revise smart.
-
2) 烯醇/共轭加成（1,2 vs 1,4）
- $\alpha,\beta$-不饱和羰基在两个位置可被进攻：羰基碳（1,2）与 $\beta$-碳（1,4/Michael）[7]Source: asksia-cheatsheet-chem2522.pdfR-X + terminal alkyne Cycle: oxidative addition > transmetalation > reductive elimination . Catalytic in Pd, mild, tolerant of functional groups = green & widely used in pharma. 15b . Imines, Acetals & Protecting Groups + N/O Carbonyl + 1° amine > imine (C=N); + 2° amine > enamine. Acid-catalysed, water removed to drive the equilibrium. Carbonyl + 2 ROH > acetal = a protecting group for C=O (stable to base & nucleophiles, removed by aqueous acid). But every protecting group adds steps = poor atom economy (principle 8 - reduce derivatives). 15c . Enols & Conjugate A & B Addition REACTIVITY Keto-enol tautomerism: the keto form dominates, but the enol is the nucleophile in a-substitution (halogenation, the aldol). a, ß-unsaturated carbonyl is electrophilic at the carbonyl C (1,2-addition) and at the B-C: 1,4 / Michael / conjugate addition . Soft nucleophiles & stabilised enolates favour 1,4. C=O MAKE . Functional groups . Substitution/elimination . Carbonyl . Named C-C coupling . Redox . Polymers . Sustainable REVISION SHEET . ALL TOPICS STRUCTURE-PROPERTY H2 / Pd catalytic CLASSIFY FIRST Sonogashira polar protic CARBONYL Revision aid . check the official unit outline for assessment . 0 2026 good luck. revise smart. CHEM2522 Sustainable Chemical Manufacture UNIVERSITY OF SYDNEY . SCHOOL OF CHEMISTRY EXAM REVISION Sem 1 2026 · SIDE 1 OF 2 Whole-unit revision . all topics[14]Source: asksia-cheatsheet-chem2522.pdfCarbonyl + 1° amine > imine (C=N); + 2° amine > enamine. Acid-catalysed, water removed to drive the equilibrium. Carbonyl + 2 ROH > acetal = a protecting group for C=O (stable to base & nucleophiles, removed by aqueous acid). But every protecting group adds steps = poor atom economy (principle 8 - reduce derivatives). 15c . Enols & Conjugate A & B Addition REACTIVITY Keto-enol tautomerism: the keto form dominates, but the enol is the nucleophile in a-substitution (halogenation, the aldol). a, ß-unsaturated carbonyl is electrophilic at the carbonyl C (1,2-addition) and at the B-C: 1,4 / Michael / conjugate addition . Soft nucleophiles & stabilised enolates favour 1,4. C=O MAKE . Functional groups . Substitution/elimination . Carbonyl . Named C-C coupling . Redox . Polymers . Sustainable REVISION SHEET . ALL TOPICS STRUCTURE-PROPERTY H2 / Pd catalytic CLASSIFY FIRST Sonogashira polar protic CARBONYL Revision aid . check the official unit outline for assessment . 0 2026 good luck. revise smart.
- 软亲核体、稳定烯醇盐倾向 1,4 加成（材料明确说）[7]Source: asksia-cheatsheet-chem2522.pdfR-X + terminal alkyne Cycle: oxidative addition > transmetalation > reductive elimination . Catalytic in Pd, mild, tolerant of functional groups = green & widely used in pharma. 15b . Imines, Acetals & Protecting Groups + N/O Carbonyl + 1° amine > imine (C=N); + 2° amine > enamine. Acid-catalysed, water removed to drive the equilibrium. Carbonyl + 2 ROH > acetal = a protecting group for C=O (stable to base & nucleophiles, removed by aqueous acid). But every protecting group adds steps = poor atom economy (principle 8 - reduce derivatives). 15c . Enols & Conjugate A & B Addition REACTIVITY Keto-enol tautomerism: the keto form dominates, but the enol is the nucleophile in a-substitution (halogenation, the aldol). a, ß-unsaturated carbonyl is electrophilic at the carbonyl C (1,2-addition) and at the B-C: 1,4 / Michael / conjugate addition . Soft nucleophiles & stabilised enolates favour 1,4. C=O MAKE . Functional groups . Substitution/elimination . Carbonyl . Named C-C coupling . Redox . Polymers . Sustainable REVISION SHEET . ALL TOPICS STRUCTURE-PROPERTY H2 / Pd catalytic CLASSIFY FIRST Sonogashira polar protic CARBONYL Revision aid . check the official unit outline for assessment . 0 2026 good luck. revise smart. CHEM2522 Sustainable Chemical Manufacture UNIVERSITY OF SYDNEY . SCHOOL OF CHEMISTRY EXAM REVISION Sem 1 2026 · SIDE 1 OF 2 Whole-unit revision . all topics[14]Source: asksia-cheatsheet-chem2522.pdfCarbonyl + 1° amine > imine (C=N); + 2° amine > enamine. Acid-catalysed, water removed to drive the equilibrium. Carbonyl + 2 ROH > acetal = a protecting group for C=O (stable to base & nucleophiles, removed by aqueous acid). But every protecting group adds steps = poor atom economy (principle 8 - reduce derivatives). 15c . Enols & Conjugate A & B Addition REACTIVITY Keto-enol tautomerism: the keto form dominates, but the enol is the nucleophile in a-substitution (halogenation, the aldol). a, ß-unsaturated carbonyl is electrophilic at the carbonyl C (1,2-addition) and at the B-C: 1,4 / Michael / conjugate addition . Soft nucleophiles & stabilised enolates favour 1,4. C=O MAKE . Functional groups . Substitution/elimination . Carbonyl . Named C-C coupling . Redox . Polymers . Sustainable REVISION SHEET . ALL TOPICS STRUCTURE-PROPERTY H2 / Pd catalytic CLASSIFY FIRST Sonogashira polar protic CARBONYL Revision aid . check the official unit outline for assessment . 0 2026 good luck. revise smart.
-
3) Sonogashira（命名偶联）考法
-
4) 氧化还原“工具箱”（你材料目前只截到一部分）
- 氧化：$1^\circ$ 醇 → 醛（PCC/Swern/TEMPO）→ 酸（KMnO$_4$/CrO$_3$/Jones）；$2^\circ$ 醇 → 酮[5]Source: asksia-cheatsheet-chem2522.pdfWHY PURITY MATTERS Degree of polymerisation vs conversion p: P XN = 1/(1-P) 0. 90 0. 95 0. 99 0. 995 = step-growth needs near-complete conversion for useful chain length. A single impurity or stoichiometric imbalance caps M - hence the purity demand. Compiled by AskSia . mapped to the CHEM2522 syllabus . asksia. ai/cheatsheet/usyd- chem2522 16 . Oxidation & Reduction THE TOOLKIT OXIDATION (ADD O / REMOVE H) 1º alcohol > aldehyde (PCC, Swern, TEMPO) > acid (KMnO4, CrO3/Jones). 2° alcohol - ketone. Green oxidants: O2, H2O2 (by-product = H2O), catalytic TEMPO. REDUCTION (ADD H / REMOVE O) REAGENT STRENGTH REDUCES NaBH4 mild[9]Source: asksia-cheatsheet-chem2522.pdfXN = 1/(1-P) 0. 90 0. 95 0. 99 0. 995 = step-growth needs near-complete conversion for useful chain length. A single impurity or stoichiometric imbalance caps M - hence the purity demand. Compiled by AskSia . mapped to the CHEM2522 syllabus . asksia. ai/cheatsheet/usyd- chem2522 16 . Oxidation & Reduction THE TOOLKIT OXIDATION (ADD O / REMOVE H) 1º alcohol > aldehyde (PCC, Swern, TEMPO) > acid (KMnO4, CrO3/Jones). 2° alcohol - ketone. Green oxidants: O2, H2O2 (by-product = H2O), catalytic TEMPO. REDUCTION (ADD H / REMOVE O) REAGENT STRENGTH REDUCES NaBH4 mild aldehyde, ketone LiAIHA strong
- 绿色氧化剂：O$_2$、H$_2$O$_2$（副产物 H$_2$O）、催化 TEMPO[5]Source: asksia-cheatsheet-chem2522.pdfWHY PURITY MATTERS Degree of polymerisation vs conversion p: P XN = 1/(1-P) 0. 90 0. 95 0. 99 0. 995 = step-growth needs near-complete conversion for useful chain length. A single impurity or stoichiometric imbalance caps M - hence the purity demand. Compiled by AskSia . mapped to the CHEM2522 syllabus . asksia. ai/cheatsheet/usyd- chem2522 16 . Oxidation & Reduction THE TOOLKIT OXIDATION (ADD O / REMOVE H) 1º alcohol > aldehyde (PCC, Swern, TEMPO) > acid (KMnO4, CrO3/Jones). 2° alcohol - ketone. Green oxidants: O2, H2O2 (by-product = H2O), catalytic TEMPO. REDUCTION (ADD H / REMOVE O) REAGENT STRENGTH REDUCES NaBH4 mild[9]Source: asksia-cheatsheet-chem2522.pdfXN = 1/(1-P) 0. 90 0. 95 0. 99 0. 995 = step-growth needs near-complete conversion for useful chain length. A single impurity or stoichiometric imbalance caps M - hence the purity demand. Compiled by AskSia . mapped to the CHEM2522 syllabus . asksia. ai/cheatsheet/usyd- chem2522 16 . Oxidation & Reduction THE TOOLKIT OXIDATION (ADD O / REMOVE H) 1º alcohol > aldehyde (PCC, Swern, TEMPO) > acid (KMnO4, CrO3/Jones). 2° alcohol - ketone. Green oxidants: O2, H2O2 (by-product = H2O), catalytic TEMPO. REDUCTION (ADD H / REMOVE O) REAGENT STRENGTH REDUCES NaBH4 mild aldehyde, ketone LiAIHA strong
- 还原剂表格在你摘录里被截断了（只看到 NaBH$_4$、LiAlH$_4$ 开头），如果你把那一页完整内容补充，我可以把“强弱与能还原什么”整理成必背表[9]Source: asksia-cheatsheet-chem2522.pdfXN = 1/(1-P) 0. 90 0. 95 0. 99 0. 995 = step-growth needs near-complete conversion for useful chain length. A single impurity or stoichiometric imbalance caps M - hence the purity demand. Compiled by AskSia . mapped to the CHEM2522 syllabus . asksia. ai/cheatsheet/usyd- chem2522 16 . Oxidation & Reduction THE TOOLKIT OXIDATION (ADD O / REMOVE H) 1º alcohol > aldehyde (PCC, Swern, TEMPO) > acid (KMnO4, CrO3/Jones). 2° alcohol - ketone. Green oxidants: O2, H2O2 (by-product = H2O), catalytic TEMPO. REDUCTION (ADD H / REMOVE O) REAGENT STRENGTH REDUCES NaBH4 mild aldehyde, ketone LiAIHA strong
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八、聚合物（Polymers）：最常考的公式、概念与“为什么纯度极重要”
-
1) Step-growth 的 Carothers 方程（必考公式）
- 数均聚合度（Degree of polymerisation, $X_n$）与转化率 $p$：[5]Source: asksia-cheatsheet-chem2522.pdfWHY PURITY MATTERS
Degree of polymerisation vs conversion p:
P
XN = 1/(1-P)
0. 90
0. 95
0. 99
0. 995
= step-growth needs near-complete conversion for useful chain length. A single impurity or stoichiometric imbalance caps M - hence the purity demand.
Compiled by AskSia . mapped to the CHEM2522 syllabus . asksia. ai/cheatsheet/usyd- chem2522
16 . Oxidation & Reduction
THE TOOLKIT
OXIDATION (ADD O / REMOVE H)
1º alcohol > aldehyde (PCC, Swern, TEMPO) > acid (KMnO4, CrO3/Jones). 2° alcohol - ketone. Green oxidants: O2, H2O2 (by-product = H2O), catalytic TEMPO.
REDUCTION (ADD H / REMOVE O)
REAGENT
STRENGTH
REDUCES
NaBH4
mild[9]Source: asksia-cheatsheet-chem2522.pdfXN = 1/(1-P)
0. 90
0. 95
0. 99
0. 995
= step-growth needs near-complete conversion for useful chain length. A single impurity or stoichiometric imbalance caps M - hence the purity demand.
Compiled by AskSia . mapped to the CHEM2522 syllabus . asksia. ai/cheatsheet/usyd- chem2522
16 . Oxidation & Reduction
THE TOOLKIT
OXIDATION (ADD O / REMOVE H)
1º alcohol > aldehyde (PCC, Swern, TEMPO) > acid (KMnO4, CrO3/Jones). 2° alcohol - ketone. Green oxidants: O2, H2O2 (by-product = H2O), catalytic TEMPO.
REDUCTION (ADD H / REMOVE O)
REAGENT
STRENGTH
REDUCES
NaBH4
mild
aldehyde, ketone
LiAIHA
strong[18]Source: asksia-cheatsheet-chem2522.pdfNo single number means "green" - name which trade-off the question tests.
Formula Belt SIDE 2
Xn = 1/(1-p) . Đ = Mw/Mn ≥1 splitting n+1 . reactivity: RCOCl>ester>amide Sn2 inversion . E2 anti-periplanar green: catalysis . renewable . degrade
asksia. ai/cheatsheet/ usyd-chem2522 . side 2/2
AskSia CHEATSHEET SERIES
20 . Polymer Properties MOLAR MASS
AVERAGES & DISPERSITY ΜΠ = Ση;Μ;/ Ση; (number avg) Mw = Ση;Μ12/Ση;Μ; (weight avg) Đ = M/Mn ≥ 1 (dispersity) Đ = 1 = perfectly uniform; step-growth ~2; controlled radical > low Đ.
THERMAL & ORDER
· Tg glass transition (amorphous softens); Tm melts (crystalline)
· Tacticity - iso / syndio / atactic; regular = crystalline, higher Tm
21 · Sustainable Polymers
· Polyamide (nylon) - diacid + diamine > amide links + H2O.
· Polycarbonate - bisphenol + carbonate source.
Need exact stoichiometry & high purity (Carothers) for high MW. The ester/amide links are also the handle for chemical recycling (hydrolysis/solvolysis back to monomer).
19b . Nature's Step- Growth BIOPOLYMERS
The largest condensation polymers are biological: proteins (amino acids - peptide/amide bonds + H2O), polysaccharides (sugars >> glycosidic bonds + H2O), nucleic acids (phosphodiester). All are hydrolysable = inherently degradable - the design template for sustainable polymers.
19c . Worked . Carothers
WHY PURITY MATTERS
Degree of polymerisation vs conversion p:
P
- $$X_n=\frac{1}{1-p}$$
- 考点意义：step-growth 要得到“有用的链长”，必须 $p$ 非常接近 1（接近完全转化）[5]Source: asksia-cheatsheet-chem2522.pdfWHY PURITY MATTERS Degree of polymerisation vs conversion p: P XN = 1/(1-P) 0. 90 0. 95 0. 99 0. 995 = step-growth needs near-complete conversion for useful chain length. A single impurity or stoichiometric imbalance caps M - hence the purity demand. Compiled by AskSia . mapped to the CHEM2522 syllabus . asksia. ai/cheatsheet/usyd- chem2522 16 . Oxidation & Reduction THE TOOLKIT OXIDATION (ADD O / REMOVE H) 1º alcohol > aldehyde (PCC, Swern, TEMPO) > acid (KMnO4, CrO3/Jones). 2° alcohol - ketone. Green oxidants: O2, H2O2 (by-product = H2O), catalytic TEMPO. REDUCTION (ADD H / REMOVE O) REAGENT STRENGTH REDUCES NaBH4 mild[9]Source: asksia-cheatsheet-chem2522.pdfXN = 1/(1-P) 0. 90 0. 95 0. 99 0. 995 = step-growth needs near-complete conversion for useful chain length. A single impurity or stoichiometric imbalance caps M - hence the purity demand. Compiled by AskSia . mapped to the CHEM2522 syllabus . asksia. ai/cheatsheet/usyd- chem2522 16 . Oxidation & Reduction THE TOOLKIT OXIDATION (ADD O / REMOVE H) 1º alcohol > aldehyde (PCC, Swern, TEMPO) > acid (KMnO4, CrO3/Jones). 2° alcohol - ketone. Green oxidants: O2, H2O2 (by-product = H2O), catalytic TEMPO. REDUCTION (ADD H / REMOVE O) REAGENT STRENGTH REDUCES NaBH4 mild aldehyde, ketone LiAIHA strong
- 为什么 purity matters（常见问答题）：一点点杂质或当量比偏差就会“封顶”分子量 $M$，因此对高纯度、严格计量特别敏感[5]Source: asksia-cheatsheet-chem2522.pdfWHY PURITY MATTERS Degree of polymerisation vs conversion p: P XN = 1/(1-P) 0. 90 0. 95 0. 99 0. 995 = step-growth needs near-complete conversion for useful chain length. A single impurity or stoichiometric imbalance caps M - hence the purity demand. Compiled by AskSia . mapped to the CHEM2522 syllabus . asksia. ai/cheatsheet/usyd- chem2522 16 . Oxidation & Reduction THE TOOLKIT OXIDATION (ADD O / REMOVE H) 1º alcohol > aldehyde (PCC, Swern, TEMPO) > acid (KMnO4, CrO3/Jones). 2° alcohol - ketone. Green oxidants: O2, H2O2 (by-product = H2O), catalytic TEMPO. REDUCTION (ADD H / REMOVE O) REAGENT STRENGTH REDUCES NaBH4 mild[9]Source: asksia-cheatsheet-chem2522.pdfXN = 1/(1-P) 0. 90 0. 95 0. 99 0. 995 = step-growth needs near-complete conversion for useful chain length. A single impurity or stoichiometric imbalance caps M - hence the purity demand. Compiled by AskSia . mapped to the CHEM2522 syllabus . asksia. ai/cheatsheet/usyd- chem2522 16 . Oxidation & Reduction THE TOOLKIT OXIDATION (ADD O / REMOVE H) 1º alcohol > aldehyde (PCC, Swern, TEMPO) > acid (KMnO4, CrO3/Jones). 2° alcohol - ketone. Green oxidants: O2, H2O2 (by-product = H2O), catalytic TEMPO. REDUCTION (ADD H / REMOVE O) REAGENT STRENGTH REDUCES NaBH4 mild aldehyde, ketone LiAIHA strong[18]Source: asksia-cheatsheet-chem2522.pdfNo single number means "green" - name which trade-off the question tests. Formula Belt SIDE 2 Xn = 1/(1-p) . Đ = Mw/Mn ≥1 splitting n+1 . reactivity: RCOCl>ester>amide Sn2 inversion . E2 anti-periplanar green: catalysis . renewable . degrade asksia. ai/cheatsheet/ usyd-chem2522 . side 2/2 AskSia CHEATSHEET SERIES 20 . Polymer Properties MOLAR MASS AVERAGES & DISPERSITY ΜΠ = Ση;Μ;/ Ση; (number avg) Mw = Ση;Μ12/Ση;Μ; (weight avg) Đ = M/Mn ≥ 1 (dispersity) Đ = 1 = perfectly uniform; step-growth ~2; controlled radical > low Đ. THERMAL & ORDER · Tg glass transition (amorphous softens); Tm melts (crystalline) · Tacticity - iso / syndio / atactic; regular = crystalline, higher Tm 21 · Sustainable Polymers · Polyamide (nylon) - diacid + diamine > amide links + H2O. · Polycarbonate - bisphenol + carbonate source. Need exact stoichiometry & high purity (Carothers) for high MW. The ester/amide links are also the handle for chemical recycling (hydrolysis/solvolysis back to monomer). 19b . Nature's Step- Growth BIOPOLYMERS The largest condensation polymers are biological: proteins (amino acids - peptide/amide bonds + H2O), polysaccharides (sugars >> glycosidic bonds + H2O), nucleic acids (phosphodiester). All are hydrolysable = inherently degradable - the design template for sustainable polymers. 19c . Worked . Carothers WHY PURITY MATTERS Degree of polymerisation vs conversion p: P
- 数均聚合度（Degree of polymerisation, $X_n$）与转化率 $p$：[5]Source: asksia-cheatsheet-chem2522.pdfWHY PURITY MATTERS
Degree of polymerisation vs conversion p:
P
XN = 1/(1-P)
0. 90
0. 95
0. 99
0. 995
= step-growth needs near-complete conversion for useful chain length. A single impurity or stoichiometric imbalance caps M - hence the purity demand.
Compiled by AskSia . mapped to the CHEM2522 syllabus . asksia. ai/cheatsheet/usyd- chem2522
16 . Oxidation & Reduction
THE TOOLKIT
OXIDATION (ADD O / REMOVE H)
1º alcohol > aldehyde (PCC, Swern, TEMPO) > acid (KMnO4, CrO3/Jones). 2° alcohol - ketone. Green oxidants: O2, H2O2 (by-product = H2O), catalytic TEMPO.
REDUCTION (ADD H / REMOVE O)
REAGENT
STRENGTH
REDUCES
NaBH4
mild[9]Source: asksia-cheatsheet-chem2522.pdfXN = 1/(1-P)
0. 90
0. 95
0. 99
0. 995
= step-growth needs near-complete conversion for useful chain length. A single impurity or stoichiometric imbalance caps M - hence the purity demand.
Compiled by AskSia . mapped to the CHEM2522 syllabus . asksia. ai/cheatsheet/usyd- chem2522
16 . Oxidation & Reduction
THE TOOLKIT
OXIDATION (ADD O / REMOVE H)
1º alcohol > aldehyde (PCC, Swern, TEMPO) > acid (KMnO4, CrO3/Jones). 2° alcohol - ketone. Green oxidants: O2, H2O2 (by-product = H2O), catalytic TEMPO.
REDUCTION (ADD H / REMOVE O)
REAGENT
STRENGTH
REDUCES
NaBH4
mild
aldehyde, ketone
LiAIHA
strong[18]Source: asksia-cheatsheet-chem2522.pdfNo single number means "green" - name which trade-off the question tests.
Formula Belt SIDE 2
Xn = 1/(1-p) . Đ = Mw/Mn ≥1 splitting n+1 . reactivity: RCOCl>ester>amide Sn2 inversion . E2 anti-periplanar green: catalysis . renewable . degrade
asksia. ai/cheatsheet/ usyd-chem2522 . side 2/2
AskSia CHEATSHEET SERIES
20 . Polymer Properties MOLAR MASS
AVERAGES & DISPERSITY ΜΠ = Ση;Μ;/ Ση; (number avg) Mw = Ση;Μ12/Ση;Μ; (weight avg) Đ = M/Mn ≥ 1 (dispersity) Đ = 1 = perfectly uniform; step-growth ~2; controlled radical > low Đ.
THERMAL & ORDER
· Tg glass transition (amorphous softens); Tm melts (crystalline)
· Tacticity - iso / syndio / atactic; regular = crystalline, higher Tm
21 · Sustainable Polymers
· Polyamide (nylon) - diacid + diamine > amide links + H2O.
· Polycarbonate - bisphenol + carbonate source.
Need exact stoichiometry & high purity (Carothers) for high MW. The ester/amide links are also the handle for chemical recycling (hydrolysis/solvolysis back to monomer).
19b . Nature's Step- Growth BIOPOLYMERS
The largest condensation polymers are biological: proteins (amino acids - peptide/amide bonds + H2O), polysaccharides (sugars >> glycosidic bonds + H2O), nucleic acids (phosphodiester). All are hydrolysable = inherently degradable - the design template for sustainable polymers.
19c . Worked . Carothers
WHY PURITY MATTERS
Degree of polymerisation vs conversion p:
P
-
2) 分子量平均与分散度（Đ）
- 定义（材料给了公式形式）[18]Source: asksia-cheatsheet-chem2522.pdfNo single number means "green" - name which trade-off the question tests.
Formula Belt SIDE 2
Xn = 1/(1-p) . Đ = Mw/Mn ≥1 splitting n+1 . reactivity: RCOCl>ester>amide Sn2 inversion . E2 anti-periplanar green: catalysis . renewable . degrade
asksia. ai/cheatsheet/ usyd-chem2522 . side 2/2
AskSia CHEATSHEET SERIES
20 . Polymer Properties MOLAR MASS
AVERAGES & DISPERSITY ΜΠ = Ση;Μ;/ Ση; (number avg) Mw = Ση;Μ12/Ση;Μ; (weight avg) Đ = M/Mn ≥ 1 (dispersity) Đ = 1 = perfectly uniform; step-growth ~2; controlled radical > low Đ.
THERMAL & ORDER
· Tg glass transition (amorphous softens); Tm melts (crystalline)
· Tacticity - iso / syndio / atactic; regular = crystalline, higher Tm
21 · Sustainable Polymers
· Polyamide (nylon) - diacid + diamine > amide links + H2O.
· Polycarbonate - bisphenol + carbonate source.
Need exact stoichiometry & high purity (Carothers) for high MW. The ester/amide links are also the handle for chemical recycling (hydrolysis/solvolysis back to monomer).
19b . Nature's Step- Growth BIOPOLYMERS
The largest condensation polymers are biological: proteins (amino acids - peptide/amide bonds + H2O), polysaccharides (sugars >> glycosidic bonds + H2O), nucleic acids (phosphodiester). All are hydrolysable = inherently degradable - the design template for sustainable polymers.
19c . Worked . Carothers
WHY PURITY MATTERS
Degree of polymerisation vs conversion p:
P
- $$M_n=\frac{\sum n_i M_i}{\sum n_i}\quad(\text{number average})$$
- $$M_w=\frac{\sum n_i M_i^2}{\sum n_i M_i}\quad(\text{weight average})$$
- $$\mathrm{Đ}=\frac{M_w}{M_n}\ge 1$$
- 记忆点（材料给的经验值）[18]Source: asksia-cheatsheet-chem2522.pdfNo single number means "green" - name which trade-off the question tests.
Formula Belt SIDE 2
Xn = 1/(1-p) . Đ = Mw/Mn ≥1 splitting n+1 . reactivity: RCOCl>ester>amide Sn2 inversion . E2 anti-periplanar green: catalysis . renewable . degrade
asksia. ai/cheatsheet/ usyd-chem2522 . side 2/2
AskSia CHEATSHEET SERIES
20 . Polymer Properties MOLAR MASS
AVERAGES & DISPERSITY ΜΠ = Ση;Μ;/ Ση; (number avg) Mw = Ση;Μ12/Ση;Μ; (weight avg) Đ = M/Mn ≥ 1 (dispersity) Đ = 1 = perfectly uniform; step-growth ~2; controlled radical > low Đ.
THERMAL & ORDER
· Tg glass transition (amorphous softens); Tm melts (crystalline)
· Tacticity - iso / syndio / atactic; regular = crystalline, higher Tm
21 · Sustainable Polymers
· Polyamide (nylon) - diacid + diamine > amide links + H2O.
· Polycarbonate - bisphenol + carbonate source.
Need exact stoichiometry & high purity (Carothers) for high MW. The ester/amide links are also the handle for chemical recycling (hydrolysis/solvolysis back to monomer).
19b . Nature's Step- Growth BIOPOLYMERS
The largest condensation polymers are biological: proteins (amino acids - peptide/amide bonds + H2O), polysaccharides (sugars >> glycosidic bonds + H2O), nucleic acids (phosphodiester). All are hydrolysable = inherently degradable - the design template for sustainable polymers.
19c . Worked . Carothers
WHY PURITY MATTERS
Degree of polymerisation vs conversion p:
P
- Đ = 1：完全均一
- step-growth 常见 Đ $\sim 2$
- controlled radical 倾向较低 Đ
- 定义（材料给了公式形式）[18]Source: asksia-cheatsheet-chem2522.pdfNo single number means "green" - name which trade-off the question tests.
Formula Belt SIDE 2
Xn = 1/(1-p) . Đ = Mw/Mn ≥1 splitting n+1 . reactivity: RCOCl>ester>amide Sn2 inversion . E2 anti-periplanar green: catalysis . renewable . degrade
asksia. ai/cheatsheet/ usyd-chem2522 . side 2/2
AskSia CHEATSHEET SERIES
20 . Polymer Properties MOLAR MASS
AVERAGES & DISPERSITY ΜΠ = Ση;Μ;/ Ση; (number avg) Mw = Ση;Μ12/Ση;Μ; (weight avg) Đ = M/Mn ≥ 1 (dispersity) Đ = 1 = perfectly uniform; step-growth ~2; controlled radical > low Đ.
THERMAL & ORDER
· Tg glass transition (amorphous softens); Tm melts (crystalline)
· Tacticity - iso / syndio / atactic; regular = crystalline, higher Tm
21 · Sustainable Polymers
· Polyamide (nylon) - diacid + diamine > amide links + H2O.
· Polycarbonate - bisphenol + carbonate source.
Need exact stoichiometry & high purity (Carothers) for high MW. The ester/amide links are also the handle for chemical recycling (hydrolysis/solvolysis back to monomer).
19b . Nature's Step- Growth BIOPOLYMERS
The largest condensation polymers are biological: proteins (amino acids - peptide/amide bonds + H2O), polysaccharides (sugars >> glycosidic bonds + H2O), nucleic acids (phosphodiester). All are hydrolysable = inherently degradable - the design template for sustainable polymers.
19c . Worked . Carothers
WHY PURITY MATTERS
Degree of polymerisation vs conversion p:
P
-
3) Tg / Tm / tacticity（结构—性质）
- Tg：玻璃化转变（无定形变软）；Tm：熔点（晶区熔融）[18]Source: asksia-cheatsheet-chem2522.pdfNo single number means "green" - name which trade-off the question tests. Formula Belt SIDE 2 Xn = 1/(1-p) . Đ = Mw/Mn ≥1 splitting n+1 . reactivity: RCOCl>ester>amide Sn2 inversion . E2 anti-periplanar green: catalysis . renewable . degrade asksia. ai/cheatsheet/ usyd-chem2522 . side 2/2 AskSia CHEATSHEET SERIES 20 . Polymer Properties MOLAR MASS AVERAGES & DISPERSITY ΜΠ = Ση;Μ;/ Ση; (number avg) Mw = Ση;Μ12/Ση;Μ; (weight avg) Đ = M/Mn ≥ 1 (dispersity) Đ = 1 = perfectly uniform; step-growth ~2; controlled radical > low Đ. THERMAL & ORDER · Tg glass transition (amorphous softens); Tm melts (crystalline) · Tacticity - iso / syndio / atactic; regular = crystalline, higher Tm 21 · Sustainable Polymers · Polyamide (nylon) - diacid + diamine > amide links + H2O. · Polycarbonate - bisphenol + carbonate source. Need exact stoichiometry & high purity (Carothers) for high MW. The ester/amide links are also the handle for chemical recycling (hydrolysis/solvolysis back to monomer). 19b . Nature's Step- Growth BIOPOLYMERS The largest condensation polymers are biological: proteins (amino acids - peptide/amide bonds + H2O), polysaccharides (sugars >> glycosidic bonds + H2O), nucleic acids (phosphodiester). All are hydrolysable = inherently degradable - the design template for sustainable polymers. 19c . Worked . Carothers WHY PURITY MATTERS Degree of polymerisation vs conversion p: P
- tacticity：iso / syndio / atactic；越规整越易结晶 → Tm 更高[18]Source: asksia-cheatsheet-chem2522.pdfNo single number means "green" - name which trade-off the question tests. Formula Belt SIDE 2 Xn = 1/(1-p) . Đ = Mw/Mn ≥1 splitting n+1 . reactivity: RCOCl>ester>amide Sn2 inversion . E2 anti-periplanar green: catalysis . renewable . degrade asksia. ai/cheatsheet/ usyd-chem2522 . side 2/2 AskSia CHEATSHEET SERIES 20 . Polymer Properties MOLAR MASS AVERAGES & DISPERSITY ΜΠ = Ση;Μ;/ Ση; (number avg) Mw = Ση;Μ12/Ση;Μ; (weight avg) Đ = M/Mn ≥ 1 (dispersity) Đ = 1 = perfectly uniform; step-growth ~2; controlled radical > low Đ. THERMAL & ORDER · Tg glass transition (amorphous softens); Tm melts (crystalline) · Tacticity - iso / syndio / atactic; regular = crystalline, higher Tm 21 · Sustainable Polymers · Polyamide (nylon) - diacid + diamine > amide links + H2O. · Polycarbonate - bisphenol + carbonate source. Need exact stoichiometry & high purity (Carothers) for high MW. The ester/amide links are also the handle for chemical recycling (hydrolysis/solvolysis back to monomer). 19b . Nature's Step- Growth BIOPOLYMERS The largest condensation polymers are biological: proteins (amino acids - peptide/amide bonds + H2O), polysaccharides (sugars >> glycosidic bonds + H2O), nucleic acids (phosphodiester). All are hydrolysable = inherently degradable - the design template for sustainable polymers. 19c . Worked . Carothers WHY PURITY MATTERS Degree of polymerisation vs conversion p: P
-
4) 结构—性质简表（材料的规则）
- 支化：更难紧密堆积（材料给出 HDPE > LDPE 的对比方向）[8]Source: asksia-cheatsheet-chem2522.pdf21b · Structure -> Property RULES Branching \ = packs tighter = denser & . stronger (HDPE > LDPE) · Chain length / M 1 = higher Tm, strength, viscosity Polar groups / H-bonds (nylon) = stronger, higher Tm · Plasticiser = lowers Ta (rigid PVC > flexible) 21c . Measuring Molar METHODS Mass GPC / SEC - size-exclusion; gives the full distribution > Mn, Mw, Đ · End-group analysis (NMR/titration) > Mn (low MW only) 22 . Greener Process PRINCIPLES 5,6,9 Toolkit · Green solvents - water, scCO2, ionic liquids, bio-solvents (2-MeTHF, ethanol); avoid chlorinated & VOCs · Biocatalysis - enzymes; mild, aqueous, enantioselective 23 . Worked . Atom Economy SHOW THE NUMBER Q. Wittig vs substitution to make an alkene - which is greener by AE? Wittig expels Ph3P=O (M, 278) - a large by- product = low atom economy despite high yield. An elimination or a catalytic metathesis keeps more atoms in product. LESSON high yield # green. Quote AE/E-factor, then name the by-product driving waste. 24 . Exam Discipline DON'T LOSE MARKS Assign every spectral peak - reconcile to one structure "Is it green?" = give a number + name the waste
- 链长/分子量：越大 → Tm、强度、黏度倾向更高[8]Source: asksia-cheatsheet-chem2522.pdf21b · Structure -> Property RULES Branching \ = packs tighter = denser & . stronger (HDPE > LDPE) · Chain length / M 1 = higher Tm, strength, viscosity Polar groups / H-bonds (nylon) = stronger, higher Tm · Plasticiser = lowers Ta (rigid PVC > flexible) 21c . Measuring Molar METHODS Mass GPC / SEC - size-exclusion; gives the full distribution > Mn, Mw, Đ · End-group analysis (NMR/titration) > Mn (low MW only) 22 . Greener Process PRINCIPLES 5,6,9 Toolkit · Green solvents - water, scCO2, ionic liquids, bio-solvents (2-MeTHF, ethanol); avoid chlorinated & VOCs · Biocatalysis - enzymes; mild, aqueous, enantioselective 23 . Worked . Atom Economy SHOW THE NUMBER Q. Wittig vs substitution to make an alkene - which is greener by AE? Wittig expels Ph3P=O (M, 278) - a large by- product = low atom economy despite high yield. An elimination or a catalytic metathesis keeps more atoms in product. LESSON high yield # green. Quote AE/E-factor, then name the by-product driving waste. 24 . Exam Discipline DON'T LOSE MARKS Assign every spectral peak - reconcile to one structure "Is it green?" = give a number + name the waste
- 极性基团/氢键（如 nylon）：更强、Tm 更高[8]Source: asksia-cheatsheet-chem2522.pdf21b · Structure -> Property RULES Branching \ = packs tighter = denser & . stronger (HDPE > LDPE) · Chain length / M 1 = higher Tm, strength, viscosity Polar groups / H-bonds (nylon) = stronger, higher Tm · Plasticiser = lowers Ta (rigid PVC > flexible) 21c . Measuring Molar METHODS Mass GPC / SEC - size-exclusion; gives the full distribution > Mn, Mw, Đ · End-group analysis (NMR/titration) > Mn (low MW only) 22 . Greener Process PRINCIPLES 5,6,9 Toolkit · Green solvents - water, scCO2, ionic liquids, bio-solvents (2-MeTHF, ethanol); avoid chlorinated & VOCs · Biocatalysis - enzymes; mild, aqueous, enantioselective 23 . Worked . Atom Economy SHOW THE NUMBER Q. Wittig vs substitution to make an alkene - which is greener by AE? Wittig expels Ph3P=O (M, 278) - a large by- product = low atom economy despite high yield. An elimination or a catalytic metathesis keeps more atoms in product. LESSON high yield # green. Quote AE/E-factor, then name the by-product driving waste. 24 . Exam Discipline DON'T LOSE MARKS Assign every spectral peak - reconcile to one structure "Is it green?" = give a number + name the waste
- 增塑剂：降低 Tg（PVC 例子）[8]Source: asksia-cheatsheet-chem2522.pdf21b · Structure -> Property RULES Branching \ = packs tighter = denser & . stronger (HDPE > LDPE) · Chain length / M 1 = higher Tm, strength, viscosity Polar groups / H-bonds (nylon) = stronger, higher Tm · Plasticiser = lowers Ta (rigid PVC > flexible) 21c . Measuring Molar METHODS Mass GPC / SEC - size-exclusion; gives the full distribution > Mn, Mw, Đ · End-group analysis (NMR/titration) > Mn (low MW only) 22 . Greener Process PRINCIPLES 5,6,9 Toolkit · Green solvents - water, scCO2, ionic liquids, bio-solvents (2-MeTHF, ethanol); avoid chlorinated & VOCs · Biocatalysis - enzymes; mild, aqueous, enantioselective 23 . Worked . Atom Economy SHOW THE NUMBER Q. Wittig vs substitution to make an alkene - which is greener by AE? Wittig expels Ph3P=O (M, 278) - a large by- product = low atom economy despite high yield. An elimination or a catalytic metathesis keeps more atoms in product. LESSON high yield # green. Quote AE/E-factor, then name the by-product driving waste. 24 . Exam Discipline DON'T LOSE MARKS Assign every spectral peak - reconcile to one structure "Is it green?" = give a number + name the waste
-
5) 测分子量的方法（考“用哪个测什么”）
- GPC/SEC（体积排阻）：给完整分布 → $M_n, M_w, \mathrm{Đ}$[8]Source: asksia-cheatsheet-chem2522.pdf21b · Structure -> Property RULES Branching \ = packs tighter = denser & . stronger (HDPE > LDPE) · Chain length / M 1 = higher Tm, strength, viscosity Polar groups / H-bonds (nylon) = stronger, higher Tm · Plasticiser = lowers Ta (rigid PVC > flexible) 21c . Measuring Molar METHODS Mass GPC / SEC - size-exclusion; gives the full distribution > Mn, Mw, Đ · End-group analysis (NMR/titration) > Mn (low MW only) 22 . Greener Process PRINCIPLES 5,6,9 Toolkit · Green solvents - water, scCO2, ionic liquids, bio-solvents (2-MeTHF, ethanol); avoid chlorinated & VOCs · Biocatalysis - enzymes; mild, aqueous, enantioselective 23 . Worked . Atom Economy SHOW THE NUMBER Q. Wittig vs substitution to make an alkene - which is greener by AE? Wittig expels Ph3P=O (M, 278) - a large by- product = low atom economy despite high yield. An elimination or a catalytic metathesis keeps more atoms in product. LESSON high yield # green. Quote AE/E-factor, then name the by-product driving waste. 24 . Exam Discipline DON'T LOSE MARKS Assign every spectral peak - reconcile to one structure "Is it green?" = give a number + name the waste
- 端基分析（NMR/滴定）：主要给 $M_n$，适合低分子量[8]Source: asksia-cheatsheet-chem2522.pdf21b · Structure -> Property RULES Branching \ = packs tighter = denser & . stronger (HDPE > LDPE) · Chain length / M 1 = higher Tm, strength, viscosity Polar groups / H-bonds (nylon) = stronger, higher Tm · Plasticiser = lowers Ta (rigid PVC > flexible) 21c . Measuring Molar METHODS Mass GPC / SEC - size-exclusion; gives the full distribution > Mn, Mw, Đ · End-group analysis (NMR/titration) > Mn (low MW only) 22 . Greener Process PRINCIPLES 5,6,9 Toolkit · Green solvents - water, scCO2, ionic liquids, bio-solvents (2-MeTHF, ethanol); avoid chlorinated & VOCs · Biocatalysis - enzymes; mild, aqueous, enantioselective 23 . Worked . Atom Economy SHOW THE NUMBER Q. Wittig vs substitution to make an alkene - which is greener by AE? Wittig expels Ph3P=O (M, 278) - a large by- product = low atom economy despite high yield. An elimination or a catalytic metathesis keeps more atoms in product. LESSON high yield # green. Quote AE/E-factor, then name the by-product driving waste. 24 . Exam Discipline DON'T LOSE MARKS Assign every spectral peak - reconcile to one structure "Is it green?" = give a number + name the waste
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6) 可持续聚合物与可回收性（答题点）
- polyamide（nylon）：二酸 + 二胺 → 酰胺键 + H$_2$O（缩合）[18]Source: asksia-cheatsheet-chem2522.pdfNo single number means "green" - name which trade-off the question tests. Formula Belt SIDE 2 Xn = 1/(1-p) . Đ = Mw/Mn ≥1 splitting n+1 . reactivity: RCOCl>ester>amide Sn2 inversion . E2 anti-periplanar green: catalysis . renewable . degrade asksia. ai/cheatsheet/ usyd-chem2522 . side 2/2 AskSia CHEATSHEET SERIES 20 . Polymer Properties MOLAR MASS AVERAGES & DISPERSITY ΜΠ = Ση;Μ;/ Ση; (number avg) Mw = Ση;Μ12/Ση;Μ; (weight avg) Đ = M/Mn ≥ 1 (dispersity) Đ = 1 = perfectly uniform; step-growth ~2; controlled radical > low Đ. THERMAL & ORDER · Tg glass transition (amorphous softens); Tm melts (crystalline) · Tacticity - iso / syndio / atactic; regular = crystalline, higher Tm 21 · Sustainable Polymers · Polyamide (nylon) - diacid + diamine > amide links + H2O. · Polycarbonate - bisphenol + carbonate source. Need exact stoichiometry & high purity (Carothers) for high MW. The ester/amide links are also the handle for chemical recycling (hydrolysis/solvolysis back to monomer). 19b . Nature's Step- Growth BIOPOLYMERS The largest condensation polymers are biological: proteins (amino acids - peptide/amide bonds + H2O), polysaccharides (sugars >> glycosidic bonds + H2O), nucleic acids (phosphodiester). All are hydrolysable = inherently degradable - the design template for sustainable polymers. 19c . Worked . Carothers WHY PURITY MATTERS Degree of polymerisation vs conversion p: P
- 这些酯/酰胺键也是化学回收的“把手”：水解/溶剂解回单体[18]Source: asksia-cheatsheet-chem2522.pdfNo single number means "green" - name which trade-off the question tests. Formula Belt SIDE 2 Xn = 1/(1-p) . Đ = Mw/Mn ≥1 splitting n+1 . reactivity: RCOCl>ester>amide Sn2 inversion . E2 anti-periplanar green: catalysis . renewable . degrade asksia. ai/cheatsheet/ usyd-chem2522 . side 2/2 AskSia CHEATSHEET SERIES 20 . Polymer Properties MOLAR MASS AVERAGES & DISPERSITY ΜΠ = Ση;Μ;/ Ση; (number avg) Mw = Ση;Μ12/Ση;Μ; (weight avg) Đ = M/Mn ≥ 1 (dispersity) Đ = 1 = perfectly uniform; step-growth ~2; controlled radical > low Đ. THERMAL & ORDER · Tg glass transition (amorphous softens); Tm melts (crystalline) · Tacticity - iso / syndio / atactic; regular = crystalline, higher Tm 21 · Sustainable Polymers · Polyamide (nylon) - diacid + diamine > amide links + H2O. · Polycarbonate - bisphenol + carbonate source. Need exact stoichiometry & high purity (Carothers) for high MW. The ester/amide links are also the handle for chemical recycling (hydrolysis/solvolysis back to monomer). 19b . Nature's Step- Growth BIOPOLYMERS The largest condensation polymers are biological: proteins (amino acids - peptide/amide bonds + H2O), polysaccharides (sugars >> glycosidic bonds + H2O), nucleic acids (phosphodiester). All are hydrolysable = inherently degradable - the design template for sustainable polymers. 19c . Worked . Carothers WHY PURITY MATTERS Degree of polymerisation vs conversion p: P
- 生物大分子（蛋白质、多糖、核酸）都是缩合聚合且可水解 → “天然可降解”的设计模板[18]Source: asksia-cheatsheet-chem2522.pdfNo single number means "green" - name which trade-off the question tests. Formula Belt SIDE 2 Xn = 1/(1-p) . Đ = Mw/Mn ≥1 splitting n+1 . reactivity: RCOCl>ester>amide Sn2 inversion . E2 anti-periplanar green: catalysis . renewable . degrade asksia. ai/cheatsheet/ usyd-chem2522 . side 2/2 AskSia CHEATSHEET SERIES 20 . Polymer Properties MOLAR MASS AVERAGES & DISPERSITY ΜΠ = Ση;Μ;/ Ση; (number avg) Mw = Ση;Μ12/Ση;Μ; (weight avg) Đ = M/Mn ≥ 1 (dispersity) Đ = 1 = perfectly uniform; step-growth ~2; controlled radical > low Đ. THERMAL & ORDER · Tg glass transition (amorphous softens); Tm melts (crystalline) · Tacticity - iso / syndio / atactic; regular = crystalline, higher Tm 21 · Sustainable Polymers · Polyamide (nylon) - diacid + diamine > amide links + H2O. · Polycarbonate - bisphenol + carbonate source. Need exact stoichiometry & high purity (Carothers) for high MW. The ester/amide links are also the handle for chemical recycling (hydrolysis/solvolysis back to monomer). 19b . Nature's Step- Growth BIOPOLYMERS The largest condensation polymers are biological: proteins (amino acids - peptide/amide bonds + H2O), polysaccharides (sugars >> glycosidic bonds + H2O), nucleic acids (phosphodiester). All are hydrolysable = inherently degradable - the design template for sustainable polymers. 19c . Worked . Carothers WHY PURITY MATTERS Degree of polymerisation vs conversion p: P
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九、绿色工艺工具箱（常考：给出更绿替代）
-
1) Green solvents（背“推荐 + 避免”）
- 推荐：水、超临界 CO$_2$（scCO$_2$）、离子液体、生物溶剂（2-MeTHF、乙醇）[8]Source: asksia-cheatsheet-chem2522.pdf21b · Structure -> Property RULES Branching \ = packs tighter = denser & . stronger (HDPE > LDPE) · Chain length / M 1 = higher Tm, strength, viscosity Polar groups / H-bonds (nylon) = stronger, higher Tm · Plasticiser = lowers Ta (rigid PVC > flexible) 21c . Measuring Molar METHODS Mass GPC / SEC - size-exclusion; gives the full distribution > Mn, Mw, Đ · End-group analysis (NMR/titration) > Mn (low MW only) 22 . Greener Process PRINCIPLES 5,6,9 Toolkit · Green solvents - water, scCO2, ionic liquids, bio-solvents (2-MeTHF, ethanol); avoid chlorinated & VOCs · Biocatalysis - enzymes; mild, aqueous, enantioselective 23 . Worked . Atom Economy SHOW THE NUMBER Q. Wittig vs substitution to make an alkene - which is greener by AE? Wittig expels Ph3P=O (M, 278) - a large by- product = low atom economy despite high yield. An elimination or a catalytic metathesis keeps more atoms in product. LESSON high yield # green. Quote AE/E-factor, then name the by-product driving waste. 24 . Exam Discipline DON'T LOSE MARKS Assign every spectral peak - reconcile to one structure "Is it green?" = give a number + name the waste
- 避免：含氯溶剂与 VOCs（挥发性有机物）[8]Source: asksia-cheatsheet-chem2522.pdf21b · Structure -> Property RULES Branching \ = packs tighter = denser & . stronger (HDPE > LDPE) · Chain length / M 1 = higher Tm, strength, viscosity Polar groups / H-bonds (nylon) = stronger, higher Tm · Plasticiser = lowers Ta (rigid PVC > flexible) 21c . Measuring Molar METHODS Mass GPC / SEC - size-exclusion; gives the full distribution > Mn, Mw, Đ · End-group analysis (NMR/titration) > Mn (low MW only) 22 . Greener Process PRINCIPLES 5,6,9 Toolkit · Green solvents - water, scCO2, ionic liquids, bio-solvents (2-MeTHF, ethanol); avoid chlorinated & VOCs · Biocatalysis - enzymes; mild, aqueous, enantioselective 23 . Worked . Atom Economy SHOW THE NUMBER Q. Wittig vs substitution to make an alkene - which is greener by AE? Wittig expels Ph3P=O (M, 278) - a large by- product = low atom economy despite high yield. An elimination or a catalytic metathesis keeps more atoms in product. LESSON high yield # green. Quote AE/E-factor, then name the by-product driving waste. 24 . Exam Discipline DON'T LOSE MARKS Assign every spectral peak - reconcile to one structure "Is it green?" = give a number + name the waste
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2) Biocatalysis（酶催化）
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3) 催化指标：TON / TOF（定义 + 计算题）
- 你材料里给了一个算例：TON = 800，TOF = 400 h$^{-1}$（并提示真实 TON 会被失活限制）[13]Source: asksia-cheatsheet-chem2522.pdfweak aromatic C=C c-0 1450-1600 1000-1300 strong C=O fine print: amide ~1650 < acid ~1710 = ketone 1715 < aldehyde 1725 < ester 1735 < acyl chloride 1800. Conjugation lowers C=O by ~30. 3 7b · Reading an IR Spectrum QUESTIONS 1. C=O? strong, sharp 1650-1750 = carbonyl present 2. Broad O-H / N-H? 2500-3550 = acid/alcohol/amine 3. C-H above or below 3000? = sp2/aromatic vs sp3 Tell-tales: aldehyde = C=O + twin C-H (Fermi) ~2720/2820; nitrile = sharp 2250; anhydride = two C=O bands. 7c . Distinguish by IR ISOMER TRAP TON = 0. 8 / 0. 001 = 800 TOF = 800 / 2 = 400 h-1 Industrial/enzyme catalysts reach TON 106- 109. Real TON is capped by deactivation (poisoning, leaching, sintering) - recyclability is the green prize. REVISION SHEET . ALL TOPICS Compiled by AskSia . mapped to the CHEM2522 syllabus . asksia. ai/cheatsheet/usyd- chem2522 Revision aid . check the official unit outline for assessment . 0 2026 flip - for side 2 . synthesis, mechanisms & polymers CHEM2522 Sustainable Chemical Manufacture UNIVERSITY OF SYDNEY . SCHOOL OF CHEMISTRY[15]Source: asksia-cheatsheet-chem2522.pdfstrong * C=C alkene 1620-1680 weak aromatic C=C c-0 1450-1600 1000-1300 strong C=O fine print: amide ~1650 < acid ~1710 = ketone 1715 < aldehyde 1725 < ester 1735 < acyl chloride 1800. Conjugation lowers C=O by ~30. 3 7b · Reading an IR Spectrum QUESTIONS 1. C=O? strong, sharp 1650-1750 = carbonyl present 2. Broad O-H / N-H? 2500-3550 = acid/alcohol/amine 3. C-H above or below 3000? = sp2/aromatic vs sp3 Tell-tales: aldehyde = C=O + twin C-H (Fermi) ~2720/2820; nitrile = sharp 2250; anhydride = two C=O bands. 7c . Distinguish by IR ISOMER TRAP TON = 0. 8 / 0. 001 = 800 TOF = 800 / 2 = 400 h-1 Industrial/enzyme catalysts reach TON 106- 109. Real TON is capped by deactivation (poisoning, leaching, sintering) - recyclability is the green prize. REVISION SHEET . ALL TOPICS Compiled by AskSia . mapped to the CHEM2522 syllabus . asksia. ai/cheatsheet/usyd- chem2522
- 虽然摘录里没把“TON/TOF 的通用定义”写成一句话，但从算例可直接用作考试计算框架：
- $$TON=\frac{\text{amount (or moles) product}}{\text{amount (or moles) catalyst}}$$（对应 0.8/0.001 这种比值）[13]Source: asksia-cheatsheet-chem2522.pdfweak aromatic C=C c-0 1450-1600 1000-1300 strong C=O fine print: amide ~1650 < acid ~1710 = ketone 1715 < aldehyde 1725 < ester 1735 < acyl chloride 1800. Conjugation lowers C=O by ~30. 3 7b · Reading an IR Spectrum QUESTIONS 1. C=O? strong, sharp 1650-1750 = carbonyl present 2. Broad O-H / N-H? 2500-3550 = acid/alcohol/amine 3. C-H above or below 3000? = sp2/aromatic vs sp3 Tell-tales: aldehyde = C=O + twin C-H (Fermi) ~2720/2820; nitrile = sharp 2250; anhydride = two C=O bands. 7c . Distinguish by IR ISOMER TRAP TON = 0. 8 / 0. 001 = 800 TOF = 800 / 2 = 400 h-1 Industrial/enzyme catalysts reach TON 106- 109. Real TON is capped by deactivation (poisoning, leaching, sintering) - recyclability is the green prize. REVISION SHEET . ALL TOPICS Compiled by AskSia . mapped to the CHEM2522 syllabus . asksia. ai/cheatsheet/usyd- chem2522 Revision aid . check the official unit outline for assessment . 0 2026 flip - for side 2 . synthesis, mechanisms & polymers CHEM2522 Sustainable Chemical Manufacture UNIVERSITY OF SYDNEY . SCHOOL OF CHEMISTRY[15]Source: asksia-cheatsheet-chem2522.pdfstrong * C=C alkene 1620-1680 weak aromatic C=C c-0 1450-1600 1000-1300 strong C=O fine print: amide ~1650 < acid ~1710 = ketone 1715 < aldehyde 1725 < ester 1735 < acyl chloride 1800. Conjugation lowers C=O by ~30. 3 7b · Reading an IR Spectrum QUESTIONS 1. C=O? strong, sharp 1650-1750 = carbonyl present 2. Broad O-H / N-H? 2500-3550 = acid/alcohol/amine 3. C-H above or below 3000? = sp2/aromatic vs sp3 Tell-tales: aldehyde = C=O + twin C-H (Fermi) ~2720/2820; nitrile = sharp 2250; anhydride = two C=O bands. 7c . Distinguish by IR ISOMER TRAP TON = 0. 8 / 0. 001 = 800 TOF = 800 / 2 = 400 h-1 Industrial/enzyme catalysts reach TON 106- 109. Real TON is capped by deactivation (poisoning, leaching, sintering) - recyclability is the green prize. REVISION SHEET . ALL TOPICS Compiled by AskSia . mapped to the CHEM2522 syllabus . asksia. ai/cheatsheet/usyd- chem2522
- $$TOF=\frac{TON}{t}$$（材料用 2 h 做除法得到 400 h$^{-1}$）[13]Source: asksia-cheatsheet-chem2522.pdfweak aromatic C=C c-0 1450-1600 1000-1300 strong C=O fine print: amide ~1650 < acid ~1710 = ketone 1715 < aldehyde 1725 < ester 1735 < acyl chloride 1800. Conjugation lowers C=O by ~30. 3 7b · Reading an IR Spectrum QUESTIONS 1. C=O? strong, sharp 1650-1750 = carbonyl present 2. Broad O-H / N-H? 2500-3550 = acid/alcohol/amine 3. C-H above or below 3000? = sp2/aromatic vs sp3 Tell-tales: aldehyde = C=O + twin C-H (Fermi) ~2720/2820; nitrile = sharp 2250; anhydride = two C=O bands. 7c . Distinguish by IR ISOMER TRAP TON = 0. 8 / 0. 001 = 800 TOF = 800 / 2 = 400 h-1 Industrial/enzyme catalysts reach TON 106- 109. Real TON is capped by deactivation (poisoning, leaching, sintering) - recyclability is the green prize. REVISION SHEET . ALL TOPICS Compiled by AskSia . mapped to the CHEM2522 syllabus . asksia. ai/cheatsheet/usyd- chem2522 Revision aid . check the official unit outline for assessment . 0 2026 flip - for side 2 . synthesis, mechanisms & polymers CHEM2522 Sustainable Chemical Manufacture UNIVERSITY OF SYDNEY . SCHOOL OF CHEMISTRY[15]Source: asksia-cheatsheet-chem2522.pdfstrong * C=C alkene 1620-1680 weak aromatic C=C c-0 1450-1600 1000-1300 strong C=O fine print: amide ~1650 < acid ~1710 = ketone 1715 < aldehyde 1725 < ester 1735 < acyl chloride 1800. Conjugation lowers C=O by ~30. 3 7b · Reading an IR Spectrum QUESTIONS 1. C=O? strong, sharp 1650-1750 = carbonyl present 2. Broad O-H / N-H? 2500-3550 = acid/alcohol/amine 3. C-H above or below 3000? = sp2/aromatic vs sp3 Tell-tales: aldehyde = C=O + twin C-H (Fermi) ~2720/2820; nitrile = sharp 2250; anhydride = two C=O bands. 7c . Distinguish by IR ISOMER TRAP TON = 0. 8 / 0. 001 = 800 TOF = 800 / 2 = 400 h-1 Industrial/enzyme catalysts reach TON 106- 109. Real TON is capped by deactivation (poisoning, leaching, sintering) - recyclability is the green prize. REVISION SHEET . ALL TOPICS Compiled by AskSia . mapped to the CHEM2522 syllabus . asksia. ai/cheatsheet/usyd- chem2522
- 论述点：工业/酶催化可到 TON $10^6$–$10^9$；真实 TON 常被 poisoning、leaching、sintering 等失活限制，“可回收性”是绿色关键[13]Source: asksia-cheatsheet-chem2522.pdfweak aromatic C=C c-0 1450-1600 1000-1300 strong C=O fine print: amide ~1650 < acid ~1710 = ketone 1715 < aldehyde 1725 < ester 1735 < acyl chloride 1800. Conjugation lowers C=O by ~30. 3 7b · Reading an IR Spectrum QUESTIONS 1. C=O? strong, sharp 1650-1750 = carbonyl present 2. Broad O-H / N-H? 2500-3550 = acid/alcohol/amine 3. C-H above or below 3000? = sp2/aromatic vs sp3 Tell-tales: aldehyde = C=O + twin C-H (Fermi) ~2720/2820; nitrile = sharp 2250; anhydride = two C=O bands. 7c . Distinguish by IR ISOMER TRAP TON = 0. 8 / 0. 001 = 800 TOF = 800 / 2 = 400 h-1 Industrial/enzyme catalysts reach TON 106- 109. Real TON is capped by deactivation (poisoning, leaching, sintering) - recyclability is the green prize. REVISION SHEET . ALL TOPICS Compiled by AskSia . mapped to the CHEM2522 syllabus . asksia. ai/cheatsheet/usyd- chem2522 Revision aid . check the official unit outline for assessment . 0 2026 flip - for side 2 . synthesis, mechanisms & polymers CHEM2522 Sustainable Chemical Manufacture UNIVERSITY OF SYDNEY . SCHOOL OF CHEMISTRY[15]Source: asksia-cheatsheet-chem2522.pdfstrong * C=C alkene 1620-1680 weak aromatic C=C c-0 1450-1600 1000-1300 strong C=O fine print: amide ~1650 < acid ~1710 = ketone 1715 < aldehyde 1725 < ester 1735 < acyl chloride 1800. Conjugation lowers C=O by ~30. 3 7b · Reading an IR Spectrum QUESTIONS 1. C=O? strong, sharp 1650-1750 = carbonyl present 2. Broad O-H / N-H? 2500-3550 = acid/alcohol/amine 3. C-H above or below 3000? = sp2/aromatic vs sp3 Tell-tales: aldehyde = C=O + twin C-H (Fermi) ~2720/2820; nitrile = sharp 2250; anhydride = two C=O bands. 7c . Distinguish by IR ISOMER TRAP TON = 0. 8 / 0. 001 = 800 TOF = 800 / 2 = 400 h-1 Industrial/enzyme catalysts reach TON 106- 109. Real TON is capped by deactivation (poisoning, leaching, sintering) - recyclability is the green prize. REVISION SHEET . ALL TOPICS Compiled by AskSia . mapped to the CHEM2522 syllabus . asksia. ai/cheatsheet/usyd- chem2522
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十、你按这份做题：Final 最稳的“复习顺序”
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1) 每天快速刷的“高产出顺序”（建议）
- 先把 指标公式背熟：AE、E-factor、PMI、DBE、n+1、（Cl/Br 同位素）[10]Source: asksia-cheatsheet-chem2522.pdf12. Inherently safer chemistry (accident prevention) Prevention > remediation is the spine: principles 1, 2, 9 do most of the exam work. 1b . Worked . Atom Economy TWO ROUTES Target = ethanol (C2HBO, M, 46): Hydration CH2=CH2 + H2O -> C2H5OH AE = 46/(28+18) = 100% (addition, no by- product). Fermentation C 6H1206 -> 2 C2H5OH + 2 CO2 AE = (2-46)/180 = 51% - CO2 is lost mass, but the feedstock is renewable. = greenness trades AE vs feedstock vs energy. Quote all three, don't crown a winner on AE alone. 2 . Sustainability Metrics CALCULATE THESE Yield tells you nothing about waste. A 100% yield reaction can still be wasteful if half the reactant mass ends up as by- product. That's why we measure atoms and mass. ATOM ECONOMY TROST 1991 % ATOM ECONOMY AE = (M, desired product / E Mr all products) x 100 = Mr product / E Mr reactants x 100 Theoretical (uses the balanced equation, ignores yield). Addition & rearrangement > 100% AE ; substitution & especially elimination/condensation lose atoms. E-FACTOR SHELDON ENVIRONMENTAL FACTOR E = mass of waste / mass of product ideal E = 0 (zero waste) INDUSTRY TONNAGE E-FACTOR Bulk chems 104-106 <1-5 Fine chems 102-104[12]Source: asksia-cheatsheet-chem2522.pdf13C + DEPT H count & connectivity 1H (6, integ, J) Rings / Tt count DBE from formula Formula Belt SIDE 1 | ΑΕ = Mc (prod)/ ΣΜ, (react) x100 E = waste / product . PMI = E+1 DBE = (2C+2+N-H-X)/2 splitting = n+1 . M+1 = 1. 1% . nC Cl 3:1 . Br 1:1 (M:M+2) asksia. ai/cheatsheet/ usyd-chem2522 . side 1/2 AskSia CHEATSHEET SERIES THE 6 . Structure Elucidation WORKFLOW Combine the techniques - each answers a different question: · 1H/13C NMR > carbon-hydrogen skeleton (how connected?) STEP 1 ALWAYS: DBE DEGREES OF UNSATURATION (IHD/DBE) DBE = (2C + 2 + N - H - X) / 2 (0 is ignored). Ring or n-bond = 1 each. DBE ≥ 4 = suspect a benzene ring (3 C=C + 1 ring). C=O = 1, C=N = 2, C=C = 2. 7 . IR Spectroscopy CM-1 Bond stretching frequency . /(k/u): stronger bond & lighter atoms = higher cm-1. Read the diagnostic 4000-1500 region; 1500-500 is the "fingerprint". BOND / GROUP CM-1 NOTE O-H alcohol[16]Source: asksia-cheatsheet-chem2522.pdfRings / Tt count DBE from formula Formula Belt SIDE 1 | ΑΕ = Mc (prod)/ ΣΜ, (react) x100 E = waste / product . PMI = E+1 DBE = (2C+2+N-H-X)/2 splitting = n+1 . M+1 = 1. 1% . nC Cl 3:1 . Br 1:1 (M:M+2) asksia. ai/cheatsheet/ usyd-chem2522 . side 1/2 AskSia CHEATSHEET SERIES THE 6 . Structure Elucidation WORKFLOW Combine the techniques - each answers a different question: · 1H/13C NMR > carbon-hydrogen skeleton (how connected?) STEP 1 ALWAYS: DBE DEGREES OF UNSATURATION (IHD/DBE) DBE = (2C + 2 + N - H - X) / 2 (0 is ignored). Ring or n-bond = 1 each. DBE ≥ 4 = suspect a benzene ring (3 C=C + 1 ring). C=O = 1, C=N = 2, C=C = 2. 7 . IR Spectroscopy CM-1 Bond stretching frequency . /(k/u): stronger bond & lighter atoms = higher cm-1. Read the diagnostic 4000-1500 region; 1500-500 is the "fingerprint". BOND / GROUP CM-1 NOTE O-H alcohol 3200-3550 broad O-H carb. acid
- 再练 结构解析流程：DBE → IR 三问 → MS → $^1$H（积分+裂分）→ $^{13}$C/DEPT（信号数+对称）[12]Source: asksia-cheatsheet-chem2522.pdf13C + DEPT H count & connectivity 1H (6, integ, J) Rings / Tt count DBE from formula Formula Belt SIDE 1 | ΑΕ = Mc (prod)/ ΣΜ, (react) x100 E = waste / product . PMI = E+1 DBE = (2C+2+N-H-X)/2 splitting = n+1 . M+1 = 1. 1% . nC Cl 3:1 . Br 1:1 (M:M+2) asksia. ai/cheatsheet/ usyd-chem2522 . side 1/2 AskSia CHEATSHEET SERIES THE 6 . Structure Elucidation WORKFLOW Combine the techniques - each answers a different question: · 1H/13C NMR > carbon-hydrogen skeleton (how connected?) STEP 1 ALWAYS: DBE DEGREES OF UNSATURATION (IHD/DBE) DBE = (2C + 2 + N - H - X) / 2 (0 is ignored). Ring or n-bond = 1 each. DBE ≥ 4 = suspect a benzene ring (3 C=C + 1 ring). C=O = 1, C=N = 2, C=C = 2. 7 . IR Spectroscopy CM-1 Bond stretching frequency . /(k/u): stronger bond & lighter atoms = higher cm-1. Read the diagnostic 4000-1500 region; 1500-500 is the "fingerprint". BOND / GROUP CM-1 NOTE O-H alcohol[17]Source: asksia-cheatsheet-chem2522.pdfEdits by # attached H: CH & CH3 up, CH2 down, quaternary C absent (the give-away for C=O & substituted aromatic). COUNTING SIGNALS = SYMMETRY # of signals = # of chemically distinct environments. Benzene = 1 13C; para- disubstituted ring = 4 (two pairs equivalent). Fewer signals than carbons = symmetry - a fast structural clue. 11 . Worked . C4H8O PUT IT TOGETHER MS M+ = 72. DBE = (2. 4+2-8)/2 = 1 = one C=O or C=C/ring. IR 1715 cm-1 strong = ketone C=O (no broad O-H, no ~2720 aldehyde C-H, no 1735 ester). 1H NMR triplet 1. 0 (3H), quartet 2. 4 (2H), singlet 2. 1 (3H) = ethyl + isolated methyl on C=O. butan-2-one, CH3COCH2CH3. MS loss of 15 (>57) and 29 (>43, CH3CO+) confirm a- cleavage either side of C=O. ---- SIA - Reconcile every piece of data to one structure - if a single peak doesn't fit, the structure is wrong. Examiners build the trap on the one ignored signal. 11b . Worked . C8H8O SPOT THE RING DBE = (2. 8+2-8)/2 = 5 = benzene ring (4) + one more (a C=O). IR 1685 (conjugated C=O). 1H: 5H multiplet 7. 4-8. 0 (mono-substituted ring) + singlet 2. 6 (3H, CH3CO). = acetophenone, C&H;COCH3. 13C ~198 (C=O); m/z 105 (PhCO+) & 77 (C6H5*) confirm. Which Technique? RECAP QUESTION USE Mass / formula MS (M+1, isotopes) Functional groups? IR (C=0, O-H, N-H) # unique C; C type 13C + DEPT H count & connectivity 1H (6, integ, J)[20]Source: asksia-cheatsheet-chem2522.pdfC=O ketone/aldehyde 190-220 DEPT Edits by # attached H: CH & CH3 up, CH2 down, quaternary C absent (the give-away for C=O & substituted aromatic). COUNTING SIGNALS = SYMMETRY # of signals = # of chemically distinct environments. Benzene = 1 13C; para- disubstituted ring = 4 (two pairs equivalent). Fewer signals than carbons = symmetry - a fast structural clue. 11 . Worked . C4H8O PUT IT TOGETHER MS M+ = 72. DBE = (2. 4+2-8)/2 = 1 = one C=O or C=C/ring. IR 1715 cm-1 strong = ketone C=O (no broad O-H, no ~2720 aldehyde C-H, no 1735 ester). 1H NMR triplet 1. 0 (3H), quartet 2. 4 (2H), singlet 2. 1 (3H) = ethyl + isolated methyl on C=O. butan-2-one, CH3COCH2CH3. MS loss of 15 (>57) and 29 (>43, CH3CO+) confirm a- cleavage either side of C=O. ---- SIA - Reconcile every piece of data to one structure - if a single peak doesn't fit, the structure is wrong. Examiners build the trap on the one ignored signal. 11b . Worked . C8H8O SPOT THE RING DBE = (2. 8+2-8)/2 = 5 = benzene ring (4) + one more (a C=O). IR 1685 (conjugated C=O). 1H: 5H multiplet 7. 4-8. 0 (mono-substituted ring) + singlet 2. 6 (3H, CH3CO). = acetophenone, C&H;COCH3. 13C ~198 (C=O); m/z 105 (PhCO+) & 77 (C6H5*) confirm. Which Technique? RECAP QUESTION USE Mass / formula MS (M+1, isotopes) Functional groups? IR (C=0, O-H, N-H) # unique C; C type
- 再练 机理分叉题：SN1/SN2/E1/E2（速率式、底物、溶剂、立体、重排、Zaitsev/Hofmann）[6]Source: asksia-cheatsheet-chem2522.pdfRevision aid . check the official unit outline for assessment . 0 2026 flip - for side 2 . synthesis, mechanisms & polymers CHEM2522 Sustainable Chemical Manufacture UNIVERSITY OF SYDNEY . SCHOOL OF CHEMISTRY EXAM REVISION Sem 1 2026 . SIDE 2 OF 2 Synthesis . mechanisms . polymers SIDE 2/2 polymers 12 · Functional Groups REACTIVITY MAP Reactivity lives at the functional group; the carbon skeleton is mostly inert. Two master patterns: · Polar / ionic - a nucleophile (electron- rich, 8-) attacks an electrophile (electron- poor, 8+). Curly arrows go from Nu to E. . Radical - homolysis, single-electron (fish-hook) arrows; chain initiation/propagation/termination. Electrophilic carbons: C-X (halide), C=O (carbonyl). Nucleophiles: OH", RO", CN", NH3, enolates, RMgX (carbanion equiv. ). 13 . Substitution & Elimination En1/2 Sn2 Sn1 Steps 1 (concerted) 2 (carbocation) Rate k[RX][Nu] k[RX][11]Source: asksia-cheatsheet-chem2522.pdfEXAM REVISION Sem 1 2026 . SIDE 2 OF 2 Synthesis . mechanisms . polymers SIDE 2/2 polymers 12 · Functional Groups REACTIVITY MAP Reactivity lives at the functional group; the carbon skeleton is mostly inert. Two master patterns: · Polar / ionic - a nucleophile (electron- rich, 8-) attacks an electrophile (electron- poor, 8+). Curly arrows go from Nu to E. . Radical - homolysis, single-electron (fish-hook) arrows; chain initiation/propagation/termination. Electrophilic carbons: C-X (halide), C=O (carbonyl). Nucleophiles: OH", RO", CN", NH3, enolates, RMgX (carbanion equiv. ). 13 . Substitution & Elimination En1/2 Sn2 Sn1 Steps 1 (concerted) 2 (carbocation) Rate k[RX][Nu] k[RX] Substrate 1° > 2° 3° > 2°[19]Source: asksia-cheatsheet-chem2522.pdfStereo inversion racemisation Solvent Nu polar aprotic strong weak ok E2: concerted, anti-periplanar H & LG, strong base, rate k[RX] [base]; E1: via carbocation, rate k[RX]. Both follow Zaitsev (more-substituted alkene) - except a bulky base (t-BuO-) gives Hofmann (less- substituted). The fork: strong bulky base + heat = elimination; good Nu, weaker base = substitution. 3º + weak Nu/protic = Sn1/E1 mix. 13b . Nucleophiles & Leaving Groups RANK THEM Leaving group best->worst: I" > Br" > CI- >> F -; TsO- & H2O good. A weak base is a good LG (stable once it leaves); OH-, RO", NH2- are poor LGs. Nucleophilicity 1 with negative charge & less steric bulk. Basicity # nucleophilicity: in polar aprotic they track; in polar protic the bigger, more-polarisable ion wins (I" > F-). 13c · Carbocation Stability DRIVES Sn1/E1 Order 3° > 2° > 1º > methyl (hyperconjugation + induction); benzylic/allylic are extra-stable (resonance). An unstable cation rearranges (1,2-hydride or alkyl shift) to a more stable one - the classic Sn1/E1 "wrong product" trap. 13d . Mechanism Arrows METHOD MARKS Arrow starts at a lone pair or bond, points where electrons go · Never start an arrow at H+ or a + charge Conserve charge & atoms each step Double-head = 2e- (polar); fish-hook = 1e- (radical)
- 最后刷 聚合物公式与性质题：Carothers、Đ、Tg/Tm、结构-性质规则、测量方法[5]Source: asksia-cheatsheet-chem2522.pdfWHY PURITY MATTERS Degree of polymerisation vs conversion p: P XN = 1/(1-P) 0. 90 0. 95 0. 99 0. 995 = step-growth needs near-complete conversion for useful chain length. A single impurity or stoichiometric imbalance caps M - hence the purity demand. Compiled by AskSia . mapped to the CHEM2522 syllabus . asksia. ai/cheatsheet/usyd- chem2522 16 . Oxidation & Reduction THE TOOLKIT OXIDATION (ADD O / REMOVE H) 1º alcohol > aldehyde (PCC, Swern, TEMPO) > acid (KMnO4, CrO3/Jones). 2° alcohol - ketone. Green oxidants: O2, H2O2 (by-product = H2O), catalytic TEMPO. REDUCTION (ADD H / REMOVE O) REAGENT STRENGTH REDUCES NaBH4 mild[8]Source: asksia-cheatsheet-chem2522.pdf21b · Structure -> Property RULES Branching \ = packs tighter = denser & . stronger (HDPE > LDPE) · Chain length / M 1 = higher Tm, strength, viscosity Polar groups / H-bonds (nylon) = stronger, higher Tm · Plasticiser = lowers Ta (rigid PVC > flexible) 21c . Measuring Molar METHODS Mass GPC / SEC - size-exclusion; gives the full distribution > Mn, Mw, Đ · End-group analysis (NMR/titration) > Mn (low MW only) 22 . Greener Process PRINCIPLES 5,6,9 Toolkit · Green solvents - water, scCO2, ionic liquids, bio-solvents (2-MeTHF, ethanol); avoid chlorinated & VOCs · Biocatalysis - enzymes; mild, aqueous, enantioselective 23 . Worked . Atom Economy SHOW THE NUMBER Q. Wittig vs substitution to make an alkene - which is greener by AE? Wittig expels Ph3P=O (M, 278) - a large by- product = low atom economy despite high yield. An elimination or a catalytic metathesis keeps more atoms in product. LESSON high yield # green. Quote AE/E-factor, then name the by-product driving waste. 24 . Exam Discipline DON'T LOSE MARKS Assign every spectral peak - reconcile to one structure "Is it green?" = give a number + name the waste[18]Source: asksia-cheatsheet-chem2522.pdfNo single number means "green" - name which trade-off the question tests. Formula Belt SIDE 2 Xn = 1/(1-p) . Đ = Mw/Mn ≥1 splitting n+1 . reactivity: RCOCl>ester>amide Sn2 inversion . E2 anti-periplanar green: catalysis . renewable . degrade asksia. ai/cheatsheet/ usyd-chem2522 . side 2/2 AskSia CHEATSHEET SERIES 20 . Polymer Properties MOLAR MASS AVERAGES & DISPERSITY ΜΠ = Ση;Μ;/ Ση; (number avg) Mw = Ση;Μ12/Ση;Μ; (weight avg) Đ = M/Mn ≥ 1 (dispersity) Đ = 1 = perfectly uniform; step-growth ~2; controlled radical > low Đ. THERMAL & ORDER · Tg glass transition (amorphous softens); Tm melts (crystalline) · Tacticity - iso / syndio / atactic; regular = crystalline, higher Tm 21 · Sustainable Polymers · Polyamide (nylon) - diacid + diamine > amide links + H2O. · Polycarbonate - bisphenol + carbonate source. Need exact stoichiometry & high purity (Carothers) for high MW. The ester/amide links are also the handle for chemical recycling (hydrolysis/solvolysis back to monomer). 19b . Nature's Step- Growth BIOPOLYMERS The largest condensation polymers are biological: proteins (amino acids - peptide/amide bonds + H2O), polysaccharides (sugars >> glycosidic bonds + H2O), nucleic acids (phosphodiester). All are hydrolysable = inherently degradable - the design template for sustainable polymers. 19c . Worked . Carothers WHY PURITY MATTERS Degree of polymerisation vs conversion p: P
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十一、你下一步想要我怎么“救命式”帮你（你回我一个选项就行）
- A）你把你们 final 的题型/题目截图发我：我按题型出“答题模板”（比如结构解析题怎么写满分步骤）
- B）我给你做一套 “必考公式+必考判断题”20 题小测（做完我按错题给你补漏）
- C）你告诉我你最虚的模块：
- 绿色指标（AE/E/PMI）
- 光谱解析（IR/MS/NMR）
- SN1/SN2/E1/E2
- 聚合物（Carothers/Đ/Tg/Tm）
我就只讲那一块，讲到你会为止（并配题）
- （可选）如果你愿意，我也可以把你这门课的“你最容易丢分的点/你的薄弱模块”记住，下次你说“复习 CHEM2522”，我就直接按你的薄弱点优先带你冲刺。
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