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Chemistry
Posted 6 months ago

(i) Identify A\mathbf{A} and provide a mechanism to account for its formation.
i).
C10H6 N2\mathrm{C}_{10} \mathrm{H}_{6} \mathrm{~N}_{2}
ii). KCN\mathrm{KCN}
3
A
(ii) Identify B\mathbf{B} and provide a mechanism to account for its formation.
i). nBuLin-\mathrm{BuLi}
ii). CO2\mathrm{CO}_{2}
C9H6O2 S\mathrm{C}_{9} \mathrm{H}_{6} \mathrm{O}_{2} \mathrm{~S}
4
iii). H\mathrm{H}^{\oplus}
B
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Answer from Sia
Posted 6 months ago
Solution
1
Identify Compound A: To identify compound A with the molecular formula C10H6N2C_{10}H_{6}N_{2}, we need to consider the reagents used in its synthesis. The use of PhCOCl suggests acylation, and KCN indicates a nucleophilic substitution where a cyano group replaces a leaving group
2
Mechanism for the formation of A: The mechanism likely involves the formation of a ketone from the starting material 3 via Friedel-Crafts acylation followed by a nucleophilic substitution with KCN to introduce the cyano group
3
Identify Compound B: To identify compound B with the molecular formula C9H6O2SC_{9}H_{6}O_{2}S, we need to consider the reagents used in its synthesis. The use of n-BuLi suggests deprotonation, CO2 indicates carboxylation, and H+ suggests an acid work-up, likely leading to the formation of a carboxylic acid
4
Mechanism for the formation of B: The mechanism likely involves the deprotonation of the starting material 4 by n-BuLi to form a carbanion, followed by carboxylation with CO2 to introduce a carboxyl group, and finally, protonation with H+ to yield the carboxylic acid
1 Answer
Compound A is likely a naphthalene derivative with a ketone and a cyano group. The mechanism involves Friedel-Crafts acylation followed by nucleophilic substitution with KCN.
2 Answer
Compound B is likely a thiophene derivative with a carboxylic acid group. The mechanism involves deprotonation by n-BuLi, carboxylation with CO2, and acid work-up with H+.
Key Concept
The identification of organic compounds and their mechanisms of formation is based on the molecular formula and the reagents used in the synthesis.
Explanation
Compound A is synthesized through acylation and nucleophilic substitution, while Compound B is synthesized through deprotonation, carboxylation, and protonation.

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