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青州's Question
Chemistry
Posted 5 months ago

In a specialized organic chemistry research experiment, a scientist synthesizes a novel compound "Theta" with a molecular formula C10H14O2\mathrm{C}_{10} \mathrm{H}_{14} \mathrm{O}_{2}. When "Theta" undergoes ozonolysis followed by reductive workup with zinc and acetic acid, it yields two different compounds: "lota" (C6H12O)\left(\mathrm{C}_{6} \mathrm{H}_{12} \mathrm{O}\right) and "Kappa" (C4H6O2)\left(\mathrm{C}_{4} \mathrm{H}_{6} \mathrm{O}_{2}\right). Analyze these results to deduce the structure of "Theta" and identify the likely structures of "Iota" and "Kappa." Also, explain the type of chemical reactions involved in each step
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Answer from Sia
Posted 5 months ago
Solution
1
Identify the reaction: The given reaction involves ozonolysis followed by reductive workup with zinc and acetic acid. Ozonolysis is a reaction where ozone (O3\mathrm{O}_3) cleaves double bonds in alkenes to form carbonyl compounds. The reductive workup with zinc and acetic acid converts the ozonides into aldehydes or ketones
2
Analyze the molecular formulas: The molecular formula of "Theta" is C10H14O2\mathrm{C}_{10} \mathrm{H}_{14} \mathrm{O}_{2}. After ozonolysis, it yields "Iota" (C6H12O\mathrm{C}_{6} \mathrm{H}_{12} \mathrm{O}) and "Kappa" (C4H6O2\mathrm{C}_{4} \mathrm{H}_{6} \mathrm{O}_{2}). This suggests that "Theta" contains a double bond that is cleaved to form these two products
3
Determine the structure of "Theta": Given the products, "Theta" likely has a structure that includes a double bond between two carbon atoms. The cleavage of this double bond during ozonolysis would result in the formation of "Iota" and "Kappa"
4
Identify the structures of "Iota" and "Kappa": - "Iota" (C6H12O\mathrm{C}_{6} \mathrm{H}_{12} \mathrm{O}) is likely a ketone or aldehyde with a six-carbon chain. - "Kappa" (C4H6O2\mathrm{C}_{4} \mathrm{H}_{6} \mathrm{O}_{2}) is likely a compound with a four-carbon chain and two oxygen atoms, possibly a carboxylic acid or ester
5
Propose the structure of "Theta": Considering the molecular formulas and the products of ozonolysis, "Theta" could be a compound like 1,2-dimethylcyclohexene. Upon ozonolysis, this would yield a six-carbon ketone (Iota) and a four-carbon carboxylic acid (Kappa)
Answer
The structure of "Theta" is likely 1,2-dimethylcyclohexene. "Iota" is a six-carbon ketone, and "Kappa" is a four-carbon carboxylic acid.
Key Concept
Ozonolysis and reductive workup reactions
Explanation
Ozonolysis cleaves double bonds in alkenes to form carbonyl compounds, and reductive workup with zinc and acetic acid converts ozonides into aldehydes or ketones.

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