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Question
Chemistry
Posted 10 months ago

Please design the synthetic route of the following transformation
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Answer from Sia
Posted 10 months ago
Solution
1
Identify the starting material and desired product: The starting material is cyclohexane, and the desired product is a cyclopentane with an attached carbonyl group forming an ester with methanol (OMe)
2
Consider possible reactions: To transform cyclohexane to the desired product, we need to perform a ring contraction and introduce a carbonyl group, followed by esterification
3
Ring contraction: Cyclohexane can be converted to cyclopentane through a series of reactions that may involve a diazonium intermediate formed from an aminocyclohexane precursor
4
Functional group introduction: Once the cyclopentane ring is formed, a carbonyl group can be introduced through oxidation reactions, such as using a strong oxidizing agent like chromium trioxide $\text{CrO}_3$ or pyridinium chlorochromate (PCC)
5
Esterification: The final step is to convert the carboxylic acid to an ester using methanol in the presence of an acid catalyst, such as sulfuric acid $\text{H}_2\text{SO}_4$
Answer
The synthetic route involves ring contraction of cyclohexane to form cyclopentane, oxidation to introduce the carbonyl group, and esterification with methanol to form the final product.
Key Concept
Synthetic route design for organic transformations
Explanation
The process involves identifying the necessary reactions to convert the starting material into the desired product, considering the need for ring contraction, functional group introduction, and esterification.

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