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Show how you would synthesize the following compound beginning with acetoacetic ester. 1589.0 logra

Show how you would synthesize the following compound beginning with acetoacetic ester. 1589.0 logra

Organic Chemistry
Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter21: Benzene And The Concept Of Aromaticity
Section: Chapter Questions
Problem 21.58P
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**Title: Synthesis of a Cyclopentanone Derivative Using Acetoacetic Ester** **Objective:** To outline a method for synthesizing the specified compound, starting with acetoacetic ester. **Compound Structure:** The target compound features: - A five-membered cyclopentanone ring. - An ester functional group (carbonyl attached to an oxygen linked to another carbon). - A ketone group on the left side of the structure. **Synthesis Steps:** 1. **Starting Material:** - Use acetoacetic ester as the starting compound. This molecule contains a β-keto ester structure, ideal for further transformations. 2. **Base-Induced Alkylation:** - Deprotonate the acetoacetic ester at the active methylene group using a strong base (e.g., sodium ethoxide). - Perform an alkylation reaction by introducing the necessary alkyl halide to form a substituted acetoacetic ester. 3. **Ester Hydrolysis and Decarboxylation:** - Hydrolyze the ester group using an acid or base to convert it into a carboxylic acid. - Follow this by decarboxylation to expel carbon dioxide, yielding a β-keto acid. 4. **Cyclization:** - Undergo intramolecular condensation to form the cyclopentanone ring structure, facilitated by specific conditions or catalysts. 5. **Final Adjustments:** - Ensure the compound matches the target structure, particularly focusing on any necessary stereochemistry or additional functional groups. **Conclusion:** The effective synthesis of the cyclopentanone derivative from acetoacetic ester involves a sequence of strategic transformations, capitalizing on the reactive sites of the starting material to construct the desired compound with high specificity.
Transcribed Image Text:**Title: Synthesis of a Cyclopentanone Derivative Using Acetoacetic Ester** **Objective:** To outline a method for synthesizing the specified compound, starting with acetoacetic ester. **Compound Structure:** The target compound features: - A five-membered cyclopentanone ring. - An ester functional group (carbonyl attached to an oxygen linked to another carbon). - A ketone group on the left side of the structure. **Synthesis Steps:** 1. **Starting Material:** - Use acetoacetic ester as the starting compound. This molecule contains a β-keto ester structure, ideal for further transformations. 2. **Base-Induced Alkylation:** - Deprotonate the acetoacetic ester at the active methylene group using a strong base (e.g., sodium ethoxide). - Perform an alkylation reaction by introducing the necessary alkyl halide to form a substituted acetoacetic ester. 3. **Ester Hydrolysis and Decarboxylation:** - Hydrolyze the ester group using an acid or base to convert it into a carboxylic acid. - Follow this by decarboxylation to expel carbon dioxide, yielding a β-keto acid. 4. **Cyclization:** - Undergo intramolecular condensation to form the cyclopentanone ring structure, facilitated by specific conditions or catalysts. 5. **Final Adjustments:** - Ensure the compound matches the target structure, particularly focusing on any necessary stereochemistry or additional functional groups. **Conclusion:** The effective synthesis of the cyclopentanone derivative from acetoacetic ester involves a sequence of strategic transformations, capitalizing on the reactive sites of the starting material to construct the desired compound with high specificity.
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Given is organic compound.

We can synthesize this compound by acetoacetic ester synthesis reactions.


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