Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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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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Step 1: Interpretation of given problem
Given is organic compound.
We can synthesize this compound by acetoacetic ester synthesis reactions.
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