Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter23: Addition To A Carbonyl
Section: Chapter Questions
Problem 39CTQ
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Transcribed Image Text:**Exercise 3: Acetoacetic Ester Synthesis**
Propose an acetoacetic ester synthesis to make 5-ethyl-6-methyl-2-heptanone.
**Explanation:**
This question asks you to design a synthetic route using acetoacetic ester. The goal is to create the specified ketone, 5-ethyl-6-methyl-2-heptanone, using known reagents and reaction steps. The acetoacetic ester synthesis typically involves:
1. **Formation of an enolate ion** from the acetoacetic ester by treatment with a base.
2. **Alkylation** of the enolate ion with an appropriate alkyl halide.
3. **Hydrolysis and decarboxylation** of the resulting compound to yield the desired ketone.
Consider the molecular structure of 5-ethyl-6-methyl-2-heptanone as you select which alkyl halides to use and ensure that the necessary carbon skeleton is constructed through the synthesis.
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