3. Propose an acetoacetic ester synthesis to make 5-ethyl-6-methyl-2-heptanone.

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
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Chapter23: Addition To A Carbonyl
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**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.
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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