4. Which of the following compounds can be prepared by a malonic ester synthesis? Show the alkyl halide you would use in each case. (a) Ethyl pentanoate ⒸEthyl 2-methylbutanoate (b) Ethyl 3-methylbutanoate (d) Ethyl 2,2-dimethylpropanoate

4. Which of the following compounds can be prepared by a malonic ester synthesis? Show the alkyl halide you would use in each case. (a) Ethyl pentanoate ⒸEthyl 2-methylbutanoate (b) Ethyl 3-methylbutanoate (d) Ethyl 2,2-dimethylpropanoate

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

Chapter19: Enolate Anions And Enamines

Section: Chapter Questions

Problem 19.48P

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Question

4. Which of the following compounds can be prepared by a malonic ester synthesis? Show the alkyl halide you
would use in each case.
(a) Ethyl pentanoate
© Ethyl 2-methylbutanoate
(b) Ethyl 3-methylbutanoate
(d) Ethyl 2,2-dimethylpropanoate

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Step 1: Malonic-ester synthesis

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Step 2: Malonic-ester synthesis of ethyl pentanoate

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Step 3: Malonic-ester synthesis of ethyl-3-methylbutanoate and ethyl-2-methylbutanoate

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