Provide the reaction mechanism for this reaction and identify the final product. OEt NaOEt, EtOH

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
Chapter7: Alkynes
Section: Chapter Questions
Problem 7.29P
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Provide the reaction mechanism for this reaction and identify the final product.
OEt
NaOEt, EtOH
Transcribed Image Text:Provide the reaction mechanism for this reaction and identify the final product. OEt NaOEt, EtOH
Expert Solution
Step 1

The given reaction is an example of the claisen condensation reaction which results in the formation of a beta-keto ester.

In the given reaction the two esters present are ethyl benzoate and ethyl butanoate. The ethyl benzoate does not consists of any hydrogen atom present at the alpha carbon of the carbonyl group, while there are two hydrogen atoms present on the alpha carbon of the carbonyl group in ethyl butanoate. So the first step of the reaction mechanism involves the abstraction of one of the hydrogen presents on the alpha carbon by the base NaOEt whic results in the formation of a carbanion. 

 

Chemistry homework question answer, step 1, image 1

Step 2

In the next step, the carbanion formed will act as a nucleophile and attacks on the carbonyl carbon of the ethyl benzoate followed by the removal of EtO- to form a beta-keto ester. 

Chemistry homework question answer, step 2, image 1

 

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