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Predict the products of self-condensation of the following

Chapter 16, Problem 36P

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QUESTION:

Predict the products of self-condensation of the following esters.

(a) methyl propanoate + \(\mathrm{NaOCH}_{2}\)      (b) ethyl phenylacetate + \(\mathrm{NaOCH}_{2} \mathrm{CH}_{2}\)

Equation transcription:

Text transcription:

{NaOCH}{2}

{NaOCH}{2}{CH}{2}

Questions & Answers

QUESTION:

Predict the products of self-condensation of the following esters.

(a) methyl propanoate + \(\mathrm{NaOCH}_{2}\)      (b) ethyl phenylacetate + \(\mathrm{NaOCH}_{2} \mathrm{CH}_{2}\)

Equation transcription:

Text transcription:

{NaOCH}{2}

{NaOCH}{2}{CH}{2}

ANSWER:

Solution:

Here we have to predict the products of self-condensation of the following esters

Step 1

In self-condensation reaction, a chemical compound containing a carbonyl group acts both as the electrophile and the nucleophile.

(a) methyl propanoate + NaOCH3

+ NaOCH3 

(Methyl propanoate)    (Sodium methoxide)                  (1-methoxypentan-1,3-dione)

Methyl propanoate on addition with sodium methoxide  undergoes self condensation reaction and forms 1-methoxypentan-1,3-dione.

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