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Chapter 18: Q37P (page 906)

Diazomethane can be used to convert a carboxylic acid to a methyl ester. Propose a mechanism for this reaction.

Short Answer

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Diazomethane constitutes a molecule comprising methylene carbon and dinitrogen connected to it. It is made by the decomposition of several derivatives of N-methyl-N-nitrosamines. The treatment of carboxylic acid with diazomethane produces methyl esters.

Step by step solution

01

Diazomethane

Diazomethane constitutes a molecule comprising methylene carbon and dinitrogen connected to it. It is made by the decomposition of several derivatives of N-methyl-N-nitrosamines. The treatment of carboxylic acid with diazomethane produces methyl esters.

02

The mechanism for the conversion of carboxylic acid to an ester using diazomethane

The first step involves the protonation of diazomethane by the carboxylic acid that forms a carboxylate ion.

This ion attacks the methyl group of CH3-N2, in which CH3-N2 is a good alkylating agent and N2is a good leaving group. This leads to the formation of methyl ester and N2. The mechanism is given below.

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