Answered: Which one of the following carboxylic…

Which one of the following carboxylic acid derivatives can undergo nucleophilic acyl substitution without the need of an acid to catalyze the reaction? O CH3C=N ОН `NH2

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter19: Aldehydes And Ketones: Nucleophilic Addition Reactions

Section19.SE: Something Extra

Problem 28VC

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Question

Which one of the following carboxylic acid derivatives can undergo nucleophilic acyl
substitution without the need of an acid to catalyze the reaction?
O CH3C=N
ОН
`NH2

Expert Solution

Step 1

Nucleophilic acyl substitution (acyl transfer reaction) occurs by a two-step mechanism.

First, attack of the carbonyl carbon atom of an acyl derivative by a nucleophile yields a tetrahedral intermediate.

The tetrahedral intermediate can then eject a leaving group.

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