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
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
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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Transcribed Image Text: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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