EBK ESSENTIAL ORGANIC CHEMISTRY
EBK ESSENTIAL ORGANIC CHEMISTRY
3rd Edition
ISBN: 8220100659461
Author: Bruice
Publisher: PEARSON
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Chapter 11.12, Problem 23P
Interpretation Introduction

Interpretation:

To arrange the given amides in decreasing order of reactivity towards acid-catalyzed hydrolysis reaction.

Concept introduction:

The normal reaction of an amide with water does not give good yield of product. As amides are least reactive carboxylic acid derivatives so to increase the reactivity of amides a mineral acid is added. The addition of acid increases the reactivity of amide by making more electrophilic carbonyl carbon and it also helps in the elimination of amine part from amide via protonating the amine group during reaction and make it a good leaving group.

The reaction of water and amides in presence of acid gives a carboxylic acid as a product. The reaction eqaution is written as,

EBK ESSENTIAL ORGANIC CHEMISTRY, Chapter 11.12, Problem 23P

The reactivity of amide also depends upon the leaving tendency of amine part from acyl group. The weaker the base better will be the leaving group. The basicity of amines is decreased by decreasing the electron density from nitrogen atom of amine.

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EBK ESSENTIAL ORGANIC CHEMISTRY

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