EP ESSENTIAL ORG.CHEM.-MOD.MASTERING
EP ESSENTIAL ORG.CHEM.-MOD.MASTERING
3rd Edition
ISBN: 9780133858501
Author: Bruice
Publisher: PEARSON CO
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Chapter 11, Problem 47P
Interpretation Introduction

Interpretation:

The reaction mechanism for the formation of an anhydride from the reaction of butanedioic acid and thionyl chloride has to be proposed.

Concept introduction:

Dicarboxylic acid reacts with thionyl chloride and undergoes nucleophilic substitiution reaction at one carboxylic group to form acyl chloride.

Acyl chloride is the most reactive carboxylic derivative functional group and hence nucleophilic OH group of the second carboxylic group attacks the carbonyl group of the acyl group. Chloride ion leaves as the leaving group and cyclic anhydride product from the dicarboxylic acid is formed.

Example:

  EP ESSENTIAL ORG.CHEM.-MOD.MASTERING   , Chapter 11, Problem 47P

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EP ESSENTIAL ORG.CHEM.-MOD.MASTERING

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