Essential Organic Chemistry, Global Edition
Essential Organic Chemistry, Global Edition
3rd Edition
ISBN: 9781292089034
Author: Paula Yurkanis Bruice
Publisher: PEARSON
Question
Book Icon
Chapter 11.14, Problem 27P
Interpretation Introduction

Interpretation:

To write the mechanism for the reaction of an acyl chloride with acetate ion to form an acid anhydride.

Concept introduction:

The reaction of an acyl chloride with acetate ion is a nucleophilic substitution reaction. The acetate ion acts as a nucleophile and attacks the carbonyl carbon of the acyl chloride. The attack results in the formation of a tetrahedral intermediate. Some chloride group attached to the carbonyl carbon acts as a leaving group in the reaction and results in the collapse of the tetrahedral intermediate to form the corresponding anhydride.

Blurred answer
Students have asked these similar questions
Propose a mechanism for the reaction of bisphenol A with phosgene.
When a student treated butanedioic acid with thionyl chloride, she was surprised to find that the product she obtained was an anhydride rather than an acyl chloride. Propose a mechanism to explain why she obtained an anhydride.
Propose mechanisms for the nucleophilic acyl substitutions to form ethyl benzoate andN-methylacetamide

Chapter 11 Solutions

Essential Organic Chemistry, Global Edition

Knowledge Booster
Background pattern image
Similar questions
SEE MORE QUESTIONS
Recommended textbooks for you
  • Text book image
    Organic Chemistry
    Chemistry
    ISBN:9781305080485
    Author:John E. McMurry
    Publisher:Cengage Learning
    Text book image
    Organic Chemistry
    Chemistry
    ISBN:9781305580350
    Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
    Publisher:Cengage Learning
    Text book image
    Introduction to General, Organic and Biochemistry
    Chemistry
    ISBN:9781285869759
    Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
    Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9781305080485
Author:John E. McMurry
Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Text book image
Introduction to General, Organic and Biochemistry
Chemistry
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Cengage Learning