Essential Organic Chemistry Study Guide & Solution Manual, Books a la Carte Edition
Essential Organic Chemistry Study Guide & Solution Manual, Books a la Carte Edition
3rd Edition
ISBN: 9780134255644
Author: Bruice, Paula Yurkanis
Publisher: PEARSON
Question
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Chapter 11.14, Problem 28P

(a)

Interpretation Introduction

Interpretation:

The acyl chloride and carboxylate ion that could be used to form the given mixed anhydride have to be found.

Concept Introduction:

Mixed anhydrides are unsymmetrical anhydrides which have different alkyl groups.

Example:

  Essential Organic Chemistry Study Guide & Solution Manual, Books a la Carte Edition, Chapter 11.14, Problem 28P , additional homework tip  1

The acetyl chloride and carboxylate ion that could be used to form any given mixed anhydride can be analysed using the simple retro analysis as shown here:

  Essential Organic Chemistry Study Guide & Solution Manual, Books a la Carte Edition, Chapter 11.14, Problem 28P , additional homework tip  2

(b)

Interpretation Introduction

Interpretation:

The other reagents that could be used to form the given mixed anhydride have to be found.

Concept Introduction:

Mixed anhydrides are unsymmetrical anhydrides which have different alkyl groups.

Example:

Essential Organic Chemistry Study Guide & Solution Manual, Books a la Carte Edition, Chapter 11.14, Problem 28P , additional homework tip  3

Any anhydride can be obtained using the following two pairs of reagents:

  1. 1. Acetyl chloride and a carboxylate ion.

  Essential Organic Chemistry Study Guide & Solution Manual, Books a la Carte Edition, Chapter 11.14, Problem 28P , additional homework tip  4

  1. 2. Two different carboxylic acids if mixed or unsymmetrical anhydride has to be formed or two same carboxylic acids if symmetrical anhydride has to be formed.

  Essential Organic Chemistry Study Guide & Solution Manual, Books a la Carte Edition, Chapter 11.14, Problem 28P , additional homework tip  5

For any simple anhydride, the two carboxylic acids from which it has been formed can be found by the simple retro analysis as shown here:

  Essential Organic Chemistry Study Guide & Solution Manual, Books a la Carte Edition, Chapter 11.14, Problem 28P , additional homework tip  6

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Essential Organic Chemistry Study Guide & Solution Manual, Books a la Carte Edition

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