Essential Organic Chemistry, Global Edition
Essential Organic Chemistry, Global Edition
3rd Edition
ISBN: 9781292089034
Author: Paula Yurkanis Bruice
Publisher: PEARSON
Question
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Chapter 11.8, Problem 16P

(a)

Interpretation Introduction

Interpretation:

To predict the products of the following transesterification reaction.

  ethyl benzoate + excess isopropanol + HCl

Concept Introduction:

Transesterification is the process of formation of a new ester molecule from the reaction of alcohol and an ester.  This is like hydrolysis of ester but here nucleophile is alcohol molecule instead of H2O.  As alkoxide groups have same basicity, therefore, an excess amount of alcohol is used.  The addition of an acid also increases the rate of reaction by protonating the carbonyl oxygen atom.  A general transesterification is written as,

Essential Organic Chemistry, Global Edition, Chapter 11.8, Problem 16P , additional homework tip  1

(b)

Interpretation Introduction

Interpretation:

To predict the products of the following transesterification reaction.

  phenyl acetate + excess ethanol + HCl

Concept Introduction:

Transesterification is the process of formation of a new ester molecule from the reaction of alcohol and an ester.  This is like hydrolysis of ester but here nucleophile is alcohol molecule instead of H2O.  As alkoxide groups have same basicity, therefore, an excess amount of alcohol is used.  The addition of an acid also increases the rate of reaction by protonating the carbonyl oxygen atom.  A general transesterification is  written as,

Essential Organic Chemistry, Global Edition, Chapter 11.8, Problem 16P , additional homework tip  2

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