Pearson eText for Essential Organic Chemistry -- Instant Access (Pearson+)
Pearson eText for Essential Organic Chemistry -- Instant Access (Pearson+)
3rd Edition
ISBN: 9780137533268
Author: Paula 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,

Pearson eText for Essential Organic Chemistry -- Instant Access (Pearson+), 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,

Pearson eText for Essential Organic Chemistry -- Instant Access (Pearson+), Chapter 11.8, Problem 16P , additional homework tip  2

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+ HCl →? Draw the molecule on the canvas by choosing buttons from the Tools (for bonas), Atoms and Advanced Template toolbars. The single bond is active by default. + M C + H± 2D EXP. CONT. K ? L 1 H₁₂C [1] A HCN O S CH3 CH 3 CI Br HC H₂ CH CH CH3 - P F

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Pearson eText for Essential Organic Chemistry -- Instant Access (Pearson+)

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