EBK ESSENTIAL ORGANIC CHEMISTRY
EBK ESSENTIAL ORGANIC CHEMISTRY
3rd Edition
ISBN: 8220100659461
Author: Bruice
Publisher: PEARSON
Question
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Chapter 11, Problem 52P

(a)

Interpretation Introduction

Interpretation:

The mechanism for the given reaction has to be proposed.

Concept introduction:

Carboxylic acid shows nucleophilic acyl substitution reaction.  The acid protonates the oxygen of carboxylic acid which results in increased electrophilicity of the carbonyl carbon.  The water molecule acts as a nucleophile and gets attached to the carbonyl carbon of the carboxylic acid.  The tetrahedral intermediate is formed stays in equilibrium with protonated and unprotonated form.  The H2O group gets eliminated from the tetrahedral intermediate to again from the carboxylic acid.

(b)

Interpretation Introduction

Interpretation:

To predict the reside of labeled oxygen in the product when a carboxylic acid is dissolved in isotopically labeled methanol and acid catalyst is added to it.

Concept introduction:

Carboxylic acid reacts with alcohol in the presence of a strong acid to form an ester. Carbonyl oxygen of carboxylic acid gets protonated by the acid resulting in increased electrophilicity of the carbonyl carbon. Alcohol can act as a nucleophile which gets attached to the carbonyl carbon after that tetrahedral intermediate is formed. A proton is removed from alkoxy group (OR) group then the hydroxy group gets eliminated to form an ester.

(c)

Interpretation Introduction

Interpretation:

To predict the labeled reside in the product when ester is dissolved in isotopically labeled water(H2O18) and acid catalyst is added to them.

Concept introduction:

Ester undergoes hydrolysis when dissolved in water with acid. Carbonyl oxygen of ester gets protonated by the acid resulting in increased electrophilicity of the carbonyl carbon. Water can act as a nucleophile which gets attached to the carbonyl carbon of ester after that tetrahedral intermediate is formed. A proton is removed from OH2 group then the alkoxy (OR) group gets eliminated to producecarboxylic acid and water.

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Chapter 11 Solutions

EBK ESSENTIAL ORGANIC CHEMISTRY

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