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The mechanism for hydrolysis of an ester in aqueous acid involves formation of a tetrahedral carbonyl addition intermediate. Evidence in support of this mechanism comes from an experiment designed by Myron Bender. He first prepared ethyl benzoate enriched with oxygen-18 in the carbonyl oxygen and then carried out acid-catalyzed hydrolysis of the ester in water containing no enrichment in oxygen-18. If he stopped the experiment after only partial hydrolysis and isolated the remaining ester, the recovered ethyl benzoate lost a portion of its enrichment in oxygen-18. In other words, some exchange had occurred between oxygen-18 of the ester and oxygen-16 of water. Show how this observation bears on the formation of a tetrahedral carbonyl addition intermediate during acid-catalyzed ester hydrolysis.

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Organic Chemistry

8th Edition
William H. Brown + 3 others
Publisher: Cengage Learning
ISBN: 9781305580350

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Section
BuyFindarrow_forward

Organic Chemistry

8th Edition
William H. Brown + 3 others
Publisher: Cengage Learning
ISBN: 9781305580350
Chapter 18, Problem 18.21P
Textbook Problem
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The mechanism for hydrolysis of an ester in aqueous acid involves formation of a tetrahedral carbonyl addition intermediate. Evidence in support of this mechanism comes from an experiment designed by Myron Bender. He first prepared ethyl benzoate enriched with oxygen-18 in the carbonyl oxygen and then carried out acid-catalyzed hydrolysis of the ester in water containing no enrichment in oxygen-18. If he stopped the experiment after only partial hydrolysis and isolated the remaining ester, the recovered ethyl benzoate lost a portion of its enrichment in oxygen-18. In other words, some exchange had occurred between oxygen-18 of the ester and oxygen-16 of water. Show how this observation bears on the formation of a tetrahedral carbonyl addition intermediate during acid-catalyzed ester hydrolysis.

Interpretation Introduction

Interpretation:

Way in which the given observation bears on the formation of a terahedral carbonyl addition intermediate during acid-catalysed easter hydrolyis, the corresponding transformation has to be shown.

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,

Organic Chemistry, Chapter 18, Problem 18.21P

Explanation of Solution

This observation can only be explained by proposing reversible formation of a tetrahedral carbonyl addition intermediate and assumption that exchange of oxygen-18 in this manner is more rapid than collapse of the intermediate to give benzoic acid and ethanol...

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Chapter 18 Solutions

Organic Chemistry
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