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Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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Step 1 Introduction

On hydrolysis, esters undergo cleavage to produce carboxylic acid and alcohol. The reaction occurs in the presence of an aqueous acid(H₂SO₄) or an aqueous base(NaOH).

The mechanism of base hydrolysis involves the following steps.

The nucleophilic attack of carbonyl carbon by Hydroxyl ion(OH^-) resulting in tetrahedral intermediate.
The tetrahedral intermediate disintegrates by the release of the alkoxide group reforming carbonyl group.
Thus, acid is produced from the tetrahedral intermediate, and the alkoxide group converts to alcohol.

The mechanism of acid hydrolysis involves the following steps.

Protonation of ester carbonyl making it more electrophilic.
Water oxygen acts as the nucleophile attacking the electrophilic C=O group forming a tetrahedral intermediate.
Deprotonation of water group attached to the tetrahedral intermediate.
Alkoxide group is made a good leaving group by protonation.
Neutral methanol gets released.
Deprotonation of oxonium ion results in a carboxylic acid.

NOTE: According to Bartleby guidelines, one question should be answered. I am answering Q5.

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