Chapter 11.8, Problem 17P

Interpretation Introduction

Interpretation:

To write the mechanism for the acid-catalyzed transesterification of ethyl acetate and methanol.

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 ${\text{H}}_{\text{2}}\text{O}$. 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,