Answered: H* R `OH R A tert-butyl ester…

Introductory Chemistry: An Active Learning Approach

6th Edition

ISBN:9781305079250

Author:Mark S. Cracolice, Ed Peters

Publisher:Mark S. Cracolice, Ed Peters

Chapter21: Organic Chemistry

Section: Chapter Questions

Problem 56E

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Question

Fischer esterification cannot be used to prepare tert-butyl esters. Instead, carboxylic acids are treated with 2-methyIpropene in the presence of an acid catalyst to generate them.

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(a) Why does the Fischer esterification fail for the synthesis of tert-butyl esters?
(b) Propose a mechanism for the 2-methylpropene method.

H*
R
`OH
R
A tert-butyl ester
2-Methylpropene
(Isobutylene)

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

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