Predict the products, propose mechanisms for the reactions of carboxylic acidderivatives with reducing agents, alcohols, amines, and organometallic reagentssuch as Grignard, organolithium, and organocuprate reagents

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter16: Chemistry Of Benzene: Electrophilic Aromatic Substitution
Section16.4: Substituent Effects In Electrophilic Substitutions
Problem 9P: Predict the major products of the following reactions: (a) Nitration of bromobenzene (b) Bromination...
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Predict the products, propose mechanisms for the reactions of carboxylic acid
derivatives with reducing agents, alcohols, amines, and organometallic reagents
such as Grignard, organolithium, and organocuprate reagents

Expert Solution
Step 1

Most of the carboxylic acids on reduction with reducing agents lead to the formation of primary alcohols. These reductions are normally carried out using a strong reducing agent, such as lithium aluminum hydride. Carboxylic acids are also reduced to alcohols in the presence of diborane. The carboxylic acid derivatives are also reduced by lithium aluminum hydride. The reaction and mechanism involved are as follows:

Chemistry homework question answer, step 1, image 1

Step 2

Carboxylic acids react with alcohols in the presence of an acid catalyst to form esters. This is known as the esterification reaction. The reaction of an acid and alcohol is shown below.

Chemistry homework question answer, step 2, image 1

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