REACTIONS OF CARBOXYLIC ACID DERIVATIVES

Introduction

Reactions

Carboxylic acids

Preparation

Introduction

This page focuses on the preparation of and reactions of carboxylic acid derivatives.

Reactions

Carboxylic acids

Preparation

Oxidative cleavage of alkynes

Oxidation of primary alcohols

Oxidation of alkylbenzenes. Note the necessity of a proton at the benzylic position.

Saponification of esters with sodium hydroxide followed by H3O+

Acid-catalyzed hydrolysis of esters

Acid-catalyzed hydrolysis of nitriles. Note that this mechanism includes hydrolysis of amides.

Treating carbon dioxide with a Grignard reagent and then H3O+ to form a carboxylic acid

Reactions

Reduction of a carboxylic acid with LAH.

Fischer esterification. Note the reversibility of all the steps: you can treat an ester with H3O+ to get the carboxylic acid.

Conversion to acid chloride with thionyl chloride and pyridine.

Acid chlorides

Reactions

Hydrolysis of acid chlorides

Alcoholysis of acid chlorides

Aminolysis of acid chlorides. Note that you can use NH3, NRH2, or NR2H to form primary, secondary, and tertiary amides, respectively.

Reduction of acid chloride to primary alcohol using LAH and H3O+ workup

Reduction of acid chloride using lithium tri(t-butoxy)aluminum hydride and water workup

Reduction of acid chloride using Grignard reagent

Reduction of acid chloride using Gilman reagent

Synthesis of acid anhydride

Acid anhydrides

Reactions that use acid anhydrides are very similar to those of acid chlorides, with a different leaving group. Thus a full discussion will be omitted here, as acid chloride reactions have been discussed extensively. Of particular note, however, is the use of acid anhydrides to protect alcohols. Deprotection can be achieved with sodium hydroxide. Amines can also be protected and deprotected.