Reactions of Carboxylic Acids

Carboxylic acids undergo acid/base reactions as we saw in a previous section in this chapter.

By way of nucleophilic acyl substitution, carboxylic acids can be converted into various carboxylic acid derivatives (i.e. acid haildes, anhydries, esters and amides).  We will look at these reactions as we examine each of the carboxylic acid derivatives.

Carboxylic acids can be reduced to primary alcohols.

Reduction of Carboxylic Acids.

Carboxylic acids can be reduced to primary alcohols using LiAlH₄ (LAH) or BH₃.

Lithium aluminum hydride (LAH) is a powerful oxidizing reagent.

Borane (BH₃) will selectively reduce a carboxyl group in the presence of other carbonyls (aldehydes/ketones).

For example, the following compound when treated with borane results in the ketone not getting reduced.

If lithium aluminum hydride were employed both carbonyls would get reduced.