Carboxylic acids can be reduced to primary alcohols with LiAlH4 or with BH3 followed by work-up with aqueous acid. In the reduction with LiAlH4, an intermediate aldehyde is formed, which is rapidly reduced to give the primary alcohol.
Heavy metal salts of carboxylic acids undergo decarboxylation on heating in organic solvents. In the presence of Br2, the radical intermediate is trapped as an alkyl bromide (the Hunsdiecker reaction).
Carboxylic acids can be converted into acid halides by reaction with SOCl2, phosgene, or PBr3.
Carboxylic acids can be converted into esters by reaction with the corresponding alcohol in the presence of an acid catalyst (Fischer esterification), by alkylation of the carboxylate anion with an alkyl halide in an SN2 reaction, or by reaction with diazomethane (methyl esters only).
Reactions of Carboxylic Acids