ABSTRACT

Carboxylic acids are molecules that possess a –CO2H functional group. Carboxylic acids are produced from the oxidation of primary acids or aldehydes with Jones reagent or a Pinnick oxidation, respectively. Carboxylic acids are Brønsted–Lowry acids with moderate acidity that react to generate carboxylate anions, good and weakly basic nucleophiles. Carboxylic acids are moderate nucleophiles, at the carbonyl oxygen atom, and weakly acidic at the α-carbon. The dominant reactivity that will be considered in this chapter is electrophilicity at the carbonyl carbon atom, which can be enhanced by Lewis and Brønsted–Lowry acids. Readers will be introduced to means of converting carboxylic acid into various carboxylic acid derivatives: acid chlorides, acid anhydrides, esters, and amides.