Chapter 18 Carboxylic Acid Derivatives and Acyl Substitution

Carboxylic acid derivatives also contain a carbonyl unit, but they have a leaving group attached to the acyl carbon that facilitates acyl substitution reactions. Carboxylic acids contain a carbonyl that is connected to an OH unit in a COOH unit called the carboxyl group. The IUPAC nomenclature for carboxylic acids identifies the longest continuous chain for the acid that contains the CO2H unit. The nomenclature of each acid derivative is based on the carboxylic acid precursor, the “parent” acid. Esters are a combination of a carboxylic acid and an alcohol. Sulfonic acids form acid halides, anhydrides, esters, and amides. A detergent is a surfactant is usually an alkylbenzene sulfonate but more soluble in hard water than a soap.

Carboxylic Acids

Dicarboxylic Acids

Acid chlorides, Anhydrides, Esters, Amides

Sulfonic Acids

Acyl Substitution

Hydrolysis of Acid Chlorides and Anhydrides

Hydrolysis of Esters

Hydrolysis of Amides

Preparation of Acid Chlorides and Anhydrides

Preparation of Esters

Lactones

Preparation of Amides

Lactams and Imides

Reactions of Carboxylic Acid Derivatives

Nitriles and Organocuprates

Dicarboxylic Acid Derivatives

Baeyer-Villiger Oxidation

Sulfonic Acid Derivatives

Nitriles

Reactions of Acid Derivatives

Spectroscopy of Acid Derivatives

Fatty Acids and Lipids