Carboxylic acid derivatives include acid halides, acid anhydrides, esters, amides, and nitriles. Acid halides have the ending -oyl followed by the name of the halide, such as chloride. Anhydrides have the ending -oicanhydride, esters have a prefix for the alkyl group and the ending -oate, and nitriles have the ending -nitrile.
Derivatives of Carboxylic Acid
Carboxylic acid derivatives include carboxylate, acid chloride, acid anhydride, ester, amide, and nitrile.
Acid halides are named by substituting -yl for -ic, followed by the name of the halide.
Examples of Acid Halides
Using the IUPAC system, acid halides are named by substituting the -yl ending for the -ic ending and adding the name of the halide at the end.
An acid anhydride is an organic compound that contains two carbonyl groups (C=O) bound to the same oxygen atom with (RCO)2O stoichiometry. To name acid anhydrides, replace acid with anhydride. If the molecule has different acyl groups, they should be listed in alphabetical order.
Examples of Acid Anhydrides
Using the IUPAC system, acid anhydrides are named by substituting anhydride for acid. Multiple acyl groups are listed in alphabetical order.
An ester is an organic compound that contains a carboxyl unit in which a hydroxyl group is replaced by an alkyl or aryl group, giving it R−C(=O)OR′ or R−COOR′ stoichiometry. Ester derivatives of carboxylic acids are given two names. The first name denotes the alkyl group attached to the sp3-hybridized oxygen; the second name indicates the carboxylic acid. Then -ate is substituted for -ic or -oic.
Examples of Esters
Using the IUPAC system, esters are named by first naming the alkyl group attached to the sp3-hybridized oxygen; the second name indicates the carboxylic acid. Then substitute -ate for -ic or -oic. For example, a two-carbon ester that has a three-carbon group attached to the oxygen would be named propyl acetate.
An amide is an organic compound that contains a carbonyl (C=O) linked to a nitrogen atom through a C−N bond. It has a general RC(=O)NRR′ stoichiometry. To name an amide, substitute the -oic or -ic acid with -amide. Substituents located on the N are indicated by an N in the name.
Examples of Amides
Formamide is a one-carbon primary amide, and N,N-dimethylformamide is a one-carbon tertiary amide.
A nitrile is an organic compound that has a carbon triple bonded to a nitrogen with RCN stoichiometry; it is also called a cyano group. To name nitriles, substitute -onitrile or -nitrile for the -ic or -oic acid suffix. Nitriles are also commonly referred to by their common names, which may include cyanide.
Examples of Nitriles
Ethanenitrile is a two-carbon nitrile, and 2-methylpropanenitrile is a three-carbon nitrile.
