Nomenclature of carboxylic acid derivatives

Acid Anhydrides When both acyl groups are the same, the word acid in the corresponding carboxylic acid is replaced by anhydride. When the two acyl groups are different, their corresponding carboxylic acids are cited in alphabetical order. 

The alkyl group and the acyl group of an ester are specified independently. Esters 

Aryl esters, that is, compounds of the type RCOAr, are named in an analogous way. 

Amides When naming amides, replace the -ic acid or -oic acid of the corresponding carboxylic acid with -amide. Substituents, irrespective of whether they are attached to the acyl group or the amide nitrogen, are listed in alphabetical order. Substitution on nitrogen is indicated by the locant N-. 

Similar to the -carbonyl chloride suffix for acyl chlorides, -carboxamide is used when an amide group is attached to a ring. 

The hydrolysis of a carboxylic acid derivative is but one example of a nucleophilic acyl substitution. Nucleophilic acyl substitutions connect the various classes of carboxylic acid derivatives, with a reaction of one class often serving as preparation of another. These reactions provide the basis for a large number of functional group transformations both in synthetic organic chemistry and in biological chemistry. 

Also included in this chapter is a discussion of the chemistry of nitriles, compounds of the type RC=N. Nitriles may be hydrolyzed to carboxylic acids or to amides and, so, are indirectly related to the other functional groups presented here. 

With the exception of nitriles (RC N), all carboxylic acid derivatives consist of an acyl O 

Although acyl fluorides, bromides, and iodides are aU known classes of organic compounds, they are encountered far less frequently than are acyl chlorides. Acyl chlorides will be the only acyl halides discussed in this chapter. 

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Table 22.2 summarizes the most important points about the nomenclature of carboxylic acid derivatives. 

Summary Nomenclature of Carboxylic Acid Derivatives and Nitriles... 

NOMENCLATURE OF CARBOXYLIC ACID DERIVATIVES The Acyl Group and Acid Derivatives... 

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