20.1 Nomenclature of Carboxylic Acid Derivatives The hydrolysis of a carboxylic acid derivative is but one example of a nucleophilic acyl substitution. Nucleophilic acyl substitutions connect the various classes of car- boxylic 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 trans- formations both in synthetic organic chemistry and in biological chemist 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. 20.1 NOMENCLATURE OF CARBOXYLIC ACID DERIVATIVES with the exception of nitriles (RCEn, all carboxylic acid derivatives consist of an acyl group(RC-)attached to an electronegative atom. Acyl groups are named by replacing the-ic acid ending of the corresponding carboxylic acid by -yl. Acy! halides are named by placing the name of the appropriate halide after that of the acyl group CHaCO CH,=CHCH,CCI Acetyl chloride p-Fluorobenzoyl bromide Although acyl fluorides, bromides, and iodides are all known classes of organic com- pounds, they are encountered far less frequently than are acyl chlorides. Acyl chlorides will be the only acyl halides discussed in this chapter In naming carboxylic acid anhydrides in which both acyl groups are the same, we simply specify the acyl group and add the word"anhydride. "When the acyl groups are different, they are cited in alphabetical order. O CH3COCCH3 C6HSCOCC6H ChS COC(CH2)5CH Acetic anhydride Benzoic anhydride The alkyl group and the acyl group of an ester are specified independently. Esters are named as alkyl alkanoates. The alkyl group Rof RCoR'is cited first, followed by the acyl portion RC-. The acyl portion is named by substituting the suffix -ate for the ending of the corresponding acid. CH3COCH2CH3 CH3CH, COCH3 -CoCH,CHCI Ethyl acetate Methyl propanoate 2-Chloroethyl benzoate Back Forward Main MenuToc Study Guide ToC Student o MHHE WebsiteThe hydrolysis of a carboxylic acid derivative is but one example of a nucleophilic acyl substitution. Nucleophilic acyl substitutions connect the various classes of car￾boxylic 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 trans￾formations 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 RCPN. Nitriles may be hydrolyzed to carboxylic acids or to amides and, so, are indirectly related to the other functional groups presented here. 20.1 NOMENCLATURE OF CARBOXYLIC ACID DERIVATIVES With the exception of nitriles (RCPN), all carboxylic acid derivatives consist of an acyl group attached to an electronegative atom. Acyl groups are named by replacing the -ic acid ending of the corresponding carboxylic acid by -yl. Acyl halides are named by placing the name of the appropriate halide after that of the acyl group. Although acyl fluorides, bromides, and iodides are all known classes of organic com￾pounds, they are encountered far less frequently than are acyl chlorides. Acyl chlorides will be the only acyl halides discussed in this chapter. In naming carboxylic acid anhydrides in which both acyl groups are the same, we simply specify the acyl group and add the word “anhydride.” When the acyl groups are different, they are cited in alphabetical order. The alkyl group and the acyl group of an ester are specified independently. Esters are named as alkyl alkanoates. The alkyl group R of is cited first, followed by the acyl portion . The acyl portion is named by substituting the suffix -ate for the -ic ending of the corresponding acid. CH3COCH2CH3 O Ethyl acetate CH3CH2COCH3 O Methyl propanoate COCH2CH2Cl O 2-Chloroethyl benzoate RC± O X RCOR O X CH3COCCH3 O X O X Acetic anhydride C6H5COCC6H5 O X O X Benzoic anhydride C6H5COC(CH2)5CH3 O X O X Benzoic heptanoic anhydride F CBr O p-Fluorobenzoyl bromide CHCH2CCl O CH2 3-Butenoyl chloride CH3CCl O Acetyl chloride (RC±) O X 20.1 Nomenclature of Carboxylic Acid Derivatives 775 Back Forward Main Menu TOC Study Guide TOC Student OLC MHHE Website