Carboxylic Acid Derivatives Acid Chlorides Acid Anhydrides Esters Amides Nitriles Nucleophilic Acyl Substitution
Carboxylic Acid Derivatives Acid Chlorides Acid Anhydrides Esters Amides Nitriles Nucleophilic Acyl Substitution
300 Examples l°amides￥ (MW55-60) bp(C) 200 N-methyl2°amides O N.N-dimethyl 3 amides CH3一C- NH2 222 0 acid 100 acids●x CH3一C-OH 118 chlorides nitriles A CHCH2CH2OH 97 1°alcohols CHCH2-C=N 97 methyl￥ 0 0 esters H-C一OCH 32 CH:CH2CH2CH3 0 -100 ○n-alkanes 20 60 100 140 180 molecular weight
Reactivity of Acid Derivatives Reactivity Derivative Leaving group Basicity more reactive less basic acid chloride Ci- anhydride ester 0-R amide -NH2 less reactive carboxylate more basic
Reactivity of Acid Derivatives
Interconversions of acid derivatives O acid chloride RCCI R anhydride SOCl2 R-C-OR' ester amide R-C-NH2 carboxylate R一C一
Nucleophilic Acyl Substitution R-C-X+Nuc:R-C-Nuc+:X- carboxylic acid acyl halide anhydride 0 R-C-O-R'R一C-NH, ester amide
Nucleophilic Acyl Substitution