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
I.U.P.A.C.Nomenclature (uses carboxylic acid template) 八人3 drop "ic acid"add "yl chloride" drop "acid"add "anhydride" pentanoyl chloride pentanoic anhydride OCH3 NH2 "alkyl"drop "ic acid"add "ate" drop "oic acid"add "amide" methyl pentanoate pentanamide CN drop "ic acid"add "e nitrile" pentanenitrile
I.U.P.A.C. Nomenclature (uses carboxylic acid template) O Cl O O O O OCH3 O NH2 CN pentanoyl chloride pentanoic anhydride methyl pentanoate pentanamide pentanenitrile drop "ic acid" add "yl chloride" drop "acid" add "anhydride" "alkyl" _ drop "ic acid" add "ate" drop "oic acid" add "amide" drop "ic acid" add "e_nitrile
Acid Chlorides OCH3 CCI o-me thoxybe nzoyl chloride (E)2-octe noyl chloride 0 CH3O CH2CCI (p-me thoxyphe nylace tyl chloride
Acid Chlorides CCl OCH3 O o-methoxybenzoyl chloride O Cl (E) 2-octenoyl chloride CH2 CCl O CH3 O (p-methoxyphenyl)acetyl chloride
Acid Anhydrides CH butanoic anhydride ace tic be nzoic anhydride butyric anhydride OH HO succinnic acid succinnic anhydride
Acid Anhydrides O O O butanoic anhydride butyric anhydride C O C O O CH3 acetic benzoic anhydride O O O succinnic anhydride OH O O HO succinnic acid
Esters COCH2CH2CH propyl be nzoate (Z cyclope ntyl 2-bute noate 0 COCH-CH(CH3) CH-COCHCH3 isobutyl cyclohe xane carboxylate e thyl phe nylace tate
Esters COCH2 CH2 CH3 O O O propyl benzoate (Z) cyclopentyl 2-butenoate COCH2 CH(CH3 ) 2 O isobutyl cyclohexanecarboxylate CH2 COCH2 CH3 O ethyl phenylacetate
Amides CNH2 CH H2N meta me thylbe nzamide 2-e thyl-3-me thylpe ntanamide o-e thyl-B-me thylvale ramide CN(CH3)2 HCN H N-be nzylformamide N,N-dime thylcyclope ntane carboxamide
Amides CH3 CNH2 O meta methylbenzamide H2N O 2-ethyl-3-methylpentanamide -ethyl--methylvaleramide CN(CH3) 2 O N,N-dimethylcyclopentanecarboxamide HCN O H N-benzylformamide