《有机化学》课程PPT教学课件（Organic Chemistry, William A. Price, Ph.D. PPT, La Salle University, L.G.WADE, JR., 8th Edition）Carboxylic Acid Derivatives

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