Nucleophilic acyl substitution

Amide formation: p-anisidine (an aniline) with Ac2O gives N-(4-methoxyphenyl)acetamide.

Acid chloride formation: nicotinic acid (a carboxylic acid) with SOCl2 gives nicotinoyl chloride (the acid chloride).

Fischer esterification: adipic acid (a carboxylic acid) with CH3CH2OH; H2SO4; toluene, Δ gives diethyl adipate (the ester).

Nitrile hydrolysis: 2-methylbenzonitrile with H2SO4; H2O, Δ gives 2-methylbenzoic acid (the carboxylic acid).

Amide dehydration to nitrile: fumaramide with P2O5; Δ gives fumaronitrile.

Saponification: (4-nitrophenyl)methyl acetate (an ester) with NaOH, Δ; aq. CH3OH gives 4-nitrobenzyl alcohol (the benzylic alcohol).

Amide hydrolysis: caprolactam (a seven-membered lactam) with 1) aq. HCl; 2) Amberlite resin gives 6-aminohexanoic acid (the carboxylic acid).

Ester from acid chloride: tert-butanol (a tertiary alcohol) and acetyl chloride (an acid chloride) with CH3CH2OCH2CH3, Δ gives tert-butyl acetate (the ester).

Anhydride formation: 2-furancarboxylic acid with Ac2O, NaOAc; benzene, Δ gives furan carboxylic-acetic acid anhydride and acetic acid (the carboxylic acid).

Other acyl substitution: benzoyl chloride (an acid chloride) with KSH gives thiobenzoic acid (the acyl substitution product).

Anhydride opening: citraconic anhydride (a cyclic anhydride) with H2O gives citraconic acid (the half-ester or diacid).

Lactamization: methyl 4-amino-4-methylpentanoate (a primary amine) with CH3CH2OH; 55-60 °C gives 5,5-dimethylpyrrolidin-2-one (the five-membered lactam).

Anhydride formation: benzoic acid (a carboxylic acid) and acetic anhydride gives acetic benzoic anhydride and acetic acid (the carboxylic acid).

Amide formation: aniline and diketene with Δ; benzene gives acetoacetanilide (the amide).

Nitrile hydrolysis: ethyl 2,4-dicyano-2-phenylbutanoate (a nitrile) with aq. HCl; AcOH, Δ gives 2-phenylpentanedioic acid (the carboxylic acid).

Amide dehydration to nitrile: isobutyramide with P2O5; Δ gives isobutyronitrile.

Amide dehydration to nitrile: nicotinamide with P2O5; Δ gives 3-cyanopyridine (the nitrile).

Acid chloride formation: monomethyl sebacate (a carboxylic acid) with SOCl2; Δ gives methyl 10-chloro-10-oxodecanoate (the acid chloride).

Amide formation: piperidine (a secondary amine) with NaOH, H2O gives benzoylpiperidine (the amide).

Amide formation: methyl 10-chloro-10-oxodecanoate (an acid chloride) with NH4OH; 8 °C gives 9-carbamoyl-nonanoic acid methyl ester (the amide).

Fischer esterification: lactic acid (a carboxylic acid) with iPrOH, H2SO4; benzene, Δ gives isopropyl lactate (the ester).

Amide dehydration to nitrile: cyanoacetamide with PCl5, Δ gives malononitrile.

Acid chloride formation: butyric acid (a carboxylic acid) with SOCl2; Δ gives butyryl chloride (the acid chloride).

Fischer esterification: mandelic acid (a carboxylic acid) with CH3CH2OH; HCl, Δ gives ethyl mandelate (the ester).

Anhydride opening: succinic anhydride (a cyclic anhydride) with CH3OH; Δ gives monomethyl succinate (the half-ester or diacid).

Amide formation: ethyl benzoylacetate (a β-keto ester) with xylene, Δ gives 3-oxo-3-phenylpropionanilide (the amide).

Transesterification: methyl acrylate (an α,β-unsaturated ester) with p-TsOH; n-BuOH, Δ; hydroquinone gives butyl acrylate (the α,β-unsaturated ester).

Saponification: diethyl 2-benzylpropanedioate (a malonate ester) with 1) KOH; 2) HCl gives benzylmalonic acid (the carboxylic acid).

Acid chloride formation: 4-nitrobenzoic acid (a carboxylic acid) with PCl5, Δ gives 4-nitrobenzoyl chloride (the acid chloride).

Fischer esterification: acetonedicarboxylic acid with CH3CH2OH; (2 equiv.); HCl gives diethyl acetonedicarboxylate (the β-keto ester).

Carbamate formation: 2-methyl-1-naphthol (a phenol) with Et3N; PhMe gives (2-methylnaphthalen-1-yl) N-methylcarbamate.

Transesterification: morpholine-2,5-dione (a six-membered lactone) with 1); KOEt; THF; 2) AcOH gives ethyl 2-[(2-hydroxyacetyl)amino]acetate (the ester).

Saponification: 2,2,5-trimethyl-5-phenyl-1,3-dioxolan-4-one (a five-membered lactone) with 1); NaOH; 2) HCl / H2O gives atrolactic acid (the carboxylic acid) and acetone (the methyl ketone).

Amide formation: aniline with CH2Cl2 gives 2-methylacetanilide (the amide).

Amide formation: phthaloyl chloride (an acid chloride) with 1); Et3N; CH2Cl2; 2) HCl / H2O gives tert-butyl 1,4-dioxo-2,3-benzoxazine-3-carboxylate (the amide).

Amide formation: cyclohexanecarbonyl chloride (an acid chloride) with Et3N; CH2Cl2 gives N-methylcyclohexanecarboxamide.

Amide formation: 5,5-dimethyl-3-(3-methylbenzoyl)imidazolidine-2,4-dione (an imide) with MeCN gives N,N-diethyl-m-toluamide.

Amide formation: p-toluidine (an aniline) with AcOH gives 4-methylacetanilide (the amide).

Ester from acid chloride: benzoin (a benzylic alcohol) with Ac2O; AcOH, H2SO4 gives benzoin acetate (the ester).

Nitrile hydrolysis: 3-butenenitrile with HCl, H2O; Δ gives 3-butenoic acid (the carboxylic acid).

Anhydride formation: acetyl chloride (an acid chloride) and acetic acid (a carboxylic acid) with pyridine gives acetic anhydride.

Lactamization: 4-aminocyclohexanecarboxylic acid (a primary amine) with Dowtherm A; Δ gives the six-membered lactam.

Amide formation: glycine (a primary amine) with Ac2O, H2O gives acetylglycine (the amide).

Amide hydrolysis: caprolactam (a seven-membered lactam) with HCl, H2O; Δ gives 6-aminohexanoic acid (the carboxylic acid).

Acid chloride formation: isobutyric acid (a carboxylic acid) with SOCl2 gives isobutyryl chloride (the acid chloride).

Amide formation: isobutyryl chloride (an acid chloride) with NH4OH gives isobutyramide.

Nitrile hydrolysis: 3-aminopropionitrile with Ba(OH)2; H2O, 90 °C gives beta-alanine (the carboxylic acid).

Nitrile hydrolysis: sodium cyanoacetate (a nitrile) with aq. NaOH gives disodium malonate (the carboxylate).

Other acyl substitution: a carbamate with i-PrLi (adds to C=S; the alkoxide then displaces OtBu from the Boc group) gives the acyl substitution product and the acyl substitution product.

Saponification: methyl 3-nitrobenzoate (an ester) with 1) aq. NaOH, Δ; 2) HCl gives 3-nitrobenzoic acid (the carboxylic acid).

Amide dehydration to nitrile: cyanoacetamide with POCl3, Δ; ethylene dichloride gives malononitrile.

Amide formation: ethyl lactate (an ester) with liquid NH3 gives lactamide.

Acid chloride formation: a carboxylic acid with SOCl2; Δ gives the acid chloride.

Nitrile hydrolysis: phenylacetonitrile with HCl, H2O gives benzeneacetamide.

Amide hydrolysis: N-(2-bromo-4-methylphenyl)acetamide with 1) aq. HCl, Δ (amide hydrolysis); 2) NaOH gives 2-bromo-4-methylaniline.

Amide formation: glycine (a primary amine) with NaOH, H2O; 2) HCl gives hippuric acid (the amide).

Amide hydrolysis: an amide with HCl; H2O, Δ gives (+-)-methionine (the carboxylic acid).

Fischer esterification: oxalic acid (a carboxylic acid) with CH3CH2OH; (2 equiv.); CCl4, Δ gives diethyl oxalate (the ester).

Amide dehydration to nitrile: chloroacetamide with P2O5, Δ; trimethylbenzene gives chloroacetonitrile.

Fischer esterification: oxalic acid (a carboxylic acid) with CH3OH; (2 equiv.); H2SO4 gives dimethyl oxalate (the ester).

Fischer esterification: 3-chloro-1-propanol (a primary alcohol) with p-TsOH, AcOH; benzene, Δ gives 3-chloropropyl acetate (the ester).

Amide formation: cyclohexanecarbonyl chloride (an acid chloride) with (CH3)2NH; benzene gives N,N-dimethylcyclohexanecarboxamide.

Acid chloride formation: cyclohexanecarboxylic acid with SOCl2; Δ gives cyclohexanecarbonyl chloride (the acid chloride).

Saponification: tert-butyl 2-decylacrylate (an α,β-unsaturated ester) with 1) KOH, CH3CH2OH, Δ; 2) H2SO4, H2O gives 2-decyl acrylic acid (the α,β-unsaturated carboxylic acid).

Ester from acid chloride: 4-methylbenzoyl chloride (an acid chloride) with (CH3)3COLi gives 1,1-dimethylethyl 4-methylbenzoate (the ester).

Ester from acid chloride: a 1,2-diol with acetyl chloride gives the ester.

Nitrile hydrolysis: glutaronitrile with HCl, H2O; Δ gives glutaric acid (the carboxylic acid).

Acid chloride formation: itaconic acid (a carboxylic acid) with PCl5 (2 equiv.); Δ gives 2,2-methylenesuccinyl dichloride (the acid chloride).

Amide formation: aniline gives benzanilide (the amide).

Fischer esterification: a carboxylic acid with CH3COCl; CH3OH gives the ester.

Acid chloride formation: O-acetylmandelic acid (a carboxylic acid) with SOCl2 gives 1-(chloroformyl)benzyl acetate (the acid chloride).