17 10 Reaction with Primary Amines Imines Some

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17. 10 Reaction with Primary Amines: Imines

17. 10 Reaction with Primary Amines: Imines

Some reactions of aldehydes and ketones progress beyond the nucleophilic addition stage Acetal formation

Some reactions of aldehydes and ketones progress beyond the nucleophilic addition stage Acetal formation Imine formation Compounds related to imines Enamines The Wittig reaction

Some reactions of aldehydes and ketones progress beyond the nucleophilic addition stage Acetal formation

Some reactions of aldehydes and ketones progress beyond the nucleophilic addition stage Acetal formation Imine formation Compounds related to imines Enamines The Wittig reaction

Imine (Schiff's Base) Formation H 2 N • • + C O • •

Imine (Schiff's Base) Formation H 2 N • • + C O • • HN C • • O • • R R a carbinolamine • • N R C (imine) + H 2 O H

Example O CH + CH 3 NH 2 CH=NCH 3 + H 2 O

Example O CH + CH 3 NH 2 CH=NCH 3 + H 2 O N-Benzylidenemethylamine (70%)

Example O CH + CH 3 NH 2 OH CH NHCH 3 CH=NCH 3

Example O CH + CH 3 NH 2 OH CH NHCH 3 CH=NCH 3 + H 2 O N-Benzylidenemethylamine (70%)

Example O + (CH 3)2 CHCH 2 NH 2 NCH 2 CH(CH 3)2 +

Example O + (CH 3)2 CHCH 2 NH 2 NCH 2 CH(CH 3)2 + H 2 O N-Cyclohexylideneisobutylamine (79%)

Example O + (CH 3)2 CHCH 2 NH 2 OH NHCH 2 CH(CH 3)2

Example O + (CH 3)2 CHCH 2 NH 2 OH NHCH 2 CH(CH 3)2 NCH 2 CH(CH 3)2 + H 2 O N-Cyclohexylideneisobutylamine (79%)

Some reactions of aldehydes and ketones progress beyond the nucleophilic addition stage Acetal formation

Some reactions of aldehydes and ketones progress beyond the nucleophilic addition stage Acetal formation Imine formation Compounds related to imines Enamines The Wittig reaction

Some reactions of aldehydes and ketones progress beyond the nucleophilic addition stage Acetal formation

Some reactions of aldehydes and ketones progress beyond the nucleophilic addition stage Acetal formation Imine formation Compounds related to imines Enamines The Wittig reaction

Reaction with Derivatives of Ammonia H 2 N G + R 2 C O

Reaction with Derivatives of Ammonia H 2 N G + R 2 C O R 2 C N G + H 2 O

Reaction with Derivatives of Ammonia H 2 N G + R 2 C H

Reaction with Derivatives of Ammonia H 2 N G + R 2 C H 2 N OH hydroxylamine O R 2 C N G + H 2 O R 2 C NOH oxime

Example O CH 3(CH 2)5 CH + H 2 NOH CH 3(CH 2)5 CH

Example O CH 3(CH 2)5 CH + H 2 NOH CH 3(CH 2)5 CH + H 2 O (81 -93%)

Reaction with Derivatives of Ammonia H 2 N G + R 2 C H

Reaction with Derivatives of Ammonia H 2 N G + R 2 C H 2 N OH O R 2 C N G + H 2 O R 2 C NOH hydroxylamine oxime H 2 N R 2 C NH 2 hydrazine etc. NNH 2 hydrazone

Example O C + H 2 NNH 2 C (73%) + H 2 O

Example O C + H 2 NNH 2 C (73%) + H 2 O

Example O CCH 3 + H 2 NNH phenylhydrazine NNH CCH 3 a phenylhydrazone

Example O CCH 3 + H 2 NNH phenylhydrazine NNH CCH 3 a phenylhydrazone (87 -91%) + H 2 O

Example O O CH 3(CH 2)9 CCH 3 + H 2 NNHCNH 2 semicarbazide

Example O O CH 3(CH 2)9 CCH 3 + H 2 NNHCNH 2 semicarbazide O NNHCNH 2 CH 3(CH 2)9 CCH 3 + H 2 O a semicarbazone (93%)

17. 11 Reaction with Secondary Amines: Enamines

17. 11 Reaction with Secondary Amines: Enamines

Some reactions of aldehydes and ketones progress beyond the nucleophilic addition stage Acetal formation

Some reactions of aldehydes and ketones progress beyond the nucleophilic addition stage Acetal formation Imine formation Compounds related to imines Enamines The Wittig reaction

Some reactions of aldehydes and ketones progress beyond the nucleophilic addition stage Acetal formation

Some reactions of aldehydes and ketones progress beyond the nucleophilic addition stage Acetal formation Imine formation Compounds related to imines Enamines The Wittig reaction

Enamine Formation H H C • • R 2 N H C O •

Enamine Formation H H C • • R 2 N H C O • • R 2 N C (enamine) + H 2 O C C • • O • • H

Example O N H + (heat in benzene) N (80 -90%)

Example O N H + (heat in benzene) N (80 -90%)

Example O N H (heat in benzene) + via N OH N

Example O N H (heat in benzene) + via N OH N