PhOCH, H Classes of Amides ·1°amide has one C-N bond(twoN-H) ·2°amide or M-substituted amide has two C-N bonds (one N-H). ·3°amide or M,W-disubstituted amide has three C-N bonds(no N-H). > Chapter 21 6
Chapter 21 6 Classes of Amides • 1 amide has one C-N bond (two N-H). • 2 amide or N-substituted amide has two C-N bonds (one N-H). • 3 amide or N,N-disubstituted amide has three C-N bonds (no N-H). =>
Naming Amides COOH ·For1°amide,drop-icor-oic acid from the carboxylic acid name,add -amide. ·For2°and3°amides,the alkyl groups bonded to nitrogen are named with N- to indicate their position. O CH3 N-ethyl-N,2-dimethylpropanamide CH:CHC-N-CH2CH3 N-ethyl-N-methylisobutyramide CH3 => Chapter 21
Chapter 21 7 Naming Amides • For 1 amide, drop -ic or -oic acid from the carboxylic acid name, add -amide. • For 2 and 3 amides, the alkyl groups bonded to nitrogen are named with Nto indicate their position. CH3 CHC N O CH2 CH3 CH3 CH3 N-ethyl-N,2-dimethylpropanamide N-ethyl-N-methylisobutyramide =>
H Cyclic Amides COOH Reaction of-NH2 and-COOH on same molecule produces a cyclic amide,lactam. To name,add word lactam to the IUPAC acid name or replace the -ic acid of common name with -olactam. 4-aminopentanoic acid lactam -H y-valerolactam CH3 => Chapter 21 8
Chapter 21 8 Cyclic Amides • Reaction of -NH2 and -COOH on same molecule produces a cyclic amide, lactam. • To name, add word lactam to the IUPAC acid name or replace the -ic acid of common name with -olactam. N O CH3 H 4-aminopentanoic acid lactam -valerolactam =>
PhOCH,C Nitriles CH H COOH cylated .-C=N can be hydrolyzed to carboxylic acid,so nitriles are acid derivatives. Nitrogen is sp hybridized,lone pair tightly held,so not very basic.(pK about 24). acetonitrile propyne Cnapter21 9
Chapter 21 9 Nitriles • -CN can be hydrolyzed to carboxylic acid, so nitriles are acid derivatives. • Nitrogen is sp hybridized, lone pair tightly held, so not very basic. (pKb about 24). =>
PhOCH, CH Naming Nitriles COOH For IUPAC names,add -nitrile to the alkane name. Common names come from the carboxylic acid.Replace -ic acid with -onitrile. Br C≡N CH:CHCH-CH2CH2CN 5-bromohexanenitrile -bromocapronitrile Cyclohexanecarbonitrile => Chapter 21 10
Chapter 21 10 Naming Nitriles • For IUPAC names, add -nitrile to the alkane name. • Common names come from the carboxylic acid. Replace -ic acid with -onitrile. CH3 CHCH2 CH2 CH2 CN Br 5-bromohexanenitrile -bromocapronitrile C N Cyclohexanecarbonitrile =>