Reactions of Amines Hofmann Elimination 量 Amines can be converted into alkenes by an elimination reaction NH2 is a poor leaving group and must be converted into a better leaving group Amine is methylated with excess iodomethane to produce a quaternary ammonium salt Quaternary ammonium salt undergoes elimination upon heating with silver oxide NH2 Excess +N(CH3)3 I +N(CH3)3 Ag2O CH3CH2CH2CH2CHCH3 CH3CH2CH2CH2CHCH3 CH3CH2CH2CH2CH=CH2 H20,heat 1-Methylpentylamine (1-Methylpentyl)trimethyl- Hex-1-ene(60%) ammonium iodide Hofmann Elimination ▪ Amines can be converted into alkenes by an elimination reaction ▪ NH2 - is a poor leaving group and must be converted into a better leaving group ▪ Amine is methylated with excess iodomethane to produce a quaternary ammonium salt ▪ Quaternary ammonium salt undergoes elimination upon heating with silver oxide Reactions of Amines