Synthesis of Amines Alkylations of ammonia and alkylamines often yield mixtures of products CH3(CH2)6CH2Br +:NH3 CH3(CH2)6CH2NH2+[CH3(CH2)6CH2]2NH 1-Bromooctane Octylamine (45%) Dioctylamine(43%) +[CH3(CH2)6CH2]3N:+[CH3(CH2)6CH2J4N Br Trace Trace Primary amines are more efficiently prepared using the azide ion,Na as the nucleophile CH2CH2Br CH2CH2N-N=N CH2CH2NH2 NaN3 1.LiAlHa,ether Ethanol 2.H20 1-Bromo-2- 2-Phenylethyl azide 2-Phenylethylamine phenylethane (89%)• Alkylations of ammonia and alkylamines often yield mixtures of products • Primary amines are more efficiently prepared using the azide ion, N3 - , as the nucleophile Synthesis of Amines