Ch18 Amines(pdf) - KFUPM Open Courseware

Alkylation of AmmoniaExampleBut the method doesn't work well in practice.Usually gives a mixture of primary, secondary,and tertiary amines, plus the quaternary salt.CH 3 (CH 2 ) 6 CH 2 BrNH 3CH 3 (CH 2 ) 6 CH 2 NH 2NH 3RXRNH 2RXR 2 NHR 4 N + X –RXR 3 NRXAs octylamine is formed, it competes withammonia for the remaining 1-bromooctane.1Reaction of octylamine with 1-bromooctane1gives N,N-dioctylamine.ExampleCH 3 (CH 2 ) 6 CH 2 BrNH 3CH 3 (CH 2 ) 6 CH 2 NH 2(45%)CH 3 (CH 2 ) 6 CH 2 NHCH2 (CH 2 ) 6 CH 3(43%)As octylamine is formed, it competes withammonia for the remaining 1-bromooctane.1Reaction of octylamine with 1-bromooctane1gives N,N-dioctylamine.+The Gabriel Synthesis of Primary Alkylamines