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Dolbier HW Solutions 532 - 626 AMINES(d Acetyl chloride...

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( d ) Acetyl chloride reacts with benzylamine to form an amide. ( e ) Acetic anhydride also gives an amide with benzylamine. ( f ) Primary amines react with ketones to give imines. ( g ) These reaction conditions lead to reduction of the imine formed in part ( f ). The overall reac- tion is reductive amination. ( h ) Amines are nucleophilic and bring about the opening of epoxide rings. ( i ) In these nucleophilic ring-opening reactions the amine attacks the less sterically hindered car- bon of the ring. ( j ) With excess methyl iodide, amines are converted to quaternary ammonium iodides. C 6 H 5 CH 2 NH 2 Benzylamine C 6 H 5 CH 2 N(CH 3 ) 3 I Benzyltrimethylammonium iodide Methyl iodide 3CH 3 I C 6 H 5 CH 2 NH 2 C 6 H 5 CH 2 NHCH 2 CHCH 3 Benzylamine 1-( N -Benzylamino)-2-propanol 1,2-Epoxypropane H 2 C
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