Dolbier HW Solutions 533

Dolbier HW Solutions 533 - 627 AMINES(k Nitrous acid forms...

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( k ) Nitrous acid forms from sodium nitrite in dilute hydrochloric acid. Nitrosation of benzylamine in water gives benzyl alcohol via a diazonium ion intermediate. Benzyl chloride will also be formed by attack of chloride on the diazonium ion. 22.32 ( a ) Aniline is a weak base and yields a salt on reaction with hydrogen bromide. ( b ) Aniline acts as a nucleophile toward methyl iodide. With excess methyl iodide, a quaternary ammonium salt is formed. ( c ) Aniline is a primary amine and undergoes nucleophilic addition to aldehydes and ketones to form imines. ( d ) When an imine is formed in the presence of hydrogen and a suitable catalyst, reductive ami- nation occurs to give an amine. ( e ) Aniline undergoes N -acylation on treatment with carboxylic acid anhydrides. ( f ) Acyl chlorides bring about N -acylation of arylamines. ( g ) Nitrosation of primary arylamines yields aryl diazonium salts. C 6 H 5 NH 2 C 6 H 5 N HSO 4 2 NaNO 2 , H 2 SO 4 H 2
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