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Question
What is the action of Benzene Sulphonyl Chloride on primary, secondary and tertiary
amines?
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Solution
Reaction of primary amine with benzene sulphonyl chloride gives corresponding
N-alkyl benzene sulphonylamide.
Owing to the presence of strong electron withdrawing sulphonyl group, hydrogen
attached to nitrogen atom in N-alkyl benzene sulphonylamide is strongly acidic
and dissolves in aqueous KOH. On acidification of this solution, insoluble amide
gets regenerated.
Reaction of secondary amine with benzene sulphonyl chloride gives N,N-dialkyl
benzene sulphonylamide.
N,N-dialkyl benzene sulphonylamide does not contain acidic hydrogen. Hence, it is not acidic and is insoluble in aqueous KOH. It is also insoluble in acid.
Due to absence of hydrogen atom directly attached to the nitrogen atom, tertiary
amines do not react with benzene sulphonyl chloride. The unreacted tertiary
amine is insoluble in aqueous KOH but soluble in acid.
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