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Question

An organic compound A (C3H9N) reacts with benzene-sulphonyl chloride to give a solid insoluble in alkali. The structure of A is :
  1. CH3NHC2H5
  2. Insufficient data to predict
  3. (CH3)3N
  4. CH3CH2CH2NH2


Solution

The correct option is A CH3NHC2H5
Primary amines when react with Hinsberg reagent (benzene sulphonyl chloride) formed a product which is soluble in alkali. Whereas secondary amine performing same reaction gives a product which is insoluble in alkali. Tertiary amines do not react with Hinsberg reagent. Hence this test is used to distinguish between 1o, 2o and 3o amines.
Compound (A) gives alkali insoluble product with this reagent and is 2o amine.

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