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Which of the following amines will form a product that is soluble in KOH, on reaction with Hinsberg’s reagent?(a) Isopropylamine(b) Diethylamine(c) N,N-Dimethylpropylamine(d) N,N-DimethylanilineI had been asked this question in an internship interview.Query is from Amines Chemical Reactions topic in chapter Amines of Chemistry – Class 12

Answer»

The correct answer is (a) Isopropylamine

To explain: The reaction of Hinsberg’s reagent with Isopropylamine GIVES N-isopropylbenzene sulphonamide. The lone HYDROGEN attached to the N atom is strongly acidic due to the presence of strong electron WITHDRAWING sulphonyl group. Hence, is it soluble in ALKALI like KOH.



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