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Which of the following amines will form a product that is soluble in KOH, on reaction with Hinsberg’s reagent?

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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-Dimethylaniline

I had been asked this question in an internship interview.

Query is from Amines Chemical Reactions topic in chapter Amines of Chemistry – Class 12

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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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