JEE Main · 2021 · 26 Feb 2021 · Shift 1 · Compounds Containing Nitrogen

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An amine on reaction with benzenesulphonyl chloride produces a compound insoluble in alkaline solution. This amine can be prepared by ammonolysis of ethyl chloride. The correct structure of amine is:

(A) $CH_{3} CH_{2} CH_{2} NHCH_{3}$
(B)(see structure)
✓ Correct
(C) $CH_{3} CH_{2} NH_{2}$
(D) $CH_{3} CH_{2} CH_{2} N - CH_{2} CH_{3}$

Answer: (B)

Solution

A benzenesulphonyl-chloride (Hinsberg) product that is insoluble in alkali arises from a secondary amine: the sulphonamide has no N–H left to ionise in base. Ammonolysis of ethyl chloride (with the halide in excess) yields the secondary amine diethylamine,

(C_{2} H_{5})_{2} N H

, which satisfies both clues. Ethylamine (C) is primary and would give an alkali-soluble sulphonamide; the secondary amines in (A) and (D) carry a propyl group and cannot be made from ethyl chloride alone. Hence the amine is diethylamine, option B.

JEE Main · 2021 · 26 Feb 2021 · Shift 1 · Single correct option

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JEE Main · 2021 · 26 Feb 2021 · Shift 1 · Compounds Containing Nitrogen

Solution

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