An organic compound $[\mathrm{A}]\left(\mathrm{C}_{4} \mathrm{H}_{11} \mathrm{~N}\right)$, shows optical activity and gives $\mathrm{N}_{2}$ gas on treatment with $\mathrm{HNO}_{2}$. The compound [A] reacts with $\mathrm{PhSO}_{2} \mathrm{Cl}$ producing a compound which is soluble in KOH . The structure of A is:

JEE Main · 2023 · 31 Jan 2023 · Shift 2 · Compounds Containing Nitrogen

An organic compound

[A] (C_{4} H_{11} N)

, shows optical activity and gives

N_{2}

gas on treatment with

HNO_{2}

. The compound [A] reacts with

PhSO_{2} Cl

producing a compound which is soluble in KOH . The structure of A is:

(A)(see structure)
(B)(see structure)
(C)(see structure)
(D)(see structure)
✓ Correct

Answer: (D)

Solution

Brisk evolution of nitrogen with nitrous acid is the mark of a primary amine, and a Hinsberg product soluble in potassium hydroxide confirms that the amine is primary, since only a primary amine gives an N-H bearing sulphonamide that dissolves in alkali. Optical activity further demands a stereocentre. The only

C_{4} H_{11} N

primary amine carrying a chiral carbon is

C H_{3} C H_{2} CH (N H_{2}) C H_{3}

. The structure of A is butan-2-amine.

JEE Main · 2023 · 31 Jan 2023 · Shift 2 · Single correct option

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JEE Main · 2023 · 31 Jan 2023 · Shift 2 · Compounds Containing Nitrogen

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