JEE Main · 2023 · 15 Apr 2023 · Shift 1 · Compounds Containing Nitrogen

Consider the following sequence of reactions:

The product 'B' is

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

Answer: (B)

Solution

Treating aniline with sodium nitrite and acid at

0 - 5^{\circ} C

diazotises the amino group, giving benzenediazonium salt as intermediate A. This diazonium ion is a weak electrophile that couples at the position para to the strongly activating dimethylamino group of N,N-dimethylaniline. Coupling joins the two rings through an azo bridge, so product B is p-(N,N-dimethylamino)azobenzene,

C_{6} H_{5} - N = N - C_{6} H_{4} - N (C H_{3})_{2}

JEE Main · 2023 · 15 Apr 2023 · Shift 1 · Single correct option

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