The final major product of the following reaction is: (i) $\mathrm{Ac}_{2}\mathrm{O} /$ Pyridine (ii) $\mathrm{Br}_{2}, \mathrm{FeCl}_{3}$ (iii) $\mathrm{OH}^{-} / \Delta$ Me

JEE Main · 2020 · 05 Sep 2020 · Shift 2 · Hydrocarbons

The final major product of the following reaction is:
(i)

Ac_{2} O /

Pyridine
(ii)

Br_{2}, FeCl_{3}

(iii)

OH^{-} /Δ

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

Answer: (D)

Solution

The amino group is first capped as an acetamide with acetic anhydride, which moderates its strong activating power so that substitution is clean and directed. Bromination with

Br X_{2} / FeCl X_{3}

then enters para to the acetamido group, a position that also fits the methyl group's own ortho/para direction. Warm hydroxide finally hydrolyses the acetyl cap to restore the free amine. The major product is the toluidine carrying bromine para to the amino group.

JEE Main · 2020 · 05 Sep 2020 · Shift 2 · Single correct option

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