In the reaction (1) $\mathrm{NaOH} / \mathrm{Br}_{2}$ Product T is

JEE Advanced · 2010 · 11 Apr 2010 · Paper 2 · Compounds Containing Nitrogen

In the reaction

(1)

NaOH / Br_{2}

Product T is

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

Answer: (C)

Solution

The reaction sequence shows a Hofmann bromamide degradation. The starting amide undergoes rearrangement with NaOH/Br₂ to give an amine with one carbon less. The subsequent reaction with benzoyl chloride (PhCOCl) gives an N-substituted benzamide. Product T is the para-toluidine derivative of benzoic acid:

CH X_{3} - C X_{6} H X_{4} - NH - CO - C X_{6} H X_{5}

JEE Advanced · 2010 · 11 Apr 2010 · Paper 2 · Single correct option

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