The hydrocarbon shown is heated with alkaline KMnO4 and acidified, the product is converted with SOCl2, then NH3, and finally treated with Br2/NaOH (Hofmann bromamide). Which structure is the final organic product?

JEE Main levelSingle correct optionDifficulty 2 of 3si265

The hydrocarbon shown is heated with alkaline $KMnO X_{4}$ and acidified, the product is converted with $SOCl X_{2}$ , then $NH X_{3}$ , and finally treated with $Br X_{2}$ /NaOH (Hofmann bromamide). Which structure is the final organic product?

The hydrocarbon shown is toluene. Oxidation gives benzoic acid (D);

SOCl X_{2}

and

NH X_{3}

give benzamide (B); the Hofmann degradation loses the carbonyl carbon as carbonate and gives aniline (A), not benzylamine (C).