JEE Main · 2023 · 06 Apr 2023 · Shift 1 · Compounds Containing Nitrogen

Compound P is neutral and of molecular formula ${\mathrm{C}}_{14}{\mathrm{H}}_{13}\mathrm{ON}$, pointing to an amide. Acid hydrolysis cleaves the amide into a carboxylic acid and an amine. The residue Q gives effervescence with sodium bicarbonate, so Q is a carboxylic acid; the oily liquid R freed on adding alkali reacts with Hinsberg's reagent to give a sulphonamide soluble in sodium hydroxide, which is the test for a primary amine. An amide that hydrolyses to a carboxylic acid and a primary aromatic amine, and whose formula carries the extra carbon shown by ${\mathrm{C}}_{14}$, is N-phenyl-4-methylbenzamide: it yields 4-methylbenzoic acid as Q and aniline as R. The structure consistent with all the tests is N-phenyl-4-methylbenzamide.