JEE Main 2026 Jan 28 Shift 1, Chemistry Q13: Preparation of Amines

Reaction (1): In benzanilide (PhNHCOPh), nitration directs to the more activated ring (the aniline-derived ring); the product drawn places NO${}_2$ on the wrong ring, so the major product shown is incorrect.

Reaction (2): Gabriel phthalimide synthesis fails with aryl halides because the SN${}^2$ step does not work on sp${}^2$ aryl carbons; no reaction.

Reaction (3): Carbylamine of PhCH${}_2$NH${}_2$ gives Ph-CH${}_2$-NC. Reduction with Sn/HCl gives a secondary amine PhCH${}_2$NHCH${}_3$ — but the standard reduction of isocyanide to the amine is normally with H${}_2$/Pt, not Sn/HCl, and Sn/HCl conditions do not cleanly give the depicted product as the major product. Your institute treats this as incorrect.

Reaction (4): Propanamide undergoing Br${}_2$ + 4 KOH (alc.) gives Hofmann bromamide degradation, producing the amine with one fewer carbon (ethylamine), together with KBr, K${}_2$CO${}_3$ and H${}_2$O. This is the textbook outcome and is the correct major product.

$\therefore$ Option (4).