JEE Advanced 2025 Paper 2 Q07 Chemistry Organic Reactions & Mechanisms Amines & Diazonium Hard

JEE Advanced 2025 Paper 2 · Q07 · Amines & Diazonium

For the reaction sequence given below, the correct statement(s) is(are):

o-xylene -> [(i) $KMnO_4$, $H^+$, heat (ii) $NH_3$, heat, $-2 H_2O$] -> X -> [(i) strong heating (ii) ethanolic $KOH$ (iii) $R-Br$] -> Y -> [$NaOH$] -> aromatic compound + Z.

  1. A. Both X and Y are oxygen containing compounds.
  2. B. Y on heating with $CHCl_3/KOH$ forms isocyanide.
  3. C. Z reacts with Hinsberg's reagent.
  4. D. Z is an aromatic primary amine.
JEE Advanced multi-correct — pick every correct option, then check.
Reveal answer + step-by-step solution

Correct answer:A, C

Solution

Identify the path: o-xylene oxidises to phthalic acid; $-2 H_2O$ on heating with $NH_3$ gives phthalimide (X). X has two $C=O$ groups -> oxygen containing. K-phthalimide (after ethanolic $KOH$ deprotonation) reacts with $R-Br$ ($S_N2$) to give N-alkyl phthalimide (Y). Y still contains the imide $C=O$ groups -> oxygen containing. (A) TRUE. Hydrolysis of Y with $NaOH$ (Gabriel synthesis) gives sodium/disodium phthalate (the aromatic compound) and primary aliphatic amine $R-NH_2$ (Z). (B) Carbylamine ($CHCl_3/KOH$) reacts with primary AMINES to form isocyanides. Y is an imide, NOT a primary amine; it does not give isocyanide. FALSE. (C) Hinsberg's reagent ($PhSO_2Cl$) reacts with primary amines to give N-substituted sulphonamides soluble in $NaOH$. Z is a primary (aliphatic) amine, hence reacts. TRUE. (D) Z is an aliphatic primary amine, NOT aromatic. FALSE. Correct: (A), (C).

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