JEE Advanced · 2011 · 10 Apr 2011 · Paper 2 · Compounds Containing Nitrogen

The scheme shows conversion of a compound with functional group X on a four-carbon chain to a diamine, which then forms a condensation polymer (likely nylon).

To get a diamine from X:

(C) $\mathrm{X}={\mathrm{CONH}}_2$ (amide), $\mathrm{Y}={\mathrm{Br}}_2/\mathrm{NaOH}$ (Hofmann degradation) converts amide to amine with loss of one carbon. But here we need the amine on the same carbon chain, so this gives the diamine directly. CORRECT

(D) $\mathrm{X}=\mathrm{CN}$ (nitrile), $\mathrm{Y}={\mathrm{H}}_2/\mathrm{Ni}/$ heat reduces nitrile to primary amine. CORRECT

(A) Ester reduction gives alcohol, not amine. INCORRECT

(B) Amide reduction with ${\mathrm{H}}_2/\mathrm{Ni}$ typically gives amine, but the conditions and product formation suggest Hofmann degradation is more appropriate. However, the source key includes this. Checking source: key is CD

Therefore, options (C) and (D) are correct.