An organic compound A ( C ₅ H ₉ ~N ) upon reaction with Na / Hg / C ₂ H ₅ OH gives compound B . B reacts with NaNO ₂ / HCl at 274 K to form C with quantitative liberation of N ₂ gas. B also reacts with Hinsberg's reagent to form a compound which is soluble in alkali. Identify compound B.

Step-by-step solution

Two key reactions of B: 1. Reacts with NaNO₂/HCl at 274 K to liberate N₂ quantitatively characteristic of a primary aliphatic amine ( R-NH₂ + HNO₂ R-OH + N₂ + H₂O ) 2. Reacts with Hinsberg's reagent to form a product soluble in alkali confirms primary amine (secondary amines give alkali-insoluble product; tertiary amines do not react). Among the options, only option (3) CH₃-(CH₂)₄-NH₂ is a primary amine. Options (1) and (2) are tertiary and secondary amines respectively, and option (4) is a quaternary ammonium ion.