Q.Complete the following reactions -
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Start your 14-day free trial to unlock the full solution →Nitriles, amides and nitro compounds can each be reduced to primary amines by suitable reagents (LiAlH₄, Br₂/KOH via Hofmann degradation, and Sn/HCl respectively).
- Reduction of a nitrile by LiAlH₄: R–C≡N + 4[H] —(LiAlH₄)→ R–CH₂–NH₂ (A nitrile is reduced all the way to a primary amine, with the carbon skeleton unchanged.)
- Hofmann bromamide degradation of an amide: R–CONH₂ + Br₂ + 4KOH → R–NH₂ + 2KBr + K₂CO₃ + 2H₂O (This is a degradation reaction — the amine formed has ONE CARBON LESS than the starting amide, since the carbonyl carbon is lost as carbonate.)
- Reduction of a nitro compound by Sn/HCl: R–NO₂ + 6[H] —(Sn/HCl)→ R–NH₂ + 2H₂O (Catalytic hydrogenation, or Sn/HCl, Fe/HCl, Zn/HCl etc. reduces a nitro group to an amine.) OR (alternative part) — reasoning:
(i) Aniline is a weaker base than cyclohexylamine because in aniline the lone pair of electrons on the N atom is delocalised (through resonance) into the benzene ring, making it less available for protonation/donation; also, N in aniline is closer to sp² hybridised (due to conjugation) so its lone pair is held more tightly. In cyclohexylamine, N is fully sp³ hybridised and its lone pair is fully available, plus the alkyl (cyclohexyl) group is electron-donating (+I effect), increasing electron density on N. Both effects make cyclohexylamine the stronger base.
(ii) AgCl dissolves in methylamine solution because methylamine acts as a ligand (through the N lone pair) and forms a soluble complex ion with Ag⁺, [Ag(CH₃NH₂)₂]⁺, similar to how AgCl dissolves in ammonia to form [Ag(NH₃)₂]⁺. Formation of this stable, soluble complex removes free Ag⁺ from solution, shifting the AgCl dissolution equilibrium forward (Le Chatelier), so the sparingly soluble AgCl dissolves. …
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