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Q.Complete the following reactions -

(i) RCN + 4H --[LiAlH4]--> ___
(ii) RCONH2 + Br2 + 4KOH --> ___ + ___ + ___ + ___
(iii) RNO2 + H --[Sn/HCl]--> ___ + ___ OR Explain the reason -
(i) Aniline is a weaker base than cyclohexyl amine.
(ii) Silver chloride dissolves in methyl amine solution.
(iii) It is difficult to prepare pure amine by ammonolysis of alkyl halide.
Madhya Pradesh MpbseMP Board Higher Secondary 2019Subjective· 3mImportance★★★★★
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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).

  1. 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.)
  2. 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.)
  3. 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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