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ChemistryNEET 2024Preparation and reactions; diazonium salts

Amines

Identify the major product C formed in the following reaction sequence:

CH3CH2CH2I→NaCNA→partial hydrolysisOH−B→(major)Br2/NaOHC\mathrm{CH_3CH_2CH_2I \xrightarrow{NaCN} A \xrightarrow[\text{partial hydrolysis}]{OH^-} B \xrightarrow[\text{(major)}]{Br_2 / NaOH} C}

  1. A.butylamine
  2. B.butanamide
  3. C.α\alpha-bromobutanoic acid
  4. D.propylamine✓

Solution

CH3CH2CH2I\mathrm{CH_3CH_2CH_2I} with NaCN gives butanenitrile (A). Partial hydrolysis converts the nitrile to the amide, butanamide (B). Hofmann bromamide degradation with Br2/NaOH\mathrm{Br_2/NaOH} removes one carbon, giving propylamine (C).

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