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Topic: Diazonium salts in synthesis· Organic Compounds Containing Nitrogen

The product formed from the following reaction sequence is[benzonitrile] [(iii) H_2O](i) LiAlH_4, H_2O;\ (ii) NaNO_2 + HCl

The product formed from the following reaction sequence is

[benzonitrile] \(\xrightarrow[\text{(iii) } H_2O]{\text{(i) } LiAlH_4, H_2O;\ \text{(ii) } NaNO_2 + HCl}\)

benzonitrile with reagents arrow and four product structures: benzyl alcohol, benzamide, benzyl diazonium chloride, benzyl chloride

1. [structure in figure]

2. [structure in figure]

3. [structure in figure]

4. [structure in figure]

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Answer: 1. [structure in figure]

Key idea: follow each step.

  1. \(\mathrm{LiAlH_4}\) reduces the nitrile \(\mathrm{C_6H_5CN}\) to the primary amine \(\mathrm{C_6H_5CH_2NH_2}\) (benzylamine).
  2. \(\mathrm{NaNO_2+HCl}\) gives nitrous acid, which converts an aliphatic primary amine into an unstable diazonium salt.
  3. The diazonium salt reacts with water, losing \(\mathrm{N_2}\), to give \(\mathrm{C_6H_5CH_2OH}\), benzyl alcohol.

Benzyl diazonium chloride is too unstable to be the final product.

Doubtly AI · 30 Oct 2026 AI-generated · not yet verified Report
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