Question:

Which of the following is not a correct method of the preparation of benzylamine from cyanobenzene ?

Show Hint

Benzylamine (C6H5CH2NH2) needs full reduction of -C≡N to -CH2NH2 (H2/Ni or LiAlH4). Acid hydrolysis of the nitrile gives benzoic acid, which NaBH4 cannot reduce.
Updated On: Nov 5, 2026
  • (i) \(\mathrm{SnCl_2 + HCl(gas)}\)    (ii) \(\mathrm{NaBH_4}\)
  • \(\mathrm{H_2/Ni}\)
  • (i) \(\mathrm{LiAlH_4}\)    (ii) \(\mathrm{H_3O^+}\)
  • (i) \(\mathrm{HCl/H_2O}\)    (ii) \(\mathrm{NaBH_4}\)
Show Solution
collegedunia
Verified By Collegedunia

The Correct Option is D

Solution and Explanation

Target: C6H5CN → C6H5CH2NH2.
(2) H2/Ni reduces -C≡N to -CH2NH2: correct method.
(3) LiAlH4 followed by aqueous work-up reduces the nitrile to the primary amine: correct method.
(4) HCl/H2O hydrolyses the nitrile to benzoic acid (C6H5COOH); NaBH4 does not reduce a carboxylic acid, so no benzylamine is formed: not a correct method.
(1) SnCl2/HCl (Stephen reduction) converts the nitrile to benzaldehyde (via the imine), and NaBH4 would then give benzyl alcohol, not benzylamine, so this sequence also does not give the amine.
Both (1) and (4) fail on strict analysis; the NTA key treats option (4) as the answer.
Answer: (4) (i) HCl/H2O (ii) NaBH4
Was this answer helpful?
0
0