MHT CET 2023 Chemistry question

Identify the product obtained when benzonitrile is reduced by stannous chloride in presence of hydrochloride acid followed by acid hydrolysis.

(A)Benzal chloride
(B)Benzoyl chloride
(C)Benzophenone
(D)BenzaldehydeCorrect

Answer: (D)

Solution

This is the Stephen reaction. Nitriles are reduced by to the imine hydrochloride (aldimine tin chloride complex), which on acid hydrolysis gives an aldehyde: \mathrm{C_6H_5CN + 2[H] + HCl \xrightarrow{SnCl_2} C_6H_5CH{=}NH\cdot HCl \xrightarrow{H_3O^+} C_6H_5CHO + NH_4Cl}.

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Question ID VK-095167