JEE Main Chemistry question

A substituted benzyl chloride bearing an aromatic iodo substituent is treated with NaCN in DMF. The structure of the major product is

(A)[product with ring –CN at two positions, –Cl retained on the side chain]
(B)[product with the side-chain –CH₂Cl converted to –CH₂CN, aromatic C–I retained, but also bearing an extra ring –Cl]
(C)[product with the side-chain –CH₂Cl converted to –CH₂CN, and the aromatic C–I replaced as well]
(D)[product with the side-chain –CH₂Cl converted to –CH₂CN, aromatic C–I retained unchanged]Correct

Answer: (D)

Solution

The substrate carries two different carbon–halogen bonds: an aliphatic, primary benzylic and an aromatic bond. The aliphatic chloride is readily attacked by the cyanide nucleophile in an -type substitution (-CH_2Cl \rightarrow -CH_2CN), while the

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Question ID VK-148055