Aniline is treated successively with (i) NaNO2 / dil. HCl at 273-278 K, (ii) CuCN/KCN, (iii) LiAlH4 in dry ether followed by aqueous work-up. The final product is

JEE Main levelSingle correct optionDifficulty 2 of 3nc061

Aniline is treated successively with (i) $NaNO X_{2}$ / dil. $HCl$ at 273-278 K, (ii) $CuCN / KCN$ , (iii) $LiAlH X_{4}$ in dry ether followed by aqueous work-up. The final product is

Step (i) gives

C X_{6} H X_{5} N X_{2} X^{+} Cl X^{-}

, step (ii) (Sandmeyer) replaces

N X_{2} X^{+}

CN

to give benzonitrile.

LiAlH X_{4}

reduces

- C \equiv N

- CH X_{2} NH X_{2}

, so the product has one more carbon than aniline:

C X_{6} H X_{5} CH X_{2} NH X_{2}