Benzonitrile is treated separately with (X) C2H5MgBr then H3O+, and (Y) one equivalent of DIBAL-H at low temperature then H3O+. The organic products X and Y are respectively

1-phenylpropan-1-one and benzaldehyde

benzaldehyde and 1-phenylpropan-1-one

1-phenylpropan-1-ol and benzyl alcohol

1-phenylbutan-1-one and benzylamine

1-phenylpropan-1-one and benzaldehyde

JEE Advanced levelSingle correct optionDifficulty 3 of 3co026

Benzonitrile is treated separately with (X) $C X_{2} H X_{5} MgBr$ then $H X_{3} O X^{+}$ , and (Y) one equivalent of DIBAL-H at low temperature then $H X_{3} O X^{+}$ . The organic products X and Y are respectively

The Grignard carbon adds once to

C \equiv N

and hydrolysis of the imine gives the ketone

C X_{6} H X_{5} COC X_{2} H X_{5}

. DIBAL-H adds one hydride to give the aldimine, which is hydrolysed to

C X_{6} H X_{5} CHO