Cyclohexanone is treated with (i) CH3NH2, trace acid, water removed; (ii) NaBH4, CH3OH; (iii) aqueous work-up. The product is

JEE Advanced levelSingle correct optionDifficulty 3 of 3o1156

Cyclohexanone is treated with (i) $CH X_{3} NH X_{2}$ , trace acid, water removed; (ii) $NaBH X_{4}$ , $CH X_{3} OH$ ; (iii) aqueous work-up. The product is

Step (i) forms the imine

C X_{6} H X_{10} = N - CH X_{3}

NaBH X_{4}

reduces C=N (reductive amination) to the secondary amine, so the product is

C X_{6} H X_{11} - NH - CH X_{3}

. Cyclohexanol would result only if the ketone were reduced before imine formation.