Cyclohex-2-en-1-one is treated successively with (i) NaBH4/CeCl3 in methanol (1,2-reduction), (ii) H2, Pd-C, (iii) PCC in CH2Cl2. The final product is

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JEE Advanced levelSingle correct optionDifficulty 3 of 3ro016

Cyclohex-2-en-1-one is treated successively with (i) $NaBH X_{4}$ / $CeCl X_{3}$ in methanol (1,2-reduction), (ii) $H X_{2}$ , Pd-C, (iii) PCC in $CH X_{2} Cl X_{2}$ . The final product is

Acyclohexanol
Bcyclohex-2-en-1-one
Ccyclohexanone
Dcyclohexene

Answer: C

(i) Luche conditions reduce only the C=O: cyclohex-2-en-1-ol. (ii) The C=C is hydrogenated: cyclohexanol. (iii) PCC oxidises the secondary alcohol to the ketone: cyclohexanone.

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Cyclohex-2-en-1-one is treated successively with (i) NaBHX4​/CeClX3​ in methanol (1,2-reduction), (ii) HX2​, Pd-C, (iii) PCC in CHX2​ClX2​. The final product is

Answer: C

More questions on Catalytic hydrogenation and metal hydride reductions (LiAlH4, NaBH4, DIBAL)

Cyclohex-2-en-1-one is treated successively with (i) $NaBH X_{4}$ / $CeCl X_{3}$ in methanol (1,2-reduction), (ii) $H X_{2}$ , Pd-C, (iii) PCC in $CH X_{2} Cl X_{2}$ . The final product is