JEE Advanced 2016 · Paper 2 · Chemistry Q31

ChemistryMultiple correct+4 / -2Question 31 of 54

Reagent(s) which can be used to bring about the following transformation is(are)

\ce{LiAlH4}

\ce{(C2H5)2O}

\ce{BH3}

in THF

\ce{NaBH4}

\ce{C2H5OH}

Raney

\ce{Ni/H2}

in THF

Answer and worked solution

Official answer: C, D

Only the aldehyde must be reduced. The COOH, the tert-butyl ester and the epoxide must survive.

(A) $\ce{LiAlH4}$ also reduces the acid and the ester, and can open the epoxide. False.
(B) $\ce{BH3}$ reduces carboxylic acids rapidly. False.
(C) $\ce{NaBH4}$ in ethanol reduces aldehydes chemoselectively. True.
(D) Raney Ni/H₂ reduces the aldehyde under mild conditions (the official choice). True.

(C), (D)

Topics:Oxidation and reduction Acid derivatives

JEE Advanced 2016 · Paper 2, Chemistry question 31