JEE Advanced levelOne or more correct optionsDifficulty 3 of 3co162
Ethyl 3-oxobutanoate, CHX3COCHX2COOCX2HX5, is treated with different reducing agents under the stated conditions. Which statements are correct?
ANaBHX4 in ethanol at 0 ∘C gives ethyl 3-hydroxybutanoate
BExcess LiAlHX4 in dry ether, followed by aqueous work-up, gives butane-1,3-diol
CNaBHX4 in ethanol at 0 ∘C gives butane-1,3-diol
DNX2HX4, hot KOH in ethylene glycol leaves the ester group unchanged
Answer: A, B
NaBHX4 reduces only the ketone, giving the hydroxy ester. LiAlHX4 reduces both ketone and ester to alcohols, giving butane-1,3-diol (ethanol is also released). Hot KOH hydrolyses the ester, so the last statement is wrong.