Alcohols Phenols And Ethers Question 83

Question: A compound of the formula $ C_4H _{10}O $ reacts with sodium and undergoes oxidation to give a carbonyl compound which does not reduce Tollen’s reagent, the original compound is

Options:

A) Diethyl ether

B) n-Butyl alcohol

C) Isobutyl alcohol

D) sec-Butyl alcohol

Show Answer

Answer:

Correct Answer: D

Solution:

[d] Since the compound $ (C_4H _{10}O) $ react with sodium, it must be alcohol (option b, c, or d). As it is oxidised to carbonyl compound which does not reduce Tollen’s reagent, the carbonyl compound should be a ketone and the $ C_4H _{10}O $ should be a secondary alcohol, i.e. sec-butyl alcohol; other two given alcohols are $ 1{}^\circ $ .