JEE Main · 2021 · 27 Aug 2021 · Shift 1 · Alcohols Phenols and Ethers

In the following sequence of reactions, the final product D is :

Answer: (C)

Solution

Propyne is deprotonated by sodium amide to its acetylide, which displaces bromide from

BrC H_{2} C H_{2} CH (OH) C H_{3}

to give

C H_{3} - C \equiv C - C H_{2} C H_{2} CH (OH) C H_{3}

. Hydrogenation over

Pd - C

reduces the triple bond fully to the secondary alcohol heptan-2-ol,

C H_{3} (C H_{2})_{4} CH (OH) C H_{3}

. Mild oxidation with

Cr O_{3}

turns this secondary alcohol into a ketone, so the final product is heptan-2-one,

C H_{3} (C H_{2})_{4} COC H_{3}

JEE Main · 2021 · 27 Aug 2021 · Shift 1 · Single correct option