Chapter 9.SE, Problem 50AP

Interpretation Introduction

Interpretation:

Sodium acetylide undergoes addition reaction with ketones to give an alcohol. How this reaction can be used to prepare 1,3-butadiene is to be shown.

Concept introduction:

Acetylides undergo addition reaction with ketones to give an ynol. The ynol can be dehydrated by warming with dilute H₂SO₄ to an enyne. The enyne is reduced with H₂ in the presence of Lindlar catalyst when the triple bond alone gets reduced to a double bond resulting in a diene.

To show:

How the reaction, the addition of alkynes to ketones to give an alcohol, can be used to prepare 1,3-butadiene.