Chapter 25, Problem 25.22P

Interpretation Introduction

Interpretation:

The alkyne from which the compound shown can be produced via a dissolving metal reduction is to be drawn.

Concept introduction:

When an alkyne is treated with metal dissolved in liquid ammonia ($\text{-}78°\text{C}$), the triple bond is reduced to a double bond. A dissolving metal reduction of an alkyne produces the E alkene almost exclusively. This is an anti-hydrogenation reaction in which two H atoms, overall, add to the triple bond in a trans fashion.