Chapter 9, Problem 9.46P

Interpretation Introduction

Interpretation:

It is to be shown how $\text{pent-2-yne}$ can be made from two different alkyl bromides.

Concept introduction:

Alkynide anions ($\text{RC}\equiv {\text{C}}^{-}$) can behave as strong nucleophiles. They are formed when terminal alkynes are treated with a strong base such as sodium hydride. In an acid-base reaction, the weakly held hydrogen atom attached to the terminal carbon atom of the alkyne is abstracted by a strong base. When alkynide anions are treated with alkyl halides, a new carbon-carbon bond is formed. An unsymmetrical internal alkyne can be made using two different alkynide anions and two different alkyl halides.