Chapter 10, Problem 10.59P

Interpretation Introduction

Interpretation:

It is to be explained why a terminal alkyne, when a product of $\text{E2}$ reaction, requires three equivalents of base ${\text{(NaNH}}_{\text{2}}\text{)}$.

Concept introduction:

$\text{E2}$ reactions are favored when the H and the leaving group on adjacent atoms are anticoplanar. One equivalent of strong base is required to carry out one $\text{E2}$ reaction. In vicinal dihalide, two $\text{E2}$ reactions are carried out to form the alkyne as the product. The proton at the terminal alkyne is acidic; a strong base can take away the acidic proton.