Chapter 7.10, Problem 23P

Interpretation Introduction

Interpretation:

The value of ${\text{pK}}_{\text{a}}$ of conjugate acid of the base which can remove proton from a terminal alkyne to form an acetylide ion should be identified.

Concept Introduction:

In a reaction which strongly favours the formation of products, the base used to remove proton from the acid should be stronger than the base formed when the proton is removed.

Order of electronegativity of carbon atoms:

$\text{sp}\text{>}{\text{sp}}^{\text{2}}\text{>}{\text{sp}}^{\text{3}}$

Most electronegative is the $\text{sp}$ hybridized carbon atom.

The most acidic compound will be the hydrogen which is attached to the most electronegative carbon.