Chapter 6, Problem 6.17P

Interpretation Introduction

Interpretation:

The stronger acid between ${\text{CH}}_{\text{3}}{\text{-NH}}_{\text{3}}^{\text{+}}$ and $\text{HC}\equiv {\text{NH}}^{\text{+}}$ is to be determined.

Concept introduction:

For a given compound, the hybridization of the atom to which proton is attached affects the acidity of that compound. The stability of a charged species increases as the effective electronegativity of an atom bearing a negative charge increases. The effective electronegativity of an atom increases in the order ${\text{sp}}^{\text{3}}{\text{< sp}}^{\text{2}}\text{< sp}$_. The effective stability of a charged species decreases as the effective electronegativity of an atom bearing the positive charge increases.