Chapter 6, Problem 6.63P

Interpretation Introduction

Interpretation:

It is to be explained why though phenol (${\text{C}}_{\text{6}}{\text{H}}_{\text{5}}\text{OH}$) is substantially more acidic than methanol (${\text{CH}}_{\text{3}}\text{OH}$), benzoic acid (${\text{C}}_{\text{6}}{\text{H}}_{\text{5}}{\text{CO}}_{\text{2}}\text{H}$) is not much more acidic than acetic acid (${\text{CH}}_{\text{3}}{\text{CO}}_{\text{2}}\text{H}$).

Concept introduction:

The stability of the compound depends on the type of atom on which a charge appears, which is followed by the extent of charge delocalization via resonance. Electron withdrawing groups stabilize the nearby negative charge whereas electron donating groups destabilize the nearby negative charge. Carboxylic acids are more acidic than alcohols due to resonance effects. The acid is stronger if it has a more stable conjugate base. The conjugate base of an acid is more stable if it forms more resonance structures as it is able to stabilize the negative charge.