Chapter 17.2, Problem 5P

Interpretation Introduction

Interpretation:

The observation that p-nitrobenzyl alcohol is more acidic than benzyl alcohol but p-methoxybenzyl alcohol is less acidic is to be explained.

Concept introduction:

Alcohols are acidic because the alkoxide ion formed due to loss of H⁺ is stabilized by solvation. Aromatic alcohols with electron releasing substituent groups on the ring are less acidic and those with electron attracting substituent groups are more acidic.

To explain:

The observation that p-nitrobenzyl alcohol is more acidic than benzyl alcohol but p-methoxybenzyl alcohol is less acidic.