Chapter 23, Problem 23.36P

Interpretation Introduction

Interpretation:

The major product of nitration of phenol where the ortho position is labeled with deuterium $\left(\text{D}\right)$, it is to be predicted and the relative amounts of each of those products to be determined.

Concept introduction:

The nitration is the electrophilic aromatic substitution reaction. The aromatic ring on reaction with nitric acid or with a mixture of concentrated nitric acid and sulfuric acid undergoes substitution of one of the ring hydrogen by nitro group and forms nitrobenzene, this is called nitration. The deuterium is an isotope of hydrogen when attached to benzene that can also be replaced by nitro group on nitration. The electron donating groups activates the aromatic ring and increases the electron density at ortho-para position comparatively than meta position. That means electrophilic aromatic substitution preferably occurs at ortho-para position. The phenol gives $\text{50-50\%}$ of ortho and para products on electrophilic aromatic substitution reaction.