Chapter 23, Problem 23.60P

Interpretation Introduction

Interpretation:

The bromination of naphthalene does not require the Lewis acid catalyst, it is to be explained.

Concept introduction:

Due to the aromatic nature of compounds other than benzene, their $\text{π}$ system similar to benzene’s, are resistant to electrophilic addition. Instead, treating these compounds with electrophiles tends to lead to substitution to preserve their aromaticity. Electrophilic aromatic substitution on naphthalene generally favors the $\text{α}$ product over the $\text{β}$ product. This means that the arenium ion produced when an electrophile attaches to the $\text{α}$ position is more stable than when it attaches to the $\text{β}$ position. Thus, naphthalene’s arenium ion intermediate is more stable than benzene intermediate.