In the electrophilic aromatic substitution of naphthalene at the (C-1) position, how many major reso — Aromatic Hydrocarbons Chemistry Question
Question
In the electrophilic aromatic substitution of naphthalene at the $\alpha$ (C-1) position, how many major resonance structures can be drawn for the intermediate arenium ion that maintain a fully intact, completely conjugated benzenoid ring?
💡 Solution & Explanation
When an electrophile attacks naphthalene at the C-1 ($\alpha$) position, the positive charge is delocalized within the attacked ring. Exactly 2 of the resulting resonance structures allow the adjacent ring to remain a fully conjugated, intact benzenoid ring. This significantly lowers the energy of the transition state compared to $\beta$ -attack, which only has 1 such intact benzenoid structure.