Compare the structural and reactive properties of naphthalene with those of benzene. Which of the fo — Aromatic Hydrocarbons Chemistry Question

💡 Solution & Explanation

Naphthalene is more reactive than benzene towards EAS because its arenium ion intermediate retains a fully intact benzene ring, providing greater stabilization and lower activation energy compared to the benzene arenium ion. The C-1 to C-2 bond has more double bond character (it is a double bond in 2 of the 3 major resonance structures) making it shorter than the C-2 to C-3 bond (a double bond in only 1). Naphthalene is a benzenoid compound, and its resonance energy ($\approx 61$ kcal/mol) is less than double that of benzene ($2 \times 36 = 72$ kcal/mol).