Aromatic HydrocarbonshardMCQ SINGLE

In the electrophilic aromatic substitution of naphthalene, attack at the (C-1) position is kineticalAromatic Hydrocarbons Chemistry Question

Question

In the electrophilic aromatic substitution of naphthalene, attack at the $\alpha$ (C-1) position is kinetically preferred over attack at the $\beta$ (C-2) position. Which of the following best explains this regioselectivity?

Answer: A

💡 Solution & Explanation

In the electrophilic aromatic substitution of naphthalene, attack at the $\alpha$ (C-1) position yields an intermediate (arenium ion) that has two canonical forms preserving a fully intact, low-energy benzenoid ring. Attack at the $\beta$ (C-2) position yields an intermediate with only one such benzenoid canonical form. Since the transition state resembling the $\alpha$ -intermediate has a lower energy, $\alpha$ -attack is faster and kinetically favored.

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