In the electrophilic aromatic substitution of naphthalene, attack at the (C-1) position is kinetically preferred over attack at the (C-2) position. Which of the following best explains this regioselec

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?

Prashant Kotian · Accepted Answer

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

💡 Solution & Explanation

Practice 22,000+ questions like this