During the Fries rearrangement, a phenyl ester is heated with anhydrous . What is the identity of the migrating electrophilic intermediate, and what are the major products formed?

Question

During the Fries rearrangement, a phenyl ester is heated with anhydrous $AlCl_3$. What is the identity of the migrating electrophilic intermediate, and what are the major products formed?

Prashant Kotian · Accepted Answer

Correct answer: B. The Fries rearrangement involves the Lewis acid-mediated cleavage of the ester bond to generate a highly electrophilic acylium ion. This ion then attacks the highly activated aromatic ring via Friedel-Crafts-like acylation, yielding a mixture of ortho and para-hydroxyaryl ketones.

💡 Solution & Explanation

Practice 22,000+ questions like this