Benzil → Benzilic Acid Rearrangement (1,2-Migration): Mechanism + Exam Traps

Convert 1,2-diketones (classic: benzil) into α-hydroxycarboxylic acids under basic conditions via nucleophilic addition followed by a 1,2-aryl shift.

• Reaction: Benzil → Benzilic Acid Rearrangement (1,2-Migration)
• What it does: Convert 1,2-diketones (classic: benzil) into α-hydroxycarboxylic acids under basic conditions via nucleophilic addition followed by a 1,2-aryl shift.
• Typical reagents: OH−, then H3O+
• Key intermediate: Tetrahedral intermediate
• Driving force: Formation of strong C=O / oxidation state stabilization
• Exam type: Predict product
• Exam type: Rearrangement logic
• Exam type: Driving force