Reaction Mechanism
The Dakin oxidation starts with nucleophilic addition of a hydroperoxide anion to the carbonyl carbon, forming a tetrahedral intermediate (2). The intermediate collapses, causing -aryl migration, hydroxide elimination, and formation of a phenyl ester (3). The phenyl ester is subsequently hydrolyzed: nucleophilic addition of hydroxide from solution to the ester carbonyl carbon forms a second tetrahedral intermediate (4), which collapses, eliminating a phenoxide and forming a carboxylic acid (5). Finally, the phenoxide extracts the acidic hydrogen from the carboxylic acid, yielding the collected products (6).
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