The reaction of an a-diketone with concentrated sodium or
Chapter 17, Problem 17.25(choose chapter or problem)
The reaction of an a-diketone with concentrated sodium or potassium hydroxide to give the salt of an a-hydroxyacid is given the general name benzil-benzilic acid rearrangement. It is illustrated by the conversion of benzil to sodium benzilate and then to benzilic acid. Propose a mechanism for this rearrangement. Benzil (an -diketone) Sodium benzilate Ph9C9C9Ph Ph9C9C9O2Na 1 NaOH 1 O O O H2O HCl H2O Ph HO Benzilic acid Ph9C9C9OH O Ph HO
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