1 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. O O НО О Но о H,O Ph—С—С—Рh + NaOH 7 Ph —С—С—O Nat HCI Ph—С—С—ОН H,O Ph Ph Benzil Sodium benzilate Benzilic acid (an a-diketone)
1 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. O O НО О Но о H,O Ph—С—С—Рh + NaOH 7 Ph —С—С—O Nat HCI Ph—С—С—ОН H,O Ph Ph Benzil Sodium benzilate Benzilic acid (an a-diketone)
Chapter19: Aldehydes And Ketones: Nucleophilic Addition Reactions
Section19.SE: Something Extra
Problem 28VC
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