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)
Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter17: Carboxylic Acids
Section: Chapter Questions
Problem 17.24P
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![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)](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Ff0b4b4bb-8aaf-4f9a-aac7-b82bc89c72cf%2F62a07fe5-c87a-4524-a79a-e964d7c495f4%2F6yp4yhs.jpeg&w=3840&q=75)
Transcribed Image Text: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)
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