: Synthesis of Benzilic Acid

Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
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Experiment 5: Synthesis of Benzilic Acid
In this experiment, benzilic acid will be prepared by causing a rearrangement
of the a-diketone benzil. (Preparation of benzil is described in Part 2 of this
experiment.) The rearrangement of benzil proceeds as follows:
K*
K* o O
||
Ph-C
КОН
Ph-C
C-Ph
Ph-
Ċ-OH
-C-OH
Benzil
Ph
Ph
ОН О
ОН О
= Ph
Ph-C-C-o K*
Ph—C—С—ОН
Ph
Ph
Potassium benzilate
Benzilic acid
The driving force for he reaction is provided by the formation of a stable
carboxylate salt (potassium benzilate). Once this salt is produced,
acidification yields benzilic acid.
Transcribed Image Text:Experiment 5: Synthesis of Benzilic Acid In this experiment, benzilic acid will be prepared by causing a rearrangement of the a-diketone benzil. (Preparation of benzil is described in Part 2 of this experiment.) The rearrangement of benzil proceeds as follows: K* K* o O || Ph-C КОН Ph-C C-Ph Ph- Ċ-OH -C-OH Benzil Ph Ph ОН О ОН О = Ph Ph-C-C-o K* Ph—C—С—ОН Ph Ph Potassium benzilate Benzilic acid The driving force for he reaction is provided by the formation of a stable carboxylate salt (potassium benzilate). Once this salt is produced, acidification yields benzilic acid.
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