Experiment No: 02:

Object: Synthesis of 5,5-diphenylhydantoin from benzil.

Theory: In 1838, Justus von Liebig found that treating benzil (1,2-diphenylethan-1,2dione) with hydroxide gave, after acid quench, 2-hydroxy-2,2-diphenylacetic acid,
which he called benzilic acid. The mechanism of this benzilic acid rearrangement
starts with attack of hydroxide on one of the carbonyl groups. The tetrahedral
intermediate can collapse in a reaction reminiscent of a semipinacol rearrangement.

Procedure: 1.
Added 1.325g benzil and 0.75g urea in to a 100mL round-bottomed flask
2.
Added 40 mL of 95% ethanol and 4 mL of 5% KOH solution.
3.
Reflux the mixture with stirring for 2 hours on sand bath.
4.
Cooled the reaction mixture and then removed the sparingly insoluble solid by
gravity filtration.
5.
Cooled the filtrate further in an ice-water bath and acidify the filtrate with 6M
sulfuric (pH 1.5~3). The white powdered solid was obtained.
6.
Collected the product by filtration, and washed it thoroughly with water to
remove the inorganic salt.
7.
Recrystallized the crude product from 95% ethanol.
8.
The white needle-shape crystal was obtained.

Reaction:

Mechanism: -