This document summarizes the rearrangement of benzilic acid from benzil. It introduces benzilic acid and notes that it can be prepared through rearrangement of the 1,2-α-diketone benzil. The document then outlines the preparation of benzil, the rearrangement mechanism involving nucleophilic addition and migration, and properties of the resulting benzilic acid including its white crystalline structure and solubility in alcohols. Hazards of benzilic acid are also mentioned, noting it is very hazardous if in contact with skin or eyes or if ingested or inhaled, and that it is chemically stable under recommended storage conditions.

1. Rearrangement of benzilic acid
Prepared by:
Aras jabar & shaxawan rahim
university of silemany
school of science
chemistry department

2. Content:
 Introduction
 Preparation of benzil
 Rearrangement of benzilic acid
 Mechanism
 Migration
 IR spectrum
 Property of benzilic acid
 Hazardouse of benzilic acid

3. Introduction
 Benzilic acid will be prepared by causing a
rearrangement of a α-diketone benzil
 The major condition of this rearrangement ,we must
have 1,2-α-diketone

4. Preparation of benzil

5. Rearrangement of benzilic acid

6. Mechanism
Nucleophilic
addition
rearrangement phenyl migration
proton transfer

7. Rearrangement

8. Migratory aptitude
> >

9. Rearrangement of nitro benzil

10. If we have cyclic compound

11. IR spectrum for benzil

12. IR spectrum for benzilic acid

13. Property of Product
Benzilic acid is a white crystalline aromatic acid
soluble in many primary alcohols. It can be prepared
by heating mixture of benzil, alcohol and potassium
hydroxide. The other preparation way is through
benzaldehyde, which dimerizates to benzil and it is
further transformed by benzilic acid rearrangement
to benzilic acid.

14. application
Doering extended the reaction to the formation of the
corresponding ester by replacing the normal alkali by alkoxides.
Thus benzil may directly be converted into alkyl benzilate by
treatment with sodium alkoxide.

15. application
The reaction may be used for the preparation of α-hydroxy acids from the easily
accessible starting materials.
It is important to note that as the ethoxide and isopropoxide ions reduce benzil to
benzoin these reagents do not carry out benzilic rearrangement.

16. Hazardous of Benzilic Acid
Potential Acute Health Effects: Very hazardous in case of skin
contact (irritant), of eye contact (irritant). Hazardous in case of
ingestion, of inhalation. Inflammation of the eye is characterized
by redness, watering, and itching. Skin inflammation is
characterized by itching.
Chemical stability : Stable under
recommended storage conditions.
Hazardous combustion products : Under fire conditions,
hazardous fumes will be present and product flammable at
high temperature and product of combustion (CO,CO2).

17. Thank you