Rearrangement of benzilic acid

prepared by
aras jabar & shaxawan rahim
students in university of sulaimani

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

2. C ontent: 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,CO 2 ) .

17. Thank you