structural elucidation of camphor

Structural elucidation of camphor

1. STRUCTURAL ELUCIDATION OF CAMPHOR Under the guidance of: Dr. A. SRI DEVI, M.pharm,Ph.D. Submitted by: K.KAVYA 1 st yr,M.pharmacy, Pharmaceutical chemistry, SPMVV. 1

2. CONTENTS : Introduction Uses Structural elucidation of camphor Synthesis Conclusion Reference 2

3. CAMPHOR Camphor is derived from the wood of camphor laurel ( Cinnamomum camphora ) and other releated trees of laurel family. Camphor is a bicyclic mono terpenoid. Camphor is a white, crystalline substance with strong odour and pangent taste. It is waxy and flammable substance. 3

4. It is obtained through steam distillation, purification and sub limation of wood, twigs &bark of the tree. Melting point:180 c and boiling point is 204 c It is optically active. 4

5. Uses: Topical analgesic Antiseptic Muscle relaxant Anti inflammatory Contraceptive Cough suppressant Insect repellant Flavour in soaps & cosmetics 5

6. General structure of camphor : IUPAC Name :1,7,7-Trimethyl bicyclo[2.2.1]heptan-2-one 6

7. STRUCTURAL ELUCIDATION OF CAMPHOR: Camphor molecular formula C 10 H 16 O . Nature of oxygen atom: Camphor as it forms oxime with NH 2 OH & phenyl hydrazine. C 10 H 16 O+ H 2 NOH C 10 H 16 =NOH Camphor Hydroximine camphor oxime Presence of bicyclic ring system: The parent hydrocarbon of camphor has molecular formula C 10 H 18 which correspond to the molecular formula of bicyclic compounds( C n H 2n-2 ). 7

8. Presence of six membered ring: when distilled with ZnCl 2 / P 2 O 5 it forms p-cymene. O C 8 H 14 - C - CH 2 P-cymene 8 ZnCl 2 P 2 O5

9. Presence of –COCH 2 group : camphor is confirmed by its formation to isonitroso derivative with amylnitrile and hydrochloride. Camphor C 8 H 14 - C - CH 2 O C 8 H 14 NOH O Iso nitrso compound 9 Amylnitrile HCl

10. Camphor on oxidation with HNO 3 gives camphoric acid and camphoronic acid. Camphoronic acid is saturated tricarboxylic acid & on distillation at atom pressure gives. C 9 H 14 O 6 + +CO 2 [O] C 10 H 16 O HNO 3 C 10 H 16 O 4 [O] C 9 H 14 O 6 Isobutyric acid Trimethyl succinic acid 10 distillation

11. Bredt suggested that comphoronic acid is 2,3-di methyl – 1,2,3-butanetri carboxylic acid , hence having 3-CH 3 group so camphor must have 3-methyl group. camphoronic acid 11

12. On the basis of the formula of camphoric acid C 10 H 16 O 4 it was found that camphoric acid is a cyclopentane derivative & the structure was proposed as: camphoric acid 12

13. Bredt proposed the following reaction to show the relationship between camphor, camphoric acid, and camphoronic acid and established the structure of camphor. camphoric acid camphor camphoronic acid [o] [o] 13

14. 14

15. Conclusion : we concluded in the camphor it presence of six membered ring , ketone group, oxene group and it oxidized to form camphoric acid &camphoronic acid . 15

16. Reference: Organic chemistry of natural products :by O.P.Agrawal. Chemistry of natural products :by Gurdeep .R.Chatwal Classical Methods in Structure Elucidation of Natural Products : R. W. Hoffmann Chemistry of natural products-SV.Bhat ,BH Nagasampagi, M.Sivakumar www.google.com 16

17. 17