- Tardigrade
- Question
- Chemistry
- A biologically active compound, Bombykol ( C 16 H 30 O ) is obtained from a natural source. The structure of the compound is determine by the following reactions. (a) On hydrogenation, Bombykol gives a compound A, C 16 H 34 O, which reacts with acetic anhydride to give an ester. (b) Bombykol also reacts with acetic anhydride to give another ester, which on oxidative ozonolysis ( O 3 / H 2 O 2) gives a mixture of butanoic acid, oxalic acid and 10-acetoxy decanoic acid. Determine the number of double bonds in Bombykol. Write the structures of compound A and Bombykol. How many geometrical isomers are possible for Bombykol?
Q.
A biologically active compound, Bombykol is obtained from a natural source. The structure of the compound is determine by the following reactions.
(a) On hydrogenation, Bombykol gives a compound , which reacts with acetic anhydride to give an ester.
(b) Bombykol also reacts with acetic anhydride to give another ester, which on oxidative ozonolysis gives a mixture of butanoic acid, oxalic acid and 10-acetoxy decanoic acid.
Determine the number of double bonds in Bombykol. Write the structures of compound and Bombykol. How many geometrical isomers are possible for Bombykol?
Solution:
From oxidation products, structure of starting compound can be
deduced as :
