Question

Treating ${\mathbf{PGC}}_{\mathbf{2}}$with a strong base such as sodium tert-butoxide followed by the addition of acid converts it to${\mathbf{PGA}}_{\mathbf{2}}$ . Propose a mechanism for this reaction

Short answer

Mechanism of the reaction

Step-by-step solution

Prostaglandins

The lipid groups present in the tissues of the body of many organisms are prostaglandins. Here, the phosphate group is the hydrophilic part which is the head of the molecule and the fatty acid group acts as the hydrophobic part which is two tails.

Constituents of prostaglandins

The prostaglandins are mainly a five-membered ring with one oxygen atom attached to the ring. In general, it is designated as X. X stands for various functional groups.

About the mechanism

The abstraction of a proton from the alpha carbon that is present adjacent to the carbonyl group takes place due to tert-butoxide ion. It will result in the formation of an oxide ion upon electron rearrangements.

The electron pair in the oxide ion is donated to the ring. The double bond present in the ring undergoes an electrophilic addition reaction resulting in the formation of ${\text{PGA}}_2$.

Mechanism of the reaction