Mechanism of 5‐(iodomethyl)oxolan‐2‐one synthesis from 4‐pentenoic acid and iodine in acetonitrile There is a question in my organic chemistry textbook with an answer. What it doesn't explain (and neither does my theory textbook, I checked) is the mechanism involved in the reaction. The reaction is as follows:



Can someone help me?
https://en.wikipedia.org/wiki/Iodolactonization
I+ reacts with the CC-π electron donor. A cyclic iodonium three-membered ring intermediate is formed. The carboxylate group opens the electrophilic intermediate to form the product lactone. 5-membered rings (gamma-lactones) https://en.wikipedia.org/wiki/Lactone are prefered due to optimum entropic and enthalpic parameters of activation.