In my organic chemistry textbook it states that protonated epoxides are usually attacked at the more substituted side due to more positive charge and carbocation character on that carbon. But, if one side of a protonated epoxide is primary and the other secondary, SN2 is very fast for the primary side and gives the major product (see image).

Wikipedia says that "Oxymercuration is very regioselective and ... the water nucleophile will always preferentially attack the more substituted carbon." So, I'm wondering why something like this doesn't happen for the intermediate with a similar three-membered ring during oxymercuration-demercuration.

enter image description here


Your Answer

By clicking “Post Your Answer”, you agree to our terms of service, privacy policy and cookie policy

Browse other questions tagged or ask your own question.