Master Organic Chemistry Reaction Guide

Oxymercuration of Alkenes to form Ethers using Hg(OAc)2

Description: When an alkene is treated with an alcohol in the presence of mercuric acetate [Hg(OAc)2] it will add to the more substituted position of the alkene (Markovnikoff) to give an ether. The mercury can then be removed using NaBH4.

The rest of this page is available to MOC Members only.
To get access to this page, plus over 1500 quizzes, the Reaction Encyclopedia, Org 1 / Org 2 summary sheets, and flashcards, sign up here for only 30 cents/ day!


Real-Life Example:
Org. Synth. 1940, 20, 81
DOI Link: 10.15227/orgsyn.020.0081

Click to Flip


Comment section

11 thoughts on “Oxymercuration of Alkenes to form Ethers using Hg(OAc)2

    1. Great question!

      It’s adjacent to an electron-withdrawing ketone. Normally you would expect the more substituted carbon to be the best at stabilizing positive charge, but the electron-withdrawing influence of the ketone means that it is in fact the less substituted carbon that is better at stabilizing positive charge.

      Similar “anti-Markovnikov” selectivity is observed in addition to alkenes where one side has a CF3 group or other electron-withdrawing groups.

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.