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.
This page is available to MOC Members only.
Sign up here for about 30 cents/ day!
Real-Life Example:
Org. Synth. 1940, 20, 81
DOI Link: 10.15227/orgsyn.020.0081
Click to Flip
okay lang. add more example.
In the last example why wasn’t ROH used along with Hg(OAc)2
the OH end of the alkene is the ROH in this case
That is absolutely correct Taylor. Thanks.
The title says “to form alcohols” but isn’t that “ether” instead?
Fixed. Thank you!
For the removal of mercuric acetate why must sodium borohydride be added in a basic condition?
why is the double bond positioned on the outside of the ring (for step 1)?
I wouldn’t say that it’s positioned on the outside of the ring. It’s an attempt to show the double bond of the ring forming a three-membered ring with mercury.