Organic Chemistry/Introduction to reactions/Oxymercuration/demercuration

Oxymercuration is a process by which water is added to an alkene through treatment of the alkene with mercury(II) acetate [Hg(O₂CCH₃)₂, usually abbreviated Hg(OAc)₂] in an aqueous tetrahydrofuran (THF) solvent. Rarely this reaction is referred to as Oxymercuration/reduction. This reaction looks just like Markovnikov. addition of water across a double bond, however there is no carbocation intermediate, so there is no rearrangement. You will learn that NaBH₄ is a common reducing agent.

Equations

Addition of water by oxymercuration               1. Hg(OAc)2, H2O/THF H2C=CH2 --------------> H3C-CH2OH                2. NaBH4