Organic Chemistry/Introduction to reactions/Oxymercuration/demercuration

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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[edit]

Addition of water by oxymercuration


              1. Hg(OAc)2, H2O/THF
H2C=CH2 --------------> H3C-CH2OH
               2. NaBH4