4.

5 Oxymercuration [Hg(OAc)2/ROH]

 Oxymercuration-demercuration is the reaction

when alkene treated with mercuric salt [Hg(OAc)2]
(Mercury II acetate) and alcohol [ROH], and ether is
formed.
 Mercuration is an electrophilic addition of a mercuric salt to an
alkene, and the resulting compound is an alkyl-mercury
derivate, from which the mercury can be removed in a
subsequent step.
 And the overall reaction is called oxymercuration-
demercuration.

 Oxymercuration is anti stereospecific and regioselective.

 This outcome implies a mechanism similar to that for
electrophilic addition reactions.
Mechanism of Oxymercuration-Demercuration
1. The mercury reagent initially dissociates to give
an acetate ion and a cation mercury species.
2. This mercury cation then attacks an alkene double bond,
furnishing a mercurinium ion.
3. Markovnikov rule regioselectivity: The alcohol that is present
attacks the more substituted carbon to give an alkylmercuric
acetate intermediate.
4. Demercuration: Replacement of mercury by hydrogen is
achieved by sodium borohydride reduction through a complex and
only incompletely understood mechanism. It is not stereospecific.