Oxymercuration-Demercuration This is another alternative for converting alkenes to alcohols with Markovnikov orientation.This method has the advantage of not involving free carbocationic species,and thus removes the possibility of rearrangements CC=C Hg(OAc)2 H20 HO HgOAc HO H (Markovnikov orientation) The reagent is called mercuric acetate,and is usually abbreviated to Hg(OAc)2In solution it ionizes into acetate ion and a positively charged mercury species which is very electrophilic. 0 0 CH,-C-O一Hg-O-C-CH, CH-C-O-Hg+ + CH-C-O Hg(OAc) +Hg(OAc) -OAc 2013 Prson Educalion ine OAc mercurinium ion Oxymercuration is the +Hg(OAc) electrophilic attack of this species on a double bond, giving a 3 membered ring compound called a mercurinium ion. Cho8 Reacns of Alkenes (landscape) Page 12 Ch08 Reacns of Alkenes (landscape) Page 12 Oxymercuration-Demercuration This is another alternative for converting alkenes to alcohols with Markovnikov orientation. This method has the advantage of not involving free carbocationic species, and thus removes the possibility of rearrangements. The reagent is called mercuric acetate, and is usually abbreviated to Hg(OAc)2 In solution it ionizes into acetate ion and a positively charged mercury species which is very electrophilic. Oxymercuration is the electrophilic attack of this species on a double bond, giving a 3 membered ring compound called a mercurinium ion