Chemical reaction of an alkene with mercuric acetate to form an alcohol
Oxymercuration reaction[1]
In organic chemistry, the oxymercuration reaction is an electrophilic addition reaction that transforms an alkene (R2C=CR2) into a neutral alcohol. In oxymercuration, the alkene reacts with mercuric acetate (AcO−Hg−OAc) in aqueous solution to yield the addition of an acetoxymercury (−HgOAc) group and a hydroxy (−OH) group across the double bond. Carbocations are not formed in this process and thus rearrangements are not observed. The reaction follows Markovnikov's rule (the hydroxy group will always be added to the more substituted carbon) and it is an anti addition (the two groups will be trans to each other).[2][3][4]
Oxymercuration followed by reductive demercuration is called an oxymercuration–reduction reaction or oxymercuration–demercuration reaction. This reaction, which is almost always done in practice instead of oxymercuration, is treated at the conclusion of the article.
^Organic Syntheses OS 6:766 Link
^Loudon, Marc G. (2002). "Addition Reactions of Alkenes". Organic Chemistry (fourth ed.). Oxford University Press. pp. 165–168.
^McGraw-Hill Higher Education (2000). Oxymercuration–Demercuration of Alkenes.
^Andreas Schleifenbaum (2001). "Oxymercuration". Reaktionen, Reagenzien und Prinzipien. Archived from the original on 29 August 2004.
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