page_title: Oxymercuration reaction
section_title: Other applications
hierarchical_section_title: Oxymercuration reaction / Other applications
caption_attribution_description: English: other applications of oxymercuration reaction
context_page_description: The oxymercuration reaction is an electrophilic addition organic reaction that transforms an alkene into a neutral alcohol. In oxymercuration, the alkene reacts with mercuric acetate in aqueous solution to yield the addition of an acetoxymercury group and a hydroxy group across the double bond. Carbocations are not formed in this process and thus rearrangements are not observed. The reaction follows Markovnikov's rule and it is an anti addition.
  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.
context_section_description: Oxymercuration is not limited to an alkene reacting with water. Using an alkyne instead of an alkene yields an enol, which tautomerizes into a ketone. Using an alcohol instead of water yields an ether. In both cases, Markovnikov's rule is observed.
  Using a vinyl ether in the presence of an alcohol allows the transfer of the alkoxy group (RO–) from the alcohol to the ether. An allyl alcohol and a vinyl ether under the conditions of oxymercuration–reaction can give R–CH=CH–CH₂–O–CH=CH₂, which is suitable for a Claisen rearrangement.
caption: Other applications of oxymercuration
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