Illustrated Glossary of Organic Chemistry

Oxymercuration-demercuration: A reaction in which an alkene is reacted with a Hg²⁺ salt and an oxygen nucleophile (water or an alcohol), to form an organomercury intermediate. The intermediate's carbon-mercury bond is then converted to a carbon-hydrogen bond by treatment with NaBH₄. The overall reaction coverts an alkene into an alcohol when the nucleophile is water, or an alkene into an ether when the nucleophile is an alcohol.

Oxymercuration-demercuration of 1-methylcyclohexene with water and mercuric acetate followed by reaction with NaBH₄ gives a tertiary alcohol. The overall reaction is electrophilic addition of water to the alkene following Markovnikov's rule.


Oxymercuration-demercuration of 1-methylcyclohexene with methanol and mercuric trifluoroacetate followed by reaction with NaBH₄ gives an ether. The overall reaction is electrophilic addition of methanol to the alkene following Markovnikov's rule.