Oxymercuration–demercuration

Definition

Oxymercuration–demercuration is a two-step organic chemical reaction process that adds water (H2O) across the double bond of alkenes, in a regioselective manner, to form alcohols without the rearrangement typically seen in acid-catalyzed hydration. First, oxymercuration involves the addition of mercury acetate and water across the alkene's double bond, followed by demercuration, where sodium borohydride reduces the intermediate to produce an alcohol.

Related terms

Alkenes:

Unsaturated hydrocarbons containing at least one carbon-carbon double bond, serving as starting materials in oxymercuration–demercuration.

Markovnikov's rule: A rule indicating that during addition reactions to unsymmetrical alkenes, the hydrogen atom bonds with the carbon having more hydrogen atoms, while groups like OH attach to carbon atoms having fewer hydrogen atoms; however, this rule is not directly applicable in oxymercuration-demercuration due to its non-rearrangement nature.

Hydration reaction: A chemical reaction where a molecule of water is added to a substance; in organic chemistry, it often refers to adding water across double bonds of alkenes to form alcohols