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In organic chemistry, the oxymercuration reaction is an electrophilic addition reaction that transforms an alkene (R 2 C=CR 2) 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 ...
When alkenes undergo hydrobromination, the alkyl bromides are formed Markovnikov. Alkyne oxymercuration-demercuration: In this reaction, HgSO 4 reacts with an alkyne in a Markovnikov regioselective manner to form an enol that is tautomerized into a ketone. This process utilizes anti addition of an OH group to the more substituted carbon, making ...
In organic chemistry, an alkene, or olefin, ... Oxymercuration-reduction: alcohols electrophilic addition of mercuric acetate, then reduction Prins reaction:
Hydroboration–oxidation reaction is a two-step hydration reaction that converts an alkene into an alcohol. [1] The process results in the syn addition of a hydrogen and a hydroxyl group where the double bond had been. Hydroboration–oxidation is an anti-Markovnikov reaction, with the hydroxyl group attaching to the less-substituted carbon.
In general oxymercuration reactions of alkenes and alkynes using mercuric compounds proceed via organomercury intermediates. A related reaction forming phenols is the Wolffenstein–Böters reaction .
Formation of a secondary alcohol via alkene reduction and hydration is shown: The hydroboration-oxidation and oxymercuration-reduction of alkenes are more reliable in organic synthesis. Alkenes react with N-bromosuccinimide and water in halohydrin formation reaction. Amines can be converted to diazonium salts, which are then hydrolyzed.
Mercury sulfate, as well as other mercury(II) compounds, are commonly used as catalysts in oxymercuration-demercuration, a type of electrophilic addition reaction that results in hydration of an unsaturated compound. The hydration of an alkene gives an alcohol. The regioselectivity is that predicted by Markovnikov's rule.
General overview of addition reactions. Top to bottom: electrophilic addition to alkene, nucleophilic addition of nucleophile to carbonyl and free-radical addition of halide to alkene. Depending on the product structure, it could promptly react further to eject a leaving group to give the addition–elimination reaction sequence.