What is oxymercuration reduction with example?

Oxymercuration demercuration is an addition reaction that can be used to turn an alkene into alcohol. In this reaction, an alkene reacts with mercury (II) acetate (Hg(OAc)2) in aqueous THF, followed by reduction with sodium borohydride (NaBH4).

What is the mechanism of oxymercuration Demercuration reaction?

In an oxymercuration–demercuration reaction, an alkene is treated with mercury(II) acetate, Hg(OAc)2, and the product is treated with sodium borohydride. The net result is a Markovnikov addition product in which the OH group bonds to the more substituted carbon atom of the alkene.

What type of reaction is oxymercuration Demercuration?

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.

What is the reactant and reagent used in oxymercuration and Demercuration?

This reaction involves a mercury acting as a reagent attacking the alkene double bond to form a Mercurinium Ion Bridge. A water molecule will then attack the most substituted carbon to open the mercurium ion bridge, followed by proton transfer to solvent water molecule.

Is oxymercuration anti addition?

Oxymercuration is very regioselective and is a textbook Markovnikov reaction; ruling out extreme cases, the water nucleophile will always preferentially attack the more substituted carbon, depositing the resultant hydroxy group there. Stereochemically, oxymercuration is an anti addition.

What is Oxymercuration reduction reaction?

The oxymercuration reaction is an electrophilic addition organic reaction that transforms an alkene into a neutral alcohol. Oxymercuration followed by reductive demercuration is called an oxymercuration–reduction reaction or oxymercuration–demercuration reaction.

Is oxymercuration a hydration reaction?

2. This reaction is electrophilic hydration.

What is oxymercuration reduction reaction?

What is the product of oxymercuration?

Oxymercuration is the reaction of an alkene with mercury(II) acetate in aqueous THF, followed by reduction with sodium borohydride. The final product is an alcohol.

What is oxymercuration reduction reaction in organic chemistry?

Oxymercuration–reduction. Therefore, the oxymercuration-reduction reaction is the net addition of water across the double bond. Any stereochemistry set up by the oxymercuration step is scrambled by the demercuration step, so that the hydrogen and hydroxy group may be cis or trans from each other.

What is the product of oxymercuration and demercuration?

In practice, the mercury adduct product created by the oxymercuration reaction is almost always treated with sodium borohydride (NaBH 4) in aqueous base in a reaction called demercuration. In demercuration, the acetoxymercury group is replaced with a hydrogen in a stereochemically insensitive reaction known as reductive elimination.

What is the difference between demercuration and reduction reaction?

In demercuration, the acetoxymercury group is replaced with a hydrogen in a stereochemically insensitive reaction known as reductive elimination. The combination of oxymercuration followed immediately by demercuration is called an oxymercuration–reduction reaction.

Is Markovnikov’s rule applicable to oxymercuration?

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.