What is the mechanism of oxymercuration Demercuration?

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 is oxymercuration and Demercuration reaction?

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 difference between oxymercuration and Demercuration?

The key difference between oxymercuration and demercuration is that oxymercuration involves an electrophilic addition where an alkene transforms into a neutral alcohol, whereas demercuration involves the conversion of an alkene into Hg2+ salt and an organomercury intermediate.

Is oxymercuration Demercuration anti or syn?

anti addition
Stereochemically, oxymercuration is an anti addition. As illustrated by the second step, the nucleophile cannot attack the carbon from the same face as the mercury ion because of steric hindrance.

Which product is formed in oxymercuration-Demercuration reaction?

Alkene hydration using the oxymercuration-demercuration reaction pathway reliably produces the Markovnikov product without carbocation rearrangment as shown in the example below. Oxymercuration-Demercuration is a two step pathway used to produce alcohols.

What reagents are used in oxymercuration-Demercuration?

Hint:In Oxymercuration – demercuration reaction alkene is converted to alcohol. In this reaction the reagent used is mercury (II) acetate in tetrahydrofuran which is used as the solvent.

Is oxymercuration-Demercuration a racemic?

This indicates that the product is a racemic mixture. There is no stereochemical control in acid-catalyzed hydration reactions.

What type of reaction is oxymercuration?

Oxymercuration-Demercuration Mechanism. This mechanism is similar to the previous electrophilic addition reactions. The major difference is that a mercurium ion bridge stabilizes the carbocation intermediate so that it cannot rearrange. Metals are electropositive.

What is the final product of oxymercuration-Demercuration reaction?

Study Notes. 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.

Which product is formed in oxymercuration Demercuration reaction?

What is the final product of oxymercuration Demercuration reaction?

Is oxymercuration Demercuration a racemic?