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 is Alkoxymercuration Demercuration?

Alkoxymercuration-demercuration is a two step pathway used to produce ethers that proceeds in a Markovnikov manner and is stereospecific (anti addition). The two steps of alkoxymerecuration-demercuraton take place on opposite faces of the double bond creating trans stereochemistry.

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.

How many steps are in Oxymercuration-Demercuration?

two step
Oxymercuration-Demercuration is a two step pathway used to produce alcohols.

What is meant by the oxymercuration Demercuration reaction illustrate it with an 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). Weber reported this reaction in a journal in 1971.

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

What is the product of this Alkoxymercuration Demercuration reaction?

Alkoxymercuration-demercuration is a reaction in which an alkene (a compound containing a carbon-carbon double bond) is reacted with an alcohol in the presence of mercuric acetate that initially yields what’s called an alkoxymercury intermediate, which produces an ether after reduction with sodium borohydride.

Is Alkoxymercuration anti markovnikov?

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.

How do you synthesize ethers?

Keep in mind there are multiple ways. The Williamson ether synthesis, alkoxymercuration of alkenes, and also the acid catalyzed substitution. Draw the electron arrow pushing mechanism for the formation of diethyl ether in the previous problem.

What is the mechanism of alkoxymercuration – demercuration?

The mechanism of the fourth step is beyond the scope of first year organic chemistry. Notice that overall, the alkoxymercuration – demercuration mechanism follows Markovnikov’s regioselectivity with the OR group attached to the most substituted carbon and the H attached to the least substituted carbon.

What is the mechanism of action of mercuric acetate on alkene?

In the first step of the mechanism, a reaction takes place between the alkene and mercuric acetate, forming a three-membered ring system with a positive charge on the mercury atom.

Does the oxymercuration – demercuration mechanism follow Markovnikov’s regioselectivity?

Notice that overall, the oxymercuration – demercuration mechanism follows Markovnikov’s Regioselectivity with the OH group attached to the most substituted carbon and the H attached to the least substituted carbon.

What is the mechanism of hydration of alkenes?

In the previous post, we talked about the acid-catalyzed hydration of alkenes which leads to the formation of alcohols: Let’s quickly recall the mechanism. The reaction starts with protonation of the double bond which leads to the more stable carbocation.