What is the mechanism of Oxymercuration?
What is the mechanism of Oxymercuration?
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 double bond. Carbocations are not formed in this process and thus rearrangements are not observed.
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 final product of Oxymercuration Demercuration reaction?
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 the mechanism of oxymercuration-demercuration reaction?
Oxymercuration-Demercuration: The mechanism. Let’s look at the mechanism of Oxymercuration-Demercuration reaction and understand how it prevents possible rearrangement reactions. In the first step, the mercuric acetate, Hg (OAc) 2, dissociates into a mercuric cation: This cation is very electrophilic and is attacked by the double bond.
How are carbocations formed in the oxymercuration reaction?
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 double bond. Carbocations are not formed in this process and thus rearrangements are not observed.
What is the demercuration reaction mechanism of alkenes?
This organic chemistry video tutorial provides a basic introduction into the alkoxymercuration demercuration reaction mechanism of alkenes into ethers.Subscr… This organic chemistry video tutorial provides a basic introduction into the alkoxymercuration demercuration reaction mechanism of alkenes into ethers.Subscr…
Where do the two steps of alkoxymerecuration-demercuraton take place?
The two steps of alkoxymerecuration-demercuraton take place on opposite faces of the double bond creating trans stereochemistry. This reaction follows electrophilic addition mechanism we have learned. The major difference is that a mercurium ion bridge stabilizes the carbocation intermediate so that it cannot rearrange.