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 Demercuration used for?
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 product of oxymercuration?
alcohol
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. It is important that you recognize the similarity between the mechanisms of bromination and oxymercuration.
Is oxymercuration Demercuration stereoselective?
Oxymercuration is a special electrophilic addition. It is anti-stereospecific and regioselective.
How many steps are in Oxymercuration Demercuration?
two step
Oxymercuration-Demercuration is a two step pathway used to produce alcohols.
What is syn addition?
Syn addition is the addition of two substituents to the same side (or face) of a double bond or triple bond, resulting in a decrease in bond order but an increase in number of substituents. Generally the substrate will be an alkene or alkyne. The classical example of this is bromination (any halogenation) of alkenes.
What does Demercuration mean?
Illustrated Glossary of Organic Chemistry – 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.
What is anti addition?
Anti addition: An addition reaction in which two substituents are added to opposite sides (or faces) of a double bond or triple bond.
Does alkene undergo oxymercuration?
Alkenes do not undergo hydration upon treatment with water even at very high temperatures. Using an indirect method, such as oxymercuration-reduction, also known as oxymercuration-demercuration or, simply, oxymercuration. …
Does Oxymercuration add syn or anti?
Stereochemically, oxymercuration is an anti addition. With 1-methyl-4-t-butylcyclohexene, oxymercuration yields only one product – still anti addition across the double bond – where water only attacks the more substituted carbon.
What does mercury acetate do?
Mercury(II) acetate is the chemical compound with the formula Hg(O2CCH3)2. Commonly abbreviated Hg(OAc)2, this compound is employed as a reagent to generate organomercury compounds from unsaturated organic precursors. It is a white water-soluble solid, but samples appear yellowish with time owing to decomposition.
Is hydration syn or anti?
The hydroboration mechanism has the elements of both hydrogenation and electrophilic addition and it is a stereospecific (syn addition), meaning that the hydroboration takes place on the same face of the double bond, this leads cis stereochemistry.