What is Hg OAc 2 do?

What is Hg OAc 2 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.

Is Hg OAc 2 an electrophile?

The classic case of nucleophilic donation to a coordinated alkene occurs with mercury (II) salts such as mercuric chloride, HgCl2, or mercuric acetate, Hg(OAc)2. This reaction qualifies as an electrophilic addition because, as in the previous cases, it begins with donation of a π-bonding pair to an electrophile.

What are the reagents for 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 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.

What does Hg OAc 2 do to an alkene?

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.

Does oxymercuration have intermediate?

Oxymercuration-Demercuration Mechanism. This mechanism is similar to the previous electrophilic addition reactions. The fourth step of the reaction pathway is the reduction of the organomercury intermediate with sodium borohydride under basic conditions.

What does HG OAc 2 do to an alkene?

Is rearrangement possible in Oxymercuration Demercuration?

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. The mercurium ion stabilizes the carbocation so that it does not rearrange.

Is Alkoxymercuration Demercuration anti Markovnikov?

Alkoxymercuration-demercuration is a two step pathway used to produce ethers that proceeds in a Markovnikov manner and is stereospecific (anti addition).

Why is Hydroboration syn addition?

Stereochemistry of hydroboration The hydroboration reaction is among the few simple addition reactions that proceed cleanly in a syn fashion. Since the bonding of the double bond carbons to boron and hydrogen is concerted, it follows that the geometry of this addition must be syn.

What product will form Hg OAc 2?

NaBH4, HO. TsC1, pyridine. KCN.

When does Hg ( OAc 2 ) form a mercuric cation?

The process begins when mercuric acetate, Hg (OAc) 2, dissociates to form a mercuric cation: The mercuric cation is a powerful electrophile and is subject to attack by a nucleophile, such as the π bond of an alkene.

What kind of reagent is mercury ( II ) acetate?

Commonly abbreviated Hg (OAc) 2, this compound is employed as a reagent to generate organomercury compounds from unsaturated organic precursors. Mercury (II) acetate is a crystalline solid consisting of isolated Hg (OAc) 2 molecules with Hg-O distances of 2.07 Å.

Which is the reagent in the first step of oxymercuration?

Oxymercuration-demercuration is the reaction sequence in which mercuric acetate acts as the reagent. In the first step (oxymercuration), treatment of an alkene with this species in the presence of water leads to the corresponding addition product.