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Alkene oxymercuration-demercuration: Stereospecific: Can only be anti addition – water kicks out the mercury from underneath the intermediate three-membered ring. The reaction is considered Markovnikov as it results in water addition with same regiospecificity as a direct hydration reaction. Alkene hydroboration-oxidation
In practice, the mercury adduct product created by the oxymercuration reaction is almost always treated with sodium borohydride (NaBH 4) in aqueous base in a reaction called demercuration. In demercuration, the acetoxymercury group is replaced with a hydrogen in a stereochemically insensitive reaction [6] known as reductive elimination. The ...
The rule states that with the addition of a protic acid HX or other polar reagent to an asymmetric alkene, the acid hydrogen (H) or electropositive part gets attached to the carbon with more hydrogen substituents, and the halide (X) group or electronegative part gets attached to the carbon with more alkyl substituents.
Conversion of 2,5-dimethylhexyne-2,5-diol to 2,2,5,5-tetramethylte-trahydrofuran-3-one. Mercury sulfate, as well as other mercury(II) compounds, are commonly used as catalysts in oxymercuration-demercuration, a type of electrophilic addition reaction that results in hydration of an unsaturated compound.
Mercury(II) acetate, also known as mercuric acetate is a chemical compound, the mercury(II) salt of acetic acid, with the formula Hg(O 2 CCH 3) 2.Commonly abbreviated Hg(OAc) 2, this compound is employed as a reagent to generate organomercury compounds from unsaturated organic precursors.
Tetrakis(acetoxymercurio)methane [5]. In part reflecting the strength of the C-Hg bond, organomercury compounds are generated by many methods. [6] Indeed, mercury may adsorb onto laboratory glassware, such that laboratories performing mercury experiments may have difficulty avoiding C–Hg bond formation.
Poison Profits. A HuffPost / WNYC investigation into lead contamination in New York City
The reaction thus provides a more stereospecific and complementary regiochemical alternative to other hydration reactions such as acid-catalyzed addition and the oxymercuration–reduction process. The reaction was first reported by Herbert C. Brown in the late 1950s [2] and it was recognized in his receiving the Nobel Prize in Chemistry in 1979.