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Oxymercuration reaction [1] In organic chemistry , the oxymercuration reaction is an electrophilic addition reaction that transforms an alkene ( R 2 C=CR 2 ) into a neutral alcohol . In oxymercuration, the alkene reacts with mercuric acetate ( AcO−Hg−OAc ) in aqueous solution to yield the addition of an acetoxymercury ( −HgOAc ) group and ...
The general chemical equation for the hydration of alkenes is the following: RRC=CH 2 + H 2 O → RRC(OH)-CH 3. A hydroxyl group (OH −) attaches to one carbon of the double bond, and a proton (H +) adds to the other. The reaction is highly exothermic. In the first step, the alkene acts as a nucleophile and attacks the proton, following ...
This reductive coupling can be viewed as involving two steps. First is the formation of a pinacolate (1,2-diolate) complex, a step which is equivalent to the pinacol coupling reaction. The second step is the deoxygenation of the pinacolate, which yields the alkene, this second step exploits the oxophilicity of titanium.
Formation of a secondary alcohol via alkene reduction and hydration is shown: The hydroboration-oxidation and oxymercuration-reduction of alkenes are more reliable in organic synthesis. Alkenes react with N -bromosuccinimide and water in halohydrin formation reaction .
[6] [12] Treatment of the intermediate silylperoxide with 1 drop of concentrated HCl in methanol leads to the hydroperoxide product. Isayama's work with modp ligand detailed. Both Mukaiyama [13] and Magnus [14] describe conditions for an α-enone hydroxylation reaction using Mn(dpm) x in the presence of oxygen and phenylsilane. An asymmetric ...
When alkenes undergo hydrobromination, the alkyl bromides are formed Markovnikov. Alkyne oxymercuration-demercuration: In this reaction, HgSO 4 reacts with an alkyne in a Markovnikov regioselective manner to form an enol that is tautomerized into a ketone. This process utilizes anti addition of an OH group to the more substituted carbon, making ...
The Bamford–Stevens reaction has not proved useful for the stereoselective generation of alkenes via thermal decomposition of metallated tosylhydrazones due to the indiscriminate 1,2-rearrangement of the carbene center, which gives a mixture of products. By replacing an alkyl group with a trimethylsilyl (TMS) group on N-aziridinylimines ...
The model is named after Michael J. S. Dewar, [1] Joseph Chatt and L. A. Duncanson. [2] [3] The alkene donates electron density into a π-acid metal d-orbital from a σ-symmetry bonding orbital between the carbon atoms. The metal donates electrons back from a (different) filled d-orbital into the empty π * antibonding orbital. Both of these ...