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The reaction is highly exothermic. In the first step, the alkene acts as a nucleophile and attacks the proton, following Markovnikov's rule. In the second step an H 2 O molecule bonds to the other, more highly substituted carbon. The oxygen atom at this point has three bonds and carries a positive charge (i.e., the molecule is an oxonium ...
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 a hydroxy (−OH) group across the ...
Whereas many hydroxylations insert O atoms into C−H bonds, some reactions add OH groups to unsaturated substrates. The Sharpless dihydroxylation is such a reaction: it converts alkenes into diols. The hydroxy groups are provided by hydrogen peroxide, which adds across the double bond of alkenes. [12]
Oxygen and nitrogen heterocycles dominate due to their abundance in natural products and pharmaceuticals. Some examples are shown below (the red alkene indicates C-C bond formed through RCM). [3] In addition to terminal alkenes, tri- and tetrasubstituted alkenes have been used in RCM reactions to afford substituted cyclic olefin products. [32]
The chemical reaction called Sharpless asymmetric dihydroxylation can be used to produce chiral diols from alkenes using an osmate reagent and a chiral catalyst. Another method is the Woodward cis-hydroxylation (cis diol) and the related Prévost reaction (anti diol), which both use iodine and the silver salt of a carboxylic acid.
The Schenck ene reaction or the Schenk reaction is the reaction of singlet oxygen with alkenes to yield hydroperoxides. The hydroperoxides can be reduced to allylic alcohols or eliminate to form unsaturated carbonyl compounds. It is a type II photooxygenation reaction, and is discovered in 1944 by Günther Otto Schenck. [1]
In organic chemistry, ozonolysis is an organic reaction where the unsaturated bonds are cleaved with ozone (O 3). Multiple carbon–carbon bond are replaced by carbonyl (C=O) groups, such as aldehydes, ketones, and carboxylic acids. The reaction is predominantly applied to alkenes, but alkynes and azo compounds are also susceptible to cleavage.
The Prins reaction is an organic reaction consisting of an electrophilic addition of an aldehyde or ketone to an alkene or alkyne followed by capture of a nucleophile or elimination of an H + ion. [ 1 ] [ 2 ] [ 3 ] The outcome of the reaction depends on reaction conditions.