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Such reactions are said to be anti-Markovnikov, since the halogen adds to the less substituted carbon, the opposite of a Markovnikov reaction. The anti-Markovnikov rule can be illustrated using the addition of hydrogen bromide to isobutylene in the presence of benzoyl peroxide or hydrogen peroxide. The reaction of HBr with substituted alkenes ...
In 1869, a Russian chemist named Vladimir Markovnikov demonstrated that the addition of HBr to alkenes usually but not always resulted in a specific orientation. Markovnikov's rule, which stems from these observations, states that in the addition of HBr or another hydrogen halide to an alkene, the acidic proton will add to the less substituted carbon of the double bond. [3]
Thus, H + attacks the carbon atom that carries fewer substituents so as the more stabilized carbocation (with the more stabilizing substituents) will form. This is another example of an Ad E 2 mechanism. [5] Hydrogen fluoride (HF) and hydrogen iodide (HI) react with alkenes in a similar manner, and Markovnikov-type products will be given.
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The reaction follows Markovnikov's rule (the hydroxy group will always be added to the more substituted carbon). The oxymercuration part of the reaction involves anti addition of OH group but the demercuration part of the reaction involves free radical mechanism and is not stereospecific, i.e. H and OH may be syn or anti to each other.
Vladimir Markovnikov was born on December 22, 1837, in Chernorechye near Nizhny Novgorod, Russian Empire (now Dzerzhinsk, Nizhny Novgorod Oblast, Russian Federation). Soon after his birth, his father retired and settled in a family estate received as a dowry from his wife's family at marriage, in the village of Ivanovo, Knyagininsky district of the Nizhny Novgorod province, where Markovnikov ...