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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. [2] [3] [4]
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 was prototypical in the study of free-radical additions. Early chemists discovered that the reason for the variability in the ratio of ...
Hydroboration–oxidation is an anti-Markovnikov reaction, with the hydroxyl group attaching to the less-substituted carbon. 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.
In organic chemistry, syn-and anti-addition are different ways in which substituent molecules can be added to an alkene (R 2 C=CR 2) or alkyne (RC≡CR).The concepts of syn and anti addition are used to characterize the different reactions of organic chemistry by reflecting the stereochemistry of the products in a reaction.
For terminal olefins (or acetylenes), the regioselectivity of the process can be described as Markovnikov (addition of X at the substituted end) or anti-Markovnikov (addition of X at the unsubstituted end). Catalysts are frequently employed to control the chemo-, regio-, and stereoselectivity of hydrofunctionalization reactions.
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In terms of regiochemistry, hydroboration is typically anti-Markovnikov, i.e. the hydrogen adds to the most substituted carbon of the double bond. That the regiochemistry is reverse of a typical HX addition reflects the polarity of the B δ+-H δ− bonds. Hydroboration proceeds via a four-membered transition state: the hydrogen and the boron ...
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