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The synthetic goal that is achieved by subjecting an alkene to an hydroboration-oxidation sequence is: Markovnikov addition of H2O wherein skeletal rearrangement is prevented

What is Markovnikov addition ?

  • To simplify the rule, it can also be stated as – “Hydrogen is added to the carbon with the most hydrogens and the halide is added to the carbon with the least hydrogens”.
  • While the halide group attaches to the carbon atom with the most alkyl substituents when a protic acid (HX) is introduced to an asymmetric alkene, the acidic hydrogen adheres to the carbon with the most hydrogen substituents.
  • When an unsymmetrically substituted alkene is combined with a protic acid, typically indicated by the symbol HX, Markovnikov's rule predicts the regiochemistry of the reaction.
  • It predicts that the protic acid's halide component will gravitate toward highly substituted carbon atoms whereas the hydrogen component would gravitate toward the least substituted carbon atom (the carbon atom holding the most carbon-hydrogen bonds).

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