H-X Addition to Alkenes: Hydrohalogenation

H-X Addition to Alkenes

  • Markovnikov addition, no stereochemistry
  • Two-step mechanism with carbocation intermediate.
  • Regiochemistry is controlled by carbocation stability.
    • 3o>2o>1o>Methyl (Markovnikov's rule)
  • Carbocation rearrangements are possible (e.g hydride or alky shifts).
  • Evidence for this mechanism is the observed regiochemistry and
    rearrangements.