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Hydrohalogenation
Markovnikov: Br or (X) goes on more substituted carbon of double bond. H goes to less subst.


1,2 - hydride shift
NOT on double bond, Cl to most subst. carbon
formation of a more stable carbocation


1,2 - alkyl shift
NOT on double bond, Br to most subst. carbon


Hydrohalogenation (ring expansion)
Markovnikov
4 or 5 sided, allylic double bond usually


acid-catalyzed hydration
Alcohol + hydronium


addition of Br or Cl
anti addition (180) when given possibility to be trans.
if not, racemix mixture
