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HX
H X
Markovnikov
Carbocation —> rearrangement
HX, ROOR
H X
Anti-Markovnikov
Radical Reaction
H2SO4, H2O
H OH
Markovnikov
Carbocation —> rearrangement
H2SO4, ROH
H OR
Markovnikov
Carbocation —> rearrangement
Hg(OAC)2, NaBH4, H2O
H OH
Markovnikov
Bridged intermediate, no rearrangement, anti-addition
Hg(OAC)2, NaBH4, H2O
H OR
Markovnikov
Bridged intermediate, no rearrangement, anti-addition
BH3, THF
HOOH, NaOH
H OH
Anti-Markovnikov
Syn, 4-membered transition state
H2, Pt
H H
Syn
X2
X X
Anti
X2, H2O
X OH
Markovnikov
Anti
X2, ROH
X OH
Markovnikov
Anti
mCPBA
H3O+
OH OH
Syn