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HX
X, H, Markovnikov
HBr, ROOR
Br, H, anti-Markovnikov
H3O+
OH, H, Markovnikov (hydro)
Hg(OAc)2
OH, H, Markovnikov (merc)
BH3, THF
OH, H, anti-Markovnikov, syn, + en
H2, Pt
H, H, syn, meso
Br2
Br, Br, anti, + en
Br2, H2O
Br, OH, Br = Markovnikov H, anti, + en
RCO3H
OH, OH, anti, + en
KMnO4, NaOH
OH, OH, syn, + en (cold)
OsO4, NaHSO3
OH, OH, syn, + en (os)
O3, DMS
double bond cleavage with oxygen