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Hg(OAc)2, H2O, THF (solvent)
NaBH4
Markov addition of H and OH
oxymercurtion-demurcuration
Hg(OAc)2, HOR, THF (solvent)
NaBH4
Markov addition of H and OR
alkoxymercuration-demurcuration
BH3, THF (solvent)
H2O2, NaOH
Anti-markov addition of H and OH
HBr + peroxides (ROOR), heat/light
anti-markov addition of H and Br
HX (cold, dark, no peroxides) → X = Cl, Br, or I
Markov addition of H and X