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Markovnikov Hydrohalogenation
H-Br, H-Cl, or H-I
Anti-Markovnikov Hydrohalogenation
H-Br, H-Cl, or H-I w/ ROOR
Acid-catalyzed Hydration
H3O+ or H2SO4 + H2O
Oxymercuration-Demercuration
1) Hg(OAc)2, H2O, 2) NaBH4
Hydroboration-Oxidation
1) BH3/THF, 2) H2O2, NaOH
Hydrogenation
H2 w/ Pt, Pd, or Ni
Halogenation
Cl2 or Br2
Halohydrin Formation
Br2, H2O (reactive solvent)
Anti-dihydroxylation
H3O+ (SECOND STEP ONLY)
Syn Dihydroxylation
1) OsO4, 2) Na2SO3/H2O,
1) OsO4, 2) NaHSO3/H2O, or
OsO4, NMO
Oxidative Cleavage
1) O3, 2) DMS