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HX
Hydrohalogenation (Markovnikov)
HBr, ROOR
Anti-Markovnikov hydrohalogenation (radical mechanism)
H₃O⁺
Acid-catalyzed hydration (Markovnikov)
1) Hg(OAc)₂, H₂O 2) NaBH₄
Oxymercuration-demercuration (Markovnikov, no rearrangement)
1) BH₃, THF 2) H₂O₂, NaOH
Hydroboration-oxidation (anti-Markovnikov, syn addition)
Br₂
Bromination (anti)
Br₂ / H₂O
Halohydrin formation (OH goes to more substituted carbon)
H₂, Pt
Hydrogenation (syn addition)
1) OsO₄ 2) NaHSO₃, H₂O
Syn dihydroxylation
KMnO₄ (cold)
Syn dihydroxylation
1) O₃ 2) DMS
Ozonolysis (cleavage to carbonyl compounds)