Syn Addition Br2 or Cl2 HBr, HCl, HI Anti Addition Hydrohalogenation Halogenation Catalytic Hydrogenation cat. ROOR Acid- catalyzed hydration Bromonium ion Epoxide H2SO4, H2O 1)OsO4 2)NaHSO3, H2O Nucleophiles or Bases Hydroboration- Oxidation Halohydrin formation Syn Dihydroxylation Anti- Markovnikov addition Halogen (Br + Cl) and H2O Anti Dihydroxylation 1) RCO3H 2) H3O+ Pd, Pt Markovnikov addition 1) BH3, THF 2) NaOH, H2O2 Syn Addition Br2 or Cl2 HBr, HCl, HI Anti Addition Hydrohalogenation Halogenation Catalytic Hydrogenation cat. ROOR Acid- catalyzed hydration Bromonium ion Epoxide H2SO4, H2O 1)OsO4 2)NaHSO3, H2O Nucleophiles or Bases Hydroboration- Oxidation Halohydrin formation Syn Dihydroxylation Anti- Markovnikov addition Halogen (Br + Cl) and H2O Anti Dihydroxylation 1) RCO3H 2) H3O+ Pd, Pt Markovnikov addition 1) BH3, THF 2) NaOH, H2O2
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G-Syn Addition
O-Br2 or Cl2
B-HBr, HCl, HI
B-Anti Addition
G-Hydrohalogenation
O-Halogenation
B-Catalytic Hydrogenation
I-cat. ROOR
G-Acid-catalyzed hydration
I-Bromonium ion
G-Epoxide
G-H2SO4, H2O
O-1)OsO4
2)NaHSO3, H2O
O-Nucleophiles or Bases
I-Hydroboration-Oxidation
N-Halohydrin formation
I-Syn Dihydroxylation
N-Anti-Markovnikov addition
B-Halogen (Br + Cl) and H2O
N-Anti Dihydroxylation
N-1) RCO3H
2) H3O+
O-Pd, Pt
I-Markovnikov addition
B-1) BH3, THF
2) NaOH, H2O2