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