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