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