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H₂
Pd, Pt, Ni
Catalytic Hydrogenation/Reduction
Syn addition


HX (for the example, use HBr)
Hydrohalogenation
Markovnikov


HBr, Peroxide (R−O−O−R)
Hydrobromination with Peroxide
Anti-Markov
*


H₂SO₄
Addition of Sulfuric Acid
markovnikov
*


H₂SO₄
H₂O
Acid-Catalyzed Hydration
Markovnikov
*


1.) BH₃, THF
2.) H₂O₂, OH-
Hydroboration Oxidation
Anti-markovnikov
Syn addition


1.) Hg(OAc)₂, H₂O
2.) NaBH₄, OH-
Oxymercuration-Demercuration
Markovnikov


X₂
Halogenation
Anti-addition


Br₂, H₂O
Halohydrin Formation
Markovnikov
Anti addition


CH₂
CH₂I₂, Zn(Cu)
OH-, HCCl₃
Addition of Carbene/Simmons-Smith
Syn addition


1.) OsO₄, Pyridine
2.) NaHSO₄, H₂O
Syn-Dihydroxylation


1.) KMnO₄, HO-
2.) H₂O, cold
Syn-Dihydroxylation

what reactions are anti markovnikov?
Hydrobromination with peroxide
Hydroboration Oxidation
what reactions are anti-addition?
Halogenation
Halohydrin formation
what reactions are syn addition?
Catalytic hydrogenation
Hydroboration oxidation
Addition of Carbene
Dihydroxylation