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Hydrohalogenation
H-X
Adding H and Halogen
Markovnikov
Syn and Anti
Acid Catalyzed Hydration
H3O+
adding H and OH
Markovnikov
Syn and Anti
Oxymercuration-Demercuration
1.) Hg (OAC)2, H2O
2.) NaBH4
alkenes into alcohols
Markovnikov addition
OH on more, Hg on Less
Hydroboration - Oxidation
1.) BH3 THF
2.) H2O2, NaOH
adding H and OH
Anti-Markovnikov
syn
Catalytic Hydrogenation
1.) H2, Pt
adding H and H
Not relevant
syn
Halogenation
Br2
adds Br and Br
not relevant
anti
Halohydrin Formation
1.) Br2, H2O
adds Br and OH
OH on more sub
anti
Anti-Dihydroxylation
1.) MCPBA
2.) H3O+
adds OH and OH
not relevant
anti
Syn - Dihydroxylation
1.) OsO4
2.)H2Os
adds OH and OH
not relevant
syn
Oxidative cleavage/ozonolysis
1) O3
2) DMS (CH3)2S, or (Zn/HOAC) or (Me2S)
split double bonds