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Hydrohalogenation
Reagent: HX (X is a Halogen)
Product(s): Alkyl Halide
Regiochemistry: Markovnikov
Sterochemistry: N/A
Hydrohalogenation with peroxide
Reagent: HX (X is a Halogen)
Product(s): Alkyl Halide
Regiochemistry: Anti-Markovnikov
Sterochemistry: N/A
Acid Catalyzed Hydration
Reagent: H3O+ or dilute H2SO4
Product(s): H and OH addition
Regiochemistry: Markovnikov
Sterochemistry: N/A
Oxymercuration-Demercuration
Reagent: 1) Hg(OAc)2, NucH 2) NaBH4
Product(s): H and OH addition
Regiochemistry: Markovnikov
Sterochemistry: Anti
Hydroboration-Oxidation
Reagent: 1)BH3, THF 2) H2O2, NaOH
Product(s): H and OH addition
Regiochemistry: Anti-Markovnikov
Sterochemistry: Syn
Catalytic Hydrogenation
Reagent: H2, Pt
Product(s): Alkane
Regiochemistry: N/A
Sterochemistry: Syn
Halogenation
Reagent: X2 (X is a Halogen)
Product(s): Dihalide
Regiochemistry: N/A
Sterochemistry: Anti
Halohydrin Formation
Reagent: X2, H2O
Product(s): X and OH addition
Regiochemistry: OH on more substituted
Sterochemistry: Anti
Syn Dihydroxylation
Reagent: 1) OsO4 2) NaHSO3 OR cold KMnO4, NaOH
Product(s): Diol (OH + OH)
Regiochemistry: N/A
Sterochemistry: Syn
Epoxidation
Reagent: mCPBA
Product(s): Epoxide
Regiochemistry: N/A
Sterochemistry: sterospecific
Anti Dihydroxylation
Reagent: 1)mCPBA 2) H3O+
Product(s): OH + OH
Regiochemistry: N/A
Sterochemistry: Anti
Ozzonolysis
Reagent: 1) O3 2) DMS
Product(s): Aldehyde or Ketone
Regiochemistry: N/A
Sterochemistry: N/A