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Markovnikov Hydrohalogenation
Reagent: HX
Product: Alkyl halide
Regio: Markovnikov
Stereo: None
Anti-Markovnikov Hydrohalogenation
Reagent: HBr + ROOR
Product: Alkyl halide
Regio: Anti-Markovnikov
Stereo: None
Acid-Catalyzed Hydration
Reagent: H3O+
Product: Alcohol
Regio: Markovnikov
Stereo: None
Oxymercuration-Demurcuration
Reagent: 1) Hg(OAc)2, H2O 2) NaBH4
Product: Alcohol
Regio: Markovnikov
Stereo: Anti
Hydroboration-Oxidation
Reagent: 1) BH3THF 2) H2O2, NaOH
Product: Alcohol
Regio: Anti-Markovnikov
Stereo: Syn
Hydrogenation
Reagent: H2, Pt, Pd, Ni
Product: Alkane
Regio: none
Stereo: Syn
Bromination
Reagent: Br2
Product: Dibromide
Regio: None
Stereo: Anti
Halohydrin Formation
Reagent: Br2+ H2O
Product: Halohydrin (X+OH)
Regio: OH on more substituted
Stereo: Anti
Epoxidation
Reagent: mCPBA
Product: Epoxide (three-membered ring)
Regio: None
Stereo: Syn
Anti Dihydroxylation
Reagent: Epoxide + H3O+
Product: Diol
Regio: None
Stereo: Anti
Syn Dihydroxylation
Reagent: Cold, dilute KMnO4
Product: Diol
Regio: None
Stereo: Syn
Oxidative Cleavage
Reagent: Warm, conc. KMnO4
Product: Acids or ketones
Regio: None
Stereo: None
Ozonolysis
Reagent: 1) O3 2) DMS or Zn/H2O
Product: Aldehydes/ketones
Regio: None
Stereo: None
Reagent: 1) O3 2) DMS or Zn/H2O
Product: Aldehydes/ketones
Regio: None
Stereo: None
Reagent: Warm, conc. KMnO4
Product: Acids or ketones
Regio: None
Stereo: None
Reagent: Cold, dilute KMnO4
Product: Diol
Regio: None
Stereo: Syn
Reagent: Epoxide + H3O+
Product: Diol
Regio: None
Stereo: Anti
Reagent: mCPBA
Product: Epoxide (three-membered ring)
Regio: None
Stereo: Syn
Reagent: Br2+ H2O
Product: Halohydrin (X+OH)
Regio: OH on more substituted
Stereo: Anti
Reagent: Br2
Product: Dibromide
Regio: None
Stereo: Anti
Reagent: H2, Pt, Pd, Ni
Product: Alkane
Regio: None
Stereo: Syn
Reagent: 1) BH3THF 2) H2O2, NaOH
Product: Alcohol
Regio: Anti-Markovnikov
Stereo: Syn
Reagent: 1) Hg(OAc)2, H2O 2) NaBH4
Product: Alcohol
Regio: Markovnikov
Stereo: Anti
Reagent: H3O+
Product: Alcohol
Regio: Markovnikov
Stereo: None
Reagent: HBr + ROOR
Product: Alkyl bromide
Regio: Anti-Markovnikov
Stereo: None
Reagent: HX
Product: Alkyl halide
Regio: Markovnikov
Stereo: None