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Hydrohalogenation reagents
HI/HBr/HCl
Hydrohalogenation regiochemistry
Markovnikov
Hydrohalogenation stereochemistry
racemic
Hydrohalogenation product
more substituted alkyl halide
Hydrohalogenation w/ peroxide reagents
HBr, ROOR
Hydrohalogenation w/ peroxide regiochemistry
anti-Markovnikov
Hydrohalogenation w/ peroxide stereochemistry
racemic
Hydrohalogenation w/ peroxide product
less substituted alkyl halide
Hydration reagents
H2SO4, H2O
Hydration regiochemistry
Markovnikov
Hydration stereochemistry
racemic
Hydration product
alcohol
Hydroboration/Oxidation reagents
1. BH3-THF
2. H2O2, H2O, NaOH
Hydroboration/Oxidation regiochemistry
anti-Markovnikov
Hydroboration/Oxidation stereochemistry
syn addition
Hydroboration/Oxidation product
alcohol
Halogenation reagents
Br2/Cl2, CCl4/CH2Cl2
Halogenation regiochemistry
N/A
Halogenation stereochemistry
anti addition
Halogenation product
vicinal dihalide
Oxymercuration/Demercuration reagents
Hg(OAc)2, H2O, NaBH4
Oxymercuration/Demercuration regiochemistry
Markovnikov
Oxymercuration/Demercuration stereochemistry
anti addition
Oxymercuration/Demercuration product
alcohol
Halohydrin reagents
Br2/Cl2, H2O
Halohydrin regiochemistry
Markovnikov
Halohydrin stereochemistry
anti addition
Halohydrin product
halohydrin