Alkene Electrophilic Addtion
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Alkene Addition Reactions by Increasing Electronegativity of Added Reagent

Atoms Added Reagents Name Regiochemistry Stereochemistry Subsequent Reactions
B, H diborane Hydroboration anti-Markovnikov syn Oxidation (H2O2, NaOH)
Net anti-Markovnikov Addition of Water
H, H hydrogen, transition metal Hydrogenation n/a syn n/a
C: a carbene from diazomethane, chloroform, or CH2I2/Zn Carbene Addition n/a syn n/a
C C   Cycloadditions      
H, O acid, water or alcohols Hydration, Ether Synthesis Markovnikov anti? n/a
Hg, O mercury acetate, water or alcohols Oxymercuration Markovnikov? anti Reduction (NaBH4)
Net Markovnikov Addition of Water
H, X mineral acid Hydrohalogenation Markovnikov anti? n/a
Br., H. hydrogen bromide, peroxide Bromine Radical Addition anti-Markovnikov n/a n/a
O peracid Epoxidation n/a syn Ring Opening with H3O+ Gives Anti Vicinal Diols
O, O osmium tetraoxide, potassium permanganate (Baeyer Test) Dihydroxylation n/a syn H2S Releases Syn Vicinal Diols, H2O2 regenerates the OsO4
O3 ozone Ozonolysis n/a syn Ring Opening, Addition, Reduction (Zn)
X, O halogen, water or alcohol Halohydrin or Haloether Synthesis Markovnikov? anti Epoxidation (NaOH)
X, X halogen Halogenation n/a anti n/a

 

 

 

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