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

Atoms Added Name Reagents Regiochemistry Stereochemistry Subsequent Reactions
B, H Hydroboration diborane anti-Markovnikov syn Oxidation (H2O2, NaOH)
Net anti-Markovnikov Addition of Water
H, H Hydrogenation hydrogen, transition metal n/a syn n/a
C: Carbene Addition diazomethane, chloroform, CH2I2/Zn n/a syn n/a
C C Cycloadditions        
H, O Hydration, Ether Synthesis acid, water or alcohols Markovnikov anti? n/a
Hg, O Oxymercuration Hg2+ Markovnikov? anti Reduction (NaBH4)
Net Markovnikov Addition of Water
H, X Hydrohalogenation mineral acid Markovnikov anti? n/a
Br., H. Bromine Radical Addition hydrogen bromide, peroxide anti-Markovnikov n/a n/a
O Epoxidation peracid n/a syn Ring Opening with H3O+ Gives Anti Vicinal Diols
O, O Dihydroxylation osmium tetraoxide, potassium permanganate (Baeyer Test) n/a syn n/a
O3 Ozonolysis ozone n/a syn Ring Opening, Addition, Reduction (Zn)
X, O Halohydrin or Haloether Synthesis halogen, water Markovnikov? anti Epoxidation (NaOH)
X, X Halogenation halogen n/a anti n/a

 

 

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