Alkene Electrophilic Addtion

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