CH310M/318M Organic I

Dr. Brian Pagenkopf

Alkene Reactions Summary Table

Reaction	Example Reagents	Key Intermediate?	Regio- selective?	Stereo- specific?	Markovnikov?
Addition of HX	HCl		yes	no	yes
Hydration	H2SO4, H2O		yes	no	yes
Halogenation	Br2, Cl2		NA	yes	NA
Addition of HOX	Br2, H2O		yes	yes	yes
Hydroboration and Oxidation	BH3, then NaOH, H2O2		yes	yes	Anti-Markovnikov
Oxymercuration and Reduction	Hg(OAc)2 then NaBH4		yes	no^*	yes
Dihydroxylation	OsO4		NA	yes	NA
Ozonolysis	O3		NA	NA	NA
Hydrogenation	H2/Pd	NA	NA	no	NA

* The reduction step is not stereoselective and negates any selectivity of the intermediate mercurium ion.