CH310M/318M Organic I

Dr. Brian Pagenkopf

Alkyne Reactions Summary Table. Some Old, Some New

Reaction with	Example Reagents	Alkenes	Alkynes	Regio- selective?
Addition of HX	HCl			ü
Hydration	H2SO4, H2O		*	ü
Halogenation	Br2, Cl2			NA
Hydroboration, then Oxidation	BH3, then NaOH, H2O2			ü
Hydroboration, then RCO2H	BH3, then MeCO2H		**	NA
", of	"			NA
Hydrogenation	H2/Pd			NA
", of	"			NA
"	Lindlar's	No Rxn		NA
Reduction with Li/NH3, of	Li/NH3	No Rxn		NA
Oxymercuration and Reduction	Hg(OAc)2 then NaBH4		See Hydration	ü
Reactions not shared
Ozonolysis	O3		-	NA
Dihydroxylation	OsO4		-	NA
Addition of HOX	Br2, H2O		-	ü

* Hg(II) is best used with this step. ** With (sia)₂BH