Alkene Reaction

HX alkene reaction

added X to the more substituted alkene position

markonikov

carbocation formation and shift possible

mixed addition (both wedge and dash) on chiral centers only

HBr and ROOR reaction

added Br to the less substituted alkene position

anti-markonikov

must have peroxide present and hv

Acid catalyst and H2O reaction

added OH to more substituted alkene position

markonikov

mixed addition (both wedge and dash) if on a chiral center

Hg(OAc)2 and H2O reaction

adds OH to more substituted alkene position without a carbocation shift

markonikov

Hg blocks carbocation shift

mixed addition (both wedge and dash) if on a chiral center

triangle Hg intermediate formed

BH3-THF and H2O2 reaction

adds OH to less substituted alkene position

anti-markonikov

syn addition of OH and H on the same plane at the same time 

use wedge and dashes if a chiral center is present 

H2 and Pt/Pd/Ni reaction

two H atoms are added to either side of alkene

syn addition of H on the same plane

X2 and inert solvent reaction

two X groups are added to either side of alkene

anti-addition of both X groups on opposite planes

halonium ion intermediate

X2 and H2O reaction

one X and one OH group are added to either side of an alkene

anti-addition of both on opposite planes

forms halonium ion intermediate

mCPBA/RCO3H reaction

two OH groups are added to either side of an alkene

anti-addition of both groups on opposite planes

forms an epoxide intermediate

creates trans diols

KMnO4 and NaOH cold reaction

two OH groups are added to either side of an alkene

syn addition of both groups on the same plane

creates cis diols

OsO4 and DMSO reaction

two OH groups are added to either side of an alkene

syn addition of both groups on the same plane

creates cis diols

O3 and DMS reaction

double bond is cut

O is added to either end of the double bond

forms ketones and aldehydes

KMnO4 and warm reaction

double bond is cut

O is added to either end of double bond

If there is an H at the end of a single bond it is replaced with OH

C(OH)2=O will oxidize to CO2