CHEM Reactants

CH₃CO₃H

Epoxidation

mCPBA

Epoxidation

OsO₄

DIhydroxylation (two OH’s next to each other added on same side) (Syn)

NaHSO₃

Dihydroxylation

B₂H₆

Hydroboration/Oxidation (an OH and H added on where the double bond ways, hydrogen goes on more substituted) (same stereochemistry) (wedge wedge or dash dash)

Br₂, H2O

Hydroxybromination (br and oh added) (anti addition) (oh goes on more sub)

X2 addition

br and br added on opposite side (br wedge and br dash)

H3O+

similar to H-X addition but OH goes on more substituted carbon from initial double bond

HX addition

H-Br (make H attach to less sub carbon, create carbocation, make br attack more substituted carbocation)

Epoxiation (stereochemistry)

Hydrogenation

Hydrogenation reaction