Addition Reactions of Alkenes

Alkene + HBr ROOR

Hydrohalogenation AM

Alkene + HX

Hydrohalogenation M

Alkene + 1) O3 2) DMS or Zn, HOAc

Ozonolysis (Ketone + aldehyde)

1 Alkene + 1) OsO4 2)H2O2

Syn dihydroxylation

+ EN

1

2 Alkene + KMnO4 NaOH, cold

Syn dihydroxylation

+ EN

2

Alkene + 1) RCO3H 2) H30+

Anti dihydroxylation

+ EN (Anti)

Alkene + X2 (BR or Cl), H2O

Halohydrin formation

+ EN (Anti)

Alkene + Br2 or Cl2

Dihalogenation (Anti)

Alkene + H2 Pt (or Pd, Pd/C)

Catalytic Hydrogenation

Alkene + 1) BH3, THF 2)H2O2, NaOH

Hydroboration-oxidation

+ EN (AM, no rearrangements, syn)

Alkene + 1) Hg(OAc)2 H2O 2) NaBH4

oxymercuration-demercuration (M, no rearrangements)

Alkene + H2O or Alcohol + catalytic acid

acid-catalyzed hydration M

Alkene + 1) O3 2) H2O2 or 1) KMnO4, heat 2) H3O+

Ozonolysis (Ketone +Carboxylic acid)