Addition of HCl, HBr, and HI

to

Alkene

Markovnikov regiochemistry occurs, with H adding to the less highly substituted alken carbon and halogen adding to the more highly substituted carbon.

Addition of Cl₂ and Br₂

to

Alkene

Anti addition is observed through a halonium ion intermediate.

Halohydrin Formation

Addition of water by hydroboration-oxidation

Non-Markovnikov syn addition occurs.

Addition of water by oxymercuration-demercuration

Catalytic Hydrogenation

Epoxidation with a peroxyacid

Syn additon occurs

Hydroxylation with OsO₄

Syn addition occurs

Addition of Carbenes to yeild cyclopropanes

1. Dichlorocarbene addition

2. Simmons-Smith Reaction

Hydroxylation by acid-catalyzed epoxide hydrolysis.

Anti-Sterochemistry occurs

Oxidative Cleavage of Alkenes

1. Reaction with Ozone followed by Zinc in Acetic Acid

2. Reaction with KMnO₄, in Acidic Solution

3. Cleavage of 1,2 Diols