ALKENE ADDITION REACTIONS

Markovnikov addition of H and X (Cl, Br, I) across a double bond. Carbocation rearrangements are possible.

Anti-Markovnikov addition of H and X (Cl, Br, I) across a double bond (radical mechanism)

Acid-catalyzed Markovnikov addition of H and OH across a double bond. Carbocation rearrangements are possible. Use dilute H2SO4 to promote hydration over elimination.

Oxymercuration-demercuration (Markovnikov). Carbocation rearrangements are NOT possible.

Hydroboration-oxidation (anti-Markovnikov, syn addition).

Bromination