Alkene Reactions

H2/Pd-C, Pt, or Ni

Hydrogenation (Alkane)

Br2/CCl4 or Cl2/CCl4

Halogenation (Anti addition; Vicinal dihalide)

Br2/H2O or Cl2/H2O

Halohydrin Formation (Anti addition; OH on more substituted carbon)

HX (HCl, HBr, or HI)

Hydrohalogenation (Markovnikov; Alkyl halide)

HBr/ROOR

Radical Hydrohalogenation (Anti-Markovnikov; Alkyl bromide)

H2O/H2SO4

Acid-Catalyzed Hydration (Markovnikov; Alcohol)

1. Hg(OAc)2/H2O 2. NaBH4

Oxymercuration-Demercuration (Markovnikov; Alcohol, no rearrangement)

1. BH3/THF 2. H2O2/OH-

Hydroboration-Oxidation (Anti-Markovnikov; Alcohol, syn addition)

mCPBA or RCO3H

Epoxidation (Epoxide; Stereospecific retention of alkene geometry)

OsO4, then NaHSO3/H2O

Syn Dihydroxylation (Syn addition; Vicinal cis-diol)

Cold, dilute KMnO4/OH-

Syn Dihydroxylation (Syn addition; Vicinal cis-diol)

1. O3 2. (CH3)2S

Ozonolysis (Oxidative cleavage; Aldehydes and/or ketones)

1. O3 2. H2O2

Ozonolysis (Oxidative cleavage; Carboxylic acids and/or ketones)

Hot, concentrated KMnO4

Oxidative Cleavage (Carboxylic acids and/or ketones)

Heat, pressure, catalyst

Polymerization (Addition polymer; Long-chain polymer)