Alkene Reactions -- Reactants and Solvents

Halogenation Reagents

X₂ (Usually Cl₂ or Br₂)

Halogenation Product

Anti-addition of two halides

Halohydrin Reagents

X₂ and H₂O (solvent)

NBS and H₂O / DMSO (solvent)

Halohydrin Product

Anti addition of a halide and an OH; OH added to the more substituted carbon

Hydration Reagents

H₂O and a strong acid; heat required

Hydration Product

Syn addition of OH and H; OH added to more substituted carbon

Hydrogenation Reagents

Catalyst (e.g. Pd/C), H₂

Hydrogenation Product

Syn addition of two hydrogens, “removal” of double bond

Hydroboration Reagents

BH₃/THF, H₂O₂

Hydroboration Product

Syn addition of an H and OH; OH added to LESS substituted carbon

Epoxidation Reagents

Halohydrin and a base

Alkene and carboxyl (RC(=O)OH)

Epoxidation Product

One oxygen bound to both carbons involved in initial double bond

Hydroxylation of Epoxides Reagents

Epoxide; H₃O⁺ and H₂O

Hydroxylation of Epoxides Products

Net anti addition of two OH groups, one on each carbon involved in the initial double bond

Ozonolysis Reagents

O₃, cold (-78 deg. Celsius)

Solvent: (CH₃)₂S or Zn + acetic acid

Ozonolysis Product

Cleaving of double bond; each carbon initially involved in the double bond is now double bonded to an oxygen.

Oxidation Reagents

KMnO₄ (potassium permanganate), H₃O⁺

Oxidation Product

Cleaving of double bond; each carbon initially involved in the double bond is now double bonded to an oxygen; hydrogens bonded to these carbons are replaced with OH groups.

Dehydrohalogenation Reagents

KOH, CH₃CH₂OH

Dehydrohalogenation Product

Removal of a halide and an hydrogen to form an alkene, water, and a diatomic molecule

Dehydration Reagents

Strong acid, H₂O

Solvent: THF, 50 degrees Celsius

Dehydration Product

Proton from an acid removes a hydroxyl group, forming an alkene and water