Organic Chemistry Alkene Reactions

Hydrohalogenation

1. HCl, HBr, or HI

2. Maokovnikov

3. Neither syn nor anti

4. Carbocation intermediate, rearrangements possible

Hydration: Acid Catalyzed

1. H₂O, H₂SO₄ (or another acid)

2. Maokovnikov

3. Neither syn nor anti

4. Carbocation intermediate, rearrangements possible

Hydration: Oxymercuration-Demercuration

1. a. Hg(OAc)₂, H₂O b. NaBH₄

2. Maokovnikov

3. Neither syn nor anti

4. No carbocation intermediate, bridged intermediate

Hydration: Hydroboration

1. a. BH₃·THF b. H₂O₂, NaOH

2. Anti-Maokovnikov

3. Syn

4. Concerted mechanism

Radical Addition (of HBR)

1. HBr, ROOR (peroxide), heat or light

2. Anti-Marokovnikov

3. Neither syn nor anti

4. Radical mechanism, works mostly for HBR

Allylic Bromination

1. NBS, light

2. Neither maokovnikov nor anti-maokovnikov

3. Neither syn nor anti

4. Bromide comes from NBS reacting with HBr

Halogenation

1. Br₂ , Cl₂

2. Neither maokovnikov nor anti-maokovnikov

3. Anti

4. Bridged halonium ion intermediate

Halohydrin Formation

1. Br₂/H₂O or Cl₂/H₂O

2. Maokovnikov-ish- OH goes to more substituted carbon; halogen goes to less substituted carbon

3. Anti

4. Bridged halonium ion intermediate

Halohydrin→ Epoxide

1. Base (NaOH, etc.)

2. Intramolecular SN2 reaction

3. Produces an Epoxide

4. Inversion occurs at the carbon undergoing substitution

Cyclopropanation (Carbene Addition)

1. N3, CH2I2 + Zn(Cu), or CHBr3

2. N