UH ORGANIC CHEMISTRY
Chapter 8: Alkene Reactions
Brief Summary
- Basic Addition Reactions
- Addition of H-X
- Markovnikov's Rule (Regioselectivity)
- Special Case: H-Br with Peroxide added
- Addition of H-OH (Water)
- Direct Hydration: H3O+
- Indirect Hydration
- Oxymercuration:
- 1. Hg(OAc)2/H2O 2. NaBH4
- Hydroboration
- 1. BH3 in THF 2. H2O2/OH-
- Oxymercuration:
- Other Additions:
- Alkoxymercuration: Oxymercuration (switch H2O with an alcohol molecule)
- Halogenation: X2 / CH2Cl2 OR CCl4
- Halohydrin Formation: X2/H2O
- Hydrogenation: H2 / Ni, Pd, or Pt
- Addition of H-X
- Carbene Reactions
- Carbene Addition
- Diazomethane Addition: CH2N2
- Simmons-Smith Reagent: CH2I2 / Zn(Cu)
- Diazomethane Addition: CH2N2
- Dihalogencarbene Addition
- CHBr3 Or CHCl3 / KOH
- Carbene Addition
- REDOX Reactions:
- Epoxidation: mCPBA
- Hydroxylation
- Syn-dihydroxylation
- KMnO4 in Cold, diluted condition
- OsO4/H2O2
- Anti-dihydroxylation
- Epoxide opening
- Syn-dihydroxylation
- Alkene Cleavage
- Ozonolysis : O3 / CH2Cl2 in DMS
- KMnO4 in Hot, concentrated condition