Alkene Reactions

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omi14
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123504
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Alkene Reactions
Updated:
2011-12-13 23:30:13
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alkene reaction mechanism organic chemistry
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CHM 325 Organic Chemistru
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  1. Markovnikov's rule (modified) states that...
    For electrophilic additions to alkenes, the electrophile adds in a way so that the most stable carbocation is formed.
  2. What is a hydrohalogenation reaction?
    • Addition of halides
    • Markovnikov's rule applies
  3. What is a hydration reaction?
    • Addition of water
    • Markovnikov's rule applies
    • (Strong acids ex: H2SO4)
  4. What is an acid catalyzed addition of alcohols to an alkene?
    • Like hydration reaction, but instead of water, it reacts with an alcohol (methanol, ethanol, etc.)
    • Occurs in strong acids like H2SO4
  5. What is an electrophilic addition of halogens?
    • Uses Br2 and Cl2 (F2 too violent, I2 products too unstable)
    • Inert non-polar solvent (ex: CCl4)
    • Anti addition
    • Stereospecific reaction
    • Regeoselective (nuc attacks more substituted carbon)
    • Markovnikov's rule applies
  6. What is the mechanism that opens the halonium ion with other nucleophiles?
    • Like regular electrophilic addition, except X+ is opened by a different nucleophile.
    • In water or alcohols
    • Anti addition
    • Stereospecific reaction
    • Regeoselective (nuc attacks more substituted carbon)
    • Markovnikov's rule applies
  7. What is hydration via oxymercuration-demercuration?
    • Solvents: Hg(OAc)2, THF, H2O
    • Electrophilic addition of +Hg(OAc)
    • Anti addition
    • Stereospecific
    • Regeoselective (nuc attacks more substituted carbon)
    • Markovnikov's rule applies
    • Demurcuration (removes +Hg(OAc) using NaBH4)
  8. What does OAc stand for?
  9. What does THF stand for?
    • Tetrahydrofuran
  10. What is hydration via hydroboration-oxidation?
    • Uses: BH3, -OH, H2O2, H2O
    • 1)BH3 syn addition (same side)
    • 2)Oxidation (-OH, H2O2, H2O)
    • Anti-Markovnikov alcohol product produced
    • Sterospecific
  11. What is free radical addition to alkenes?
    • Initiation:
    • Propagation:
    • Termination: Combo of any two radicals
    • Addition of HBr in H2O2
    • Free radical mechanism
    • Anti-Markovnikov
  12. What is reduction reaction?
    • \
    • Solvent can be alcohol or carboxylic acid
    • Stereospecific: Syn addition
  13. What is epoxidation reaction?
    • Concerted reaction
    • Syn addition
  14. What is acid catalyzed opening of epoxides?
    • Anti addition of O's
  15. What does MCPBA stand for?
    • m-chloroperoxybenzoic acid
  16. What is syn hydroxylation of alkenes?
  17. What is oxidative cleavage of alkenes?
    • Aldehydes can be oxidized to carboxylic acids
    • =CH2 oxidized to CO2 + H2O
  18. What is ozonolysis?
    • Products are ketones and aldehydes
    • =CH2 oxidized to H2C=O
  19. What is the structure of ethylene?
    H2C=CH2
  20. What is the structure of propylene?
    H2C=CH-CH3
  21. What is the structure of isobutylene?
  22. What is the structure of isoprene?
  23. What is the structure of styrene?

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