Organic Chemistry Chapter 12: Oxidation and Reduction

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tulipyoursweety
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250650
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Organic Chemistry Chapter 12: Oxidation and Reduction
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2013-12-08 22:33:07
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Organic Chemistry Chapter 12 Oxidation Reduction
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Organic Chemistry Chapter 12: Oxidation and Reduction
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  1. Oxidation reactions result in...
    • an increase in # of C-Z bonds
    • a decrease in # of C-H bonds
  2. reduction reactions result in...
    • decrease in # of C-Z bonds
    • increase in # of C-H bonds
  3. R-CH=CH-R (alkene) + H2 & Pd/C →
    • alkane
    • called: "hydrogenation of alkene"
    • syn addition of H's occur
    • less stable alkene reacts faster
  4. How can you reduce an alkene to an alkane?
    H2 & Pd/C
  5. R-CΞC-R (alkyne) + H2 & Pd/C →
    alkane
  6. R-CΞC-R (alkyne) + H2 & Lindlar catalyst
    • cis alkene
    • syn addition of H2 occurs
    • reaction stops after one equivalent
  7. R-CΞC-R (alkyne) + Na & NH3 (L) 
    • trans alkene
    • called: "dissolving metal reduction on alkyne"
    • anti addition of H2 occurs
  8. ketone + H2 & Pd/C →
    2° alcohol
  9. aldehyde + H2 & Pd/C →
    1° alcohol
  10. What are the only two reactions involving acetylide anion that we learned?
    acetylide anion + R-X → extended C chain

    acetylide anion + epoxide → opens epoxide, extends chain
  11. Reduction:
    1° R-X + _______ → R (removes X)
    mech?
    regiochemistry?
    • 1) LiAlH4 (LAH) Lithium aluminum hydride
    • 2) H2O
    • SN2
    • backside attack
  12. epoxide + _______ → opens epoxide
    regio/stereo chemistry?
    mechanism?
    • 1) LiAlH4 (LAH) Lithium aluminum hydride
    • 2) H2O
    • backside attach at less subst. C
    • SN2
  13. what does LAH do?
    • opens epoxides
    • reduces alkyl halides
  14. What is peroxy acid?
    R-CO3H
  15. epoxidation
    alkene --(mCPBA)--> epoxide
  16. dihydroxylation
    how do you make an anti-diol?
    alkene --(1) mCPBA, 2)NaOH, H2O)--> anti-diol
  17. syn dihydroxylation
    alkene --(1) OsO4, 2)NaHSO3, H2O)--> syn-diol
  18. Ozonolysis on internal alkene
    • alkene --(1)O3 2)Zn, H2O |or| CH3SCH3)-->
    • ketone & aldehyde or
    • 2 ketones or
    • 2 aldehydes
  19. Ozonolysis on internal alkyne
    alkyne --(1)O3 2)H2O)--> 2 carboxylic acids
  20. Ozonolysis on terminal alkyne
    alkyne + 1)O3 2) H2O --> carboxylic acid + CO2
  21. ozonolysis on terminal alkene
    alkene + 1) O3 2) CH3SCH3 --> aldehyde + formaldehyde
  22. primary alcohol + PCC -->
    aldehyde
  23. secondary alcohol + PCC -->
    ketone
  24. primary alcohol + CrO3, H2SO4, H2O -->
    carboxylic acid
  25. secondary alcohol + CrO3, H2SO4, H2O -->
    ketone
  26. alkene + KMnO4, H2O, -OH -->
    syn-diol
  27. True/False
    mCPBA is a peroxyacetic acid
    true

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