Organic Synthesis Reactions

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betweenloveandhate
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270952
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Organic Synthesis Reactions
Updated:
2014-04-17 22:17:04
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  1. Electrophilic addition of hydrogen halides (HX) to alkenes

    X = Cl, Br, I
    Reagents and Conditions:
    * HCl, HBr in ether
    * KI + H3PO4
    * room temperature
  2. Radical addition of hydrogen bromide (HBr) to alkenes

    Reagents and Conditions:
    * Radical initiators (usually peroxides)
    * Heat or light
  3. Electrophilic addition of halogens (X2) to alkenes

    X = Br, Cl
    Reagents and Conditions:
    * Br2, Cl2, (or I2) in CH2Cl2 or CCl4
    * Room temperature
  4. Electrophilic addition of halogens to alkenes in the presence of water

    X = Cl, Br
    Reagents and Conditions:
    * Br2 or Cl2 in H2O or NBS in H2O/DMSO
    * room temperature
  5. Electrophilic addition of water to alkenes

    Reagents and Conditions:
    * Acid catalyst needed with non-nucleophilic counter ion (H2SO4, HClO4, H3PO4)
    * High temperature required
    * Often reversible (rather used to make alkenes from alcohols)
  6. Oxymercuration of alkenes (formal addition of water)

    Reagents and Conditions:
    * Hg(OAc)2 in H2O (or THF/H2O)
    * Reduction step required to replace mercury with hydrogen (NaBH4)
    * Room temperature
  7. Hydroboration of alkenes (formal addition of water)

    Reagents and Conditions:
    * BH3-THF complex in THFtri-fold addition (to borane) is common, giving trialkylboranes *
    * (R3B) oxidation step necessary
    * (H2O2/−OH)room temperature or heat
  8. Hydrogenation of alkenes

    Reagents and Conditions:
    * H2 gas over heterogeneous catalysts (Pd/C, Pt, PtO2)
    * room temperature
  9. Hydroxylation of alkenes

    * KMnO4/−OH (lower yield)
    * OsO4/pyridine (higher yield but toxic and expensive)
    * Catalytic OsO4 with NMO
  10. Ozonolysis of alkenes

    Reagents and Conditions:
    * Ozone at low temperature followed by reduction with Zn/AcOH
  11. Oxidation of diols

    Reagents and Conditions:
    * 1,2-diol  treated by HIO4 in H2O/THF
    * Equivalent to ozonolysis of the corresponding alkene
  12. Oxidation of alkenes with permanganate under acidic conditions

    Reagents and Conditions:
    * Potassium permanganate under acidic or neutral conditions
  13. Electrophilic addition of hydrogen halides (HX) to alkynes

    X = Cl, Br
    Reagents and Conditions:
    * HCl, HBr in acetic acid
  14. Electrophilic addition of halogens (X2) to alkynes

    X = Cl, Br
    Reagents and Conditions:
    * Cl2, Br2 in CCl4
  15. Electrophilic addition of water to alkynes

    Reagents and Conditions:
    * HgSO4/H2O/H2SO4
    * no NaBH4 necessary to replace mercury (Hg) with hydrogen
  16. Electrophilic addition of water to alkynes

    Reagents and Conditions:
    * HgSO4/H2O/H2SO4
    * No NaBH4 necessary to replace mercury (Hg) with hydrogen
  17. Hydroboration of alkynes (formal addition of water) 

    Reagents and Conditions:
    * BH3/THF gives mixture of regioisomers for disubstituted alkynes, double addition with terminal alkynes
    * R'2BH (R' = 1,2-dimethylpropyl) may be used for monoaddition to terminal alkynes
  18. Hydroboration of alkynes (formal addition of water)

    Reagents and Conditions:
    * BH3/THF gives mixture of regioisomers for disubstituted alkynes, double addition with terminal alkynes
    * R'2BH (R' = 1,2-dimethylpropyl) may be used for monoaddition to terminal alkynes
  19. Hydrogenation of alkynes

    Reagents and Conditions:
    * Lindlar catalyst used for cis product (Pd, CaCO3, Pb(OAc)2, quinoline)
    * Lithium metal in ammonia for trans product
  20. Alkylation of acetylide anion

    X = Cl, Br, I, or other good leaving group
    Reagents and Conditions:
    * KNH2 or NaNH2 used as a base (in NH3 or THF)
    * LDA in THF used as a base
    * Primary electrophiles (alkylating agents) work well
    • stopped at Reaction #18

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