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  1. Priority of alkene naming
    • alkene> halides, alkyl or alkoxy groups
    • numbering goes through the double bond
  2. Properites of an Sn2 reaction. Example of reactants.
    • Direct substitution
    • Inversion of configuration (stereospecific via backside attack)
    • S= small
    • H= negative
    • Stronger base exchange drives reaction
    • Polar aprotic solvents (DMF, CH3CN, DMSO)
    • methyl,primary or secondary Akyl halide/Alcohol + polar aprotic solvent
  3. Properties of an Sn1 reaction. Example of reactants.
    • LG leaves then Nuc attacks
    • 2 or 3 (proton transfer) steps
    • more stable carbocation is better
    • tertiary and secondary Nuc
    • protic solvents; H20, ROH
  4. Properties of E1 reaction. Examples of reactants.
    • HEAT!
    • Zaitsev rule
    • H= + (endothermic)
    • strong base
    • primary and methyl groups only
  5. Properties of E2 reaction. Example of reactants.
    • Zaitsev unless using sterically hindered reactants (TbutylOK, tButylOH, heat)
    • tertiary and secondary Alkyl OH (NAOH, CH3OH, HEAT OR CH3CH2ONA AND CH3CH2OH, HEAT) and CH3ONA (matching alkyl groups)
    • stereospecific (reactants must be antiperiplanar= same plane but opposite sides so that LG can leave while Nuc attakcs)
    • racemic mixture
  6. HX (Cl, Br, I) + CH2Cl2 (inert solvent)
    alkenes and alkynes
    • addition of H - X across an alkene double bond
    • Markovnikov addition (H adds first to create the most stable carbocat)
    • for alkynes must be in XS, both X add to same carbon in Markovnikov
    • S, H= -
  7. H2SO4, H2O
    • adds OH and H in Markovnikov across double bond
    • H is taken from H2SO4 to create carbocat then OH adds
    • rearrangements
  8. 1.Hg(OAc)2, H2O
    • no rearrangements
    • markovnikov addition of OH and H (HgOAc group adds first then is broken when OH attacks and removed by second step) across double bond
    • bridged intermediate
  9. 1. BH3(B2H6), THF
    2. H2O2, KOH, H2O
    • Antimarkovnikov addition of of OH & H across double bond
    • stereospecific SYN addition
    • BH3 adds to create a bridged intermediate (happens 3 times) second step removes
  10. X2, CH2Cl2
    • addition of Cl2 or Br2 across double bond
    • ANTI addition
    • X2 creates a bridge then other X adds to break it
  11. X2, H20
    • ANTI addition of OH and X across double bond
    • X adds first (creates bridge) then OH breaks
  12. Br2, NaCl or Cl2, NaBr
    • ANTI addition of X1 and X2across double bond
    • solvent X goes on more substituted
  13. Halohydrin + NaOH, DMF = ?
  14. Alkene + peroxyacid (MCPBA) =?
    • Epoxides
    • know mechanism
  15. How do you make a trans 1,2 diol?
    • First make an epoxide (either from an alkene + MCPBA or Halohydrin + NAOH, DMF)
    • add NaOH or H2SO4 , H2O (H20 breaks epoxide bridge)
  16. H2, Pd-C/Pt/Ni
    Syn addition of H across the double bond
  17. How do you create a 1,2 cis diol from an alkene?
    • KMnO4, KOH, H2O
    • OR
    • OsO4, H2O2
  18. Alkenes + H2O + CHX3 = ?
    Bridge with two X attached
  19. CH2I2, Zn(Cu) + alkene
    creates a triangle
  20. HBr, ROOR, heat
    • antimarkovnikov addition of H and Br across double bond
    • first step, initiation, creats RO radical, H adds then Br becomes a radical
  21. naming alkynes
    • equal priority between double and triple bond, goes by lowest first bond encountered
    • in name -en comes before -yne
    • when numbering is equal -ene before -yne
  22. How to make an alkyne from an alkane?
    add Br2, Heat then E2 then add Br2 then add NaNH2, heat
  23. NaNH2, heat or KOH, heat
    dihalide alkyl to an alkyne
  24. xs H2, Pd-C/Pt/Ni
    alkyne to alkene
  25. H2, Lindlar's catalyst
    • SYN addition
    • alkyne to CIS alkene
  26. Na, NH3 (l)
    alkyne to trans alkene
  27. xs HX
    • 2X add across alkyne to the same C
    • markovnikov
    • no rearrangements
  28. X2 +alkyne
    • one X to each C across the alkyne
    • cis and trans (more)
  29. 2 X2, alkyne
    2 X add to each C across triple bond
  30. HgSO4, H2SO4, H2O
    • ketoenol tauterism
    • enol (OH to a C)
    • ketone (double bond O)
    • markovnikov
  31. 1.HB (>-<)2
    2.h2o2, NaOH
    • antimarkovnikov addition across triple bond
    • makes enol and aldehyde at the terminal
  32. Ch3ONa, DMF or DMSO to an alkyl halide
    SN2, halide replaced by CH3O
  33. What is this?
    Image Upload
  34. What is this structure?
    Image Upload
  35. What is this structure?
    Image Upload
  36. what is this?
    Image Upload
    • DMSO
    • dimethyl sulfide
    • aprotic
  37. what is this?
    Image Upload
    • DMF
    • dimethyl formamide
    • aprotic
  38. what is this? Upload
    • diethyl ether
    • protic
  39. RCO3H to an alkene
  40. How do you make a grignard reagent?
    • alkyl halide + Mg
    • alkyl halide + 2Li
    • both in hexane or ether or diethyl ether or THF
  41. What do organolithium reagents and grignard reagents react with?
    • aldehydes and ketones
    • breaks O double bond and then it's protonated with dil. aq acid
  42. What is an oxidation?
    • Adding bonds to oxygen
    • loss of electrons
  43. what is a reduction?
    • adding bonds to H
    • gain electrons
  44. Each bond to Oxygen counts as
  45. each bond to carbon counts as?
  46. Na2Cr2O7, H2SO4, H2O
    • addition to a primary alcohol
    • adds a double bonded oxygen to the C-OH (carboxylic acid)
  47. PCC= ?
  48. what is this?
    Image Upload
    carboxylic acid
  49. CrO3, H2SO4, H2O
    primary alcohol to carboxylic acid
  50. 1.LiAlH4, hexane/ether
    2. dil aq acid
    • carboxylic acid to a primary alcohol
    • reduces peroxides
  51. Are oxidations and reductions possible for tertiary alcohols?
  52. PCC, CH2Cl2
    primary alcohol to aldehyde
  53. TsCl, pyridine
    takes off H from alcohol to get OTs + alkyl and then that can be replaced via SN2 with KCN in DMF
  54. SOCl2/ PCl / PBr3/ P/I2
    in pyridine
    replace primary or secondary OH with whatever halide is on.
  55. 1. Sia2BH-THF
    2. H2O2, NaOH

    1. Sia2BH-THF 2. H2O2, KOH, H2O
    addition of H and OH across triple bond with anti-markovnikov
  56. Degrees of unsaturation is calculated by:
    [(Number of Carbons x 2) + 2 - Number of Hydrogens] / 2

    halides count as hydrogen and nitrogen is half a carbon
  57. how to differentiate an aldehyde and ketone?
    aldehyde has C-H stretch at 2750
  58. how to differentiate carbonyl groups?
    • aldehyde stretch C-H in 2750
    • carboxylic acid if has OH
  59. Difference between carbonyl and alkene stretch
    same area but carbonyl is much stronger peak

Card Set Information

2012-05-08 05:16:41

Final exam orgo
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