chm33721.

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sammymuthafuckinbammy
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196439
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chm33721.
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2013-01-29 22:45:54
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organic chemistry
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Description:
ochem quarter two. first exam.
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  1. what is a carbene?
    a carbon with two bonds and a lone pair.
  2. what reagent is used to make an alkyl halide?
    h-x. 
  3. what is the reactant to make an alkyl halide?
    an alkene.
  4. what regiochemistry does the synthesis of an alkyl halide have? 
    markovnikov. 
  5. what stereochemistry does the synthesis of an alkyl halide have? 
    mixed- syn/anti.
  6. does the synthesis of an alkyl halide happen through a carbocation?
    yes, rearrangement is possible. 
  7. what reagent is used to make an alkyl bromide?
    hbr with peroixides. (ro-or). 
  8. what is the reactant used to make an alkyl bromide?
    an alkene.
  9. what regiochemistry does the synthesis of an alkyl bromide have? 
    anti-markovnikov. 
  10. what stereochemistry does the synthesis of an alkyl bromide have?
    mixed- syn/anti.
  11. is the synthesis of an alkyl bromide a radical mechanism? 
    yes. 
  12. what reagent is used to make an alkyl hydrogen sulfate?
    cold h2so4
  13. what reactant is used to make an alkyl hydrogen sulfate?
    an alkene.
  14. what regiochemistry does the synthesis of an alkyl hydrogen sulfate have?
    markovnikov. 
  15. what stereochemistry does the synthesis of an alkyl hydrogen sulfate have? 
    mixed- syn/anti. 
  16. does the synthesis of an alkyl hydrogen sulfate have a carbocation?
    yes, it may rearrange. 
  17. what is the reagent for a hydration synthesis?
    h3o/h2o (from dilute h2so4).
  18. what is the reactant for a hydration synthesis?
    an alkene.
  19. what is the product of a hydration synthesis? 
    an alcohol.
  20. what is the regiochemistry of a hydration synthesis? 
    markovnikov.
  21. what is the stereochemistry of a hydration synthesis? 
    mixed- syn/anti.
  22. does a hydration synthesis have a carbocation?
    yes, it may have a rearrangement. 
  23. what are the reagents for an oxymercuration-demercuration synthesis?
    • 1) hg(oac)2, h2o. 
    • 2) nabh4.
  24. what is the reactant for an oxymercuration-demercuration synthesis? 
    an alkene.
  25. what is the product of an oxymercuration-demercuration synthesis?
    an alcohol.
  26. what is the regiochemistry of an oxymercuration-demercuration synthesis? 
    markovnikov. 
  27. what is the stereochemistry of an oxymercuration-demercuration synthesis? 
    mixed- syn/anti.
  28. does the synthesis of oxymercuration-demercuration undergo a carbocation phase?
    no. no rearrangement. 
  29. what are the reagents for a hydroboration-oxidation?
    • 1) bh3:thf. 
    • 2) h2o2, ho-. 
  30. what is the reactant for a hydroboration-oxidation? 
    an alkene. 
  31. what is the product of a hydroboration-oxidation?
    an alcohol. 
  32. what is the regiochemistry of a hydroboration-oxidation? 
    anti-markovnikov. 
  33. what is the stereochemistry of a hydroboration-oxidation? 
    syn addition. 
  34. does a hydroboration oxidation create any partial charges? 
    a large partial positive on the more substituted carbon. 
  35. what are the reagents for a protonolysis of trialkylboranes?
    • 1)bh3:thf. 
    • 2. hoac. 
  36. what is the reactant of a protonolysis of trialkylboranes? 
    an alkene. 
  37. what is the product of a protonolysis of trialkylboranes?
    an alkane (or deuteroalkane or tritio-alkane).
  38. what is the regiochemistry of a protonolysis of trialkylboranes?
    antimarkovnikov.
  39. what is the stereochemistry of a protonolysis of trialkylboranes?
    syn addition.
  40. what are the reagents of a halogenation?
    br2 or cl2 (from ccl4 or ch2cl2 solvent). 
  41. what is the reactant of a halogenation?
    an alkene.
  42. what is the product of a halogenation?
    a vicinal dihalide (two halides bonded to two adjacent carbons). 
  43. what is the regiochemistry of a halogenation?
    no rearrangements are possible.
  44. what is the stereochemistry of a halogenation?
    anti addition. 
  45. how does a halogenation occur? 
    via a halonium (bromonium) ion. 
  46. what are the reagents of a halohydrin formation?
    br2/h2o. 
  47. what is the reactant of a halohydrin formation?
    an alkene.
  48. what is the product of a halohydrin formation?
    a halohydrin. (one carbon atom has a halogen substituent, and an adjacent carbon atom has a hydroxyl substituent). 
  49. what is the regiochemistry of a halohydrin formation? 
    the hydroxyl group goes on the more substituted carbon.
  50. what is the stereochemistry of a halohydrin formation?
    anti addition.
  51. what does the water do in a halohydrin formation?
    it attacks the bromonium ion.
  52. what are the reagents for a cyclopropanation?
    ch2n2.
  53. what is the reactant for a cyclopropanation? 
    an alkene. 
  54. what is the product of a cyclopropanation?
    cyclopropane.
  55. what is the stereochemistry of a cyclopropanation?
    syn addition. 
  56. how does the cyclopropane form in a cyclopropanation?
    via a carbene. (concerted addition). 
  57. what are the reagents for a dicyclopropanation? 
    chx3, ko-tbu. 
  58. what is the reactant for a dicyclopropanation? 
    an alkene.
  59. what is the product of a dicyclopropanation?
    dihalocyclopropanation. 
  60. what is the stereochemistry of a dicyclopropanation?
    syn addition. 
  61. how does the dihalocyclopropane form?
    via a carbene. (concerted addition).
  62. what are the reagents for a syn-hydroxylation?
    • 1) oso4.
    • 2) nahso3
  63. what is the reactant for a syn-hydroxylation?
    an alkene.
  64. what is the product of a syn-hydroxylation?
    vicinal diol. (two hydroxyl groups attached to adjacent atoms). 
  65. what is the stereochemistry of a syn-hydroxylation? 
    syn addition.
  66. how does a syn-hydroxylation occur? 
    with a 1,3 dipolar addition to the alkene occurring first. 
  67. what are the reagents for an alkene oxidative cleavage? 
    • 1) o3.
    • 2) h2o2
  68. what is the product of an oxidative cleavage? 
    ketones and carboxylic acids. 
  69. what does an oxidative cleavage do? 
    oxidizes vinyl c-h bonds to c-oh. 
  70. what are the reagents for an ozonolysis?
    • 1) o3.
    • 2) zn; hoac. 
  71. what is the reactant for an ozonolysis? 
    an alkene. 
  72. what is the product of an ozonolysis? 
    ketones and aldehydes. 
  73. what does an ozonolysis NOT do? 
    oxidizes vinyl c-h bonds to c-oh. 
  74. what is the reagent for the synthesis of a dihaloalkene? 
    1 mol x2.
  75. what is the reactant for the synthesis of a dihaloalkene? 
    an alkyne. 
  76. what is the stereochemistry for the synthesis of a dihaloalkene? 
    trans. 
  77. what is the reagent for the synthesis of a tetrahaloalkane?
    2 mol x2
  78. what is the reactant for the synthesis of a tetrahaloalkane? 
    alkyne. 
  79. what is the reagent for the synthesis of a haloalkene?
    1 mol hx, alumina. 
  80. what is the reactant for the synthesis of a haloalkene?
    an alkyne.
  81. what is the stereochemistry for the synthesis of a haloalkene?
    markovnikov. 
  82. what is the preferred stereochemistry for the synthesis of a haloalkene? 
    trans. 
  83. how will the synthesis of a haloalkene be affected by the presence of peroxides? 
    anti-markovnikov addition. 
  84. what are the reagents for the synthesis of a geminal dihalide (two halides attached to the same carbon)?
    2 mol hx, alumina.
  85. what is the reactant for the synthesis of a geminal dihalide? 
    an alkyne. 
  86. what is the stereochemistry for the synthesis of a geminal dihalide? 
    markovnikov. 
  87. how will the synthesis of a geminal dihalide be affected by the presence of peroxides? 
    anti-markovnikov addition.
  88. what are the reagents of an alkyne oxidative cleavage? 
    • 1) o3.
    • 2) hoac.
  89. what is the product of an alkyne oxidative cleavage? 
    carboxylic acids. 
  90. what are the reagents of the hydration of alkynes? 
    hg+2, h3o+, h2o. 
  91. what is the product of the hydration of alkynes? 
    methyl ketone. 
  92. what is the regiochemistry of the hydration of alkynes? 
    markovnikov. 
  93. what is the intermediate of the hydration of alkynes? 
    an "enol" intermediate. 
  94. what are the reagents of the anti-markovnikov hydration of alkynes? 
    • 1) r2bh.
    • 2) h2o2, ho-. 
  95. what is the product of the anti-markovnikov hydraton of alkynes? 
    aldehydes. 
  96. what is the intermediate of the anti-markovnikov hydration of alkynes? 
    an "enol" intermediate. 

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