Chem 331 Exam 3 Addition Reactions Information

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9 Terms

1
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Syn Dihydroxylation

  • Uses OsO4, NaHSO3 or Na2SO3, and H2O

  • Does SYN addition

  • Single step

2
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Anti Dihydroxylation

  • Uses RCO3H (mCPBA) and H3O+

  • Does ANTI addition

  • Multistep (uses RCO3H to form triangle with O and then uses H3O+ to form product)

3
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Halohydrogenation

  • Uses H-X (X = halogen)

  • No stereochemistry

  • Multistep (substrate takes H and forms carbocation intermediate and then X attacks)

4
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Oxymercuration - Demurcuration (Hydration - markovnikov)

  • Uses Hg(OAc)2, H2O, and NaBH4

  • No stereochemistry

  • Single step

5
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Hydroboration - Oxidation (Hydration - antimarkovnikov)

  • Uses BH3 THF, NaOH, and H2O2

  • SYN addition

  • Multistep (uses BH3 THF to add BH2 to the less substituted carbon and an H to the more substituted carbon then NaOH and H2O2 to replace the BH2 with an OH)

6
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Hydrogenation

  • Uses H2 and Pt

  • Does SYN addition

  • Single step

7
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Halogenation

  • Uses X2 (halogen, i.e. Br2)

  • Does ANTI addition

  • Multistep (substrate takes one halogen and forms triangle, then the other halogen attacks)

8
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Halohydrin

  • Uses X2 (halogen, i.e. Br2) and H2O

  • Does ANTI addition

  • Multistep (substrate takes one halogen and forms triangle, then H2O attacks and leaves an OH on the more substituted carbon)

9
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Ozonolysis

  • Uses O3 and DMS

  • No stereochemistry

  • Single step