Organic Chemistry Chapter 9 & 10

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tulipyoursweety
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248002
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Organic Chemistry Chapter 9 & 10
Updated:
2014-02-01 02:20:27
Tags:
Preparation Reaction Alcohols Ethers Epoxides Organic Chemistry Chapter 10
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organic
Description:
Preparation and Reaction of Alcohols, Ethers and Epoxides
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  1. Preparation of alcohols
    mech?
    works best for?
    • R-X + -OH → R-OH + X-
    • mech: SN2
    • Works best for methyl and 1°
  2. Preparation of alkoxides (2)
    called?
    • Brownsted-Lowry acid-base reaction
    • R-O-H + Na+H- → R-O- Na+ + H2
  3. Preparation of ethers (4)
    called?
    mech?
    works best for?
    • (Williamson ether synthesis)
    • R-X + -OR → R-OR + X-
    • mech: SN2
    • works best for methyl and 1°
  4. Preparation of epoxides (3)
    can be?
    mech?
    • halohydrin + NaH → epoxides
    • can be any base to deprotonate OH
    • SN2 mechanism
  5. R-OH + H2SO4 or TsOH 
    - called?
    - mechanism? (3)

    • dehydration
    • secondary/tertiary: E1
    • primary: E2
  6. R-OH + POCl3 and pyridine 
    called?
    mechanism? (2)
    • dehydration
    • E2 only
  7. R-OH + H-X → 
    (3)
    mech?
    • R-X
    • secondary/tertiary: Sn1  REARRANGEMENT
    • primary: Sn2
  8. R-OH + SOCL2 and pyridine →
    R-OH + PBr3 →
    (4)
    mech?
    • R-OH + SOCL2 and pyridine → R-CL
    • R-OH + PBr3 → R-BR
    • Sn2 only
    • NEVER ON TERTIARY
  9. R-OH + TsOH 
    (2)
    configuration?
    • R-OTs
    • C-O bond is not broken, stereogenic configuration retained!
  10. R-O-R' + H-X (2 equiv) →
    (3)
    mech?
    • R-X + R'-X
    • secondary/tertiary: sn1
    • primary: sn2
  11. How do you open an epoxide?
    (4)
    ways?
    mechs?
    • epoxide + 
    • 1. nucleophile, then H2O
    • 2. acid
    • nucleophile mech is sn2 with attack at less substituted
    • acid mech is either sn1 or sn2 with attack at more substituted
  12. hydrohalogenation
    (5)
    steps?
    carbocation?
    rearrangement?
    H bonds where?
    stereochemistry?
    • alkene + H-X → alkyl halide
    • 2 steps
    • carbocation intermediate
    • rearrangement possible
    • Markovnikov's rule (H bonds to less substituted; more stable carbocation)
    • syn and anti addition occur
  13. Hydration
    How to synthesize an alcohol:
    (6)
    steps?
    carbocation?
    rearrangement?
    rule?
    stereochemistry?
    • alkene + H2O and H2SO4 → alcohol
    • three step mechanism
    • carbocation formed
    • rearrangement possible
    • Markovnikov's rule
    • syn and anti occur
  14. Hydration
    How to synthesize an ether:
    (6)
    steps?
    carbocation?
    rearrangement?
    rule?
    stereochemistry?
    • alkene + H-OR and H2SO4 → ether
    • three step mechanism
    • carbocation formed
    • rearrangement possible
    • Markovnikov's rule
    • syn and anti occur
  15. Halogenation
    (5)
    - steps?
    - what is formed?
    - rearrangement?
    - stereochemistry?
    • alkene + X-X → vicinal dihalide
    • two step mechanism
    • bridge halonium ion formed
    • no rearrangement
    • anti addition occurs
  16. halohydrin formation
    (7)
    - steps?
    - what is formed?
    - rearrangement?
    - bonds formed where?
    - stereochemistry?
    - what else does this?
    • alkene + X-X and H2O → halohydrin
    • three step mechanism
    • bridged halonium ion formed
    • no rearrangement
    • X bonds to less substituted C
    • anti addtion occurs
    • NBS in DMSO and H2O adds BR and OH in same fashion
  17. Hydroboration-oxidation
    (5)
    - steps?
    - rearrangement?
    - bonds formed where?
    - stereochemistry?
    • alkene --(1. BH3 or 9-BBN 2. H2O2, HO-)→ alcohol
    • hydroboration has one step mechanism
    • no rearrangements
    • OH bonds to less substituted C
    • Syn additino of H2O occurs

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