Organic chemistry Chapter 9

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  1. name ether:
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    • 4-chloro-3-methoxyheptane
    • DO NOT get priority in numbering
    • alphabetical order
  2. IUPAC: ether end with?
  3. common naming in ether
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    butyl ethyl ether

    • 3 words
    • alphabetical
  4. symmetrical ether common naming
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    diethyl ether
  5. Prepraparation of alcohols:
    synthesis undergoes what mechanism?
    • SN2 only
    • (no extra products)
  6. preparation of alcohols:
    reaction involves:
    ______ + _____ ----> alcohol
    alkyl halide + -OH ---> alcohol
  7. What kind of alkyl halides work for alcohol synthesis?
    • methyl/1°: best, fastest, highest yield, less sterically hindered
    • : works but has competing E2 rxn
  8. Preparation of ethers:
    reaction involves:
    ______ + _____ ----> ethers
    alkyl halides, -OR
  9. Preparation of ethers:
    prefers what kinds of R-X?
    • methyl/primary: favorite, best, high yield, less sterically hindered
    • secondary: works okay
    • tertiary: NEVER
  10. what is an epoxide?
    cyclic ether
  11. Preparation of epoxides:
    _______ + _____ ----> epoxide
    halohydrin, NaH
  12. RXNs of alcohols:
    dehydration with...
    H2SO4 (sulfuric acid) and TsOH
  13. all dehydrations form..
  14. alcohol synthesis only happens through what mechanism?
    SN2 ONLY
  15. ether synthesis happens through what mechanism?
    SN2 only
  16. H2SO4 (sulfuric acid) and TsOH rxn's with alcohols result in...
    dehydration, alkenes
  17. True/false:
    H2SO4 (sulfuric acid) and TsOH have the same effect
    • true
    • H2SO4 (sulfuric acid) = liquid
    • and TsOH = solid
  18. Mechanism for H2SO4 (sulfuric acid) and TsOH on methyl/primary alcohol
    E2, no E1 b/c primary carbocation is too unstable
  19. Mechanism for H2SO4 (sulfuric acid) and TsOH rxn on secondary and tertiary
    E1 (carbocation intermediate)
  20. Secondary carbocations can do what for stabilization?
  21. three ways to do dehydration
    • H2SO4 (sulfuric acid)
    • TsOH
    • POCl3 + pyridine
  22. POCL3 + pyridine mechanism
    E2 only, results in alkene
  23. How to convert alcohol into alkyl halide
    R-OH --(H-X)--> R-X + H2O
  24. Mechanism for R-OH into R-X with methyl/primary
  25. Mechanism for R-OH into R-X with secondary/tertiary
  26. What does SOCl2 + pyridine do?
    converts alcohols (R-OH) to R-Cl
  27. mechanism for SOCl2 + pyridine
    • SN2 only
  28. What does PBr3 do?
    converts R-OH into R-Br
  29. mechanism for PBr3
    • SN2 only = inversion
    • no rearrangements!
  30. ether + alkyl halide = ?
    2 alkyl halides
  31. what mechanism does conversion of ethers into alkyl halides undergo?
    can do SN1 and SN2, both, or double up on one (two steps)
  32. Ring opening of epoxides with strong nucleophile will...
    attack, then protonate
  33. ring opening of epoxides with weak nucleophile will...
    protonate, then attack
  34. strong acids will open epoxides from...
    more substituted carbon
  35. nucleophiles will open epoxides from...
    least hindered (substituted) carbon
  36. TsCl adds on a...
Card Set
Organic chemistry Chapter 9
alcohols, ethers and epoxides: naming, reactions
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