Organic Chemistry Chapter 7 & 8: Alkyl halides and elimination and substitution

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tulipyoursweety
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Organic Chemistry Chapter 7 & 8: Alkyl halides and elimination and substitution
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2013-10-29 04:59:57
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Organic chemistry alkyl halides elimination reactions substitution
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CHEM 273: Organic Chemistry, Chapter 7 and 8
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  1. Dehydrohalogenation
    remove H and X from molecule and result in an alkene
  2. E2 mechanism is unimolecular or bimolecular??
    bimolecular
  3. Rate equation of E2 mechanism
    Rate = k [R - X][Base]
  4. E2 mechanism favors ______ bases.
    strong
  5. concerted
    bond breaking/making happens at the same time
  6. E2 mechanism is concerted or stepwise?
    concerted
  7. E2 mechanism favors _____ and _____ R-X
    secondary and tertiary
  8. Alkene stability depends upon:
    • 1) inductive effect
    • 2) hyper conjugation
  9. Zaitsev's Rule:
    • When doing β-elimination reactions, the hydrogen that is removed comes from the carbon with the most hydrogens.
    • |or|
    • The major product (alkene) is the least substituted.
  10. E2 elimination requires what type of orientation?
    Anti-periplanar orientation of the leaving group and the β-hydrogen
  11. E1 mechanism is unimolecular or bimolecular?
    unimolecular
  12. E1 mechanism rate equation
    Rate = k [R-X]

    (only depends on the alkyl halide conentration)
  13. E1 mechanism favors ______ bases.
    weak
  14. E1 mechanism is concerted or stepwise?
    stepwise
  15. E1 mechanism favors ______ and _______ R-X
    secondary and tertiary
  16. True/false:
    A negatively charged nucleophile is stronger than a neutral nucleophile.
    true
  17. True/false:
    A weaker base makes a stronger nucleophile.
    false
  18. True/false:
    Steric hinderance increases nucleophilicity
    false
  19. Carbocation stability:
    inductive effect
    stabilization through the bonds from R groups
  20. Carbocation stability:
    hyperconjugation
    • stabilizes empty p orbitals
    • (stabilization through space)
  21. hyperconjugation
  22. inductive effect
  23. How to determine SN1 or SN2?
    • 1. Identify/classify the alkyl halide
    •     a) methyl or 1° --> SN2
    •     b) 3° --------------> SN1
    •     c) 2° --------------> can be either
    • 2. Strength of nucleophile
    •     - strong nucleophile ---> SN2
    •     - weak nucleophile ----> SN1
  24. Which halide should never be used as a leaving group?
    F
  25. Most stable leaving group
    I (larger)

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