Organic Chemistry Chapter 18 Electrophilic Aromatic Substitution

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Organic Chemistry Chapter 18 Electrophilic Aromatic Substitution
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2014-02-24 00:55:43
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Organic Chemistry Chapter 18 Electrophilic Aromatic Substitution
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Organic Chemistry Chapter 18 Electrophilic Aromatic Substitution
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  1. Electrophilic aromatic substitution follows a ____-step mechanism
    • two
    • Reaction with an electrophile forms a carbocation, and loss of a proton regenerates aromatic ring
  2. Which step in electrophilic aromatic substitution is rate-determining?
    first
  3. Rules describing reactivity and directing effects of common substitutents:
    [1] all _______ directors except the halogens activate the benzene ring.
    ortho-para
  4. Rules describing reactivity and directing effects of common substitutents:
    [2] all ____ directors deactivate the benzene ring
    meta
  5. Rules describing reactivity and directing effects of common substitutents:
    [3] The halogens ______ the benzene ring and direct _________.
    • deactivate
    • ortho, para
  6. benzene - R
    R = alkyl
    Inductive effect?
    donating
  7. benzene - R
    R = alkyl
    Resonance effect?
    none
  8. benzene - R
    R = alkyl
    Reactivity?
    Activating
  9. benzene - R
    R = alkyl
    Directing effect?
    ortho, para
  10. benzene - Z
    Z= N or O
    Inductive effect?
    withdrawing
  11. benzene - Z
    Z= N or O
    Resonance effect?
    donating
  12. benzene - Z
    Z= N or O
    Reactivity?
    activating
  13. benzene - Z
    Z= N or O
    Directing effect?
    ortho, para
  14. benzene - X
    X= halogen
    Inductive effect?
    withdrawing
  15. benzene - X
    X= halogen
    Resonance effect?
    donating
  16. benzene - X
    X= halogen
    Reactivity?
    deactivating
  17. benzene - X
    X= halogen
    Directing effect?
    ortho, para
  18. benzene - Y
    Y= partial + or + charge
    Inductive effect?
    withdrawing
  19. benzene - Y
    Y= partial + or + charge
    Resonance effect?
    withdrawing
  20. benzene - Y
    Y= partial + or + charge
    Reactivity?
    deactivating
  21. benzene - Y
    Y= partial + or + charge
    Directing effect?
    meta
  22. Halogenation:
    benzene --(X2 + FeX3)-->
    X = Cl, Br
    • Benzene - X
    • aryl chloride or aryl bromide
  23. Polyhalogenation occurs on benzene rings substituted by...
    OH and NH2 (and related subsituents)
  24. What is halogenation of benzene ring?
    Replacement of H by Cl or Br
  25. What is nitration of benzene ring?
    Replacement of H by NO2
  26. Halogenation:
    benzene --?--> benzene-X
    X2, FeX3
  27. Nitration:
    benzene --(HNO3, H2SO4)--> ?
    • benzene-NO2
    • Nitro compound
  28. Nitration:
    benzene --?--> benzene-NO2
    HNO3, H2SO4
  29. What is sulfonation of benzene ring?
    replacement of H by SO3H
  30. Sulfonation:
    benzene --(SO3, H2SO4)--> ?
    • benzene-SO3H
    • benzenesulfonic acid
  31. Sulfonation:
    benzene --?--> benzene-SO3H
    SO3, H2SO4
  32. What is Friedel-Crafts alkylation?
    Replacement of H by R
  33. Friedel-Crafts alkylation:
    benzene --(RCl, AlCl3)--> ?
    • benzene-R
    • alkyl benzene (arene)
  34. Friedel-Crafts alkylation:
    benzene --?--> benzene-R
    (2 answers)
    • RCl, AlCl3
    • |or|
    • ROH, H2SO4
  35. Friedel-Crafts alkylation:
    [1] with alcohols
    benzene --(ROH, H2SO4)--> ?
    benzene-R
  36. Friedel-Crafts alkylation:
    [2] with alkenes
    benzene --(CH=CHR, H2SO4)--> ?
    benzene-CRCH3
  37. Can rearrangements occur in Friedel-Crafts alkylation?
    yes
  38. Friedel-Crafts alkylation:
    The carbon in the R group being attached to the benzene ring must have what type of hybridization?
    Csp3
  39. Friedel-Crafts alkylation:
    The reaction does not occur on benzene rings substituted by _____ ________ groups or ____ groups.
    • meta deactivation
    • NH2
  40. Friedel-Crafts alkylation:
    T/F: polyalkylation can occur
    True
  41. What is Friedel-Crafts acylation?
    Replacement of H by RCO
  42. Friedel-Crafts acylation:
    benzene --(RCOCl, AlCl3)--> ?
    benzene-ketone
  43. Friedel-Crafts acylation:
    benzene --?--> ketone
    RCOCl, AlCl3
  44. Friedel-Crafts acylation:
    The reaction does not occur on benzene rings substitued by what kinds of groups?
    • meta deactivating groups
    • NH2 groups
  45. Benzylic halogenation:
    benzene --(A)--> ?
    A= Br2, hv or Δ
    |or|
    A= NBS, hv or ROOR
    • benzene-CBrR
    • benzylic bromide
  46. Benzylic halogenation:
    benzene --?--> benzene-CBrR (benzylic bromide)
    • A= Br2, hv or Δ
    • |or|
    • A= NBS, hv or ROOR
  47. Oxidation of alkyl benzenes:
    benzene-CH2R --(KMnO4)--> ?
    • benzene-COOH
    • benzoic acid
  48. Oxidation of alkyl benzenes:
    benzene-CH2R --?--> benzene-COOH (benzoid acid)
    KMnO4
  49. Oxidation of alkyl benzenes requires what for reaction?
    benzylic C-H bond
  50. Reduction of ketones to alkyl benzenes:
    benzene-COR --(A)--> ?
    A= Zn(Hg), HCl
    |or|
    A= NH2NH2, NaOH
    • benzene-CH2R
    • (alkyl benzene)
  51. Reduction of ketones to alkyl benzenes:
    benzene-COR --?--> benzene-CH2R (alkyl benzene)
    • Zn(Hg), HCl
    • |or|
    • NH2NH2, NaOH
  52. Reduction of nitro groups to amino groups:
    benzene-NO2 --(A)-->
    A= H2, Pd-C
    |or|
    A= Fe, HCl
    |or|
    A= Sn, HCl
    • benzene-NH2
    • aniline
  53. Reduction of nitro groups to amino groups: benzene-NO2 --?--> benzene-NH(aniline)
    • H2, Pd-C
    • |or|
    • Fe, HCl
    • |or|
    • Sn, HCl

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