Organic Chemistry, Chapter 7

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tulipyoursweety
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243105
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Organic Chemistry, Chapter 7
Updated:
2013-10-29 04:39:13
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Organic Chemistry Alkyl halides nucleophilic substitution
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Organic Chemistry Chapter 7, Alkyl halides and nucleophilic substitution, Naming
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  1. How give common name to simple alkyl halides
    • 1st word:
    • alkyl substituent
    • 2nd word: halide ("ide"-form)
  2. What is the common name?

    CH3CH2CH2Cl
    propyl chloride
  3. What is the common name?

    CH3Br
    methyl bromide
  4. What is the common name?
    tert-butyl iodide
  5. What is the common name?
    sec-butyl floride
  6. What makes a good leaving group in nucleophilic substitution?
    • same 4 effects that stabilize a conjugate base, aslo stabilize the leaving group in nucleophilic substitution:
    • elemental effect
    • resonance
    • inductive
    • hybridization
  7. What makes a good nucleophile in a nucleophilic substitution?
    • Negatively charged species are stronger than neutral
    • stronger base = stronger nucleophile

  8. Sn2 mechanism favors ______ and ______ R-X
    1° and methyl
  9. Alkyl halides have _______ bp's and mp's than alkanes having the same number of carbons.
    higher
  10. RX is ________ in organic solvents and _________ in water.
    soluble, insoluble
  11. ______ leaving groups for nucleophilic substitution:
    Cl-    Br-    I-    H2O
    good
  12. _____ leaving groups for nucleophilic substitution:
    F-, -OH, -NH2, H-, R-
    poor
  13. bases attack ______ and nucleophiles attack _______-_________ ________.
    protons, electron-deficient atoms (usually carbons)
  14. Right-to-left across a row of the period table, nucleophilicity ________ as basicity ________.
    increases, increases
  15. As the number of R groups on the carbon with leaving group increases, the rate of an Sn2 reaction _________. Why?
    decreases, because steric hinderence caused by bulky R groups makes nucleophilic attacks from back more difficult.
  16. As the number of R groups on the carbon with the leaving group increases, the rate of an Sn1 reaction _______. Why?
    increases, because stability of intermediate carbocation formed is more stable with more R groups attached.
  17. How does inductive effect stabilize carbocation?
    electron donating R groups stabilize the positive charge through the bonds. (more R groups, the better)
  18. Transition states in endothermic reactions resemble the ________.
    products
  19. Transition states in exothermic reactions resemble the ________.
    reactants

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