Chemistry 3719 Chapter 11

  1. Why does radical halogenation of methylbenzene only give the product of substitution at the methyl group and not the benzene ring?
    Reaction at the benzene ring would result in loss of aromaticity
  2. What organic compound results when methyl benzene is oxidized with KMnO4 and H2SO4?
    Benzoic acid:

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  3. Give a name for the following molecule:

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  4. Does the following reaction give benzoic acid as the product?

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    No; there needs to be at least one benzylic H present for the oxidation to happen
  5. What properties must a molecule have in order to have aromatic stabilization?
    Planar conjugated pi system in a cycle with (4n +2) pi electrons where n = integer
  6. Why is the name 1,6-dichlorobenzene incorrect?
    It should be 1,2-dichlorobenzene in order to keep the numbers as small as possible
  7. Why does molecule A undergo SN1 solvolysis in methanol faster than molecule B?

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    The tertiary benzylic carbocation from A will be easier to form since it will be stabilized by resonance
  8. Provide an acceptable name for the following molecule:

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  9. What is the approximate pKa of the most acidic proton in the following molecule?

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    The phenol OH group will be the most acidic with a pKa of about 10
  10. Why is pyridine (A) basic but pyrrole (B) is not?

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    The lone pair on N in pyridine is not needed for the 6 pi aromatic system and so it is available for donation as a base; the lone pair on N in pyrrole is needed for the 6 pi system and so is not available
Card Set
Chemistry 3719 Chapter 11
YSU Organic Chemistry