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17.14: Solutions to Additional Exercises

  • Page ID
    183088
  • 18-1

    18-2

    18-3  This is just one possible way to synthesize it.

    18-4  The bromine should be in the meta position. Right now it is in the ortho position, from perhaps having the ethyl group present first and then the having it substituted there. BUT the ethyl group is last to form, and the aldehyde and nitro groups would both encourage a meta substitution.

    18-5  Answer: A

    18-6

    18-7

     

    18-8

    18-9  1-chloro-2-methylbenzene and 1-chloro-4-methylbenzene

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    18-11

    Halogenation, Nitration, and Sulfonation of Benzene

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    18-13:

     

    18-14:

    Answer: A

    Activating, Ortho-, Para-Directing Substituents

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    18-17:

    Deactivating, Meta-Directing Substituents

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    18-19:

     

    18-20:

    Answer: B

    Halogen Substitutes: Deactivating, but Ortho, Para-Directing

    18-21:

    Answer: B

     

    18-22:

     

    18-23:

    Effects of Multiple Substituents on Electrophilic Aromatic Substitution

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    18-26:

    Friedel-Crafts Alkylation/Acylation

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    18-28:

    Friedel-Crafts alkylation using 1-chloropropane is not the best way to synthesize propylbenzene. You will end up with (propan-2-yl)benzene as your main product due to a hydride shift occurring during an intermediate step. A better route of synthesis may be Friedel-Crafts acylation using propanoyl chloride to make 1-phenylpropan-1-one, followed by a Clemmensen reduction to obtain the final product.

     

    18-29:

    Answer: D

    Nucleophilic Aromatic Substitution

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    18-32:

    Possible route of synthesis:

    Aromatic Substitutions Using Organometallic Reagents

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    18-34:

    Possible route of synthesis:

     

    18-35:

    Answer: D

    Side-Chain Reactions of Benzene Derivatives

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    18-37:

    Answer: A

     

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