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Planar compounds

Discussion in 'DAT Discussions' started by motivated dent, Jan 4, 2009.

  1. motivated dent

    2+ Year Member

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    why is naphthalene aromatic but [10]annulene is nonaromatic? it says somethign about cis and trans but i'm lost...
    [​IMG]naphthalene
    [​IMG][10]annulene
     
  2. doc3232

    7+ Year Member

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    You don't need to know it for the DAT. It is complicated. Something about bonds bending and what not. The second one is not planar because it conforms oddly to be stable.
     
  3. gentile1225

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    remember the requirements for aromaticity:
    cyclic
    planar
    and Huckel's rue

    annulene has 10 carbons, therefore, the strain on the ring forces the carbons pi orbitals to lie in different planes.

    napthalene is basically 2 benzene rings which we known are definitely aromatic. it is cyclic, the pi orbitals of the carbons all lie in the same plane, it satisfies Huckels rule, and is fully conjugated.
     

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