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Aromatic compounds question

Discussion in 'DAT Discussions' started by Leester, May 16, 2014.

  1. Leester

    Leester

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    Apr 26, 2013
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    Hey everyone. This is one of the questions from DAT bootcamp's question of the day series. I thought the only possible answer would be III. The answer turned out to be D (I and III). I thought compound 1 would not be aromatic because is is non-planar (Above 7 Carbons). Is compound 1 considered planar?

    Thank you
     
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  3. Myce

    Myce 2+ Year Member

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    Feb 2, 2014
    I think the reason the first one is considered aromatic is because it follow's Huckel's Rule of 4n+2 (there are 14 pi electrons 4(3) + 2 = 14), is in a conjugated cyclic system, so it's most likely planar.
     
  4. SLDENTAL

    SLDENTAL 2+ Year Member

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    Mar 2, 2014
    I talked to my orgo teacher about this question and he said it is a bad question b/c can be interpreted in different ways for which is aromatic or not bc not because like u said it could be non planar
     
  5. Leester

    Leester

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    Apr 26, 2013
    Ah I see. I just remember in Chad's videos he said something like anything > 7 carbons in structure is non planar so this question was confusing. Appreciate it.
     
  6. Ari Rezaei

    Ari Rezaei Senior Member Lifetime Donor Gold Donor Classifieds Approved 5+ Year Member

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    Mar 14, 2012
    New York, NY
    Considering anything over 7 carbons as non planar and not aromatic is an OK way to think about it in a test prep sense, but there are quite a few compounds that are aromatic with more carbons. But yes, if you have 8 or 10 carbons then it won't be aromatic, so those are good to know and what the ADA will likely test on the planar concept of aromaticity.

    Also, compound 1 is an aromatic annulene, it's large enough to accommodate all the double bonds and still be planar. You can see more information here: http://en.wikipedia.org/wiki/Cyclotetradecaheptaene
     

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