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Aromatic compounds question

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

  1. Leester


    Apr 26, 2013

    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

    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.

    SLDENTAL 2+ Year Member

    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


    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

    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:

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