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TBR Orgo stuff, WTF?

Discussion in 'MCAT Study Question Q&A' started by pfaction, Apr 15, 2012.

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  1. pfaction

    pfaction 7+ Year Member

    2,198
    37
    Mar 14, 2010
    WV
    MDApps:
    Check it out:

    [​IMG]

    So in this one, the EDG is on the bottom, so the negative charge is going to be on the top. Shouldn't it be that side which attacks? I don't get this one.

    [​IMG]

    What is the answer for #65? It's said to be B but I think it's wrong. It's not allylic, it's clearly vinylic. My answer is backed up by their question 45, which says that (I dunno how to IUPAC name this) 2 hydroxy cyclopentene is an allylic alcohol.
     
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  3. kishanb87

    kishanb87

    8
    0
    Jun 20, 2011
    I saw this earlier when I was studying as well! It would help if you posted smaller images. These images are huge. I had to zoom out of my browser to look at them. Not sure if everyone will try to do that.
     
  4. Dasypus

    Dasypus

    193
    1
    Apr 25, 2011
    Dang, break tables much?

    Anyhow, it's allylic, not vinylic, because both apply but allyl is more specific than vinyl, and with IUPAC names, you go with the most specific applicable.

    With the Diels-Alder question, I don't know what 'this one' you're refering to.
     
  5. pfaction

    pfaction 7+ Year Member

    2,198
    37
    Mar 14, 2010
    WV
    MDApps:
    But why is it allylic? It's attached directly to the double bonds.
     
  6. Dasypus

    Dasypus

    193
    1
    Apr 25, 2011
    We're naming that ether. And on one side of that oxygen, it goes -CH2-CH-CH-R. That's allyl.
     

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