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Choose from Unknown - A Chiral Compound

  1. Nov 16, 2012 #1

    AGNuke

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    A C8H12 chiral hydrocarbon, X, is reduced by catalytic Hydrogenation to an achiral C8H14. Ozonolysis (Oxidative) of X gave a chiral C8H12O4 dicarboxylic acid. Choose X from the given.

    C8H12.png

    Attempt
    I first determined the chirality of the given alternatives. That rules out the 2nd option, as it is clearly symmetric. Then I just removed the double bonds, as asked in the question to see if any achiral hydrocarbon is formed. First one, I think is achiral. But I am not sure about the 3rd and 4th.

    How about my attempt and is it something that I am overlooking?
     
  2. jcsd
  3. Nov 16, 2012 #2

    Borek

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    I think you are on the right track, but I have been wrong about chiral compounds so many times in the past I no longer trust myself.
     
  4. Nov 16, 2012 #3

    AGNuke

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    Yeah me too. It was in the test paper earlier, but I had to leave this simple looking question. What a shame.

    I couldn't formulate it back then, that 1st one would be achiral after catalytic hydrogenation.
     
  5. Nov 16, 2012 #4

    chemisttree

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    The 3rd and 4th remain chiral after hydrogenation but I'm sure you already knew that.
     
  6. Nov 17, 2012 #5

    AGNuke

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    I was unable to think about them in exam.
     
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