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Chirality of naproxen

  1. Jun 6, 2014 #1
    1. The problem statement, all variables and given/known data
    determine and explain its chirality using the CIP rule
    *see attached image*

    2. Relevant equations
    CIP rules


    3. The attempt at a solution
    Hello

    I've determined that the stereocenter of this molecule is at the carbon where the carboxyl group meets the two benzene rings.

    I've done step one and rotated the stereocenter such that the hydrogen is facing back. However when deciding the priorities of the three constituents on the stereocenter I get a little confused.

    When going down the chain, towards the aromatic rings that I'll encounter a double bond. I tried reading how these fit in with the CIP rules but I find them to be quite ambiguous.

    And with the carboxyl group, when going down the chain, which direction do I have to go? Down the hydroxyl group on the double bonded oxygen? I

    Thanks
    - miniradman
     

    Attached Files:

  2. jcsd
  3. Jun 6, 2014 #2
    You have identified the correct chiral center. These are the three groups I see.

    Methyl
    Ring
    Carboxylic acid

    I do not know what CIP rules are.
     
    Last edited: Jun 6, 2014
  4. Jun 6, 2014 #3

    Borek

    User Avatar

    Staff: Mentor

    Cahn–Ingold–Prelog
     
  5. Jun 6, 2014 #4
    Your chiral carbon is attached to:

    1) A hydrogen.
    2) A carbon which is attached to 3 or so oxygen atoms (because m.ultiple bonds are counted as equivalent number of single bonds, from memory)
    3) a carbon which is attached to 3 carbon atoms (same as above).

    Can you do it now?
     
  6. Jun 7, 2014 #5
    Well since oxygen has a higher atomic number than carbon, I assume the carboxyl group has more priority.

    However, intuitively, if I were to have another single aromatic ring in place of the carboxyl group, how would I go about going down the branches? Which would then be of highest priority? I get confused on where to go once you start having to decide which branch to take.
     
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