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Homework Help: Is the resolution of ibuprofen with pyrrolidine, C4H9N, possible?

  1. Oct 29, 2012 #1
    1. The problem statement, all variables and given/known data
    Hi! I'm doing a problem that asks whether pyrrolidine, C4H9N, could be used to resolve the racemic mixture of ibuprofen. In the correct resolution, we use the chiral base (S)-(-)-α-phenylethylamine as a resolving agent. In this question, it asks whether the base pyrrolidine could be used.

    For reference, pyrrolidine looks like this!
    http://www.chm.bris.ac.uk/webproject...lidine-s-o.gif [Broken]

    and the resolution of ibuprofen with (S)-(-)-α-phenylethylamine looks like this: (it's the second image down): http://amcrasto.theeurekamoments.com/2012/07/29/isolation-of-optically-pure-s-ibuprofen/

    2. Relevant equations
    Ibuprofen is a chiral carboxlyic acid. Pyrrolidine is a cyclic secondary amine with a five-membered heterocycle containing four carbon atoms and one nitrogen atom.

    3. The attempt at a solution
    I am thinking that this has something to do with whether pyrrolidine is chiral or achiral. I know that it if it is achiral then it would not be able to resolve the racemic mixture because it would produce identical S and R forms as we started with therefore it would not be useful. To resolve a mixture, a chiral molecule must be used. The trouble is I don't know whether or not pyrrolidine is achiral or chiral. Also, if it turns out to be chiral, then I really have no idea how to tell if pyrrolidine could be used or not! Any help would be greatly appreciated!
    Last edited by a moderator: May 6, 2017
  2. jcsd
  3. Nov 1, 2012 #2


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    Do you know how to determine if a compound is chiral or not?
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