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Thursday, October 14, 2010

Are these organic molecules the same?

Cambridge pubs are not just good for the (Danish) beer, but also for the pub quizzes. Peter asked if the below molecules are the same. I did not think so, but... what do you think? He also asked if they are chiral. We got until tomorrow 20:00 BST.

11 comments:

  1. I also tentatively think that they are different and are enantiomers.
    They produce different InChIs which appears to support this:
    InChI=1S/C15H24/c1-3-13-6-10-15(11-7-13)14-8-4-12(2)5-9-14/h3,12H,4-11H2,1-2H3/b13-3-,15-14-/t12-/m1/s1
    and
    InChI=1S/C15H24/c1-3-13-6-10-15(11-7-13)14-8-4-12(2)5-9-14/h3,12H,4-11H2,1-2H3/b13-3-,15-14-/t12-/m0/s1
    for the first and second structures respectively

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  2. Yes, chiral and the two molecules shown are enantiomers. Not trivial to assign that stereocentre though.

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  3. Yes they are chiral - it is the same geometry as 1,3-dichloroallene but I don't know how to specify one enantiomer

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  4. The two structures you show are not the same - they are stereoisomers. You can verify this by trying to superimpose them - there's no way to do it without changing configurations.

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  5. This seems to be a good example of axial chirality.

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  6. Nice quiz!. Based on their non superimposability I say that they are not the same and are chiral.
    Thanks to the comments I now know about axial chirality.

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  7. On the assumption that the double bond stereochemistries are defined by the image, yes they are enantiomers.

    But this was the easier question

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  8. See http://wwmm.ch.cam.ac.uk/blogs/murrayrust/?p=2643 for a more challenging question

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  9. See this site for an in depth analysis of disymmetric chirality, including the fascinating molecule chiralane!

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  10. They are not the same. They are enantiomers. (Nearly fogot what I learned in class)

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