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.
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
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.
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.
I also tentatively think that they are different and are enantiomers.
ReplyDeleteThey 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
Yes, chiral and the two molecules shown are enantiomers. Not trivial to assign that stereocentre though.
ReplyDeleteYes they are chiral - it is the same geometry as 1,3-dichloroallene but I don't know how to specify one enantiomer
ReplyDeleteThe 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.
ReplyDeleteThis seems to be a good example of axial chirality.
ReplyDeleteNice example :-)
ReplyDeleteNice quiz!. Based on their non superimposability I say that they are not the same and are chiral.
ReplyDeleteThanks to the comments I now know about axial chirality.
On the assumption that the double bond stereochemistries are defined by the image, yes they are enantiomers.
ReplyDeleteBut this was the easier question
See http://wwmm.ch.cam.ac.uk/blogs/murrayrust/?p=2643 for a more challenging question
ReplyDeleteSee this site for an in depth analysis of disymmetric chirality, including the fascinating molecule chiralane!
ReplyDeleteThey are not the same. They are enantiomers. (Nearly fogot what I learned in class)
ReplyDelete