I've worked out five different conformations of propyl propanoate:

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I think the bisected conformations (E) should be the most stable one.

Are my rationals and suggestions in my scheme correct?

  • 3
    $\begingroup$ Your basic arguments seem fine to me. Certainly the s-trans conformations are higher energy than the s-cis conformations (like E), see here for a nice explanation. As to whether B or E is favored, I think they are very close in energy, but if I had to pick just one, then I'd choose E. A few minor points, 1) there are 8 expected low-energy conformations, you've only drawn 5, 2) stereochemistry in the ethyl group is not properly displayed in C and D (you show both a methyl and a hydrogen in the plane), but I understand what you mean. $\endgroup$ – ron Jun 23 '15 at 21:57

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