Ring Strain

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Alex Nguyen 3I
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Ring Strain

Postby Alex Nguyen 3I » Sun Mar 13, 2016 12:56 pm

Why does cyclooctene have more ring strain than cyclohexane? Does it have something to do with the double bond?

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Re: Ring Strain

Postby Chem_Mod » Sun Mar 13, 2016 5:35 pm

Cyclohexane in its chair conformation is one of the most stable cyclic molecules. Cyclooctene is unstable because in its 3D formation, the way it is actually found, it folds in on itself (as seen in the image below). When it folds in on itself, there's a lot of steric strain. In addition, in a planar octagon, each interior angle wants to be 135 degrees, but each sp3 carbon wants an angle of 109.5. Therefore there is a 25.5 degree difference causing some angle strain.
cyclooctene.PNG (11.52 KiB) Viewed 325 times

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