1
$\begingroup$

The image below shows a [3,3] sigmatropic rearrangement. My question is why does the increased temperature favour the right side? The arrangement is technically the same except for the methyl groups on different carbons.

enter image description here

Here is another example:

enter image description here

$\endgroup$
1

1 Answer 1

4
$\begingroup$

The increased temperature is necessary to overcome the activation energy of the reaction. Many [3,3] sigmatropic rearrangements have very high activation energies. The products are favored at equilibrium because they are thermodynamically more stable. For example, in the first case, you are exchanging monosubstituted alkenes for disubstituted alkenes.

$\endgroup$

Your Answer

By clicking “Post Your Answer”, you agree to our terms of service and acknowledge that you have read and understand our privacy policy and code of conduct.

Not the answer you're looking for? Browse other questions tagged or ask your own question.