Is there a requirement for the stereochemistry of the starting material in E1 reactions? Why?
1 Answer
There is no stereochemical requirement for the starting material in
An
This causes formation of the less stable alkene in cyclohexane compounds such as (

This requirement does not exist in

The β C-H bond must be able to overlap the p orbital of the carbocation , so the β C-H bond must be axial.
We can always do a ring flip, so we can always form the more stable product, 1,2-dimethylcyclohexane.

Source: http://www.masterorganicchemistry.com/2012/10/10/comparing-the-e1-and-e2-reactions/
