[g_orbital]

In principle, could cyclohexanone (either substituted or not) flip from one chair conformation to the other, like cyclohexane?
Particularly, suppose one position in the cyclohexanone is substituted by a good leaving group (say halide), in the equatorial position. From the geometric point of view, an elimination couldn't occur, because the leaving group is not antiperiplanar to the hydrogen. However, if theoretically the cyclohexanone ring could be inversed, the substituent becomes axial, making the elimination event now geometrically feasible.
What do you think?

Thanks in advance.

[spirochete]

Yes the same geometrical constraints that apply to reactions of cyclohexane also apply to cyclohexanone. 

[nj_bartel]

How does flipping about that carbon work with retention of the pi bond?