[PoetryInMotion]

Problem. Can 1-chlorobicyclo[2.2.1]heptane undergo elimation? If so, supply a mechanism for the reaction.

My thoughts. E1 is not possible, since no stable (planar) carbocation can be formed. E2 however, should be possible, since a strong base is used. As far as I can see, the highlighted hydrogen atom in the following image lies in the same plane as the chlorine atom, which should make the reaction possible, even though anti periplanar geometry would have been more favorable.

Is this reasoning correct?

[Archer]

Would the product be stable in terms of bond angles?

[PoetryInMotion]

Thanks for your answer.

It definitely won't. And the highlighted hydrogen is not periplanar to the chlorine. I did a mistake when I built my molecular model. Thus, no elimination can take place.

[spirochete]

Thanks for your answer.

It definitely won't. And the highlighted hydrogen is not periplanar to the chlorine. I did a mistake when I built my molecular model. Thus, no elimination can take place.

Archer was correct,this concept is sometimes called Bredt's rule. How big would the rings have to be for a bridgehead elimination to happen?