Why isn't allene planar?

1 Answer
May 30, 2017

I assume you mean the twisted propadiene.

https://upload.wikimedia.org/

Well, the left half of allene is perpendicular to the right half. In order for a molecule to be planar, the whole molecule has to be planar.

A simplified explanation is that the central carbon atom's #p_x# and #p_y# orbitals are aligned to make perpendicular #pi# bonds, corresponding to perpendicular #"CH"_2# groups. The same #p# orbital cannot (easily) make two parallel #pi# bonds on either side, especially if they both contain localized electrons.

https://cluster13-files.instructure.com/

(A planar allene exists, but for a much shorter amount of time than the twisted allene as it equilibrates into the twisted form.)