If Org 2 has an overall theme, it’s “resonance”. Today’s post has a very simple message. Atoms with lone pairs, π bonds, radicals, and carbocations can participate in resonance: atoms that lack any of these features cannot.
One way in which this comes up is in determining whether two alkenes are “conjugated” or not. A full discussion of conjugation is for another time, but “conjugation” is the name we give for the phenomenon where π electrons (that is, “electrons in p orbitals”) can be shared over more than 3 or more atoms.
Here’s an example of a conjugated diene and a non-conjugated dienes.
The thing is, we can also have alkenes which are conjugated with each other even through they are not directly attached. The only requirement is that we require an atom in between which can participate in resonance. This can take at least four forms:
- A carbon (or other atom) with an empty p orbital (e.g. a carbocation)
- A carbon with a half-filled p orbital (e.g. a radical)
- A carbon with a lone pair (carbanion)
- Any other atom with a lone pair (e.g. N, O, S, etc.)
In each of these we can draw resonance forms where the middle atom participates in a π bond. This implies that the electrons are being shared (“delocalized”) between this central atom and the alkenes on the side, and thus the whole system is ‘conjugated’.
Why does this matter, you may ask? Because some day, I have a hunch that you might be asked whether the following rings are conjugated or not, and you might need to come up with a good answer….