[impulse29]

I just got a new organic chem assignment, and there is one question that defies my logic, and what we've learned. We are given two cyclic 5 carbon rings, one has two double bonds, the other has one. We are supposed to remove 2 protons (forming a dianion), and account for its stability. However, since it is such a small compound, wouldn't this compound not exist? I suppose that if it were a trans configuration it would be more likely, or if one proton is lost from either side. I am not asking for the solution, just some help on my path.

Thanks,
Impulse.

[Yggdrasil]

Think about what deprotonation might do to a cyclic, conjugated molecule, especially if deprotonation allows the molecule to change from sp³ hybridization to sp² hybridization.

[impulse29]

After looking at the molecule, it made sense where the two protons would likely come from. Also, I found that using Hückel's rules, that it becomes aromatic. I thought that both positive charges would be on the 5-carbon ring with one double bond.
Thanks.