[owlpower]

I don't understand why. Both are aromatic compounds but I thought benzene has 3 C=C carbon bonds which allows for "greater" resonance.

[Borek]

Both are aromatic compounds

Are they?

[Babcock_Hall]

I find it helpful to think in terms of how a given anion can stabilize its negative charge.

[owlpower]

Why would Cyclopentadiene anion be more stable than benzene? Benzene has 3 C=C bonds, and the negative charge can be delocalised over the pi electron system.

Whereas for Cyclopentadiene I am not so sure...there are only 2 C=C bonds.

[owlpower]

Both are aromatic compounds

Are they?

Sorry, I realised Cyclopentadiene is not aromatic. I am not very clear on the aromatic rules as it isn't entirely covered in my course. From what I checked, they need to be cyclic, planar, and have a certain number of electrons...

[Borek]

Sorry, I realised Cyclopentadiene is not aromatic. I am not very clear on the aromatic rules as it isn't entirely covered in my course. From what I checked, they need to be cyclic, planar, and have a certain number of electrons...

Yes, so called https://en.wikipedia.org/wiki/Hückel%27s_rule

[Babcock_Hall]

Try drawing resonance structures of both anions.