Main Question or Discussion Point
Consider the hypothetical molecule 1,3,5-cyclohexatriene (not benzene, I am referring to a molecule where no resonance takes place - a molecule with three C=C bonds and 3 C-C bonds). Each carbon atom in this molecule would be participating in one double bond, and so each carbon atom would be sp2 hybridized. This would suggest bond angles of 120° throughout the cyclic structure, which is only true of a regular hexagon. However, C=C bonds are shorter than C-C bonds. Three C=C bonds and three C-C bonds would certainly result in a somewhat distorted hexagon. Those are clearly two conflicting results. What are your thoughts on this?