Mothballs are composed of naphthalene, [tex]\mathrm{C}_{10} \mathrm{H}_8[/tex], a molecule that consists of two six-membered rings of carbon fused along an edge, as shown in this incomplete Lewis structure: (a) Draw all of the resonance structures of naphthalene. How many are there? (b) Do you expect the [tex]\mathrm{C}[/tex] - [tex]\mathrm{C}[/tex] bond lengths in the molecule to be similar to those of [tex]\mathrm{C}-\mathrm{C}[/tex] single bonds, [tex]\mathrm{C}=\mathrm{C}[/tex] double bonds, or intermediate between [tex]\mathrm{C}-\mathrm{C}[/tex] single and [tex]\mathrm{C}=\mathrm{C}[/tex] double bonds? (c) Not all of the [tex]\mathrm{C}-\mathrm{C}[/tex] bond lengths in naphthalene are equivalent. Based on your resonance structures, how many [tex]\mathrm{C}-\mathrm{C}[/tex] bonds in the molecule do you expect to be shorter than the others?
