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Mothballs are composed of naphthalene, C10H8, C10H8, 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 C−C bond lengths in the molecule to be similar to those of C−C single bonds, C=Cdouble bonds, or intermediate between C−C single and C=C double bonds? (c) Not all of the C−C bond lengths in naphthalene are equivalent. Based on your resonance structures, how many C−C bonds in the molecule do you expect to be shorter than the others?

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