Naphthalene, like benzene, is aromatic and can be represented by three resonance structures as shown. Unlike benzene, not all the bonds in naphthalene are the same length. Which bond, A or B in the structure shown below, is longer? A B C A B
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Look at the three resonance structures of naphthalene shown in Section 15.6 and account for the fact that not all carbon-carbon bonds have the same length. The C1-C2 bond is $136 \mathrm{pm}$ long, whereas the $\mathrm{C} 2-\mathrm{C} 3$ bond is $139 \mathrm{pm}$ long.
Mothballs are composed of naphthalene, $\mathrm{C}_{10} \mathrm{H}_{8},$ 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, $C=C$ double bonds, or intermediate between $\mathrm{C}-\mathrm{C}$ single and $\mathrm{C}=\mathrm{C}$ double bonds? (c) Not all of the $\mathrm{C}-\mathrm{C}$ bond lengths in naphthalene are equivalent. Based on your resonance structures, how many $\mathrm{C}-\mathrm{C}$ bonds in the molecule do you expect to be shorter than the others?
(a) Use the concept of resonance to explain why all six $\mathrm{C}-\mathrm{C}$ bonds in benzene are equal in length. (b) Are the $\mathrm{C}-\mathrm{C}$ bond lengths in benzene shorter than $\mathrm{C}-\mathrm{C} \mathrm{sin}-$ gle bonds? Are they shorter than $\mathrm{C}=\mathrm{C}$ double bonds?
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