Dolbier HW Solutions 270

Dolbier HW Solutions 270 - form of benzene. We say that one...

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11.27 p -Dichlorobenzene has a center of symmetry. Each of its individual bond moments is balanced by an identical bond dipole oriented opposite to it. p -Dichlorobenzene has no dipole moment. o -Dichlorobenzene has the largest dipole moment. 11.28 The shortest carbon carbon bond in styrene is the double bond of the vinyl substituent; its length is much the same as the double-bond length of any other alkene. The carbon carbon bond lengths of the ring are intermediate between single- and double-bond lengths. The longest carbon carbon bond is the sp 2 to sp 2 single bond connecting the vinyl group to the benzene ring. 11.29 Move p electron pairs as shown so that both six-membered rings have an arrangement of bonds that corresponds to benzene. 11.30 ( a ) In the structure shown for naphthalene, one ring but not the other corresponds to a Kekul
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Unformatted text preview: form of benzene. We say that one ring is benzenoid, and the other is not. By rewriting the benzenoid ring in its alternative Kekul form, both rings become benzenoid. ( b ) Here a cyclobutadiene ring is fused to benzene. By writing the alternative resonance form of cyclobutadiene, the six-membered ring becomes benzenoid. Both rings are benzenoid. This six-membered ring is not benzenoid (does not correspond to Kekul form of benzene). This six-membered ring is benzenoid (corresponds to a Kekul form of benzene). Less stable More stable CH CH 2 140 pm 147 pm 134 pm Cl Cl p-Dichlorobenzene m 5 0 D m-Dichlorobenzene m 5 1.48 D Cl Cl o-Dichlorobenzene m 5 2.27 D Cl Cl 264 ARENES AND AROMATICITY...
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