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Dolbier HW Solutions 277 - 271 ARENES AND AROMATICITY 11.39...

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11.39 A good way to develop alternative resonance structures for carbocations is to move electron pairs toward sites of positive charge. Only one of the Lewis structures shown is a tertiary carbocation. o -Methylbenzyl cation has tertiary carbocation character; m -methylbenzyl cation does not. 11.40 The resonance structures for the cyclopentadienide anions formed by loss of a proton from 1-methyl-1,3-cyclopentadiene and 5-methyl-1,3-cyclopentadiene are equivalent. 11.41 Cyclooctatetraene is not aromatic. 1,2,3,4-Tetramethylcyclooctatetraene and 1,2,3,8-tetramethyl- cyclooctatetraene are constitutional isomers. Leo A. Paquette at Ohio State University synthesized each of these compounds independently of the
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