Dolbier HW Solutions 278

Dolbier HW Solutions 278 - 272 ARENES AND AROMATICITY 11.42...

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11.42 Cyclooctatetraene has eight p electrons and thus does not satisfy the (4 n 1 2) p electron require- ment of the H ü ckel rule. All of the exercises in this problem involve counting the number of p electrons in the various species derived from cyclooctatetraene and determining whether they satisfy the (4 n 1 2) p electron rule. ( a ) Adding 1 p electron gives a species (C 8 H 8 2 ) with 9 p electrons. 4 n 1 2, where n is a whole number, can never equal 9. This species is therefore not aromatic. ( b ) Adding 2 p electrons gives a species (C 8 H 8 2 2 ) with 10 p electrons. 4 n 1 2 5 10 when n 5 2. The species C 8 H 8 2 2 is aromatic. ( c ) Removing 1 p electron gives a species (C 8 H 8 1 ) with 7 p electrons. 4 n 1 2 cannot equal 7. The species C 8 H 8 1 is not aromatic. ( d ) Removing 2 p electrons gives a species (C 8 H 8 2 1 ) with 6 p electrons. 4 n 1 2 5 6 when n 5 1. The species C 8 H 8 2 1 is aromatic. (It has the same number of p electrons as benzene.) 11.43 ( a , b ) Cyclononatetraene does not have a continuous conjugated system of p electrons. Conjuga-
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