Dolbier HW Solutions 263

Dolbier HW Solutions 263 - 257 ARENES AND AROMATICITY...

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energy orbitals. There are 12 p electrons, and so the lowest 5 orbitals are each doubly occu- pied, whereas each of the next 2 orbitals orbitals of equal energy is singly occupied. 11.14 One way to evaluate the relationship between heats of combustion and structure for compounds that are not isomers is to divide the heat of combustion by the number of carbons so that heats of com- bustion are compared on a per carbon basis. As the data indicate (within experimental error), the heats of combustion per carbon of the two aro- matic hydrocarbons, benzene and [18]-annulene, are equal. Similarly, the heats of combustion per carbon of the two nonaromatic hydrocarbons, cyclooctatetraene and [16]-annulene, are equal. The two aromatic hydrocarbons have heats of combustion per carbon that are less than those of the nonaromatic hydrocarbons. On a per carbon basis, the aromatic hydrocarbons have lower potential
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