Solution

ID: past-exam-of-the-chemistry-a-course-of-the-university-of-cambridge/2023/paper-1/a5/a/ii/solution

Filling the three bonding molecular orbitals with two electrons each gives
Three isolated ethene-like bonds, evaluated with the same Hückel method parameters, have . Thus the signed delocalization energy is
Equivalently, the positive stabilization is .
Benzene has a planar cyclic conjugated system with six electrons, satisfying the count with . All three bonding molecular orbitals are filled and the antibonding levels are empty, giving the closed-shell stabilization associated with aromaticity. The conclusion uses the continuous cyclic overlap as well as the electron count.

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