Solution

ID: past-exam-of-the-chemistry-course-of-the-year-3-of-the-natural-sciences-course-of-the-university-of-cambridge/2022/paper-2a/section-b/23/e/solution

The symmetric approach preserves the C2v molecular point group with its twofold axis z and mirror planes xz and yz. The molecular ring lies in xz. Classify orbitals by reflection signs : , , , . With globally defined p-orbital phases the molecular orbital correlation diagram gives
Within either two-orbital symmetry block the lower member remains correlated with the lower product member; the non-crossing rule prevents swapping their order through an ordinary same-symmetry crossing. Crossings between different irreducible representations are allowed. The crucial consequence is that the occupied carbon pi orbital correlates to a C–O-antibonding combination, rather than both initially occupied orbitals becoming the two product bonding orbitals.
Figure 1.
Original six-orbital correlation and schematic state correlation for the symmetric oxygen addition
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