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When we talk about exchanging electron $i$ with electron $j$, we are actually changing the wavefunction according to $$\Psi(..., x_i, ..., x_j, ...) \to \Psi(..., x_j, ..., x_i, ...).$$ The operation is taken by the parity operator $P$. Applying it twice would return the wavefunction to its original form. So the following eigenvalue equation is satisfied $... 8 In short: The presence of the$\sigma_h$plane you see depends on the conformation of the methyl groups. If your example were either benzene or 1,4-dichlorobenzene, then you were be right, the molecule would contain a plane of symmetry identical to the plane defined by the benzene ring. This$\sigma_h\$ plane then could be described as in the following ...