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Example · Example 22

Q.Explain why resonance in the carbonate ion is a description of one delocalised structure, and not a molecule that rapidly oscillates between three separate Lewis structures.

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It is tempting, but incorrect, to imagine that a molecule described by resonance is literally hopping back and forth between its different contributing structures — first looking like structure 1, then an instant later like structure 2, and so on. This is not what resonance describes. Each individual resonance structure is only an approximate, incomplete two-dimensional drawing, forced by the limitation of drawing a single fixed double bond per structure; no single such drawing, on its own, can correctly represent a bonding pattern that is genuinely spread out (delocalised) over several atoms at once. The real carbonate ion has exactly one true structure at every instant — the resonance hybrid — in which the extra pi-bonding electron density is permanently and evenly shared across all three C–O bonds, never concentrated fully on just one of them the way any single canonical structure implies. This is precisely why experiment finds all three bonds to be identical in length: if the ion really did switch between the three structures, an instantaneous snapshot would sometimes s …

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