Q.Explain the structure of the molecule.
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Start your 14-day free trial to unlock the full solution →'s structure cannot be captured by a single Lewis structure. It is best described as a
resonance hybrid of three canonical forms — , , and
(Fig. 4.5 of the textbook) — and this resonance hybrid is exactly why the experimentally
measured C–O bond length (115 pm) sits between a pure C=O double bond (121 pm) and a pure C≡O
triple bond (110 pm).
Why a single Lewis structure isn't enough
A straightforward Lewis-structure treatment of gives one clean answer: carbon, with 4
valence electrons, forms a double bond with each of the two oxygens, using all 16 valence
electrons () and leaving no lone pairs on carbon. This structure — — is
perfectly valid on its own, is linear, and correctly predicts a bond angle and a nonpolar
molecule.
But a single structure like this makes a specific, checkable prediction: if both C–O bonds are
plain double bonds, they should both have the normal C=O bond length, pm. Experiment
says otherwise — the C–O bond length actually measured in is pm, noticeably shorter
than pm. Something in the simple picture is incomplete.
Bringing in resonance
This is the same situation we already saw for ozone () and the carbonate ion ():
whenever a molecule's real, experimentally measured bond length falls between the values
expected for two different bond orders, a single Lewis structure cannot be the whole truth, and
we turn to resonance.
For , the textbook gives three canonical (contributing) structures, shown together in Fig.
4.5:
- Form I: — the ordinary double-bond structure, with no formal charges.
- Form II: — one oxygen forms a single bond and carries a formal positive charge; the other forms a triple bond and carries a formal negative charge.
- Form III: — the mirror image of Form II, with the triple bond and single bond swapped between the two oxygens.
None of these three forms is the actual structure of on its own. The real molecule is a
resonance hybrid of all three — a single, stable structure whose true bonding character is
an average of the three canonical forms, not a molecule flipping between them.
Why the hybrid explains the bond length
Averaging across the three forms, each C–O bond has some triple-bond character (from whichever
form puts a triple bond on that side) mixed with mostly double-bond character (since Form I,
the pure double-bond form, contributes most heavily and is the lowest-energy, most stable of the
three canonical structures). This gives each C–O bond a bond order between 2 (pure double) and 3
(pure triple) — and a bond length correspondingly between the double-bond value (121 pm) and the
triple-bond value (110 pm).
The measured value, 115 pm, sits neatly in that intermediate range — shorter and stronger than a …
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