Comparison of Carbon Oxygen Double Bond Length in Organic Species
Consider the following molecules/species:
The correct order of carbon - oxygen double bond length is :

Options
A
B
C
D
Correct
Topics & Concepts
Step-by-Step Solution
To determine the correct order of the carbon-oxygen () bond length in the given species, we analyze the contribution of resonance structures and the resulting bond order for each species:
-
Species (Tropone / 2,4,6-Cycloheptatrien-1-one):
- The carbonyl group can polarize as follows:
- Polarisation gives a seven-membered ring carbocation containing electrons. According to Hückel's rule ( electrons with ), this ring is aromatic and exceptionally stable.
- Due to this aromatic stabilization, the dipolar single-bonded resonance structure () contributes heavily to the resonance hybrid.
- As a result, the bond has substantial single-bond character, leading to a bond order significantly less than . Thus, it has the longest carbon-oxygen bond.
-
Species (Acetate ion, ):
- The negative charge is delocalized equally over both oxygen atoms through two equivalent canonical structures:
- Due to equal resonance, the carbon-oxygen bond order is exactly:
-
Species (Acetone, ):
- It possesses a standard, highly localized carbon-oxygen double bond ().
- Without any aromatic stabilization or equivalent charge delocalization, the single-bond contributor is minimal.
- Thus, the bond order is closest to , giving it the shortest carbon-oxygen bond.
Conclusion:
Comparing the bond orders:
Since bond length is inversely proportional to bond order (), the correct order of carbon-oxygen bond lengths is:
Correct Option: D ()