Consider the following molecules/species : [figure] The correct order of carbon-oxygen double bond length is :
- x > y > z
- y > z > x
- z > x > y
- x > z > y
Answer
(4) x > z > y
Solution
Bond length of C=O increases as its double-bond character (bond order) decreases.
(y) Acetone: no conjugation ⇒ the C=O keeps full double-bond character ⇒ shortest.
(z) Acetate ion: two equivalent resonance structures, CH3-C(=O)-O CH3-C(O )=O ⇒ each C–O bond has bond order 1.5.
(x) Tropone: in the dipolar resonance form C -O the ring becomes a tropylium ion — cyclic, planar, 6 π electrons (4n + 2, n = 1) ⇒ aromatic. This aromatic stabilisation makes the dipolar form the major contributor (tropone has a large dipole moment, ≈ 4.3 D), so its C–O bond has the greatest single-bond character ⇒ longest.
∴ Carbon-oxygen bond length: x > z > y
Answer: (4)