Shown below is the structure of methyl acetate with three different α, β and γ carbon - oxygen bonds. [figure] The correct order of bond lengths of these bonds is :
- α > β > γ
- α < β < γ
- α = β = γ
- α < β = γ
Answer
(2) α < β < γ
Solution
Resonance in the ester group: the lone pair on the ether O (β-bond O) is delocalised towards C=O:
CH3- O \|C-O-CH3 CH3- O |C= O-CH3
α (C=O): double bond, slightly lengthened by resonance ⇒ shortest
β (C–O of ester): single bond with partial double-bond character ⇒ intermediate
γ (O–CH3): pure single bond to an sp3 carbon ⇒ longest
∴ α < β < γ
Answer: (2)