Comparison of Bond Lengths in Methyl Acetate
Shown below is the structure of methyl acetate with three different , and carbon - oxygen bonds.
The correct order of bond lengths of these bonds is :
Options
Step-by-Step Solution
To determine the correct order of the carbon-oxygen bond lengths in methyl acetate, we need to analyze the bond orders of the three specified bonds (, , and ) by considering their resonance structures:
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Bond ( carbonyl bond): In the main contributing canonical structure, the bond is a double bond. It participates in resonance with the adjacent oxygen atom: Due to this delocalization, the bond has a major double-bond character with a small fraction of single-bond character. Thus, its bond order is close to (approximately ). High bond order corresponds to the shortest bond length.
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Bond ( ester acyl bond): In the primary structure, the bond is a single bond. However, the lone pairs on the ester oxygen atom undergo resonance with the carbonyl group, imparting partial double-bond character to the bond (). Thus, its bond order is strictly greater than (approximately ). Consequently, its length is intermediate—shorter than a standard single bond, but longer than the double bond .
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Bond ( ester alkyl bond): The bond connects the ester oxygen to an -hybridized methyl carbon. This bond does not participate in resonance and retains a pure single-bond character with a bond order of exactly . Therefore, it is the longest bond among the three.
Comparing the bond orders:
Since bond length is inversely proportional to bond order, the order of bond lengths is:
Thus, the correct option is B.