General Organic ChemistryMedium

Question

Shown below is the structure of methyl acetate with three different $\alpha,\beta$ and $\gamma$ carbon-oxygen bonds.

The correct order of bond length of these bonds is :

Options

A.$\alpha > \beta > \gamma$
B.$\alpha < \beta < \gamma$
C.$\alpha = \beta = \gamma$
D.$\alpha < \beta = \gamma$

Solution

Sol. [Key Concept: Resonance in the ester shortens the $C - O$ single bond toward double-bond character, giving the bond-length order $\alpha < \beta < \gamma$.]

RS 1 is more stable than RS2

∴ contribution of RS1 is more than RS2 in it's R.H.

∴ Order of bond length $\alpha < \beta < \gamma$

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