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Compare the basicity of the following compounds: Benzoate ion and Formyl Benzoate ion

Accepted Answer

The benzoate ion (C6H5COO-) is more basic than the formyl benzoate ion (C6H5CO2CHO-). Here's why:

Resonance Stabilization: The negative charge on the benzoate ion is delocalized over the entire benzene ring through resonance. This stabilization makes it less likely to donate its electron pair and act as a base.

Electron-Withdrawing Group: The formyl group (CHO) in formyl benzoate is an electron-withdrawing group. This group pulls electron density away from the carboxylate group, making it less basic. The more electron-withdrawing the group, the less basic the compound.
In summary, the benzoate ion is more basic due to its greater resonance stabilization and the lack of an electron-withdrawing group compared to the formyl benzoate ion.


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