* Electron Density: The phenyl ring is directly attached to the oxygen atom of the ester group, which is electron-withdrawing. This makes the phenyl ring more electron-rich compared to the benzoate ring.
* Electrophilic Aromatic Substitution: Nitration is an electrophilic aromatic substitution reaction. Electron-rich aromatic rings are more susceptible to attack by electrophiles like the nitronium ion (NO2+).
* Resonance: The phenyl ring can participate in resonance with the carbonyl group of the ester, further increasing its electron density.
In contrast:
* The benzoate ring is directly attached to the carbonyl group, which is electron-withdrawing. This makes it less electron-rich and less reactive towards electrophilic attack.
Therefore, the phenyl ring of phenyl benzoate is more likely to undergo nitration.
