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In which of the following molecules is the pi-electron density of the aromatic ring the greatest?

1. nitrobenzene
2. phenoxide ion
3. aniline
4. anisole

Correct answer: phenoxide ion

Solution

The phenoxide ion has a negatively charged oxygen (O-) that donates its lone pair very strongly into the ring by resonance, raising ring pi-electron density the most. Aniline and anisole donate but from neutral atoms; nitrobenzene is strongly deactivating (electron-withdrawing).

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