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In which of the following aromatic compounds is the pi-electron density of the benzene ring the lowest?

1. nitrobenzene
2. anisole
3. para-nitroaniline (ring bearing both -NO2 and -NH2)
4. 1,3-dinitrobenzene

Correct answer: 1,3-dinitrobenzene

Solution

-NO2 is strongly electron-withdrawing (-M, -I) and removes pi density. Two nitro groups (dinitrobenzene) deplete the ring more than one (nitrobenzene). Anisole (-OCH3) and p-nitroaniline (the -NH2 donates) keep more density. Hence 1,3-dinitrobenzene has the minimum ring pi-electron density.

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