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Why is ethylbenzene more easily nitrated than benzene?

Cyril Gamage  Follow

The ethyl group on the benzene has a 2,4-directing effect (a relatively weak one compared to -OH or -NH2), this means it is an electron donating group that donates electrons into the delocalised ring, activating it. Because the ring is now more electron dense, it is now more nucleophilic and more susceptible to electrophilic attack thus meaning during nitration, it may not need sulfuric acid to produce the nitronium ion from nitric acid as in benzene and it may be done at lower temperatures.

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Caleb Brunson  Follow

The mechanisms for nitration of benzene and ethylbenzene are shown below.

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