Question #72513

Write down the mechanism of electrophilic substitution reaction in nitrobenzene.

Expert's answer

Answer on Question #72513, Chemistry / Organic Chemistry

Question:

Write down the mechanism of electrophilic substitution reaction in nitrobenzene.

Answer:

First of all we must understand that NO2\mathrm{NO}_2 -group in the nitrobenzene has negative inductive and negative mesomeric effect. Therefore it deactivates the benzene ring for electrophilic substitution reactions. Ortho- and para- positions of the ring are more deactivated then meta- position. See below:



Therefore the electrophile attacks meta- position and form the intermediate sigma-complex which gives the product after losing the proton.



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