BRAINCAKE3-Directing Groups
Groups that withdraw electron density from the benzene ring, such as the nitro group, -NO2, are 3-directing.
Why
The -NO2 group pulls electron density out of the ring. This lowers the electron density most at positions 2, 4 and 6, so position 3 (and the equivalent position 5) is left relatively richer in electrons, and the electrophile substitutes there.
Deactivation
Because the ring has less electron density overall, nitrobenzene reacts more slowly than benzene. Harsher conditions are needed, such as a higher temperature for a second nitration.
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All 16 lessons in Benzene · All OCR A-level Organic Chemistry topics