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Which substituent lowers the reactivity of a benzene ring toward electrophilic substitution, yet still mainly directs a new group to the ortho and para positions?
- –NH2
- –NO2
- –Cl
- –C2H5
Correct answer: –Cl
Solution
-Cl deactivates the ring (electron-withdrawing -I) yet directs o,p (lone-pair resonance donation). -NO2 deactivates but is meta-directing, so the stored answer is wrong.
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