JEE Main · 2007 · 29 Apr 2007 · Offline · Hydrocarbons

Presence of a nitro group in a benzene ring

(A)activates the ring towards electrophilic substitution
(B)renders the ring basic
(C)deactivates the ring towards nucleophilic substitution
(D)deactivates the ring towards electrophilic substitution✓ Correct

Answer: (D)

Solution

The nitro group withdraws electron density strongly from the ring, both by its inductive pull and by its

- M

resonance effect, leaving the ring electron-poor. An electron-poor ring is less attractive to the electrophiles involved in aromatic substitution, so the reaction is retarded. The nitro substituent therefore deactivates the ring towards electrophilic substitution.

JEE Main · 2007 · 29 Apr 2007 · Offline · Single correct option

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