Ncert Exercises & Solutions

In an electrophilic substitution reaction of nitrobenzene, the nitro group:

(a)	Deactivates the ring by the inductive effect.
(b)	Activates the ring by the inductive effect.
(c)	Decreases the charge density at the ortho and para positions of the ring relative to the meta position by resonance.
(d)	Increases the charge density at the meta position relative to the ortho and para positions of the ring by resonance.

1. (c) Only
2. (a) and (c)
3. (b) and (d)
4. (d) only

Hint: The -NO₂group exhibits both -I (inductive) and -R (resonance) effects.

(1, 3)

Nitro group by virtue of -I-effect withdraw electrons from the ring and increase the charged and destabilised carbocation.

In ortho, para-attack of electrophile on nitrobenzene, we are getting two structures (A) and (B) in which positive charge is appearing on the carbon atom directly attached in the nitro group.

As nitro group is electron withdrawing by nature, it decreases the stability of such product and hence meta attack is more feasible when electron withdrawing substituents are attached.

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