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Q.

A group which deactivates the benzene ring towards electrophilic substitution but directs the    incoming group towards o-and p-positions is

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a

NO2

b

Cl

c

Br

d

all

answer is D.

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Detailed Solution

  • Halogens are electron-withdrawing groups due to electronegative nature, hence they deactivate benzene ring for electrophilic substitution but are o,p-directing due to resonance. (As halogens have lone pair). 
  • In nitrobenzene, the nitro group (−NO2) is attached to the benzene ring. −NO2 group is an electron withdrawing group. It deactivates benzene ring towards electrophilic substitution reaction.
  • The resonating structure of nitrobenzene shows +ve charge develops in ortho and para positions.
  • As a result, the electron density at meta position is relatively higher than at the ortho and para position.
  • It decreases the electron density at ortho and para position thus making the electron density at meta position more than at ortho and para position.
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