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Q.

When nitrobenzene is treated with Br2 in presence of FeBr3, the major product formed is m-bromonitrobenzene. Statement which is related to obtain the m-isomer is

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a

the intermediate carbonium ion formed after initial attack of Br+ at the meta position is least destabilized

b

the electron density on meta carbon is increased than that on ortho- and para-positions

c

loss of aromaticity when Br+ attacks at the ortho and para positions and not at meta position

d

easier loss of H+ to regain aromaticity from the meta position than from ortho and para positions.

answer is B.

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Detailed Solution

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Electron withdrawing groups decrease, electron density in the o- and p-positions without effecting m-positions, thus in such cases meta positions will has relatively higher electron density than the ortho and para positions it is not increased due to -NO2 group. The intermediate carbocation formed by the attack of an electrophile on nitrobenzene will have relatively unstable resonating structure in case of ortho and para position.

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