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Question

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

A
The electron density of meta carbon is more than that on ortho and para positions
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B
Loss of aromaticity when Br+ attacks at the ortho and para positions and not at meta position
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C
Easier loss of H+ to regain aromaticity from the meta position than from ortho and para positions
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D
None of the above
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Solution

The correct option is A The electron density of meta carbon is more than that on ortho and para positions
The exact influence of a given substituent is seen as its interactions with the delocalized positive charge on the benzonium intermediate generated by bonding to the electrophile at each of the three substitution sites. Nitro groups have a positive charge on the atom bonded to the aromatic ring. Like charges of two groups are destabilized by charge repulsion so meta-products predominate as compared to others.

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