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Question

When nitrobenzene is treated with Br2 in presence of FeBr3, the major product formed is m− bromonitrobenzene. Statements which are related to the formation of m−isomer are:

A
The electron density on meta carbon is more than that on ortho and para positions
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B
The intermidiate carbonium ion formed after initial atack of Br+ at the meta position is least destabilised
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C
Loss of aromaticity when Br+ attacks at the ortho and para positions and not at meta position
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D
Easier loss of H+ to regain aromaticity from the meta position than from ortho and para positions
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Solution

The correct option is B The intermidiate carbonium ion formed after initial atack of Br+ at the meta position is least destabilised


Electron withdrawing groups such as NO2 group decrease electron density at the ortho and para-positions, thus in such cases meta positions will has relatively higher electron density than the ortho and para positions.




Meta substitution will not put the positive charge on the same carbon that bears the nitro group. Hence, the intermidiate carbonium ion formed after initial atack of Br+ at the meta position is least destabilised.

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