Question

When nitrobenzene is treated with $Br_2$ in the presence of $FeBr_3$ the major product formed is m-bromonitrobenzene. Statements which are related to obtain the m-isomer, are

• A. the electron density on meta carbon is more than that on ortho and para positions
• B. the intermediate carbonium ion formed after initial attack of $Br^+$ at the meta position is less destabilised
• 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 meta position than from ortho and para positions

Answer 1

Answer: (B)

the intermediate carbonium ion formed after initial attack of $Br^+$ at the meta position is less destabilised

Answer 2

Nitro group withdraws electrons more from ortho/para position than from meta position. Also the o-complex formed from met a attack is less destabilised than from ortho/para positions.