Question

When nitrobenzene is treated with $B{r}_2$ in the presence of $FeB{r}_3$ 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 $B{r}^{+}$ at the meta position is less destabilised
• C. loss of aromaticity when $B{r}^{+}$ 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)

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.