Question

# Account for the following: Although the Amino group is o and p directing in aromatic electrophilic substitution reactions, aniline on nitration gives a substantial amount of m-Nitroaniline?

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Solution

## Aniline on nitration gives a substantial amount of m-Nitroaniline:The Nitration process usually undergoes in the presence of an acidic medium i.e the mixture of $\mathrm{Con}{\mathrm{HNO}}_{3}$ and $\mathrm{Con}{\mathrm{H}}_{2}{\mathrm{SO}}_{4}$, which results in the protonation of the Anilinium ion, and Nitroaniline is formed.The formed Anilium ion basically acts as a deactivating group and directs the nitro $\left(-{\mathrm{NO}}_{2}\right)$ group to the meta position by forming a meta isomer of Nitroaniline.Also, the nitro group which is an electron-withdrawing group does not undergo Friedel craft reaction on ortho and para position as it deactivates the benzene ring mainly at the respective ortho and para position for electrophilic substitution reaction.Hence, aniline on nitration gives a substantial amount of m-Nitroaniline.

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