Towards electrophilic substitution, the most reactive will be
- Nitrobenzene
- Aniline
- Aniline hydrochloride
- N-Acetylaniline
Solution

Nitrobenzene and aniline hydrochloride have electron- withdrawing $\left(-\mathrm{NO}_{2}ight.$ and $\left.-\mathrm{N} \mathrm{H}_{3}^{+}ight)$ groups, hence these will undergo electrophilic substitution with difficulty. Aniline and N-acetylaniline (acetanilide) have electron-releasing groups, however $-\mathrm{NHCOCH}_{3}$ is less electron- releasing than $-\mathrm{NH}_{2}$ due to delocalisation of lone pair of electron on $\mathrm{N}$ toward carbonyl group. Hence aniline (having $-\mathrm{NH}_{2}$ ) will undergo electrophilic substitution most easily.
Asked in: JEE-TOPICTESTS-CHEMISTRY