Aniline is highly reactive towards electrophilic aromatic substitution, often leading to poly-substitution (e.g., tribromoaniline with bromine water). To strictly obtain a mono-substituted para-deriva

Question

Aniline is highly reactive towards electrophilic aromatic substitution, often leading to poly-substitution (e.g., tribromoaniline with bromine water). To strictly obtain a mono-substituted para-derivative (like p-bromoaniline or p-nitroaniline), which sequence of reactions must be employed?

Prashant Kotian · Accepted Answer

Correct answer: C. The group is a powerful activator. To tame its reactivity, it is acetylated with acetic anhydride or acetyl chloride to form acetanilide. The group is still an ortho/para director but is only moderately activating because the nitrogen lone pair is cross-conjugated with the carbonyl group. This prevents poly-substitution and oxidation, allowing for clean mono-substitution (predominantly para due to sterics), after which the acetyl group is removed via hydrolysis.

💡 Solution & Explanation

Practice 22,000+ questions like this