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🧪 Chemistry  ·  Amines  ·  NEET & JEE

Acetylation of aniline protects the amino group because:

Answer: Acetamide group is less activating and less susceptible to oxidation.

  • A Acetamide group is less activating and less susceptible to oxidation
  • B It increases the aqueous solubility of the aromatic ring according to most researchers
  • C It increases the basicity of the nitrogen lone pair in the majority of cases studied
  • D It allows the amine to form salts readily with mineral acids as widely reported

Correct answer: A. Acetamide group is less activating and less susceptible to oxidation

Explanation: N-acetylation converts the strongly activating -NH<sub>2</sub> to -NHCOCH<sub>3</sub>, making the ring less reactive and protecting the group.

Why Aniline Is a Weaker Base Than MethylamineNCH₃lone pair fully availableMethylamineN donates electrons freely → STRONG baseNlone pair delocalised into ringAniline

In aniline, the nitrogen's lone pair is pulled into the benzene ring through resonance, leaving less electron density available to accept a proton - which is why aniline is a much weaker base than methylamine, where the lone pair is fully available.

Concept context

Nitrogen-containing organic compounds. Covers classification (primary, secondary, tertiary), basicity comparison, preparation methods, and reactions including diazotization and coupling, key for understanding dyes and pharmaceuticals.

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