Unit 23: Amines

Amines unify acid-base chemistry, synthesis, biomolecular relevance, and aromatic substitution patterns, making them central to both pharmaceutical chemistry and core mechanisms.

  • Classify amines and compare their basicity in aliphatic, aromatic, and heteroatom-rich environments.
  • Predict products of reductive amination, nitro reduction, Gabriel synthesis, and common amine functional-group interconversions.
  • Understand acylation, alkylation, diazonium formation, and Hofmann elimination at a conceptual level.
  • Explain why aniline is less basic than a typical alkyl amine.

Checkpoint Questions

Q: Why is reductive amination so useful?
A: It converts a carbonyl compound into an amine while forming a new C–N bond in a controlled, chemoselective way.
Q: Why is aniline less basic than methylamine?
A: The lone pair on aniline is partially delocalized into the benzene ring, so it is less available to accept a proton.

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