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Amines — Class 12 CBSE Chemistry revision notes

A 3-page visual revision sheet for Amines, written for Class 12 CBSE Chemistry. Formulas, diagrams and the traps that cost marks, laid out to be read the night before rather than the term before. Free, and it opens inside CapCompass.

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Amines in one look

nitrogen's lone pair makes every amine a base and a nucleophile, but steric bulk and solvation decide how strong

Classification of amines

Aliphatic amine
  • N attached to sp^3 alkyl carbon(s)
  • 1° R-NH_2, 2° R_2NH, 3° R_3N, classified by carbons ON nitrogen, not the carbon skeleton
  • N lone pair sits free, not conjugated anywhere
Aromatic amine
  • N attached directly to the aromatic ring, e.g. aniline
  • same 1°/2°/3° naming, but the N lone pair conjugates into the ring
  • delocalisation makes this lone pair less available, so the ring-attached N is a weaker base

Structure of the amine nitrogen

  • nitrogen is sp^3 hybridised with a pyramidal shape, the lone pair occupying the fourth position
  • aromatic amine's N flattens toward sp^2 so its lone pair aligns with the ring's pi system
  • this lone pair makes every amine both a Lewis base (donates it) and a nucleophile

Preparation of amines

  • Gabriel phthalimide synthesis: gives a pure 1° amine only phthalimide+R-Xto N-alkylphthalimideto R-NH_2
  • reduction of a nitrile R-CN+H_2to R-CH_2NH_2
  • Hofmann bromamide degradation: one carbon shorter R-CONH_2+Br_2+NaOHto R-NH_2

Basicity of amines: the counterintuitive order

  • in the gas phase, basicity is 3°>2°>1°>NH_3: alkyl groups donate, freeing the lone pair
  • in water (the order actually tested), sterics and solvation flip this: simple alkyl amines run 2°>1°>3°>NH_3
  • reason: 3°'s cation solvates worst (fewest N-H bonds for water), so LESS stable despite most donation
  • aniline's basicity is far lower than ammonia or any aliphatic amine: lone pair tied in ring conjugation

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