Chemistry 332 - Winter 1997

Chapter 12 - Amines

New Skills

Knowledge - Level 1

the nitrogen functional groups:

amine, amide, heterocycle, nitro, azo, azide, diazonium ion

names for the common heterocyclic amines:

pyridine, pyrrole, imidazole

Concepts - Level 2

basicity of nitrogen compounds depends on the lone pair availability

interrelationship between pKb and pKa values ( pKa + pKb = 14 )

relative basicity (pKa of the conjugate acids):

alkyl amines (10) > imidazole (7) > aryl amines ~ pyridine (5)
pyrrole and amides are not basic (delocalization of the lone pair)

solubility effects / acid-base separations and extractions

(ionized forms are water-soluble, neutral forms often are not)

optical resolution via diastereomeric salts

Applications - Level 3

generate names for amines by IUPAC or common or Chem Abstracts methods

classify amines as 1° , 2°, or 3° (or 4° ammonium ions)

use substitution or reduction reactions to prepare amines

use diazonium ion substitution reactions to prepare substituted benzenes

use amines as nucleophiles in substitution reactions

Analytical Skills - Level 4 & higher

use the reactions of this and previous chapters to synthesize a target compound