Chem 336 - Spring 1999 - Organic Chemistry III
Portland State University - Dr. Carl C. Wamser


Chapter 21 Skills


Knowledge - Level 1

know the nitrogen functional groups:

amine, amide, nitro, azide, diazonium ion, N-nitrosoamine


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

write reaction mechanisms for amine reactions


Synthesis Skills - Level 5

design a synthetic sequence for a given target compound