Chem 336 - Spring 1999 - Organic Chemistry III
Portland State University - Dr. Carl C. Wamser
Chapter 21 Skills
know the nitrogen functional groups:
amine, amide, nitro, azide, diazonium ion, N-nitrosoamine
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
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
write reaction mechanisms for amine reactions
design a synthetic sequence for a given target compound