Chem 336 - Spring 2002
Organic Chemistry III
Dr. Carl C. Wamser
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)
generate appropriate names for amines
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