Organic Chemistry III

Professor Carl C. Wamser

Amines

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)

Applications - Level 3

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

Analytical Skills - Level 4

write reaction mechanisms for amine reactions

Synthesis Skills - Level 5

design a synthetic sequence for a given target compound