Amines Summary

1. Neutral amines have 3 covalent bonds and a lone pair arranged tetrahedrally around a nitrogen atom.
2. Amines undergo pyramidal inversion, this process is rapid at room temperature.
3. Amines are polar compounds which can hydrogen bond. Only 1oand 2oamines can act as
hydrogen bond donors andacceptors.

Synthesis

1oAmines

R

CH
2

NH
2

R

X

C

N

R

CN

R

X

N-K+

O

O

NR

O

O

R

NH
2

Amine

hydrolysis
Alkyl
Phthalimideor NH
2NH
2

Potassium
Phthalimide

Alkyl Halide

+

-

Amine

reduce

Nitrile

Alkyl Halide

+

cynanide

R

X

Alkyl Halide

+Azide ion

N

N

N

Alkyl Azide

R

NH
2

Amine

reduce

R

N3

Aromatic Nitro

NO2

Amine

reduce

NH2

R

O

R

NH
3

NH
2OH

NH
3

R

N

R

H

NaBH
3CN

R

N

R

H

H

1oAmine

reduce

Imine
or
Oxime

Ketone or
Aldehyde

2oAmines

R

O

R

R

N

R

R'

R'

NH2

R

N

R

R'

H

1oAmine

2oAmine

reduce

Imine

Ketone or
Aldehyde

3oAmines

R

O

R

R

N

R

R'

(R')2

NH

R

N

R

R'

R'

2oAmine

3o Amine

reduce

Iminium salt

Ketone or
Aldehyde

R'

1o, 2o, 3o

Amines

R

COOH

R

COCl

R'

NH2
R

CONHR'

R

CH
2NHR'

Amine

reduce

Amide

Amine

Acid Chlorides

Carboxylic Acids