Amines are organic compounds derived from ammonia that contain an amino group. They can be classified as primary, secondary, or tertiary based on how many carbon groups are bonded to the nitrogen. Amines have unpleasant odors, are polar, and act as weak bases. They undergo reactions like nitration, halogenation, and coupling with diazonium salts to form azo dyes. Amines are used to synthesize nylons through condensation polymerization and are also found in dyes, drugs, and other products.

1. Amine
s

2. Introduction:
Amines:
• Are derivatives of ammonia NH3.
• Contain N attached to one or more alkyl (Aliphatic amine) or
aromatic groups (Aromatic amine).
CH -NH CH -NH-CH
-NH2 amino group
CH2CH3
Ethylbenzene
NH2

3. Amines are classified into three groups:
depending on the number of carbon groups bonded to nitrogen.
CH3 CH3
 
CH3—NH2 CH3—NH CH3—N—CH3
Primary 1° Secondary 2° Tertiary 3°

4. Naming Amines
- Drop the final “-e” of the parent alkane and replace it by “-amine”.
- Use a number to locate the amino group (-NH2) on the parent chain.
IUPAC name – 1° amines
CH3 CHCH3
NH2
NH2
H2 N
NH2
1,6-HexanediamineCyclohexanamine2-Propanamine
CH3-CH-CH3
NH2
2-propanamine
CH3-CH-CH-CH3
NH2
Cl
3-chloro-2-butanamine 1,6-hexanediamine
123 1 2
3
4
1
23
4
5
6

5. Common name
Names of alkyl groups (In alphabetical order) + “amine”
CH3—CH2—NH2 ethylamine
CH3—NH —CH3 dimethylamine
CH3
|
CH3—N—CH2—CH3 ethyldimethylamine
Naming Amines

6. CH2 CH3
Ethylbenzene
CH2CH3 CH3 CH=CH
TolueneEthylbenzene Styren
CH2CH3 CH3 CH=CH2
TolueneEthylbenzene Styrene
Aniline (common name)
NO2
CH3
CH3
Aniline
4-Nitroaniline 3-Methylaniline 4-Chloro-3-methylaniline
NH2
NH2
NH2 NH2
Cl
1 2
3
4
1 2
3
1 2
3
4
CH2CH3 CH3 CH=CH
TolueneEthylbenzene Styrene

7. Naming Amines
– Take the largest group bonded to nitrogen as the parent amine.
– Name the smaller group(s) bonded to nitrogen, and show their
locations on nitrogen by using the prefix “N”.
IUPAC name – 2° and 3° amines
N
CH3
CH3
NHCH3
N,N-Dimethyl-
cyclopentanamine
N-Methylaniline
N
CH
C
NHCH3
N,N-Dimeth
cyclopentana
N-Methylanilineaniline
CH3-N-CH2-CH3
CH3
N,N-Dimethylethanamine

8. Heterocyclic amines
When N is one of the atoms of a ring.
N
HH
CH3
Pyrrolidine Pyridine Nicotine

9. Physical properties of Amines
1. They have unpleasant odors (rotting fish like ammonia).
2. They are polar compounds.
Difference in electronegativity between N - H (3.0 – 2.1 = 0.9)
3. 1° and 2° amines have hydrogen bonds (N-H).
Weaker than alcohols (O-H).
3° amines do not form hydrogen bonds (no H atom).
4. Boiling points: Hydrocarbons< Amines < Alcohols
5. Almost soluble in water (hydrogen bonding).

10. Chemical properties of Amines
They are weak bases (like ammonia): react with acids.
N
H
H
CH3 .. + H – O – H
..
..N
H
H
CH3 H
+
O – H....
..
-
Some amines present in our blood and make it approximately basic (pH = 7.4).
(to form water-soluble salts)

11. Chemical properties of Amines
C6 H5 NH2
CH3 CH2 NH2Aliphatic
Ammonia
Aromatic
3.0 - 4.0
4.74
8.5 - 9.5
Class pKb Example Name
Ethanamine
Aniline
Stronger base
Weaker base
Aliphatic amines are weak bases by comparison with inorganic bases
such as NaOH, they are strong bases among organic compounds.
Aliphatic amines are stronger bases than aromatic amines.
(slightly stronger than NH3)

12. Examples
(CH3 CH2 ) 2 NH HCl
N
CH3 COOH
N
H
(CH3 CH2 ) 2 NH2
+
Cl-
CH3 COO-
Diethylammonium
chloride
+
Pyridinium acetate
+(a)
(b) +

13. Reactions:
1- Acids.
NH2 + HCl NH3
+Cl-
(CH3CH2)2NH + CH3COOH (CH3CH2)2NH2
+
, -
OOCCH3
anilinium chloride
diethylammonium acetate

14. 2- Nitration.
NH2
HNO3
H2SO4
TAR!
(CH3CO)2O
NHCOCH3
HNO3
H2SO4
NHCOCH3
NO2
+ ortho-
H2O,OH-
∆
NH2
NO2

15. 3- Sulphonation.
NH2
+ H2SO4
NH3
SO3
cold H2SO4
NH3 HSO4

16. 4- Halogenation.
NH2
+ Br2, aq.
NH2
Br Br
Br
no catalyst needed
use polar solvent
Br2,Fe
Br
HNO3
H2SO4
Br
NO2
+ ortho-
H2/Ni
Br
NH2
polyhalogenation!

17. 5- Nitrosation.
N
H3C CH3
NaNO2, HCl
N
H3C CH3
N
O
The ring is sufficiently activated towards EAS to react
with the weak electrophile NO+

18. 6- Azo dyes. (coupling with diazonium salts)
NH2
CH3
+
N2 Cl
benzenediazonium
chloride
CH3
NH2
N
N
an azo dye

19. 7. Reactions with nitrous acid.
NH2 + HONO N N diazonium salt
R-NH2 + HONO N2 + mixture of alchols & alkenes
primary amines
secondary amines
H
N R + HONO N R
N
O
N-nitrosamine
tertiary amines
N R
R
+ HONO N R
R
N
O
p-nitrosocompound

20. USES OF AMINES
1- SYNTHESIS OF NYLON:
Nylons are condensation copolymers formed by reacting
equal parts of a diamine and a dicarboxylic acids, so that
peptide bonds form at both ends of each monomer in a
process analogous to polypeptides biopolymers.
2- Dyes:
Few are as follow.
 Methyl Orange.
 Direct Brown 138.
 Sunset Yellow FCF.
 Azo- dyes.

21. 3- Drugs:
Few are as follow.
• Chlorpromazine.
• Chlorpheniramine.
• Ephedrine.

22. The
end