This power point is about classification, nomenclature, reactions and uses of amines.

1. AMINES
Classification, Nomenclature,
Reactions and uses.

2. Introduction
Amines are organic compounds that are derived
by replacing one or more hydrogen atoms of
ammonia with hydrocarbon groups.
 Derivatives of Ammonia.
-NH2 amino group

3. AMINES CLASSIFICATION
Amines are classified as:
1°, 2°, or , 3° amines: Amines in which there are 1, 2, or 3
alkyl or aryl groups.
Methylamine
(a 1° amine)
Dimethylamine
(a 2° amine)
Trimethylamine
(a 3° amine)
CH3 - NH2 CH3 - NH CH3 - N
CH3 CH3
CH3
:
: :

4. AMINES CLASSIFICATION
Amines are further divided into aliphatic, aromatic, and
heterocyclic amines:
Aliphatic amine: An amine in which nitrogen is bonded
only to alkyl groups.
Aromatic amine: An amine in which nitrogen is bonded to
one or more aryl groups.
Heterocyclic amine: An amine in which nitrogen is one of
the atoms of a ring.
Aniline
(a 1° aromatic amine)
N-Methylaniline
(a 2° aromatic amine)
Benzyldimethylamine
(a 3° aliphatic amine)
NH2 N-H CH2 - N- CH3
CH3 CH3
:
:
:

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

6. Aniline (common name)
NH2CH2CH3 CH3 CH=CH2
TolueneEthylbenzene Styrene
CH2CH3
Ethylbenzene
CH2CH3 CH3 CH=CH
TolueneEthylbenzene Styren
CH2CH3 CH3 CH=CH2
TolueneEthylbenzene StyreneNO2
CH3
CH3
4-Nitroaniline 3-Methylaniline 4-Chloro-3-methylaniline
NH2
NH2 NH2
Cl
1 2
3
4
1 2
3
1 2
3
4

7. RULES OF NOMENCLATURE
 Name is based on longest carbon chain.
 e- of alkane is replaced with -amine.
 Substituents on nitrogen have N- prefix.
NH2CH2CH2CHCH2CH3
Br
3-bromo-1-pentanamine
CH3CH2CHCH2CH2CH3
N(CH3)2
N,N-dimethyl-3-hexanamine

8. Reactions of Amines
1. As Base.
2. Alkylation.
3. Reaction with Nitrous acid.
4. Conversion into amides.
5. Hofmann elimination from quaternary hydroxides.

9. 1. As Base
NH2 + HCl NH3
+
Cl-
(CH3CH2)2NH + CH3COOH (CH3CH2)2NH2
+
, -
OOCCH3
anilinium chloride
diethylammonium acetate

10. 2. Alkylation
RNH2
R-X
R2NH
R-X
R3N
R-X
R4N+X-
1o 2o 3o
4o salt
SN2: R-X must be 1o or CH3
CH3CH2CH2CH2Br
NH3
CH3CH2CH2CH2NH2
n-butylamine

11. 3. Reaction 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

12. 4. Conversion into Amides
R-NH2 + RCOCl  RCONHR + HCl
1o N-subst. amide
R2NH + RCOCl  RCONR2 + HCl
2o N,N-disubst. amide
R3N + RCOCl  no reaction
3o

13. 5. Hoffmann elimination
Step 1: exhaustive methylation  4o salt
Step 2: Reaction with Ag2O  4o hydroxide + AgX
Step3: heat to eliminate  alkene(s) + R3N
CH3CH2CH2CH2
(xs) CH3I
CH3CH2CH2CH2NH2 N
CH3
CH3
CH3 I-
CH3CH2CH2CH2 N
CH3
CH3
CH3 I-
Ag2O
CH3CH2CH2CH2 N
CH3
CH3
CH3 OH-
+ AgI
CH3CH2CH2CH2 N
CH3
CH3
CH3 OH
 CH3CH2CH=CH2 + (CH3)3N

14. USES OF AMINES
 Aromatic amines are mainly used as a starting material for
the production of azo dyes.
 Many drugs are designed to interfere with the action of
natural amines.
 Amines are used in making artificial fibers.
 Aromatic amines are used in detergent production

15. THANK YOU