• Amines are organic derivatives of ammonia, NH3, with one

or more alkyl groups bonded to the nitrogen atom.

••
N
R H
H
• General formula: R-NH2 (R= alkyl or aryl)

• Functional group: NH2 (amino group)

 CLASSIFICATION OF AMINES
• Amines are classified as primary (1o), secondary (2o), or
tertiary (3o) , corresponding to the number of alkyl or aryl
groups attached to N.

●● ●●
●●
R—N—H R—N—H R—N—R
H R R
1o
2o 3o
amine
amine amine
 1o ALIPHATIC AMINE

WADE:CH3
4 ed.,NH
p.848*
SOL: 8 ed., p.942*
2
CH3CHCHCH
CAREY: 5 ed., p.913
2 6 ed., p.893*
MUR:
3–methyl–1–butanamine
NOR: p.239
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2-phenyl-1-propanamine

OH
CH3 NH2

CH3CHCHCHCH3
NH
CH3 2
3–aminocyclohexanol
2,3–dimethyl–2–pentanamine
 1o AROMATIC AMINE
NH2
NH2

CH3
aniline
4–
methylaniline

3-aminobenzoic acid
 "N
- 2o ALIPHATIC AMINE
* start ado

↑
HCH ,

CHzCH2 C
HCHz

N–methyl–2–butanamine
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N–isopropyl–2–propamine
 2o AROMATIC AMINE

NHCH2CH3

CH3
N-methylaniline
N-ethyl-4-methylaniline
 3o ALIPHATIC AMINE

H3 CH2CH
C N 3

N,N–dimethyl–1–
propanamine N–ethyl–N–
methylcyclohexanamine

CH3CH2 N CH2CH3

CH3CH2

triethylamin
4–bromo–N,N–dimethyl–2–
e
 3o AROMATIC AMINE
H3 CH
C N 3
H3 CH
C 3

N,N,2,6–
tetramethylaniline N-butyl-N-ethylaniline
 PHYSICAL PROPERTIES OF AMINES

BOILING POINT

• Both primary and secondary amines can form intermolecular

hydrogen bonds.

• Primary amines have two N-H bond, hydrogen bonding is more

significant in primary amine than in secondary amine.

• Tertiary amines cannot form hydrogen bonds to each other.

 EXAMPLE:

Relative
Boiling
Amines Class molecular
points/oC
mass
CH3CH2CH2NH2 1° 59 49
CH3CH2-NH-CH3 2° 59 37
CH3 Loading…
| 3° 59 4
CH3-N-CH3

Boiling Point : CH3CH2CH2NH2 > CH3CH2NHCH3 > (CH3)3N

Explanation: All the structures of amine have same molecular mass but the boiling
point are different due to the class of amine. 1° amine> 2° amine> 3° amine
 Boiling Point : carboxylic acid > alcohol > amine > haloalkane> alkane

EXAMPLE:

Ethanoic acid > 1-propanol > propylamine > chloroethane > butane

• Only ethanoic acid, 1-propanol and propylamine can form

hydrogen bond between molecules.

• Ethanoic acids have the highest boiling point because it forms

stable dimers through hydrogen bonds.
 The hydrogen bonds of propylamine formed between its
molecules are weaker than those between 1-propanol molecules
since nitrogen is less electronegative than oxygen.

• Chloroethane is polar molecules (van der Waals forces between

molecules), and hence do not form hydrogen bonds.

• Butane is non-polar molecules (weak van der Waals forces

between molecules), do not form hydrogen bonds.

• The hydrogen bonds are stronger than van der Waals forces
 Examples
The table below compares the boiling points of organic
compounds of comparable relative molecular mass.

Amines Type Relative Boiling

molecular points/oC
mass
CH3CH2CH2CH3 alkane 58 -0.05
butane

CH3CH2Cl haloalkane 64.5 12.5

chloroethane

CH3CH2CH2NH2 amine 59 48.6

1-propanamine

CH3CH2CHO aldehyde 58 48.8

Propanal

CH3CH2CH2OH alcohol 60 97.2

1-propanol

CH3COOH Carboxylic acid 60 118

Boiling Pointethanoic
: Carboxylic
acid acid > Alcohol > Carbonyl >Amine > Haloalkane > Alkane
 Solubility of 1°, 2°, 3° amines In Water

• All amines having ≤ 5C’s are water soluble because they can form hydrogen
bond with H2O molecules.

• Amines having > 5C are water insoluble because the alkyl portion (hydrophobic
area) is too large to dissolve in the polar H2O.

• Comparing amines with the same number of carbons, 1° amines are more
soluble than 2° amines because 1° amines have two hydrogen atom that can
form in hydrogen bonding.
Comparison the solubility between 1°,2° and 3°amine in water

The most hydrogen More hydrogen bonds The least hydrogen

bonds per 1° amine per 2° amine molecule bond per 3° amine
molecule molecule
3° < 2 ° < 1 ° amine
hydrogen bonds
Increasing solubility