SUBTOPIC: AMINES

Functional group

R-NH2

1) Name of Functional group: Amino

2) Name of family: Amine

Uses
1) Morphin

2) Diazepam/Valium

3) Procaine

1
4) Lidocaine

2
Nomenclature:
1) Locate parent chain containing amino fg
2) Give amino the lowest no

Eg:

Diamines

3
Classification of amines
Primary

Secondary

Tertiary

4
Physical properties

a. Physical state and melting/boiling points

i. Very volatile liquids
ii. Has very polar amino group
iii. Primary amines and secondary amines can form hydrogen bonds
with one another.
Diagram:

iv. Tertiary amines are more volatile because they can only form
DDI among themselves. Hydrogen bonding is not possible
between tertiary amines.

Diagram:

5
 b. Solubility in water
i. Lower amines- Very soluble in water
1) Amine has very polar amino group
2) can form strong hydrogen bonds with very polar water
molecules.

Diagram:

ii. Higher amines- Less soluble

1. Amine has polar amino group

2. However, non-polar hydrocarbon chain outweighs the polarity of
amino group causing the molecule to be less polar
3. Difficult to form strong hydrogen bonds with very polar water
molecules
4. Hence, less soluble in water

c. Solubility in non polar organic solvents

i. the larger the molecule the more soluble it will be due to extensive/many
DF between amine molecules and non-polar organic solvent molecules.

6
Chemical properties
1) Weak base

b. Amines are organic bases.

i. Proton acceptors
ii. Lone pair of electrons on nitrogen atom accept proton (hydrogen
ion) from an acid to form alkylammonium ion.
iii. The process is known as protonation

Eg: R-NH2 + H+  R-NH3+

CH3NH2 + H+  CH3NH3+

c. Neutralisation reactions

i. CH3COOH + NH2CH3  CH3COONH3CH3

ii. HCl + CH3CH2NH2  CH3CH2NH3Cl

iii. HNO3 + CH3NH2  CH3NH3NO3

7
 Application in drugs
1) Procaine and Lidocaine are anaesthetics

2) They are insoluble in water due to large molar mass

3) They need to be injected into blood stream and blood is an aqueous environment
4) Administered into blood as amine salts
5) In the form of ionic compound, it can dissolve in water due to the formation of
ion-dipole interactions with very polar water molecules.

8
SUBTOPIC: AMIDES

Uses:
1) Caffeine

2) Urea

9
3) Paracetamol

Chemical properties
1) Formation of amide
a. Involves 2 stages
i. Acid-base reaction

ii. Condensation reaction

10
2) Hydrolysis
a. Acidic hydrolysis

b. Alkaline hydrolysis

11