CHAPTER 20: AMINE

19.1: Introduction of amine

1. Amine is organic derivatives of ammonia where one or more ………………………………………atom in

ammonia molecule is replaced by alkyl or aryl group.
2. Amine has rotten fish smell. General formula of aliphatic amine: ………………………………………………
3. Nomenclature:
 Parent is longest carbon chain that contain -NH 2 group.
 Replace the -e in alkane with -amine.
Eg:
………………………………………………………… ………………………………………………………

…………………………………………………………… ………………………………………………………

4. There four class of amine

a) Primary amine: R group replace …………………H atom in ammonia : ……………………………….

b) Secondary amine: R group replace …………………H atom in ammonia : ……………………………

c) Tertiary amine: R group replace …………………H atom in ammonia : ……………………………….

d) quatenary amine: Ammonium salt : ……………………………….

20.2: Physical properties of amine

1. Boiling point
 Boiling point of amine are higher than corresponding alkanes but lower than
alcohol because oxygen is more electronegative thus alcohol has stronger
……………………………………………
 Primary amine has higher boiling point than secondary and tertiary amine because
its can from more ………………………………………………
 Tertiary amine has lower boiling point than expected because its cannot form
………………………………………………….. with its molecule.

2. Solubility
 Amine with low molecular mass is soluble in water because its can form
…………………………..............................with water. The solubility in water decrease
when the hydrophobic group increase.

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  Primary amine is more soluble than secondary amine because its can form more
……………………………………………….with water.

20.3: preparation of amine

1. Reduction of nitriles (………………..) to produce primary amine.

Reagent:………………………………………. Condition: …………………………

………………………………………………………………………………………………………………….

2. Reduction of amines
Reducing agent:………………………………………………………………………………………………………………………
……………………………………………………………………………………………………………………..

3. Alkylation of ammonia/ amines

………………………………………………………………………………………………………
………………………………………………………………………………………………………
……………………………………………………………………………………………………..

4. Reduction of nitro compound (Preparation of aniline)

…………………………………………………………………………………………………….

20.4: Reaction of amine

1. Reaction undergo by amines
a) Reaction with mineral acid
b) Reaction with nirous acid
c) Reaction with acyl chloride
d) Reaction of aromatic amines with halogens

2. Reaction of amine with dilute mineral acid will form ionic salts which can crystalline out as
colourless crystal.

…………………………………………………………………………………………………………………….
3. Reaction of amine with nitrous acid required the preparation of nitrous acid in lab

……………………………………………………………………………………………………………………………………..

Nitrous acid formed can react with different class of amine to give different product.
a) Primary amines

………………………………………………………………………………………………………………..

…………………………………………………………………………………………………………………….

Observation: …………………………………………………………………….
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 …………………………………………………………………………………………………………………….

Observation: …………………………………………………………………………………………………………………
………………………………………………………………………………………………………………..

b) Secondary amines

…………………………………………………………………………………………………………………

Observation: …………………………………………………………………………….

c) Tertiary amines

………………………………………………………………………………………………………

Observation: ………………………………………………………

4. Reaction of amine with acyl chloride

………………………………………………………………………………………………………………………..

5. Reaction of aromatic amines with halogens

…………………………………………………………………………………………………………………….
Observation: ……………………………………….of bromine water decolurised and white ppt formed
6. Coupling reaction: two benzene ring from ………………………………………………………….. and
phenol/aromatic amines combine together by azo group ………………………….. to form azo dye.

…………………………………………………………………………………………………………………….

…………………………………………………………………………………………………………………….

Observation: …………………………………………………………………………………………………………

20.5: Amino acid

1. Amino acid is organic compound that having both the amino group, …………………………..and
carboxyl group,……………………………..in their structure.
2. Amino acids are basic building block of protein and occur naturally in protein as α-amino acid
which amino and carboxyl group attached to the same carbon.

……………………………………………………………………………………………….
3. Nomenclature:
 Amino acid is naming as amino derivatives of carboxylic acid

……………………………………………………………………………………………………………..
 Common name of amino acid is also used and its ends with -ine, it devotes by three
letter abbreviation.
 Glycine or Gly

………………………………………………………………………………………………….
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  Alanine or Ala

 ………………………………………………………………………………………………….

 Serine or Ser

 ………………………………………………………………………………………………….

4. Physical properties:
 Amino acid are all crystalline solids at room temperature. Its has higher
melting point than amine and carboxylic acid of similar Mr because of
strong ……………………………………… hold the zwitterion together.
 All amino acids are soluble in water because its can form
……………………………………… bond with water, but insoluble in organic
solvent.

20.6: Acid base property of amino acid

1. Amino acids contain the basic group…………………and acidic group …………………..together.The

two group undergo intramolecular acid base reaction
2. The proton,……………from ………………………group is transfer to the nitrogen atom of
……………………group to form dipolar ion known as ………………………………………..

3. With the presence of both amino and carboxyl group, amino acid have both acidic and basic
character to act as buffer. Amino acids can act as base in the presence of acid and act as acid
in the presence of base to form salt. Thus its has amphoteric properties.

………………………………………………………………………………………………………………………………..

………………………………………………………………………………………………………………………………..

4. Amino acid can exist in three form depending on of the pH of the solution

20.7: Reaction of amino acid

1. Reaction involving carboxyl group

a) Reaction with base, metal and carbonates to form salt.

…………………………………………………………………………………………………………………………………
…………………………………………………………………………………………………………………………………
…………………………………………………………………………………………………………………………………

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 b) Esterification
…………………………………………………………………………………………………………………………………

2. Reaction involving the amino group.

a) Reaction with acid to form salt and water
…………………………………………………………………………………………………………………………………

b) Reaction with acyl chloride

…………………………………………………………………………………………………………………………………

c) Reaction with nitrous acid

…………………………………………………………………………………………………………………………………

20.8: polypeptides

1. Two amino acid can react/combine together by elimination of water. This is called
condensation or dehydration reaction. An acid, ……………………… group from one amino acid
react with amino, ……………………..group and form dipeptide through peptide bond.

2. Combination of three amino acid will form large molecule called tripeptide while a further
combination of amino acid will resulting in a long chain polymer that that called
polypeptides.
Eg: Given:
Alanine (Ala): Glycerine (Gly):

a) Gly-Ala

b) Ala-Gly

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20.9: Proteins

1. Proteins is natural biopolymer which are formed from α-amino acid with general formula:

2. In protein the amino acid molecules are bonded by peptide linkage. The Mr of protein from
6000 to a few million.
3. Protein have four level of structure: Primary, secondary, tertiary and quatenary
a) Primary structure refer to polypeptide chain that have an amino terminal and carboxyl
terminal

b) Secondary structure formed when primary structure fold due to intermolecular

hydrogen bond between the -CO and -NH group in chain

4. Mixture of amino acid are form when protein is hydrolysis through heating with dilute acid
or base and catalyst by enzyme.
 During the hydrolysis the C-N bond in peptide linkage is broken down by a reaction
of water.

 In complete hydrolysis of protein, mixture of amino acid formed separately and

identify by electrophoresis or chromatography.
 In electrophoresis, the amino acid separate base on movement of ions with different
pH in electric field.
 In chromatography, amino acid moves at different rate under influence of mobile
phase. The chromatography then spray with ninhydrin for identification.
5. Proteins are form abundance in human body: hormones, haemoglobin, enzyme, muscles,
skin hair and antibody. From 20 amino acids 12 of them are non essential amino acid which
can synthesis by human body while 8 are essential amino acid that must supplied through
diet.
6. There are two classes of proteins
a) Fibrous protein – Elongated and insoluble in water which exist as structural component
in tissues. Eg: skin, muscles, hair
b) Globular protein: spherical and soluble in water and required to regulate and maintain
the physiological processes. Eg: Enzyme, antibodies and haemoglobin.