Chemistry 20

Chapter 8

Amines
 Amines

Amines:

• Are derivatives of ammonia NH3.

• Contain N attached to one or more alkyl (Aliphatic amine) or

aromatic groups (Aromatic amine).

-NH2 amino group

NH
CH22 CH3

CH3-NH2 CH3-NH-CH3

Eth ylb enzene

 Amines

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°

 Naming Amines
IUPAC name – 1° amines

The same method as we did for alcohols.

- 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.

NH2 NH2
NH2 3 5 1
CH3-CH-CH3 NH2 CH3-CH-CH-CH3
3 2
4
H2 N 6
NH2
3 2 1 CH3 CHCH31 2 4
Cl
2-Propanamine
2-propanamine Cyclohexanamine
3-chloro-2-butanamine 1,6-Hexan ediamine
1,6-hexanediamine
 Naming 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
 Aniline (common name)

NH
CH22 CH3 CH3 CH=CH

Aniline

Eth ylb enzene Toluen e Styrene

NH
CH22 CH3 CH3 NH
CH22 CH3 CH=CH
NH
CH22 CH3 CH3 CH=CH2
2 1 2
1
1 2

3 3CH3 3
4
4 CH3
Eth ylb enzene Etheylb
Toluen Cl enzene
Styren
Eth ylb
NOenzene Toluen e Styrene
2

4-Nitroaniline 3-Methylaniline 4-Chloro-3-methylaniline

 Naming Amines
IUPAC name – 2° and 3° 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”.

CH3 CH
NHCH3 NHCH
N 3 N
CH3 C
N-Meth ylan iline N,N-Dimethyl-
N-Meth ylan ilineaniline N,N-Dimeth
cyclopentan amine cyclopentan a
CH3
CH3-N-CH2-CH3 N,N-Dimethylethanamine
 Heterocyclic amines

When N is one of the atoms of a ring.

N CH3
H H

Pyrrolidine Pyridine Nicotine

 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).

 Chemical properties of Amines

They are weak bases (like ammonia): react with acids.

(to form water-soluble salts)

H H
.. -...
N.. . ..O – H
+
CH3 + H – ..
O–H CH3 N H

H H

Some amines present in our blood and make it approximately basic (pH = 7.4).
 Chemical properties of Amines

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)

Clas s pKb Example N ame

Aliph atic 3.0 - 4.0 CH3 CH2 NH2 Ethan amin e Stron ger bas e
Ammonia 4.74
Aromatic 8.5 - 9.5 C6 H5 NH2 Anilin e Weaker base
 Examples

Complete each acid-base reaction and name the salt formed.

(a) ( CH3 CH2 ) 2 NH + HCl

(b ) + CH3 COOH
N
 Examples

Complete each acid-base reaction and name the salt formed.

Solutions:

(a) (CH3 CH2 ) 2 NH + HCl (CH3 CH2 ) 2 NH2 + Cl-

D ieth ylammoniu m
chloride

(b) + CH3 COOH CH3 COO-

N N+
H Pyridinium acetate