A MINES

GONZALES, LUZVIMINDA
L.
 Types of Amines
• Alkyl Amines
CH3—NH2, CH3CH2—NH2,
• Aryl Amines

• Heterocyclic Amines
 HETEROCYCLIC AMINES

Pyrole Guanine
Pyridine

cytosine thymine uracil adenine

 Classification of Amines
• Primary Amines
R-NH2 ex. CH3—NH2
• Secondary Amines
R-NH-R’ ex. CH3
│
CH3—NH
• Tertiary Amines
R-NR”-R’ ex. CH3
│
CH3—N — CH3
• Ammonium Salts
R-NH-R’+
Nomenclature
of Amines

6
• To name an amine, the suffix –amine is added to the
alkyl root name of the parent chain.
example: CH3—NH2 Methanamine
CH3CH2—NH2 Ethanamine
• The location of the amino group on the parent chain is
indicated by a number
example: NH2
│
CH3—CH2 — CH3 2-Propanamine
• Secondary and Tertiary Amines are commonly named as
N-substituted primary amines. The largest group
bonded to nitrogen is the parent chain.
example: CH3
│
CH3—NH N-methylmethanamine
EXERCISES:
PHYSICAL
PROPERTIES
A. Polarity
- amines are polar because of N
- able to form H-bond but less than alcohols
- able to form H-bond to themselves
- tertiary amines are not able to form H-bond
B. Boiling point
- have higher BP than comparable alkanes but
lower than alcohols

FAMILY BP RANK COMPOUND

Alcohol 117o  3  propanol
Ketone 56o  4, 5 propanone/acetone
Aldehyde 49o  4, 5  propanal
Amine 49o  6 propylamine
Ether 11o  8  methyl ethyl ether
Alkane -42o  9  propane
-in comparison to the same group:
-as the number of carbon increases, BP
increases
-as the number of branching increases, BP
decreases
Type Formula Boiling point (°C)
primary CH3NH2 -6.3
primary CH3CH2NH2 16.6
primary CH3CH2CH2NH2 48.6
secondary (CH3)2NH 7.4
tertiary (CH3)3N 3.5
C. Solubility
C1-C6 are soluble in water
C6 above are slightly soluble to insoluble

D. Other physical properties

- have pungent odor

Trimethylamine – rotting fish

1,4-butanediamine – putrescine
1,5-pentanediamine – cadaverine
- Like ammonia, amines are weak bases
and is slightly more basic.
- Aromatic amines are less basic
-They are stronger bases and nucleophiles
than water

NH3 + H2O → NH4+ + OH-

RNH2 + H2O → RNH3+ + OH-
CHEMICAL
REACTIONS
Reactions with Acids
- whether soluble or insoluble in water,
amines react with strong acids to form
water-soluble salts.

3 +Cl-

+ HCl

Norepinephrine Norepinephrine
chloride
EXERCISES:

1.CH3CH2NH2 + HCl
2.(CH3)2NH + HCl
3.(CH3)3N + HCl
4. + HCl

5. + HCl
APPLICATIONS
 USES – MEDICINAL - ALKALOIDS
H

N
CH3
N
N
N
nicotine H H H

Yohimbine
H

CH3O

O OH

from Datura roots -

vasodilator & supposed
aphrodisiac
 CH3 Hallucinogen from toadstools.
CH2CH2N Combined with bufotoxin(steroid
HO CH3
with long chain amide) from hide
on toads - produces ZOMBIES.
N
H
bufotenine

CH3O
CH2CH2NH C CH3
Hormone produced in the pineal
gland (center of the brain) -
N
An increase signals sleepiness
H for humans, large increase during
melatonin
schizophrenic episode, etc.