Organic Chemistry for the 12th Class

By El Wathan
 Physical Chemical
properties properties

Identification Introduction
of amine of
class cycloamine
 Put in the right order these
compound bellow from higher to
lower boiling point!

1 a) CH3CH2OCH2CH3, (CH3CH2)2NH, and

CH3CH2CH2CH2OH
b) Methanamine, N-methylmethanamine,
N,N-dimethylmethanamine,
ethanamine, and aniline
This test is designed to
explore how far you know
Complete the reaction! about amine compound

2 a. CH3CH2NH2 + HCl 
b. CH3CH2NH2 + CH3Cl 
c. CH3NH2 + CH3COOH 

3 Draw at least 3 structures of

cycloamine that you know!
#boiling point #polar and non-polar #soluble in water
 The level of boiling point / melting point of an organic
compound is influenced by some factors, such as:

_> Number of the atoms

• CH3CH2NH2 (17oC) > CH3NH2 (-6.3oC)

_> Interaction between molecules

• CH3CH2NH2 (17oC) > (CH3)3N (3oC)

 The interactions between molecules in primary or
secondary amine is hydrogen bonding and van der walls in
tertiary amine.

Hydrogen Bonding > Van Der Walls

 hydrogen bonding
N
H
H H

N
H
H H
 Alcohol

Primary and
Secondary amine

Ether / Tertiary
amine
Hydrogen Bonding

HO------H >> HN------H

In alcohol In amine
 The level of polar effect in amine compound is influenced
by some factors, such as:

_> Interaction with water

• As more numbers of interaction in an amine
molecule with water molecule will give the
strong polar effect (soluble in water)
O
H
HO
HH

>>
N
C
H
3
H
HN
3 C
H
OH
CC
3 H
O
H
H
3
H
H
 The level of polar effect in amine compound is influenced
by some factors, such as:

_> the length of hydrocarbon chain

• As length of hydrocarbon chain in an amine
molecule will give the weak polar (non-polar)
effect (insoluble in water)
O
O
H H
H
H
Aniline
Methanamine
>>
N N
C
H
3
H
H H H
H O
O
O
H
H O H
H
H H H
#reaction #netralization #lone pair effect
 lone pair
Because of lone will give the
pair in nitrogen base character
atom in amine (Lewis base)
compound

So ... it can react with an acid compound

_> netralization reaction
• CH3CH2CH2NH2 + HCl  CH3CH2CH2NH3Cl

_> SN2 reaction (Substitution)

• because of the lone pair in nitrogen atom,
will make the amine compound can act as
nucleufil which is able to attack  carbon in
alkyl halide that has positive partial
 carbon

CH3CH2CH2Cl
_> SN2 reaction

+ -

Nu: + CH3CH2CH2-Cl
 carbon

 CH3CH2CH2Nu + Cl-
_> SN2 reaction in base solution

CH3CH2CH2NH2 + CH3Cl + NaOH

 CH3CH2CH2NHCH3 + H2O + NaCl

#Hinsberg reaction #primary #secondary #tertiary
 _> Hinsberg reaction

O O
H

_> C H 3-N H 2 + S Cl
N aO H
-N a C l
S N

-H 2 O
O O CH3

A c id H y d ro g e n

O O O
H H

_> S N
NaO H
-H 2O
S N Na
HCl
-N a C l
S N

O CH 3 CH CH
O 3 O 3

Soluble in Insoluble when

base solution adding acid
 _> Hinsberg reaction

O O
C
H3

N
aOH
_> (C
H3)2
-NH+ SC
l
-N
aCl
SN

-H
2O
O O C
H3

N
oA
ci
d H
y
dr
oge
n
O O O
C
H3 C
H3 C
H3

_> SN
N
a
OH
SN
H
Cl
SN

OC
H3 OC
H3 OC
H3

Insoluble in No change /
base solution Insoluble when
adding acid
 _> Hinsberg reaction
O O
C
H3

_> (
CH)
3
3-
N+ S
Cl
N
a
-
N
O
a
C
H
l
SNC
H
3O
H

O OC
H
3

O O
C
H
3

_> N
aO
H N
SN
CO
H
3H S
ON
a+
-
H
2O H
C C
3 H
3
C
H
3
C
OH
3 O
No change in
H base solution
N N
_>
H
C
l Cl
H
C
3 C
H
3 H
C
3 C
H
3
C
H
3 C
H
3
Soluble when
adding base
#aromatic and non-aromatic #homocyclic and heterocyclic
_> aromatic homocyclic
N
H
2
N
H
2

Aniline Benzilamine

_> non-aromatic homocyclic

N
H
2

N
H
cyclopentanamine
2
cyclohexanamine
_> aromatic heterocyclic
H
N
N
pyroline pyridine

_> non-aromatic heterocyclic

N
H
N
H pyrolidine pyperidine
Try to make conclution from this leraning of amine