REACTIONS OF ALCOHOLS
1.
Combustion (Extreme Oxidation)
a
l
c
o
h
o
l+
o
x
y
g
e
n c
a
r
b
o
n
d
i
o
x
i
d
e
+
w
a
t
e
r
2
C
H
C
H
O
H
+
6
O
4
C
O
+
6
H
O
3
2
2
2
2
2.
Elimination (Dehydration)
°
H
S
O
/
1
0
0
C
2
4
a
l
c
o
h
o
l
a
l
k
e
n
e
+
w
a
t
e
r
°
H
S
O
/
1
0
0
C
C
H
C
H
C
H
O
H
C
H
C
H
=
C
H
+
H
O
3 2 2
3
2
2
2 4
3.
Condensation
°
H
S
O
/
1
4
0
C
2
4
e
x
c
e
s
s
a
l
c
o
h
o
l
°
e
t
h
e
r+
w
a
t
e
r
H
S
O
/
1
4
0
C
2
C
H
C
H
O
H
C
H
C
H
O
C
H
C
H
+
H
O
3 2
3
2
2
3
2
2 4
4.
Substitution
L
u
c
a
s
R
e
a
g
e
n
t
Z
n
C
l
2
a
l
c
o
h
o
l+
h
y
d
r
o
g
e
n
h
a
l
i
d
e
a
l
k
y
lh
a
l
i
d
e
+
w
a
t
e
r
Z
n
C
l
C
H
C
H
O
H
+
H
C
l
C
H
C
H
C
l+
H
O
3 2
3
2
2
2
• This reaction with the Lucas Reagent (ZnCl2) is a
qualitative test for the different types of alcohols because
the rate of the reaction differs greatly for a primary,
secondary and tertiary alcohol.
• The difference in rates is due to the solubility of the
resulting alkyl halides
• Tertiary Alcohol turns cloudy immediately (the alkyl
halide is not soluble in water and precipitates out)
• Secondary Alcohol  turns cloudy after 5 minutes
• Primary Alcohol  takes much longer than 5 minutes to
turn cloudy
5.
Oxidation
• Uses an oxidizing agent such as potassium
permanganate (KMnO4) or potassium dichromate
(K2Cr2O7).
• This reaction can also be used as a qualitative test
for the different types of alcohols because there is
a distinct colour change.
dichromate  chromium 3+
(orange)  (green)
permanganate  manganese (IV) oxide
(purple)  (brown)
T
e
r
t
i
a
r
y
A
l
c
o
h
o
l
n
o
to
x
i
d
i
z
e
d
u
n
d
e
rn
o
r
m
a
lc
o
n
d
i
t
i
o
n
s
C
H
3
K
M
n
O
4
H
C C O
H
3
K
C
r
O
2
2
7
N
O
R
E
A
C
T
I
O
N
C
H
3
t
e
r
t
b
u
t
y
la
l
c
o
h
o
l
S
e
c
o
n
d
a
r
y
A
lc
o
h
o
l
k
e
to
n
e+
h
y
d
r
o
g
e
n
io
n
s
H
O
K
M
n
O
4
H
C
3
C
C
H
3
O
H
2
p
r
o
p
a
n
o
l
P
r
i
m
a
r
y
A
l
c
o
h
o
l
+
+2
H
C
K
C
r
O
2
2
7
H
C
3
C
H
3
p
r
o
p
a
n
o
n
e
a
l
d
e
h
y
d
e
+
w
a
t
e
r
c
a
r
b
o
x
y
l
i
c
a
c
i
d
+
h
y
d
r
o
g
e
n
i
o
n
s
OH
OH
H
K
M
n
O
H
4
K
M
n
O
4
+
C
H
C
H
C
H
O
H
CCC
CCC
H
+
2
H
3
2
2
H
+
H
O
K
C
r
O
2 K
2
2
7
C
r
O
2
2
7H
O H
H
H H
H
1
p
r
o
p
a
n
o
l
p
r
o
p
a
n
o
i
c
a
c
i
d
p
r
o
p
a
n
a
l
6.
Acid-Base Reactions
• Like water, alcohols can act as an acid or base,
depending on what it is reacting with.
• When they react as an acid, the alkyl oxide ion
(R-CH2O-) is formed.
e
t
h
a
n
o
l+
s
o
d
i
u
m e
t
h
o
x
i
d
e
i
o
n
+
s
o
d
i
u
m
i
o
n
+
h
y
d
r
o
g
e
n
2
C
H
C
H
O
H
+
2
N
a
3
2
+
2
C
H
C
H
O
+
2
N
a
+
H
3
2
2
• When they react as a base, the alkyl oxonium ion
(R-CH2OH2+) is formed
e
t
h
a
n
o
l+
s
u
l
f
u
r
i
c
a
c
i
d
C
H
C
H
O
H
+
H
S
O
3
2
2
4
e
t
h
y
l
o
x
o
n
i
u
m
i
o
n
+
b
i
s
u
l
f
a
t
e
i
o
n
+
C
H
C
H
O
H
H
S
O
3
2
2+
4
Preparation of Alcohols
1. Hydration of an Alkene
a
lk
e
n
e+w
a
te
r
°
H
S
O
0
0
C
2
4/1
a
lc
o
h
o
l
°
H
S
O
0
0
C
2
4/1
H
CC
H
C
H
O
2
3 +H
2
HH H
H C C C H
HH
HO
2. Oxidation of an Alkene
• This reaction uses an oxidizing agent like KMnO4 or
K2Cr2O7 to produce a “diol”.
a
lk
e
n
e+w
a
te
r
H
CC
H
C
H
O
2
3 +H
2
K
M
n
O
4
K
C
r2O
2
7
K
M
n
O
4
K
C
r2O
2
7
"
d
io
l"
HH H
HC C C H
HH
O
HO
Reactions of Ethers
1.
2.
3.
Ethers do not react with oxidizing or reducing
agents.
Combustion
ether + oxygen  carbon dioxide + water
CH3-O-CH3 + 3 O2  2 CO2 + 3 H2O
Reaction with Concentrated Binary Acids
e
th
e
r+
2
b
in
a
r
y
a
c
id
C
H
O
C
H
C
H
2
H
C
l
3
2
3+


2
a
lk
y
lh
a
lid
e
s+
w
a
te
r
H
C
C
l+
C
lC
H
C
H
H
O
3
2
3+
2
4. Reaction with Atmospheric Oxygen
This is a slow reaction in which highly unstable peroxides
are formed
ether+oxygen
C
H
C
H
H
3O
2C
3+O
2
peroxide
H
O
O
C
H
H
3C
2C
3