ALCOHOL

The Alcohol Family

1. One of member of homologous series which contain carbon,
hydrogen and oxygen.
2. General formula for alcohol is CnH2n+1OH. [n=1,2,3..]
3. Alcohol contains the hydroxyl group, -OH as their functional
group. [notes: not hydroxide ion, OH- , alcohol not is alkaly ]
4. Alcohol is neutral compound.
5. Alcohol are named by replacing -e for alkane with ol.

6. Structural formula and molecule for few alcohol.

n

Name

Mr

Molekul
Formula

12+3+ CH3OH
1 Methanol 16+1
@
= 32 CH4O

Structural formula
H
|
H C OH
|
H

H
H
12x2 +
|
|
Ethanol
C2H5OH
5 +16
H C C OH
2
very
@
+1=
|
|
important
C2H6O
46
H
H
H
H H
|
|
|
H C C C OH
C3H7OH
|
|
|
H
H H

Propan-1ol

60

Butan-1ol

74

C4H9OH

Pentan-1ol

88

C5H11OH

Hexan-1ol

102

C6H13OH

Q: Give names for this alcohol.

OH
CH3

CH2

CH

CH2

CH2

Formula: C6H13OH
Name

: HEXAN-3-OL

CH3

Naming Alcohol
1. Find the longest continous carbon chain containing OH.
2. Number the carbon beginning at the end nearer to the OH,
write the number in front of the ending ol.
3. Locate the alkyl group (branch chain), give number to the
carbon and named the alkyl group. Put the number in front of
the group.
CH3
: methyl
C2H5 atau CH2CH3
: ethyl
C3H7 atau CH2CH2CH3
: propyl
4. Complete the name for the alcohol
(ii)

CH3

CH2

OH

C CH2
|
CH3

CH2

Formula: C7H15OH
Name : 3-methyl hexan-3-ol

CH3

(iii)
OH

CH3

CH2

Formula
Name

CH

CH
|
CH3

CH2

CH3

: C7H15OH
: 4-methyl hexan-3-ol

(iii)
OH
CH3

CH
|
CH3

CH

CH CH2
|
CH3

CH2
|
CH3

Formula : C9H19OH
Name
: 2, 4 dimethyl heptan-3-ol

(iv)

CH3

CH2

C 2H 5

CH

OH

CH

CH2

CH2 CH3

Formula : C9H19OH
Name
: 5-ethyl heptan-3-ol
Physical Properties
1. Liquid at room temperature. (pg. 62) [ no gas]
2. Simple alcohol are very soluble in water, infinite solubility.
Methanol, ethanol dan propan-1-ol is miscible in all proportions
(terlarut campur dengan air dalam semua kadaran).
The rest of the alcohol less soluble or insoluble.
Isomerism
Similar to alkenes, isomerism in alcohol results from the
branching of the carbon chain and the different location of the
hydroxyl group.
You only have to know the isomerism in propanol dan butanol.
Q : Draw 2 isomers for propanol and 4 isomers for butanol,
and dan named the isomers.

Propanol

Butanol

Propanol

H H H

H C C C OH

H H H

Molecular formula: C3H7OH

Name: Propan-1-ol

H H H

HCCCH

H OH H

Molecular formula: C3H7OH

Name: Propan-2-ol

Butanol

H H H H

H C C C C OH

H H H H

Molecular formula: C4H9OH

Name: Butan-1-ol

H H H H

HCCCCH

H H OH H

Molecular formula: C4H9OH

Name: Butan-2-ol

H
H
H

H C C C OH

H HCH H

Molecular formula: C4H9OH

Name: 2-methylpropan-1-ol

H
OH
H

H C C C H

H HCH H

Molecular formula: C4H9OH

Name: 2-methylpropan-2-ol

10

ETHANOL
1. Preparation of ethanol.
i. Laboratory preparation (fermentation)
ii. Industrial production (hydration process)
Making Ethanol Fermentation
1. Two stages;
i. Fermentation
ii. Purification
- through fractional distillation at 78 oC
( boiling point of ETHANOL)
Fermentation of Glucose
1. Yeast is added to sugar or starch.
2. Anaerobic process ( takes place in the absence of oxygen).
3. Yeast releases enzymes. These enzymes break down the
sugars/starch into glucose, C6H12O6.
4. Zymase slowly decomposes the glucose to form ethanol and
carbon dioxide.

C6H12O6 (aq)

Zymase @ C2H5OH @ C2H6O

2CH3CH2OH (l) + 2CO2 (g)

o
30 C

11

Delivery tube
Conical flask
Beaker
Glucose + yeast

Lime water

When the concentration of ethanol reach 15%, the yeast dies.

Q: How to produce pure alcohol?
A: Purified the ethanol through fractional distillation.
Purification of Ethanol
1. Ethanol produced from the fermentation process is impure,
because its mix with the glucose solution.
Q : Draw labeled diagram to carry out the purification of ethanol
through fractional distillation process.

12


Thermometer

Fractioning
collum

Water out

Liebig
condenser

Retort stand
with clamp
Rounded
conical

Water
Product from
fermentation

Wire
gauge

XXXXXXXXXXXXXXX

Porcelain
chips

Water in
Distillate
(Ethanol)

Bunsen
burner

Q: Why the solution/filtrate in rounded conical must heated at

78oC.
A: The boiling point of ethanol is 78 oC.
Q: Ethanol produced may still contains of some water.
What should be done to be sure that ethanol is 100% pure?
A: Anhydrous calcium oxide or anhydrous calcium chloride is
add/put into the ethanol.

13

Q: What is the function of;

- thermometer
- porcelain chips
- Liebig condenser
A: thermometer is used to ensure that temperature is always
at 78 oC.
B: Porcelain chips is used to avoid the solution jumped/
effervesence (breaking bubbles)
C: To cooled the ethanol vapour to become liquid.
Q: Named the process in Liebig condenser.
A: Condensation
Q: What is the properties of ethanol
A: Properties;
- colourless
- volatile
- good organic solvent
- miscible with water
- highly flammable
- antiseptic
- chemically reactive

14

Q: What is the uses of ethanol

A: Uses;
-

As a solvent in perfumes/cosmetics
As a thinner in varnish, ink
As a cleaner for compact disc.
As a fuel for transport
As a raw material for the manufacture of vinegar,
As a raw material to make industrial product such as
antiseptic and cough syrup.

Industrial production of ethanol

Ethene is mix with steam is passed through concentrated
phosphoric acid (catalyst) at 300 oC (temperature) and 60
atmosphere (pressure).

@ C2H4
CH2 = CH2 +

H3PO4
concentrsted
H2O

300 o C, 60 atm

15

C2H5OH
CH3CH2OH

Chemical Properties
1. Combustion
i. Alcohol are very flammable sustances.
ii. Ethanol burns with non-smoky and blue flame and releases
lot of heat. Suitable for use as fuel, described as clean fuel.

C2H5OH
Ethanol

3O2

Oxygen

2CO2
+
Carbon
dioxide

3H2O
Water

Q: Write combustion equation for hexanol

C6H13OH
hexanol

9O2

Oxygen

6CO2
+
Carbon
dioxide

7H2O
Water

2. Oxidation
i. Ethanol can be oxidised into ethanoic acid by an oxidising agent.
[Ethanoic acid is a family of carboxilic acids]

CH3CH2OH
Etanol

2[O]

16

CH3COOH + H2O
Ethanoic acid

Q: Show the structural formula for the equation above.

H
H
|
|
H C C OH + 2[O]
|
|
H
H

H
O
|

H C C OH + H2O
|
H

Q: Named 2 solutions are commonly used as oxidising agent.

(i)

Acidified potassium manganate(VII), KMnO4

(purple to colourless / decolourised)

(ii)

Acidified potassium dichromate(VI), K2Cr2O7

(orange to green)

Q: Draw a labeled diagram for the process.

Ethanol +
potassium dikromat(VI) +
dilute sulfuric acid

Heat
Distillate
(ethanoic acid)

17

Cold
water

Distillate (ethanoic acid)

- Colourless
- Vinegar smell
- Blue litmus paper turns red (acidic properties)
3. Dehydration

- H2O

ALCOHOL

ALKENE

1. Converted ethanol into ethene and a molecule of water.

2. The elimination of water results the formation of a carbon-carbon
double bond.
3. Dehydration occur when
a. ethanol vapours is passed over a heated catalyst such as.
i- Porous pot / porcelain chips
ii- Purnice stone / aluminium oxide, Al2O3 /alumina
b. Ethanol is heated under reflux at 170 oC with excess
concentrated sulphuric acid.

CH3CH2OH
Ethanol

CH2 = CH2
Ethene

18

H2O

Q : Draw the structural molecule for the process

H
H
|
|
HCCH
|
|
H
OH

H H
|
|
H C C H + H 2O

Q : Draw labeled diagram.

Glass wool
soaked with
ethanol

Porcelain
chips
Ethene
gas

Heat

Heat

Delivery
tube

Test
tube

Water

Prepared by;
Kamal Ariffin Bin Saaim
SMKDBL
http://kemhawk.webs.com

19

Retort
stand
with
clamp