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 alkali ]

4. Alcohol is neutral compound.

5. Alcohol are named by replacing -e for alkane with ol.

6. Structural formula and molecule for few alcohol.

Molekul
n Name Mr Structural formula
Formula
H
|
12+3+
CH3OH H C OH
1 Methanol 16+1
|
= 32
H

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

H H H
| | |
H C C C OH
3 Propan-1-ol 60 C3H7OH
| | |
H H H

4 Butan-1-ol 74 C4H9OH

5 Pentan-1-ol 88 C5H11OH

6 Hexan-1-ol 102 C6H13OH

1
Q: Give names for this alcohol.

OH

CH3 CH2 CH CH2 CH2 CH3

Formula: C6H13OH

Name : Hexan-3-ol

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

(i)

OH

CH3 CH2 C CH2 CH2 CH3
|
CH3

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

(ii) OH

CH3 CH2 CH CH CH2 CH3
|
CH3

Formula : C7H15OH
Name : 4-methyl hexan-3-ol

2
 (iii)

OH

CH3 CH CH CH CH2 CH2
| | |
CH3 CH3 CH3

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

(iv)

C2H5 OH

CH3 CH2 CH CH2 CH 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.

3
Propanol

Butanol

4
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.

Zymase
C6H12O6 (aq) 2CH3CH2OH (l) + 2CO2 (g)
30 oC

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.

5
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.

Thermometer

Water out
Fractioning
collum

Liebig
condenser

Retort stand
with clamp

Rounded
Water Water in
conical
Product from
fermentation Porcelain Distillate
Wire XXXXXXXXXXXXXXX chips (Ethanol)
gauge
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.

6
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

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).

7
 H3PO4
concentrsted
CH2 = CH2 + H2O CH3CH2OH
300 o C, 60 atm

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 + 3O2 2CO2 + 3H2O

Ethanol Oxygen Carbon Water
dioxide

Q: Write combustion equation for hexanol

C6H13OH + 9O2 6CO2 + 7H2O

hexanol Oxygen Carbon Water
dioxide

2. Oxidation
i. Ethanol can be oxidised into ethanoic acid by an oxidising agent.

[Ethanoic acid is a family of carboxilic acids]

CH3CH2OH + 2[O] CH3COOH + H2O

Etanol Ethanoic acid

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)

8
Q: Draw a labeled diagram for the process.

Ethanol +
potassium dikromat(VI) +
dilute sulfuric acid

Heat

Distillate Cold
(ethanoic acid) 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 CH2 = CH2 + H2O

Ethanol Ethene

9
Q : Draw labeled diagram.

Glass wool
soaked with Porcelain
ethanol chips

Ethene
gas

Delivery Retort
Heat Heat Test stand
tube tube with
clamp

Water

10