14.

1 Properties of Alcohols
AS Chemistry A
Module 4 Core Organic Chemistry
Chapter 14 Alcohols
What are the properties and reactions of alcohols?

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14.1 Properties of Alcohols

Lesson Objectives:

Learners should be able to demonstrate and apply their

knowledge and understanding of:

The polarity of alcohols and an explanation, in

terms of hydrogen bonding, of the water
solubility and the relatively low volatility of
alcohols compared with alkanes
Classification of alcohols into primary, secondary
and tertiary alcohols
What are the properties of Alcohols?

Learning Objectives

Explain, in terms of hydrogen

bonding, the water solubility and the
relatively low volatility of alcohols

Describe the difference between

primary, secondary and tertiary
alcohols

Classify alcohols into primary,

secondary and tertiary alcohols

Starter
Draw the displayed, structural, molecular and
skeletal structure of:

2-methyl-propan-2-ol
2,2 dimethyl butanol
2 bromo,3chloro pentan-2-ol

What are the properties of Alcohols?

What are alcohols?

Alcohols are a homologous series of organic compounds
with the general formula CnH2n+1OH and names ending ol.
The functional group in alcohols is the hydroxyl group: OH.
No. of
carbon atoms

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Molecular
formula

Name

CH3OH

methanol

C2H5OH

ethanol

C3H7OH

propanol

C4H9OH

butanol

C5H11OH

pentanol

C6H13OH

hexanol
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Naming alcohols
Alcohols with three or more carbon atoms display
positional isomerism. The number of the carbon to which
the hydroxyl groups is attached is written before the ol.

propan-1-ol

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propan-2-ol

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Making Ethanol
Hydration of Ethene

Hydration of ethanol with steam

Phosphoric acid catalyst
Conditions:
High temperatures
Moderate Pressures
Operated continuously
What are the properties of Alcohols?

Making Ethanol
Fermentation

Sugar or starch (Carbohydrates) converted into

ethanol and carbon dioxide
Conditions
Carried out in solution (aq)
Relatively low temperatures (37C)
Anaerobic conditions
What are the properties of Alcohols?

Why are the boiling points of alcohol

so much higher than alkanes?
Alkane

Molecular
Mass

Boiling
Point (C)

Alcohol

Molecular
Mass

Boiling
Point (C)

Methane

16

-182

Methanol

32

65

Ethane

30

-89

Ethanol

46

78

Propane

44

-42

Propanol

60

97

Butane

58

-0.5

Butanol

74

118

Pentane

72

36

Pentanol

88

138

Hexane

86

69

Hexanol

103

155

What are the properties of Alcohols?

Volatility & boiling point

Hydrogen Bonding!!!

Hydrogen bonding is the strongest

intermolecular force

What are the properties of Alcohols?

Solubility
Alcohols can dissolve in water!

This is a result of hydrogen bonding!

Solubility of alcohols decreases with alcohol
length

Why does solubility increase with length?

What are the properties of Alcohols?

Classification of alcohols
We can classify alcohols into three categories:
Primary
Secondary
Tertiary
The classification of alcohol depends on the Alkyl
groups around the OH alcohol group
What are the properties of Alcohols?

Primary Alcohols
The -OH group is bonded to a carbon with one
other alkyl groups attached

What are the properties of Alcohols?

Secondary Alcohols
The -OH group is bonded to a carbon with two
other alkyl groups attached

What are the properties of Alcohols?

Tertiary Alcohols
The -OH group is bonded to a carbon with three
other alkyl groups attached

What are the properties of Alcohols?

Primary, secondary and tertiary

A chain of carbon atoms can be represented by R when
drawing the structure. This is referred to as an R group.

Primary (1) alcohols have one

R group attached to the carbon to
which the OH group is attached.

Secondary (2) alcohols have two

R groups attached to the carbon to
which the OH group is attached.

Tertiary (3) alcohols have three

R groups attached to the carbon to
which the OH group is attached.
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Learning Objectives (1)

A
B

Compare the oxidation of primary,

secondary and tertiary alcohols

Give an example of a chemical

test that shows oxidation has taken
place

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Describe the combustion of

alcohols

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The Combustion of Alcohols

In plentiful of oxygen alcohols burn

completely to form carbon dioxide and
water
C2H5OH(l) + 3O2(g) 2CO2(g) + 3H2O(l)
Write the molecular structure of the
combustion of (Include state symbols):
Propanol
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Oxidation of Alcohols

Primary and secondary alcohols can be

oxidised using a suitable oxidising agent
One suitable oxidising agent is acidified
dichromate ions
This is made from potassium dichromate
and sulphuric acid
Alcohol + [O], the general equation for
oxidation

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Acidified dichromate ions

During the course of an oxidation reaction

acidified dichromate ions turn from organ
to green

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Synthesis of carboxylic acids

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Oxidation of Tertiary Alcohols

Tertiary alcohols cannot be oxidised

They are resistant to oxidation!
So acidified dichromate remains orange

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Dehydration of an alcohol

An alcohol can be dehydrated to form an

alkene in the presence of an acid catalyst
(Conc phosphoric acid or conc sulphuric
acid)
This is an elimination reaction
Alcohol is heated under reflux with the
catalyst for 40 minutes.
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Dehydration of ethanol in the lab

In the lab, dehydration of ethanol can be achieved by
passing ethanol over a hot aluminium oxide catalyst.
Ethene gas is collected by displacement.
ceramic wool soaked
in ethanol

ethene gas

aluminium
oxide

water
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Esterification

An ester is formed when an alcohol is

warmed with a carboxylic acid in the
presence of an acid catalyst
The reaction is known as esterification
Concentrated sulfuric acid is often used as
the acid catalyst
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