Organic Chemistry

C11.1 Formulas and Terminology

C11.2 Naming Organic Compounds
C11.3 Fuels
C11.4 Alkanes
C11.5 Alkenes
C11.6 Alcohols
C11.7 Polymers
• Which homologous series does
the hydrocarbon, C20H42, belong
to?
• Is zingiberene (C15H24) an alkane?
Explain
your answer.
• How can you differentiate an
alkane from an alkene?

a monocyclic sesquiterpene compound that

gives ginger its distinctive flavor and is the
main component of ginger's volatile oil:
• Fuels are substances that can burn
easily in air to give out thermal energy.
• Coal, natural gas and petroleum (or
crude oil) are fossil fuels.
• They were formed from decayed plants
and animals that lived millions of years
ago.
• We use fossil fuels as sources of energy.
Fractional distillation of petroleum
• Petroleum is a dark brown, foul-smelling liquid that does
not flow easily.
• It must be refined or separated into fractions before it
can be useful.
• Petroleum can be separated into useful fractions
by fractional distillation.

How is petroleum separated in an oil refinery?

• In oil refineries, the hydrocarbons in petroleum are
separated by fractional distillation through the following
stages.
 Uses of petroleum Fractional distillation of petroleum (continued)
fractions
• The uses of different
petroleum fractions
depend on their
properties.
• Lighter fractions with
fewer carbon atoms
burn easily (e.g.,
gasoline, petrol)
• Heavier fractions are
thick and viscous, so
most of them are used
as lubricants.
How can we conserve petroleum? • Reducing the use of
petroleum by
reducing the number
of motor vehicles in
the road and taking
public transport;
• Using alternative fuels
such as solar energy;
• Improving the design
of power stations and
vehicles
so that they use
petroleum more
efficiently.
Alkanes are a
homologous series of
hydrocarbons that contain
only carbon–carbon single
covalent bonds.
 Propane, an example of an alkane

Lighters contain
alkane molecules.
These molecules
exist as a liquid in
such containers.

The skin of some fruits is

coated with alkanes.
• Alkanes are saturated hydrocarbons because they contain only
carbon–carbon single covalent bonds.
• In alkane molecules, all outer electrons of each carbon atom are
used in forming single bonds with four other atoms.
First four members of the alkane homologous series
Bonding in a methane molecule

• The physical properties of alkanes change as the

number of carbon atoms increases.
Bonding in an ethane molecule
• Alkenes are a homologous series of hydrocarbons
that contain one or more carbon–carbon double
bonds.

Ethene, an example of an alkene

Limonene (C10H16) is responsible for the

scent in citrus fruits like oranges and
lemons. Thus, it is often used in food
flavouring and perfumes.
 First three members of the alkene homologous series

• The boiling point of an alkene increases as the number

of carbon atoms in the molecule increases.
• They are unsaturated hydrocarbons because they
contain carbon–carbon double covalent bonds.
Cracking of petroleum

• Cracking is the breaking down of larger alkane molecules into smaller

molecules, using a high temperature and a catalyst.
Example:
• A catalyst may be used to speed up the process of cracking. This process is
known as catalytic cracking.
• In industries, cracking is done by passing the petroleum fraction containing
long-chain alkanes over a catalyst at a high temperature (about 500°C).
Hydrogen may sometimes be produced during cracking.
• The following reaction takes place:
How is the cracking of alkanes carried out in school laboratories?

• The cracking of alkanes can be demonstrated in the school laboratory using the
apparatus shown in the figure.
• Petroleum vapour is passed over a heated porous pot containing the catalysts
aluminium oxide and silicon dioxide.
• The product is a mixture of alkanes and alkenes.
 Why do we crack larger alkane molecules?
3 Cracking is used to produce petrol.
1 Cracking is used to produce short-chain alkenes.
• Over half the fractions obtained from the
refining of petroleum are the heavier,
less useful fractions.
• Short-chain alkenes, such as ethene and propene, are
used as starting materials for making ethanol and • Through cracking, long-chain alkanes

plastics. from petroleum fractions can be

2 Cracking is used to produce hydrogen. converted into short-chain alkanes,

which are in higher demand as they are
used to produce petrol.

• Hydrogen is the by-product in the cracking of alkanes.

Distinguishing between saturated and unsaturated hydrocarbons
• Aqueous bromine is red-brown.
• If an alkene is added to aqueous bromine, the bromine is decolourised.
• This reaction serves as a chemical test for the presence of unsaturated hydrocarbons.

Testing for the presence of unsaturated hydrocarbons

 Chemical properties of alkenes

Combustion reactions Addition reactions

1. Addition of bromine
(bromination)
2. Addition of hydrogen
(hydrogenation)
3. Addition of steam
(hydration)
• An addition reaction is a reaction in which an unsaturated organic compound
combines with another substance to form only one product.
• The addition reactions of alkenes can be represented by the general equation:

• Examples of addition reactions of alkenes:

1. Addition of bromine (bromination)
2. Addition of hydrogen (hydrogenation)
3. Addition of steam (hydration)
1 Addition of bromine (bromination)

• Aqueous bromine can be used to distinguish between alkanes and alkenes.

• This is because alkenes can undergo addition reaction with bromine.
• The addition of bromine or bromine water to an alkene is known as bromination.
Example:
 2 Addition of hydrogen (hydrogenation)

• At 200°C and in the presence of a catalyst such

as nickel, alkenes can react with hydrogen to
form alkanes.
• This reaction is known as hydrogenation.

Example:
3 Addition of steam (hydration)

• Alkenes can react with steam to produce alcohols.

• Conditions:
o Temperature = 300°C
o Pressure = 60 atm.
o Acid catalyst: phosphoric(V) acid (H3PO4)

Example:
Alcohols are a homologous series of organic compounds
which have the hydroxyl (–OH) functional group.

Propanol, an example of an alcohol

A ball-and-stick
model of ethanol

• All alcohols contain the elements carbon, hydrogen and oxygen.

 Physical properties of alcohols

• Alcohols are volatile liquids at room temperature and pressure.

• Alcohols are soluble in water. Their solubility decreases as their molecular size increases.
• The boiling points of alcohols increase as their molecular size increases.

Physical properties of some alcohols

Chemical properties of alcohols

• Alcohols burn in excess oxygen to produce carbon dioxide and water vapour.

Example:

Alcohols are commonly used Alcohol is burnt on some foods such as

to make hand sanitisers. fruit cake to give it a distinct flavour.
 Uses of ethanol
As a solvent

• It is a suitable solvent for paints, varnishes, deodorants,

perfumes and after-shave lotions. Shellac dissolved in
ethanol is used as a liquid polish.

As a fuel
• In cars
o In Brazil, ethanol obtained from sugarcane is used as fuel for motor vehicles.
o Ethanol is a cleaner fuel than petrol as it produces less air pollutants.
• In cooking
o Ethanol is the main component of methylated spirit.
o Methylated spirit contains 85% ethanol, 5% methanol and 10% water.
o It is used in spirit lamps and camping stoves for cooking.
 Polymers
• A polymer is a large molecule built up from many smaller molecules.
• These smaller molecules are called monomers.
• Different polymers are made up of different monomers.

Examples of natural and synthetic polymers

The process of joining together a large number of monomers to form a polymer is called polymerisation.

covalent bonds

polymerisation

Monomers Polymer

Polymerisation
• Addition polymerisation occurs when unsaturated monomers join to form the polymer as
the only product.
• The polymer formed is called the addition polymer.

• Alkenes can undergo addition polymerisation.

• The simplest addition polymer is poly(ethene).
• Poly(ethene) is commonly known as polythene.
Ball-and-stick model of ethene
How is poly(ethene) produced from ethene?

H H H H H H H H
C C + C C + C C + C C
H H H H H H H H

H H H H H H H H
C C + C C + C C + C C Poly(ethene) is used for making toys,
cling films, plastic containers, plastic
H H H H H H H H bottles, and plastic bags.
A section of the structure of poly(ethene)
The equation for the addition polymerisation is written as:

The repeat unit of poly(ethene) is:

The formula of a polymer can be written

using its repeat unit. Thus, the formula of
poly(ethene) can be simply written as:
How can we deduce the structural formula of a monomer from its polymer?

Let us examine this using the polymer, polystyrene as an example. A

section of the structure of polystyrene is as shown.

Polystyrene is hard, light and brittle. It

is used to make disposable containers.
The structural formula of the monomer can be determined by the steps below:

Thus, the structural formula of the monomer of polystyrene is:

 The structural formula of the monomer can be determined by the steps below:

Thus, the structural formula of the monomer of polystyrene is:

Condensation polymerisation occurs when monomers combine to form a polymer,
with the elimination of small molecules such as water, ammonia or hydrogen
chloride.
The polymer obtained from condensation polymerisation is called condensation
polymer.
There are two main groups of condensation polymers:
1. Polyamides
2. Polyesters
 Nylon – a synthetic polyamide

Nylon is made from two monomers; a dicarboxylic acid and a diamine.

Dicarboxylic acid — a molecule Diamine — a molecule

with two –COOH groups with two –NH2 groups

Monomers of nylon (The coloured rectangles represent part of the monomers.)

 Condensation polymerisation between a dicarboxylic acid and diamine to form nylon

The repeat unit of nylon is:

PET – a synthetic polyester
PET is also known as Terylene.
It is made from two monomers: a dicarboxylic acid and a diol.

Diol –– an alcohol with

Dicarboxylic acid –– an acid with two –COOH groups
two –OH groups

Monomers of PET (The coloured

rectangles represent part of the Nylon and PET are synthetic fibres. Clothes
made from synthetic fibres are shrink-proof
monomers.) and crease-proof. They are also easier to
wash and dry.
Condensation polymerisation between a dicarboxylic acid and a diol to form PET

The repeat unit of PET is:

What are the differences between addition and condensation polymerisation?

Differences between addition and condensation polymerisation