11 Organic chemistry 1

FOCUS POINTS
★ What is a homologous series?
★ What are the similarities and differences between saturated and unsaturated hydrocarbons?
★ What are polymers and why are they useful?
★ How do plastics cause environmental challenges?

You will have seen earlier in Chapter 6 that important substances, called hydrocarbons, are
obtained from petroleum. These hydrocarbons are mainly used as fuels of different types. In this
chapter you will study two families, or homologous series, of these hydrocarbons, the alkanes and
alkenes. You will examine their different structures and different physical and chemical properties.
You will see that it is possible to produce alkenes from alkanes in a process called cracking. Finally,
you will learn about a very important set of materials that are made from alkenes called polymers,
better known as plastics, and the problems that are created by overuse of these polymers.

A lot of the compounds that are present in living

things have been found to be compounds containing
11.1 Alkanes
carbon (Figure 12.1). These are known as organic Most of the hydrocarbons in petroleum belong to the
compounds. All living things are made from organic family of compounds called alkanes. The molecules
compounds based on chains of carbon atoms which within the alkane family contain carbon atoms
are not only covalently bonded to each other but covalently bonded to four other atoms by single
also covalently bonded to hydrogen, oxygen and/or bonds as shown in Figure 12.2, which shows the fully
other elements. The organic compounds are many displayed formulae of some alkanes. Because these
and varied. Some scientists suggest that there are molecules possess only carbon–carbon single covalent
more than ten million known organic compounds. bonds, they are said to be saturated hydrocarbons,
as no further atoms can be added. This can be seen
in the bonding scheme for methane (Figure 12.3). The
physical properties of the first six members of the
alkane family are shown in Table 12.1 (p. 190).

Key definition
A displayed formula shows how the various atoms are
bonded and shows all the bonds in the molecule as
individual lines.

You will notice from Figure 12.2 and Table 12.1 that
the compounds have a similar structure and similar
name endings. They also behave chemically in a
similar way. A family with these factors in common
▲ Figure 12.1 Living things contain organic compounds is called a homologous series.

188

[Link] 188 24/02/21 10:10 PM

11.1 Alkanes

Methane
H

H H
H CMethane
H

H H

H C H

H C
Ethane
H H

H CEthane
C H
H H
H H
H H

H C C H

H H

Propane Methane molecule (CH4)

H H H ▲ Figure 12.3 The covalent bonding scheme for methane

H CPropane
C C H All the members of a homologous series can also
H H
H H
H H be represented by a general formula. In the case of
H C C C H the alkanes, the general formula is:
H H H CnH2n + 2
Butane
where n is the number of carbon atoms present.
H H H H
As you go up a homologous series, in order of
H CButane
C C C H increasing number of carbon atoms, the physical
H
H
H
H
H
H
H
H properties of the compounds gradually change.
H C C C C H
For example, the melting and boiling points of the
alkanes shown in Table 12.1 gradually increase.
H H H H
This is due to an increase in the intermolecular
Pentane Going further forces as the size and mass of the molecule
H H H H H increases (Chapter 3, p. 43). As you can see from
Figure 12.2 and Table 12.1, the increase in size and
H CPentane
C C C C H
H H H
mass of the molecule is due to the addition of a
H H
H H H H H CH2 group as you descend the homologous series.
H C C C C C H

H H H H H The compounds within a homologous series

possess similar chemical properties through their
Hexane
functional group. A functional group is usually an
H H H H H H
atom or group of atoms that are present within the
H CHexane
C C C C C H molecules of the homologous series. In the case of
H H
H
H
H
H
H
H
H
H the alkanes, they are unusual in that they do not
H H
H C C C C C C H
have a functional group. For a further discussion of
functional groups, see Chapter 13, p. 206.
H H H H
H H Under normal conditions, molecules with up to
four carbon atoms are gases, those with between
five and 16 carbon atoms are liquids, while those
▲ Figure 12.2 The fully displayed formulae and molecular with more than 16 carbon atoms are solids.
models of the first six alkanes

189

[Link] 189 24/02/21 10:10 PM

11 organic chemiStry 1

Key definitions Naming the alkanes

A homologous series is a family of similar compounds All the alkanes have names ending in -ane. The rest
with similar chemical properties due to the presence of of the name tells you the number of carbon atoms
the same functional group. present in the molecule. For example, the compound
A functional group is an atom or group of atoms that whose name begins with:
determine the chemical properties of a homologous series.
» meth- has one carbon atom
» eth- has two carbon atoms
▼ Table 12.1 Some alkanes and their physical properties
» prop- has three carbon atoms
Physical » but- has four carbon atoms
state at
Molecular Melting Boiling room
and so on.
Alkane formula point/°C point/°C temperature
Methane CH4 −182 −162 Gas
Ethane C 2 H6 −183 −89 Gas
Structural isomerism
Sometimes it is possible to write more than
Propane C 3H8 −188 −42 Gas one displayed formula to represent a molecular
formula. The displayed formula of a compound
Butane C 4H10 −138 0 Gas
shows how the atoms are joined together by
the covalent bonds. For example, there are two
different compounds with the molecular formula
C4H10. The displayed and structural formulae of
Going further these two substances, along with their names and
physical properties, are shown in Figure 12.4.
H H H H
Melting Boiling Physical Melting point
Molecular point/ point/ state at room H C C C C H 138 C
Alkane formula °C °C temperature Boiling point
H H H H 0C
Pentane C5H12 −130 36 Liquid
Hexane C6H14 −95 69 Liquid
CH3CH2CH2CH3
a Butane
H H H
Melting point
C H
Test yourself H C C 159 C

H H Boiling point
1 Estimate the boiling points for the alkanes with 12 C
formulae: H C H
a C7H16
b C 8H18. H
2 Name the alkane that has the formula C7H16. CH3CH(CH3)CH3
b 2-methylpropane
▲ Figure 12.4 Displayed and structural formulae for the
two isomers of C 4H10

190

[Link] 190 24/02/21 10:10 PM

11.2 The chemical behaviour of alkanes

methane + oxygen → c arbon + water + (ΔH)

Compounds such as those in Figure 12.4 are
dioxide
known as structural isomers. Isomers are
substances which have the same molecular CH4(g) + 2O2(g) → CO2(g) + 2H2O(g)
formula but different structural formulae and The gaseous alkanes are some of the most useful
displayed formulae. The isomers in Figure 12.4 fuels. As you saw in Chapter 6, they are obtained by
have the same molecular formula, C4H10, but the fractional distillation of petroleum. Methane,
different structural and displayed formulae. better known as natural gas, is used for cooking
Butane (Figure 12.4a) has the structural formula as well as for heating offices, schools and homes
CH3CH2CH2CH3 and 2-methylpropane (Figure 12.4b) (Figure 12.5a). Propane and butane burn with very
has the structural formula CH3CH(CH3)CH3. The hot flames and they are sold as liquefied petroleum
brackets show the formula of the branch. The gas (LPG). In rural areas where there is no supply
different structures of the compounds shown in of natural gas, central heating systems can be run
Figure 12.4 have different melting and boiling on propane gas (Figure 12.5b). Butane, sometimes
points. Molecule b contains a branched chain and mixed with propane, is used in portable blowlamps
and in gas lighters.
has a lower melting point than molecule a, which
has no branched chain. All the alkane molecules
with four or more carbon atoms possess isomers.
Perhaps now you can see why there are so many
different organic compounds!
Key definitions
Structural isomers are compounds with the same
molecular formula, but different structural formulae.
The structural formula of an organic compound is
a This is burning methane
an unambiguous description of the way the atoms are
arranged, including the functional group.

Test yourself
3 Draw the displayed formulae for the isomers
of C5H12.

For further insight into isomerism, see p. 195 and

Chapter 13, p. 207.

11.2 The chemical behaviour b Central heating systems can be run on propane

of alkanes ▲ Figure 12.5

Alkanes are rather unreactive compounds. For

example, they are generally not affected by alkalis, As stated, alkanes are generally unreactive but,
acids or many other substances. Their most important like all homologous series, they will undergo
property is that they burn or combust easily. similar chemical reactions. They will react with
Gaseous alkanes, such as methane, will burn in a halogens such as chlorine. Chlorine is quite
good supply of air, forming carbon dioxide and water a reactive non-metal and will react with, for
as well as plenty of heat energy.

191

[Link] 191 24/02/21 10:10 PM

11 organic chemiStry 1

example, methane in the presence of sunlight or H

ultraviolet light. This is known as a photochemical
reaction, with the UV light providing the H C CI
activation energy (Ea) for the reaction (see Chapter H
6, p. 93). The overall chemical equation for this
process is: ▲ Figure 12.6 Chloromethane
methane + chlorine → chloromethane + h ydrogen atom to form chloromethane (see Figure 12.6).
chloride This type of reaction is known as a substitution
CH4(g) + Cl2(g) → CH3Cl(g) + HCl(g) reaction. In a substitution reaction, one atom
or group of atoms is replaced by another atom or
We can see that one hydrogen atom of the
group of atoms: this is know as monosubstitution.
methane molecule is substituted by a chlorine

Going further
Chloromethane is used extensively in the chemical severe problem since the lethal dose was only slightly
industry. For example, chloromethane is used to higher than that required to anaesthetise the patient. In
make silicones. Silicones are used in building and 1956, halothane was discovered by chemists working
construction. They are able to bond and seal materials at ICI. This is a compound containing chlorine, bromine
such as concrete, glass, granite, plastics and steel (see and fluorine which has been used as an anaesthetic
Figure 12.7). This enables them to work better and last in recent years. Its formula is CF 3CHBrCl. However,
longer. There are dangers associated with substances even this is not the perfect anaesthetic since evidence
containing chloromethane. It is a harmful substance and suggests that prolonged exposure to this substance
should be treated with caution. may cause liver damage. The search continues for even
better anaesthetics.
A group of compounds called the chlorofluorocarbons
(CFCs) were discovered in the 1930s. Because of
their inertness they had many uses, especially
as a propellant in aerosol cans. CFC-12 or
dichlorodifluoromethane, CF 2 Cl 2, was one of the
most popular CFCs in use in aerosols. Scientists
believe that CFCs released from aerosols are
destroying the ozone layer and steps are being taken to
reduce this threat.

The ozone hole problem

Our atmosphere protects us from harmful ultraviolet
radiation from the Sun. This damaging radiation is
absorbed by the relatively thin ozone layer found in the
stratosphere (Figure 12.8).
Large holes have been discovered in the last 30 years in
▲ Figure 12.7 Silicones are used carefully as adhesives
the ozone layer over Antarctica, Australasia and Europe
as well as sealants
(Figure 12.8a). Scientists think that these holes have
Early anaesthetics relied upon trichloromethane, CHCl3, been produced by CFCs such as CFC-12. CFCs escape
or chloroform. Unfortunately, this anaesthetic had a into the atmosphere and, because of their inertness,

192

[Link] 192 24/02/21 10:10 PM

11.2 The chemical behaviour of alkanes

remain without further reaction until they reach agreements are adhered to then the ozone layer will
the stratosphere and the ozone layer. In the recover by 2050.
stratosphere, the high-energy ultraviolet radiation
causes a chlorine atom to split off from the CFC 80
Thermosphere
molecule. This chlorine atom, or free radical, then
reacts with the ozone. 70
Cl(g) + O3(g) → OCl(g) + O2(g) Mesosphere Ionosphere
60
This is not the only problem with CFCs. They are also

Altitude/km
significant greenhouse gases (Chapter 11, p. 183). 50
The ozone depletion and greenhouse effects have
become such serious problems that an international 40
Ozone layer
agreement known as the Montreal Protocol Stratosphere
on Substances that Deplete the Ozone Layer was 30
agreed in 1987.
20
Research into replacements has taken place
since then, producing better alternatives called 10 Troposphere
hydrochlorofluorocarbons (HCFCs). These have
lower ozone-depletion effects and are not effective

0
60
20
20
60
greenhouse gases. The protocols of the 1980s have

10

10
been superseded by the Kyoto Protocol of 1997 and Temperature/ C
the 2016 Paris Agreement, which has been signed b The ozone layer is between 25 km and 50 km above
by 197 countries. It is believed that if the intended sea level

a This diagram comes from NASA’s ozone monitoring programme, TOMS (Total Ozone Mapping Spectrometer). The
ozone hole over the Antarctic (shown in purple and pink on the diagram) is largest in the Antarctic spring. Note: Dobson
units are a measure of the total amount of ozone in a vertical column from the ground to the top of the atmosphere
▲ Figure 12.8

193

[Link] 193 24/02/21 10:10 PM

11 organic chemiStry 1

Other uses of alkanes n is the number of carbon atoms. The alkenes

are more reactive than the alkanes because they
Besides their major use as fuels (p. 191), some of each contain a double carbon–carbon covalent
the heavier alkanes are used as waxes in candles, as bond between the carbon atoms (Figure 12.9).
lubricating oils and in the manufacture of another Molecules that possess a carbon–carbon double
family of hydrocarbons – the alkenes. covalent bond, or even a triple covalent bond, are
said to be unsaturated hydrocarbons, because
Test yourself it is possible to break one of the two bonds to
add extra atoms to the molecule. This feature of
4 Write a balanced chemical equation to
represent the combustion of propane. alkenes is very important and is responsible for
5 In what mole proportions should chlorine the characteristic properties of these organic
and methane be mixed to produce compounds. This feature is, for the alkenes, known
chloromethane? as their functional group.
6 Draw the covalent bonding diagram for
chloromethane, CH3Cl.
H H H H

C C C C
Methane – another greenhouse gas H H
H H
Methane, the first member of the alkanes, occurs
naturally. Cows produce it in huge quantities when ▲ Figure 12.9 The bonding in ethene, the simplest alkene
digesting their food. It is also formed by growing
rice. Like carbon dioxide, it is a greenhouse gas The chemical test to show the difference between
(Chapter 11, p. 183) because it acts like the glass saturated and unsaturated hydrocarbons is discussed
in a greenhouse – it will let in heat from the Sun on p. 197.
but will not let all of the heat back out again. It is
thought that the greenhouse effect may contribute Naming the alkenes
to global warming, which could have disastrous All alkenes have names ending in -ene. Alkenes,
effects for life on this planet. A great debate is especially ethene, are very important industrial
going on at the moment as to how we can reduce chemicals. They are used extensively in the plastics
the amount of methane released into the atmosphere industry and in the production of alcohols such
and hence reduce the effects of global warming. as ethanol and propanol. See Table 12.2 and
Figure 12.10.
Test yourself ▼ Table 12.2 The first three alkenes and their physical
properties
7 Use your research skills and your textbook
to find out: Physical
a any other sources of methane found in state at
nature Molecular Melting Boiling room
b how climate change might affect your Alkene formula point/°C point/°C temperature
particular environment.
Ethene C 2H4 −169 −104 Gas

Propene C 3 H6 −185 −47 Gas

11.3 Alkenes
Alkenes form another homologous series of Butene C 4 H8 −184 −6 Gas
hydrocarbons of the general formula C nH2n where

194

[Link] 194 24/02/21 10:10 PM

11.3 Alkenes

Ethene
H H Going further
C C
H H The different isomers shown in Figure 12.11 have
different melting and boiling points due to their
Propene different structures. All the alkene molecules with
four or more carbon atoms possess isomers.
H H
H
H C C C Test yourself
H
H 8 Draw the displayed formulae for the
isomers of C5H10.
Butene
H H H
H
H C C C C
H
H H
Where do we get alkenes from?
Very few alkenes are found in nature. Most of
▲ Figure 12.10 Displayed formula and shape of the first
three alkenes the alkenes used by the petrochemical industry
are obtained by breaking up larger, less useful
alkane molecules obtained from the fractional
The structural formula of ethene is CH2=CH2 and distillation of petroleum. This is usually done by a
the structural formula of propene is CH2=CHCH3. process called catalytic cracking. In this process
the alkane molecules to be ‘cracked’ (split up) are
Structural isomerism in alkenes passed over a mixture of aluminium and chromium
You saw when studying the alkanes that oxides heated to 550°C.
sometimes it is possible to write more than one
dodecane decane + ethene
displayed or structural formula to represent a
molecular formula (p. 190). These are known as C12H26(g) C10H22(g) + C2H4(g)
structural isomers. Butene and the higher alkenes (found in kerosene) shorter alkane alkene
also show structural isomerism. For example,
there are three different compounds with the Another possibility is:
molecular formula C4H8. The displayed formulae of C12H26(g) → C8H18(g) + C4H8(g)
two of these substances along with their names
and structural formulae are shown in Figure 12.11. In these reactions, hydrogen may also be formed
The structural formulae of the isomers but-1-ene during cracking. The amount of hydrogen produced
and but-2-ene give an unambiguous description depends on the conditions used. Since smaller
of the way the atoms are arranged, including the hydrocarbons are generally in greater demand than
location of the C=C double bond or functional the larger ones, cracking is used to match demand
group. The structural formulae are CH3CH2CH=CH2 (Table 12.3).
(but-1-ene) and CH3CH=CHCH3 (but-2-ene).
H H H H H H H H

H C C C C H C C C C H

H H H H H

CH3 CH2 CH=CH2 CH3CH=CHCH3

But-1-ene But-2-ene
▲ Figure 12.11 But-1-ene and but-2-ene: isomers of C4H8

195

[Link] 195 24/02/21 10:10 PM

11 organic chemiStry 1

▼ Table 12.3  Percentages of the fractions in petroleum and

the demand for them 11.4 The chemical
Fraction
Approx % in
petroleum
Approx %
demand
behaviour of alkenes
The double bond makes alkenes more reactive
Refinery gas 2 5
than alkanes in chemical reactions. For example,
Gasoline 21 28 hydrogen adds across the double bond of ethene,
Kerosene 13 8 under suitable conditions, forming ethane (Figure
Diesel oil 17 25 12.13). This type of reaction is called an addition
Fuel oil and 47 34
reaction. The usefulness of this type of reaction
bitumen is that only one product is formed.

This means that oil companies are not left with

large surpluses of fractions containing the larger
molecules.
Figure 12.12 shows the simple apparatus that can
be used to carry out thermal cracking reactions in the
laboratory. You will notice that in the laboratory we
may use a catalyst of broken, unglazed pottery. This
experiment should only ever be carried out as a teacher
demonstration.
▲ Figure 12.13 The addition of hydrogen to ethene using
Paraffin molecular models
soaked into
absorbent wool
Addition reactions
Broken porcelain
or aluminium
Hydrogenation
oxide granules Hydrogen adds across the C=C double bond in
ethene. This reaction is called hydrogenation.
The conditions necessary for this reaction to take
Delivery place are a temperature of 200°C in the presence
tube
of a nickel catalyst.
Strong
Warm heat ethene   + hydrogen ethane
C2H4(g) + H2(g)    C2H6(g)
H H H H

C C + H H H C C H
Cold water bath Crystallising dish H H H H

▲ Figure 12.12 The cracking of an alkane in the laboratory Hydrogenation reactions like the one shown with
ethene are used in the manufacture of margarines
Test yourself from vegetable oils.
9 Using the information in Table 12.2 (p. 194), Hydration
estimate the boiling point of pentene. Another important addition reaction is the one
10 Write a balanced chemical equation to used in the manufacture of ethanol. Ethanol
represent the process that takes place when has important uses as a solvent and a fuel. It is
decane is cracked. formed when water (as steam) is added across
the double bond in ethene in the presence of an
acid catalyst. For this reaction to take place, the
reactants have to be passed over a catalyst of

196

[Link] 196 24/02/21 10:10 PM

11.4 The chemical behaviour of alkenes

colour change takes place (Figure 12.14). This is

phosphoric(V) acid (absorbed on silica pellets) at
because there are no double bonds between the
a temperature of 300°C and pressure of 6000 kPa
carbon atoms of alkanes.
(1 atmosphere = 1 × 105 pascals).
300°C, 6000 kPa ethene bromine dibromoethane
ethene + steam ethanol
phosphoric(V)
acid catalyst C 2H 4(g) Br2 (in solution) C 2H 4Br2 (in solution)
C2H4(g) + H2O(g) C2H5OH(g)

H H H H H H
H H
C C + H OH H C C H C C Br Br H C C H
H H H OH H H Br Br

This reaction is reversible as is shown by the

equilibrium () sign. The conditions have been
chosen to ensure the highest possible yield of
ethanol. In other words, the conditions have been
chosen so that they favour the forward reaction.
The percentage yield is high at approximately
96%. It should be noted, however, that the
ethene is a non-renewable resource.
For a further discussion of ethanol and
alcohols generally, see Chapter 13, p. 206.
This method of manufacturing ethanol is a
continuous process. In a continuous process,
reactants are continually fed into the reaction
vessel or reactor as the products are removed.
Generally, continuous processing is employed if the
substance being made is needed on a large scale. ▲ Figure 12.14 The alkane, on the left, has no effect
on the bromine solution, but the alkene, on the right,
As you have seen, during addition reactions decolourises it
only one product is formed.

Test yourself
Halogenation – a test for 11 What is meant by the term ‘addition reaction’?
unsaturated compounds 12 How would you test the difference between
The addition reaction between bromine dissolved in ethane and ethene?
an organic solvent, or water, and alkenes is used as
a chemical test for the presence of a double bond 13 Write the displayed formula for pentene.
between two carbon atoms. When a few drops of this 14 Which of the following organic chemicals are
bromine solution are shaken with the hydrocarbon, alkanes and which are alkenes?
if it is an alkene (such as ethene), a reaction takes • Propene, C 3H6
place in which bromine joins to the alkene double • Octane, C 8H18
bond. This results in the bromine solution losing • Nonane, C9H20
• Butene, C 4H8
its red/brown colour. If an alkane, such as hexane, State why you have chosen your answers.
is shaken with a bromine solution of this type, no

197

[Link] 197 24/02/21 10:10 PM

11 organic chemiStry 1

Practical skills
Alkanes and alkenes Some statements in the student’s account have
For safe experiments/demonstrations which been underlined by the teacher.
are related to this chapter, please refer to the Answer these questions to identify how the
Cambridge IGCSE Chemistry Practical Skills experiment could be improved.
Workbook, which is also part of this series.
1 Which major safety precaution did they forget
Safety to mention at the start of the experiment?
● Eye protection must be worn. 2 Do you think the teacher would have added
a few drops from a measuring cylinder?
A student wrote the following account of an Explain your answer.
experiment carried out by the teacher to test 3 What would be the actual colour of the
which of two liquid hydrocarbons was an alkane aqueous bromine solution?
and which was an alkene. 4 How would the teacher have shaken the test
To a few drops of each liquid in separate test tubes?
tubes, they added a few drops of red aqueous 5 Would you expect only one layer in the
bromine solution from a measuring cylinder. solution after adding the aqueous bromine
They then corked the test tubes and shook them a solution? Explain your answer.
little. In one test tube the solution went colourless 6 Has the student got the identification of the
showing this hydrocarbon to be an alkane, while alkane and the alkene correct? Explain your
there was no change in colour of the other, so this answer.
must be the alkene.

11.5 Polymers molecules, like ethene, which join together in this

way are called monomers. A polymer chain, a very
Polythene is a plastic that was discovered by large molecule or a macromolecule, often consists
accident. Through the careful examination of this of many thousands of monomer units and in any
substance, when it was accidentally discovered, the piece of plastic there will be many millions of
plastics industry was born. Polythene is now produced polymer chains. Since in this polymerisation process
in millions of tonnes worldwide every year. It is made the monomer units add together to form only one
by heating ethene to a relatively high temperature product, the polymer, the process is called addition
under a high pressure in the presence of a catalyst. polymerisation.
H H H H
Key definitions
n C C C C
Polymers are large molecules built up from many small
H H H H n units called monomers.
Plastics are made from polymers.
In a chemical equation for this process, we show
that a large number of ethene molecules are adding
together by using the letter n to indicate very large
numbers of monomer molecules. The polymer formed,
in the chemical equation, is shown as a repeat unit
which repeats n times to form the polymer chain.
When small molecules like ethene join together
to form long chains of atoms, called polymers,
the process is called polymerisation. The small ▲ Figure 12.15 This model shows part of the poly(ethene)
polymer chain

198

[Link] 198 24/02/21 10:10 PM

11.5 Polymers

Poly(ethene), like many other addition polymers Other alkene molecules can also produce substances
has many useful properties including: being tough, like poly(ethene); for example, propene produces
easy to mould and an excellent insulator. One of poly(propene), which is used to make ropes and
the drawbacks however, as you will see later in this packaging.
section, is that it is not affected by the weather and In theory, any molecule that contains a carbon-
does not corrode, and therefore has disposal problems. to-carbon double covalent bond can form an addition
It can be found as a substitute for natural polymer. For example, ethene, CH=CH2, will undergo
materials in plastic bags, sandwich boxes, washing- an addition reaction to form poly(ethene).
up bowls, wrapping film, milk-bottle crates and The actual structure of the polymer can only
washing-up liquid bottles (Figure 12.16). be shown/represented by drawing the monomer as
shown in Figure 12.17. In this figure, you will see
that the double bond has been replaced by a single
bond and there are two extension bonds drawn
on either side, which show that the polymer chain
extends in both those directions.
H H H H

C C C C

H H H H
Ethene Repeat unit in
(monomer) the polymer

▲ Figure 12.17 Addition polymerisation of ethene

▲ Figure 12.16 These crates are made from poly(ethene)

Going further
Other addition polymers
Many other addition polymers have been produced.
Often the plastics are produced with particular
properties in mind, such as PVC (polyvinyl chloride or
poly(chloroethene) and PTFE (poly(tetrafluoroethene)).
Both of these plastics have monomer units similar
to ethene.

H H F F
C C C C
a Model of chloroethene, the PVC monomer
H Cl F F

PVC monomer PTFE monomer

(vinyl chloride or (tetrafluoroethene)
chloroethene)

If we use chloroethene (Figure 12.18a), the polymer we

make is slightly stronger and harder than poly(ethene)
and is particularly good for making pipes for plumbing
(Figure 12.19). b Model of part of a PVC polymer chain
▲ Figure 12.18

199

[Link] 199 24/02/21 10:10 PM

11 organic chemiStry 1

• it will withstand very high temperatures, of up to

260°C
• it forms a very slippery surface
• it is hydrophobic (water repellent)
• it is highly resistant to chemical attack.
These properties make PTFE an ideal ‘non-stick’
coating for frying pans and saucepans. Every year more
than 50 000 tonnes of PTFE are made.

F F F F
n C C C C
▲ Figure 12.19 These pipes are made from PVC F F F F n
PVC is the most versatile plastic and is the second most Monomer Polymer chain
widely used, after poly(ethene). Worldwide more than
27 million tonnes are produced annually. The properties of some addition polymers along with
If we start from tetrafluoroethene (Figure 12.20a), the their uses are given in Table 12.4.
polymer we make, PTFE, has some slightly unusual
properties:

a Model of tetrafluoroethene, the PTFE monomer      b Model of part of a PTFE polymer chain
▲ Figure 12.20

▼ Table 12.4 Some addition polymers

Plastic Monomer Properties Uses

Poly(ethene) CH2=CH2 Tough, durable Carrier bags, bowls buckets, packaging
Poly(propene) CH3CH=CH2 Tough, durable Ropes, packaging
PVC CH2=CHCl Strong, hard (less flexible than Pipes, electrical insulation, guttering
poly(ethene))
PTFE CF2=CF2 Non-stick surface, withstands high Non-stick frying pans, soles of irons
temperatures
Polystyrene CH2=CHC6H5 Light, poor conductor of heat Insulation, packaging (especially as foam)
Perspex CH2=C(CO2CH3)CH3 Transparent Used as a glass substitute

200

[Link] 200 24/02/21 10:10 PM

11.5 Polymers

Environmental challenges of result in the production of toxic gases) mean that

especially high temperatures have to be employed
plastics during the incineration process, driving energy
In the last 30 to 40 years, plastics have taken costs up.
over as replacement materials for metals, glass, » Recycling produces large quantities of black
paper and wood, as well as for natural fibres such plastic bags and sheeting for resale. However
as cotton and wool. This is not surprising since there are problems with recycling in that some
plastics are light, cheap, relatively unreactive, can plastics cannot be recycled because of their
be easily moulded and can be dyed bright colours. properties.
Unfortunately, as you saw earlier in this section, » Biodegradable plastics, as well as those polymers
they are not affected by the weather and so do that degrade in sunlight (photodegradable,
not corrode. This is both an advantage, in the way Figure 12.23a), have been developed. Other
they can be used, and a disadvantage, as it makes common categories of degradable plastics include
plastics so difficult to dispose of safely. Plastics synthetic biodegradable plastics which are broken
have contributed significantly to the household down by bacteria, as well as plastics which
waste problem, at least 10% in some countries, and dissolve in water (Figure 12.23b). The property
it is getting worse (Figure 12.21)! that allows plastic to dissolve in water has
been used in relatively new products, including
soluble capsules containing liquid detergent. Very
recently, chemists have found ways of involving
carbon dioxide and sugars in the production of
plastics that are also broken down by bacteria.
However, the vast majority of polymers are still
non-biodegradable.
There is a further huge global problem which has
been highlighted recently. That is, there are extreme
pollution problems caused by non-biodegradable
plastics and their accumulation in the world’s oceans
(see Figure 12.24). Aquatic life is being decimated
in some regions of the world. The problems with
▲ Figure 12.21 This plastic waste is ready to go to landfill plastics are causing a dramatic rethink of the role
of plastics in our society!
In the recent past, much of our plastic waste has
been used as landfill in, for example, disused
quarries. However, all over the world these sites are
getting very much harder to find and it is becoming
more and more expensive to dispose of the waste.
Also the older landfill sites are now beginning
to produce gases, including methane (which is
a greenhouse gas), which contribute to global
warming. The alternatives to dumping plastic waste
are certainly more economical and more satisfactory
but also create their problems.
» Incineration schemes have been developed to
use the heat generated from burning waste
for heating purposes (Figure 12.22). However,
problems with the combustion process (which can ▲ Figure 12.22 A plastic incineration plant

201

[Link] 201 24/02/21 10:10 PM

11 organic chemiStry 1

a This plastic bag is photodegradable ▲ Figure 12.24 Non-biodegradable plastics accumulate in

the oceans of the world

Test yourself
15 Draw the structure of the repeat unit of
the addition polymer formed from
CH3—CH2CH=CH2.
16 Draw the displayed formula of the monomer
from which the addition polymer below has
been produced.
C6H 5 H C6H 5 H C6H 5 H

C C C C C C

H H H H H H

b This plastic dissolves in water

▲ Figure 12.23

Revision checklist
After studying Chapter 11 you should be able to: ✔ State that a structural formula is a description
✔ Draw and interpret the displayed formula of of the way the atoms in a molecule are arranged,
a molecule to show all of the atoms and all including CH2=CH2.
of the bonds. ✔ Define structural isomers as compounds with the
✔ Write and interpret general formulae to show the same molecular formula, but different structural
ratio of atoms in the molecules of the compounds formulae, including C4H10 as CH3CH2CH2CH3 and
in a homologous series. CH3CH(CH3)CH3, and C4H8 as CH3CH2CH=CH2 and
✔ Identify a functional group as an atom or group CH3CH=CHCH3.
of atoms that determine the chemical properties ✔ Describe a homologous series as compounds
of a homologous series. that have the same functional group, the same
general formula, differ from one member to the
next by a –CH2– unit , show a trend in physical
properties and have similar chemical properties.

202

[Link] 202 24/02/21 10:11 PM

11.5 Polymers

✔ State that a saturated compound has molecules in ✔ Describe the manufacture of alkenes and
which all carbon–carbon bonds are single bonds. hydrogen by the cracking of larger alkanes using a
✔ State that an unsaturated compound has high temperature, 550°C, and a catalyst.
molecules in which one or more carbon–carbon ✔ Describe the reasons for the cracking of larger
bonds are double bonds or triple bonds. alkanes.
✔ Distinguish between saturated and unsaturated
✔ Name and draw the structural and displayed hydrocarbons using aqueous bromine.
formulae of unbranched alkanes and alkenes and
the products of their reactions containing up to ✔ State that in an addition reaction, only one
four carbon atoms per molecule. product is formed.
✔ Describe the properties of alkenes in terms of
✔ State the type of compound present given the addition reactions with bromine, hydrogen and
chemical name ending in -ane, -ene, or from a steam, and draw the structural or displayed
molecular, structural or displayed formula. formulae of the products.
✔ State that the bonding in alkanes is single covalent
and that alkanes are saturated hydrocarbons. ✔ Define polymers as large molecules built up from
✔ Describe the properties of alkanes as being many small units called monomers.
generally unreactive, except in terms of ✔ Describe the formation of poly(ethene) as an
combustion and substitution by chlorine. example of addition polymerisation.

✔ State that in a substitution reaction, one atom ✔ Identify the repeat units and/or linkages in
or group is replaced by another atom or group. polymers.
✔ Describe the substitution reaction of alkanes ✔ Deduce the structure or repeat unit of an addition
with chlorine as a photochemical reaction, with polymer from a given alkene and vice versa.
UV light providing the activation energy, and
draw the structural or displayed formulae of the ✔ State that plastics are made from polymers.
products, limited to monosubstitution. ✔ Describe how the properties of plastics have
implications for their disposal.
✔ State that the bonding in alkenes includes a double ✔ Describe the environmental challenges caused
carbon–carbon covalent bond and that alkenes are by plastics in terms of their disposal in landfill,
unsaturated hydrocarbons. accumulation in oceans and formation of toxic
gases from burning.

203

[Link] 203 24/02/21 10:11 PM

11 organic chemiStry 1

Exam-style questions
1 Explain the following statements. b Alkanes can be converted into substances
a Ethene is called an unsaturated which are used as solvents. To do this the
hydrocarbon.[2] alkane is reacted with a halogen, such as
b The cracking of larger alkanes into simple chlorine, in the presence of ultraviolet light.
alkanes and alkenes is important to the i Give a word and balanced chemical
petrochemical industry. [3] equation for the reaction between
c The conversion of ethene to ethanol is an methane and chlorine. [4]
example of an addition reaction. [2] ii Identify the type of reaction taking
place.[1]

2 The following question is about some of the 4 Ethene, C2H4, is the starting material for making
reactions of ethene. plastic carrier bags.
Gas B H H H H

n C C C C
Hydrogen + H H H H n
catalyst A

Burn in a Identify the type of chemical change taking

ETHENE Gas C + water place in the diagram above. [1]
air
Bromine
b Identify the product formed by this
reaction.[1]
Steam +
c i The alkene, ethene, is made by cracking
catalyst D
large alkane molecules. Describe a simple
Liquid F chemical test to show that ethene is
Liquid E present.[2]

a Give the names and formulae for ii Draw the displayed formula of any
substances A to F.[12] products formed in part c i.[1]
b i Give a word and balanced chemical
equation to represent the reaction in 5 a The majority of plastic carrier bags are
which liquid E is formed. [4] difficult to dispose of.
ii Identify the reaction conditions i Explain why carrier bags should not just be
required for the process to take place.[3] thrown away. [2]
c Give the homologous series that gas B ii Explain why plastic carrier bags should be
belongs to. [1] recycled.[2]
d Describe a chemical test which would iii Give one advantage that a plastic carrier
allow you to identify gas C.[2] bag has over one made out of paper. [1]
b A label like the one below is found on some
3 a Petroleum is a mixture of hydrocarbons which plastic carrier bags.
belong to the homologous series called the ‘This plastic carrier bag is made from a
alkanes. substance that is made from the chemical
Explain the meaning of the terms in italics.[6] elements carbon and hydrogen only. When
the carrier bag is burned, it produces carbon
dioxide and water. These substances are
natural and will not harm the environment.’

204

[Link] 204 24/02/21 10:11 PM

Exam-style questions

i Give the meaning of the term ‘element’. [2] 6 a Identify which of the following formulae
ii Identify the name given to the type of represent alkanes, which are alkenes, and
compound that contains the elements which represent neither.
carbon and hydrogen only. [1] CH3 C12H24
iii When the plastic bag burns, heat energy is C6H12 C20H42
given out. Give the name used to describe
reactions that give out heat energy. [1] C5H12 C2H4
iv The plastic bag will probably give off a C6H6 C8H18
toxic gas when it is burned in a limited C9H20 C3H7[3]
supply of air. Give the name and formula
of this gas. [2] b Draw the displayed formulae for all the
possible isomers which have the
molecular formula C6H14.[10]

205

[Link] 205 24/02/21 10:11 PM

11 Organic chemistry 2
FOCUS POINTS
★ What are the structures and formulae of the homologous series, alcohols and carboxylic acids?
★ What are the uses of ethanol and how can it be manufactured?
★ How does ethanoic acid react with metals, bases and carbonates?
★ How do condensation polymers differ from addition polymers and why is this reaction important in the
production of polyamides and polyesters?
★ Why can proteins be described as a type of polymer?

In Chapter 12, we discussed the organic compounds obtained from petroleum, the alkanes, and
how they are converted into another homologous series of hydrocarbons called the alkenes. In this
chapter you will learn that if you replace one of the hydrogen atoms on an alkane molecule with a
group such as –OH, the hydroxyl group, then you get a new homologous series called the alcohols.
Also if you replace one of the hydrogen atoms on an alkane molecule with a –COOH group then
you get a homologous series called the carboxylic acids. You will see that whichever group you
have attached, it will bring with it a new set of physical and chemical properties. These groups are
known as functional groups and it is this group of atoms that is responsible for the characteristic
reactions of the organic compound. You will also study the formation and uses of another type of
polymer known as condensation polymers. Finally, you will learn about the natural condensation
polymers, proteins.

11.6 Functional groups ▼ Table 13.1 The functional groups present in some
homologous series of organic compounds
You saw in Chapter 12 that the functional group
Class of compound Functional group
of an organic molecule is an atom or group of
atoms that determine the chemical properties of a Alcohols R–OH
homologous series. It is not surprising, therefore, Carboxylic acids R–COOH
that there are so many organic molecules given that Esters R–COOR
there are many functional groups that can replace
Amines R–NH2
an H atom of basic hydrocarbon molecules.
Table 13.1 shows some examples of functional Amides R–CONH2
groups. In the table, R represents an alkyl group or
a hydrogen atom. An alkyl group has the general
formula based on the alkanes, CnH2n+1. When n = 1, 11.7 Alcohols (R–OH)
R = CH3; when n = 2, R = C2H5, and so on. The alcohols form another homologous series with
the general formula CnH2n+1OH (or R–OH, where R
represents an alkyl group). All the alcohols possess
an –OH as the functional group. Table 13.2 shows
the names and condensed formulae of the first
four members along with their melting and boiling
points.

▲ Figure 13.1 This fruit juice contains plenty of vitamin C, or

ascorbic acid, which contains the functional group –COOH

206

[Link] 206 24/02/21 10:11 PM

11.7 Alcohols (R–OH)

▼ Table 13.2 Some members of the alcohol family

Test yourself
Melting Boiling
Alcohol Formula point/°C point/°C 1 Which of the following are alcohols?
pentanol, cyclohexane, butene, heptanol
Methanol CH3OH −94 64
Ethanol CH3CH2OH −117 78 2 What is the name of the alcohol with the
chemical formula C 8H17OH?
Propanol CH3CH2CH2OH −126 97
3 Looking at the chemical formulae of the following
Butanol CH3CH2CH2CH2OH −89 117 compounds, which is an alcohol?
C5H12    C2H5OH    C 4H10    C7H14

The alcohols are named by reference to the Alcohols have high boiling points and relatively low
corresponding alkane (see Chapter 12, p. 190), volatility. Alcohol molecules are like water molecules
always ensuring that the hydrocarbon chain is (H–OH) in that they are polar (see Chapter 11,
numbered from the end that gives the lowest p. 173).
number to the position of the –OH group. If the
–OH group is positioned at the end of the alcohol,
for example in CH3CH2CH2OH, then the position
Going further
of this group is shown by numbering the carbon Alcohol molecules are polar because of the presence
atom it is attached to as ‘1’. So this molecule of the –OH group, in which the hydrogen attached to
is called propan-1-ol, or propanol for short. If oxygen creates (within this group) a small difference
the –OH group is attached to the second carbon in charge (Figure 13.3). Other organic molecules that
atom, CH3CH(OH)CH3, then this molecule is called are polar are carboxylic acids such as ethanoic acid
(p. 211).
propan-2-ol. The displayed formulae of these
δ+
two isomers of propanol are shown in Figure 13.2 H
along with those for two isomers of butanol.
δ– δ+ δ–
H H H H H H O H O
H H
H C C C O H C C
H C C C H
H Hydrogen H
H H
H H H H O H bond
C C
Propan-1-ol H H H
H H
Propan-2-ol
a Propan-1-ol and propan-2-ol ▲ Figure 13.3 Polar –OH groups in ethanol molecules
lead to hydrogen bonding and an attraction between
H H H H H H H H neighbouring molecules

H C C C C OH H C C C C H Because of the presence of the polar –OH groups,

there is a relatively strong polar attraction between
H H H H H OH H H alcohol molecules. This polar attraction between
Butan-1-ol Butan-2-ol the charges δ+ and δ− in neighbouring molecules
b Butanol-1-ol and butan-2-ol
is called a hydrogen bond. This means that the
molecules have a much stronger attraction for each
▲ Figure 13.2 Displayed formulae of alcohols other than molecules of the corresponding alkane
of similar relative molecular mass, Mr. For example,
ethanol has an Mr value of 46 and is a liquid at room
temperature with a boiling point of 78°C, while
propane (CH3CH2CH3) has an Mr of 44 and is a gas at
room temperature with a boiling point of −42°C.

207

[Link] 207 24/02/21 10:11 PM

11 organic chemiStry 2

It is possible to think of alcohol molecules as water mixed with petrol as a fuel for cars and this use is
molecules in which an H atom has been replaced by an increasing worldwide. The ethanol used mixed with
alkyl group, for example, –C2H5 in C2H5OH. This close petrol is also unfit for human consumption.
similarity between their molecules explains why water
and alcohols with small molecules, such as methanol
and ethanol, are miscible. They mix because of the
Oxidation
presence of the polar –OH group in both molecules. Vinegar is manufactured by allowing solutions
Many other materials, such as food flavourings, containing alcohol to oxidise. Bacteria present in
are made from ethanol. As ethanol is also a the solution aid this process to take place. This
very good solvent and evaporates easily, it is type of oxidation is how different vinegars are
used extensively as a solvent for paints, glues, produced. Beer is converted to malt vinegar while
aftershave and many other everyday products wine oxidises to wine vinegar and cider to cider
(Figure 13.4). vinegar.
Ethanol can also be oxidised to ethanoic
acid (an organic acid also called acetic acid)
by powerful oxidising agents, such as acidified
potassium manganate(VII). During the reaction,
the purple colour of potassium manganate(VII)) is
removed (Figure 13.5) as the ethanol is oxidised
to ethanoic acid.
heat
ethanol + oxygen → ethanoic + water
(from acid

potassium
manganate
(VII))
CH3CH2OH(l) + 2[O] → CH3COOH(aq) + H2O(l)

▲ Figure 13.4 This aftershave contains alcohol H H H O

Ethanol is by far the most important of the alcohols H C C O H+ 2[O] H C C H2O
and is often just called ‘alcohol’. Ethanol can be H H H O H
produced by fermentation (p. 209) as well as by the Carboxylic acid group
hydration of ethene (p. 210). It is a neutral, colourless,
volatile liquid which does not conduct electricity.

Combustion
The combustion of ethanol is an important property
of ethanol. Ethanol burns quite readily with a clean,
hot flame.
ethanol + oxygen → carbon + water + (ΔH)
dioxide
CH3CH2OH(l) + 3O2(g) → 2CO2(g)  + 3H2O(g) + (ΔH) ▲ Figure 13.5 Potassium manganate(VII) turns from
purple to colourless
As methylated spirit, it is used in in domestic burners
for heating and cooking. Methylated spirit is ethanol
with small amounts of poisonous substances, such
as methanol, added to stop people drinking it. Some Test yourself
countries, like Brazil and the US, already use ethanol 4 Why does ethanol make such a good solvent?

208

[Link] 208 24/02/21 10:11 PM

11.7 Alcohols (R–OH)

Going further

Cholesterol – a complex molecule that

contains the –OH group
Cholesterol is a naturally occurring and essential
chemical. It belongs to a family of chemicals
called steroids and also contains an alcohol group
(Figure 13.6). Cholesterol is found in almost all of
the tissues in the body, including nerve cells. Levels
of cholesterol above normal (above 6.5 mmol/l) are
associated with an increased risk of heart disease.
Cholesterol hardens and blocks off arteries by building
up layers of solid material (atheroma) inside the
arteries (Figure 13.7). This is particularly serious if
the arteries that supply the heart or brain are blocked.
Simple tests are now available to monitor cholesterol a This artery is being blocked by atheroma, which may be
levels. People with high levels can be treated and can related to high levels of cholesterol in the blood
follow special low-fat and low-cholesterol diets.
CH3
CH3

CH3
CH3
CH3

HO Cholesterol

▲ Figure 13.6 The displayed formula of cholesterol

b This is a healthy artery
▲ Figure 13.7

Manufacture of ethanol The best temperature for this process to be carried

out is 25–35°C. This is because the enzymes in
Biotechnology involves making use of micro- yeast which catalyse this process will be denatured
organisms or their components, such as enzymes, at temperatures much above this, for example,
for the benefit of humans to produce, for example, at 40°C.
foods such as yoghurt and bread. One of the oldest
biotechnologies is that of fermentation. It involves glucose yeast
ethanol + carbon dioxide
a series of biochemical reactions brought about by
micro-organisms or enzymes. C6H12O6(aq) → 2C2H5OH(l) + 2CO2(g)

Fermentation The process in industry by which glucose is

Fermentation in the laboratory can be carried fermented is a batch process. A batch process
out using sugar solution. A micro-organism called is one in which each batch goes through one
yeast is added to the solution. The yeast uses the stage of the production process before moving
sugar for energy during anaerobic respiration onto the next stage. So in this case, ethanol is
(respiration without oxygen), and so the sugar is the primary product. After fermentation of the
broken down to give carbon dioxide and ethanol. glucose has finished, the ethanol in this batch has

209

[Link] 209 24/02/21 10:11 PM

11 organic chemiStry 2

to be separated from the mixture by fractional As discussed earlier, ethanol is a very useful
distillation. The process then is repeated with chemical and used in many ways. It can be
another batch of reagents. Batch processes are manufactured by two processes: fermentation of
used where small amounts of a substance are glucose and hydration of ethene. A summary of the
required. The percentage yield by this process is methods of manufacture are shown in Table 13.3.
approximately 15%. Figure 13.8 shows a simple ▼ Table 13.3 Summary of the two methods that are used to
apparatus for obtaining ethanol from glucose in make ethanol
the laboratory.
Fermentation Hydration
Conditions 37°C and so less 300°C, 6000 kPa
employed energy needed uses a catalyst of
compared to the phosphoric acid
hydration method
Processing Manufactured in Manufactured by a
batches continuous process
Sustainability Sustainable Finite source–ethene
source – the is non-renewable
glucose is
renewable
Purification Fractional Becomes pure
distillation during production
Percentage Low – about 15% High – about 96%
yield
▲ Figure 13.8 Fermenting glucose and yeast to produce
ethanol. The bag is inflated during the experiment by CO2

Hydration of ethene As you would expect, both methods of

preparation of ethanol have their advantages and
Another important addition reaction is the hydration
disadvantages. Table 13.4 shows some of these.
of ethene used in the manufacture of ethanol.
Ethanol has important uses as a solvent and a fuel. ▼ Table 13.4 Advantages and disadvantages of
It is formed when water (as steam) is added across preparation methods for ethanol
the double bond in ethene in the presence of an Advantages Disadvantages
acid catalyst. For this reaction to take place, the
Fermentation • Low energy • Slow process
reactants have to be passed over an acid catalyst consumption
(usually phosphoric(V) acid absorbed on silica • Not a continuous
pellets) at a temperature of 300°C and pressure of • Uses readily process
available
6000 kPa. materials
300º C, 6000 kPa Hydration of • Much faster • High energy
ethene + steam ethanol ethene process consumption
phosphoric(V)
acid catalyst
• Continuous • Requires ethene
process which has to
be obtained by
C2 H4 (g ) + H2 O(g ) C2H5OH(g )
cracking
H H H H

C C + H OH H C C H Test yourself
H H H OH 5 Why should being a continuous process be
an advantage for a process for making ethanol?
For a further discussion of this reaction, see
Chapter 12, p. 197.

210

[Link] 210 24/02/21 10:11 PM

11.8 Carboxylic acids

Going further 11.8 Carboxylic acids

Baking The carboxylic acids form another homologous
To make bread, fresh yeast is mixed with warm series, this time with the general formula
sugar solution and the mixture is added to the flour. CnH2n+1COOH. All the carboxylic acids possess
This dough mixture is then put into a warm place
to rise. The dough rises due to the production of
–COOH as their functional group.
carbon dioxide from aerobic respiration (respiration Table 13.5 shows the first four members of
with oxygen) by the yeast. The products of this style this homologous series along with their melting
of respiration are different to those of anaerobic and boiling points. Figure 13.9 shows the actual
respiration. arrangement as displayed formulae of the atoms
Methanoic acid
in these members of this family.
yeast O
sugar + oxygen carbon + water + (ΔH ) ▼ Table 13.5 Some members ofHthe C
carboxylic acid series
            dioxide O H
Melting Boiling
C6H12O6(aq) + 6O2(g) → 6CO2(g) + 6H2O(l) + (ΔH ) Carboxylic Structural point/ point/
acid formula °C °C
After the dough has risen, it is baked: the heat kills Methanoic HCOOH Ethanoic
9 acid 101
the yeast and the bread stops rising. acid
Methanoic acid H
O
Ethanoic O CH3COOH 17 118
New applications of biotechnology acid
H C
H C acid
Methanoic C
O H
A large number of firms throughout the world O H HO
are investing large sums of money in the newer Propanoic CH3CH2COOH −21 141
H C
biotechnology applications now in use. acid O H
» Enzymes can be isolated from micro-organisms Butanoic CH3CH2CH2COOH −6 164
and used to catalyse reactions in other processes. acid Propanoic acid
Ethanoic acid
For example, proteases are used in biological H H
H
detergents to digest protein stains such as blood Methanoic acid O Ethanoic acid O
and food. Also, catalase is used in the rubber H CO C
H C C C
H O H
industry to help convert latex into foam rubber. H C O H O
» Our ability to manipulate an organism’s genes to HO H H
H
C
H
C
make it useful to us is called genetic engineering. O H
This is being used, for example, to develop novel    H
plants for agriculture as well as making important Propanoic acid Butanoic acid
human proteins such as insulin and growth Ethanoic acid
hormone. H H H H H
H O Propanoic acid O
However, a word of caution is necessary. The new H C C OC H H CH C C C
biotechnologies may not be without dangers. For H C C O H O O H
example, new pathogens (organisms that cause H H O H   H C HC HC H
H O first
H four
disease) might be created accidentally. Also, new ▲ Figure 13.9 The displayed formulae of the
H H
pathogens may be created deliberately for use in members of the carboxylic acids
warfare. As you can imagine, there are very strict
Butanoic acid
guidelines covering these new biotechnologies, Propanoic acid
especially in the area of research into genetic Carboxylic acids
H H
H H H reacting as acids
Butanoic acid O
engineering. Methanoic
C C acid
C Cis present H in stinging nettles and
O
H H H
H C C C
ant stings. Ethanoic
O H
O acid,
H however, is theO most well
knownH H H
H H as it is the mainH constituent
C C C of C vinegar. Like
O H
other acids, ethanoic acid Haffects
H H
indicators and
will react with metals such as magnesium. However,
Butanoic acid
H H H
O
H C C C C
O H
H H H
211

[Link] 211 24/02/21 10:11 PM

11 organic chemiStry 2

whereas the mineral acids, such as hydrochloric Ethanoic acid also undergoes further typical
acid, are called strong acids, ethanoic acid is a reactions of acids with indicators turning, for
weak acid (Chapter 8, p. 118). Even though it is example, methyl orange to red.
a weak acid, it will still react with bases to form
salts. For example, the salt sodium ethanoate
(CH3COONa) is formed when ethanoic acid reacts Going further
with dilute sodium hydroxide.
Some interesting carboxylic acids
ethanoic acid + sodium → sodium + water We come across carboxylic acids in our everyday life.
hydroxide Aspirin is a frequently used painkiller. It is also able
to reduce inflammation and fever, and a low dose
CH3COOH(aq) + NaOH(aq) → CH3COONa(aq) + H2O(l) taken on a daily basis by people over the age of 50 may
prevent heart attacks.
Ethanoic acid also undergoes typical reactions of
Vitamin C, also known as ascorbic acid, is an essential
acids with metals and carbonates. In the case of
vitamin. Vitamin C is required by the body in very
the metal magnesium, the metal salt magnesium small amounts and it is obtained from foods. It is
ethanoate ((CH3COO)2Mg) and hydrogen are found in citrus fruits and brightly coloured vegetables,
produced. such as peppers and broccoli. Vitamin C prevents the
disease scurvy.
ethanoic acid + magnesium → m
agnesium + hydrogen
ethanoate
2CH3COOH(aq) + Mg(s) → (CH3COO)2Mg(aq) + H2(g)
Test yourself
Ethanoic acid reacts with carbonates such as 6 Describe the reaction that takes place between
sodium, producing the salt sodium ethanoate ethanoic acid and:
(CH3COONa), carbon dioxide and water. a calcium
b potassium carbonate
ethanoic acid + sodium → sodium + carbon + water c potassium hydroxide.
       carbonate ethanoate dioxide In each case, write a word equation as well as a
balanced chemical equation.
2CH3COOH(aq) + Na2CO3(s) → 2CH3COONa(aq) + CO2 + H2O(g)

11.9 Esters
Ethanoic acid will react with ethanol, in the Members of the ‘ester’ family have strong and
presence of a few drops of concentrated sulfuric pleasant smells. They have the general formula
acid acting as a catalyst, to produce ethyl CnH2n+1COOC xH2x+1. Esters are named after the acid
ethanoate – an ester. and alcohol from which they are derived:
conc
» name – alcohol part first, acid part second,
ethanoic + ethanol ethyl ethanoate + water
acid H 2SO4 e.g. propyl ethanoate
» formula – acid part first, alcohol part second,
CH3COOH(l) + C2H5OH(l)  CH3COOC2H5(aq) + H2O(l) e.g. CH3COOC3H7
This reaction is called esterification. Table 13.6 shows the actual arrangement of the
atoms in some of the members of this family.

212

[Link] 212 24/02/21 10:11 PM

11.9 Esters

▼ Table 13.6 The displayed formulae of some esters

Made from
Ester Alcohol Carboxylic acid Structure 3D model
Ethyl ethanoate Ethanol Ethanoic acid H O
CH3COOC 2H5 C2H5OH CH3COOH
H C C H H

O C C H
H
H H

Propyl methanoate Propan-1-ol Methanoic acid O

HCOOC 3H7 C3H7OH HCOOH H H H
H C

O C C C H

H H H

Methyl butanoate Methanol Butanoic acid H H H

O
C3H7COOCH 3 CH3OH C3H7COOH
H
H C C C C

H H H O C H

Many esters occur naturally and are responsible for

the flavours in fruits and the smells of flowers.
They are used, therefore, in some food flavourings
and in perfumes (Figure 13.10).
Fats and oils are naturally occurring esters
which are used as energy storage compounds by
plants and animals. They possess the same linkage
as PET but have different units (see p. 215).

▲ Figure 13.10 Perfumes contain esters

Test yourself
7 Which of the following organic chemicals are • Pentene, C5H10
carboxylic acids or alcohols? • Hexanol, C6H13OH
• Hexanoic acid, C5H11COOH State why you have chosen your answers.
• Butanol, C 4H9OH
• Octane, C 8H18 8 Write word and balanced chemical equations for
• Nonane, C9H20 the esterification of propanoic acid with ethanol.
• Methanoic acid, HCOOH

213

[Link] 213 24/02/21 10:11 PM

11 organic chemiStry 2

Practical skills
For safe experiments/demonstrations which Some statements in the student’s account have
are related to this chapter, please refer to the been underlined by the teacher.
Cambridge IGCSE Chemistry Practical Skills
Answer these questions to identify how the
Workbook, which is also part of this series.
account of the experiments could be improved.
Safety 1 In both cases, what strength of ethanoic acid,
● Eye protection must be worn. dilute or concentrated, and volume of acid,
5 cm3 or 50 cm3, would be used?
A student wrote the following account of two 2 In both experiments, what is the more
experiments they observed their teacher carrying scientifically correct word to use rather
out about the properties of carboxylic acids. than ‘bubbling’?
1 Some ethanoic acid was poured into a test 3 What was the gas that gave a squeaky
tube. A small piece of magnesium ribbon pop?
was added to the acid. Bubbling took place. 4 In experiment 2, how is the sodium
The test tube was corked and the gas carbonate added?
produced was tested using a lit wooden splint. 5 In experiment 2, how should the shaking
It gave a squeaky ‘pop’. The gas must be take place? Explain your answer.
oxygen. 6 In experiment 2, what was the gas that
2 Some ethanoic acid was poured into a test gave a milky colour with limewater?
tube. Some sodium carbonate was added to 7 Are there any other suggestions that you
the acid. Bubbling took place. The test tube could make to improve the account?
was corked and after about 10 seconds the
cork was removed and the gas was poured into
a test tube containing limewater. This test tube
was corked and shaken. The limewater went
slightly milky. The gas must be hydrogen.

11.10 Condensation The starting molecules for nylon are more

complicated than those for poly(ethene) and are
polymers called 1,6-diaminohexane and hexanedioic acid.
In Chapter 12 (p. 198), you studied the different Hexanedioic acid 1,6-diaminohexane
addition polymers produced from alkenes. Not all HOOC(CH2)4COOH H2N(CH2)6NH2
polymers are formed by addition reactions though.
Some are produced as a result of a different type H2N(CH2)6CONH(CH2)4COOH H2O
of reaction. In 1935, Wallace Carothers discovered
a different sort of plastic when he developed Amide link
the thermoplastic, nylon. Nylon is made by
reacting two different chemicals together, unlike The polymer chain is made up from the two
poly(ethene) which is made only from monomer starting molecules arranged alternately
units of ethene. Poly(ethene), formed by addition (Figure 13.11) due to these molecules reacting
polymerisation, can be represented by: and therefore linking up. Each time a reaction
takes place, the other product of the reaction,
–A–A–A–A–A–A–A–A–A–A– a molecule of water, is lost.
where A = monomer.

214

[Link] 214 24/02/21 10:11 PM

11.10 Condensation polymers

▲ Figure 13.11 A nylon polymer chain is made up from the

two molecules arranged alternately just like the two
different coloured poppet beads in the photo

This sort of reaction is called condensation

polymerisation. This differs from addition
polymerisation, where there is only one product.
Because an amide link is formed during the
polymerisation, nylon is known as a polyamide.
This is the same amide link as found in proteins
(p. 216). It is often called the peptide link. This ▲ Figure 13.12 Nylon fibre is formed by forcing molten
plastic through hundreds of tiny holes
type of polymerisation, in which two kinds of
monomer unit react, results in a chain of the We can obtain different polymers with different
type: properties if we carry out condensation
–A–B–A–B–A–B–A–B–A–B– polymerisation reactions between other monomer
molecules. For example, if we react ethane-1,2-diol
Generally, polyamides have the structure:
with benzene-1,4-dicarboxylic acid (terephthalic
O O O O O acid), then we produce a polymer called
C C N N C C N N C poly(ethyleneterephthalate) or PET for short.
H H H H Ethane-1,2-diol Benzene-1,4-dicarboxylic acid
HO(CH2)2OH HOOC(C6H4)COOH
Looking at this structure, it is easy to see that the
repeat unit of this polyamide is:
HO(CH2)2OCO(C6H4)COOH H2O
O O

C C N N Ester link
H H This ester link is the same linkage as in fats.
When nylon is made in industry, it forms as a solid Generally, polyesters have the structure:
which is melted and forced through small holes O O O O
(Figure 13.12). The long filaments cool and solid
C C O O C C O O
nylon fibres are produced which are stretched
to align the polymer molecules, and then dried. Like nylon, PET can be turned into yarn, which can
The resulting yarn can be woven into fabric then be woven. PET clothing is generally softer
to make shirts, ties, sheets and parachutes or than that made from nylon but both are hard
turned into ropes or racket strings for tennis and wearing. Because an ester link is formed during
badminton rackets. the polymerisation, PET is known as a polyester.

215

[Link] 215 24/02/21 10:11 PM

11 organic chemiStry 2

When this polymer is being used to make bottles, Amino acids are the building blocks of proteins.
for example, it is usually called PET. An interesting Similar to nylon (see p. 215), proteins are
feature of PET is that it can be converted back into polyamides as they contain the –CONH– group,
its monomers and so can be recycled. which is called the amide or, in the case of
proteins, the peptide link. Proteins are formed by
Test yourself condensation polymerisation.
9 Draw the displayed structures of the two Glycine Alanine
monomer units for the following polymer chain.
O O O O O
H H

C C N N C C N N C H 2N C COOH H 2N C COOH
H H H H H CH 3

10 Explain the differences between an addition

polymer and a condensation polymer.
H O H

H 2N C C N C COOH H 2O

11.11 Natural polyamides H H CH 3

Proteins are natural polyamides. They are A dipeptide

condensation polymers formed from amino acid (composed of two amino acids joined together)
monomers. Amino acid monomers have the general
structure shown below. R represents different types Protein chains formed by the reaction of many
of side chain. amino acid molecules have the general structure
shown below.
H R
O
N C C H H O R H H O
H H O H
N C C N C C N C C

There are 20 different amino acids and they R H H O R

each possess two functional groups. One is the
Further reaction with many more amino acids takes
carboxylic acid group, –COOH. The other is the
place at each end of each molecule to produce
amine group, –NH2. Two amino acids are glycine
the final protein (Figures 13.13 and 13.14). For a
and alanine.
molecule to be a protein, there must be at least
H 100 amino acids involved. Proteins make up some
R H H C H 15% of our body weight and, along with fats and
carbohydrates (such as starch and glucose), they
H2N C COOH H2N C COOH H2N C COOH are among the main constituents of food.
H H H
H O H O
General Glycine Alanine
structure N C N C N C

H O

▲ Figure 13.13 General structure of a protein

216

[Link] 216 24/02/21 10:11 PM

11.11 Natural polyamides

A chain S S

H 2N Gly Ile Val Glu Gln Cys Cys Thr Ser Ile Cys Ser Leu Tyr Gin Leu Glu Asn Tyr Cys Asn COOH

1 5 10 15
S
S
S S
B chain

H 2N Phe Val Asn Gin His Leu Cys Gly Ser His Leu Val Glu Al a Leu Tyr Leu Val Cys Gly Glu

1 5 10 15 20 Ar g

Gly

Phe
HOOC Thr Lys Pr o Thr Trp Phe

30 25

▲ Figure 13.14 The structure of a protein – human insulin (the different coloured circles represent different amino acids
in this protein)

Test yourself
11 How many amino acids have to be involved before
O H H
the biopolymer is called a protein?
12 a Give the molecular formula of the amino acid C C N
valine (see diagram). HO CH H
b During a condensation reaction involving this
H3C CH3
amino acid which two functional groups react?

217

[Link] 217 24/02/21 10:11 PM

11 organic chemiStry 2

Revision checklist
After studying Chapter 11 you should be able to: ✔ Describe the formation of ethanoic acid by the
✔ Write the general formulae for the homologous oxidation of ethanol with acidified potassium
series alcohols and carboxylic acids. manganate(VII) as well as by bacterial oxidation
during vinegar production.
✔ Name and draw the structural and displayed
✔ Describe the reaction of a carboxylic acid with
formulae of unbranched alcohols, including an alcohol to give an ester.
propan-1-ol, propan-2-ol, butan-1-ol and ✔ Name and draw the displayed formulae of the
butan-2ol, and carboxylic acids, as well as the unbranched esters which can be made from
products of their reactions containing up to four unbranched alcohols and carboxylic acids, each
carbon atoms per molecule. containing up to four carbon atoms.
✔ Deduce the structure or repeat unit of a
✔ State the type of compound present given the
condensation polymer from given monomers.
chemical name ending in -ol or -oic acid or from a ✔ Describe the differences between condensation
molecular, structural or displayed formula. and addition polymerisation.
✔ Describe the manufacture of ethanol by ✔ Describe and draw the structure of nylon (a
fermentation of glucose and the catalytic addition polyamide) and PET (a polyester).
of steam to ethene. ✔ Describe proteins as natural polyamides.
✔ Describe the advantages and disadvantages of the ✔ Draw the general structure of a natural
two methods for manufacturing ethanol. polyamide.
✔ Describe the combustion of alcohols. ✔ Describe and draw the structure of proteins.
✔ State the uses of ethanol as a solvent and a fuel.
✔ Describe the reactions of carboxylic acids with
metals, bases and carbonates including names
and formulae of the salts produced.

218

[Link] 218 24/02/21 10:11 PM

Exam-style questions

Exam-style questions 3 a Copy the following table and complete it by

giving the displayed formulae for ethanol and
ethanoic acid.
1 a The functional group of the homologous
series alcohols is –OH. Explain what is Ethane Ethanol Ethanoic acid
meant by the terms in italics.[4] H H
b Give the general formula of the homologous H C C H
series of alcohols. [1]
H H [4]
c Butan-1-ol is used as a solvent for paints. It
can be made by the hydration of but-1-ene.
b Describe a simple chemical test that
i Give an equation for the reaction that
could be used to distinguish ethanol from
takes place to produce butan-1-ol. [3]
ethanoic acid.[3]
ii Identify the reaction conditions for this
reaction to take place. [3] c i Identify the class of compound
d Butan-1-ol will undergo bacterial oxidation produced when ethanol reacts with
if left in the air. Give the name of the ethanoic acid. [1]
organic substance formed by this ii What catalyst is required for this
oxidation process and give its formula. [2] reaction?[1]
2 A piece of cheese contains protein. Proteins iii Give a word and balanced chemical
are natural polymers made up of amino acids. equation for this reaction. [4]
There are 20 naturally occurring amino acids.
The displayed formulae of two amino acids are
shown below. 4 a Ethanoic acid is a weak acid. Describe what
Glycine Alanine you understand by the term weak acid. [1]
H H
b Ethanoic acid will react with sodium
H 2N C COOH H 2N C COOH carbonate. Write a word and balanced
H CH3 chemical equation for the reaction. [4]
c Ethanoic acid will react with metals such
a Identify the type of polymerisation as magnesium. Write a word and balanced
involved in protein formation. [1] chemical equation for the reaction. [4]
b Give the molecular formulae of the two d Ethanoic acid will react with bases such as
amino acids shown. [2] sodium hydroxide.
c Sketch a displayed formula to represent the i What do you understand by the term
product formed by the reaction between ‘base’?[2]
the amino acids shown above. [2] ii Give another example of a base. [1]
iii Write a word and balanced chemical
equation for the reaction. [4]

219

[Link] 219 24/02/21 10:11 PM

13 Organic chemistry 2

5 a Identify which carboxylic acids and alcohols 6 a Identify the polymerisation process that is
you use to make the following esters: used to make both nylon and PET. [1]
i butyl methanoate [2] b Give the starting materials for making:
ii ethyl methanoate [2] i nylon [2]
iii propyl propanoate. [2] ii PET. [2]
b Identify which esters would be made using c Give the name and formula of the small
the following carboxylic acids and alcohols: molecule produced during the polymerisation
i ethanoic acid and butan-1-ol [1] reactions to produce both nylon and PET. [2]
ii methanoic acid and methanol [1] d Give the name of the chemical link that holds
iii propanoic acid and butan-1-ol. [1] together:
c Sketch the displayed formulae of the i nylon [1]
following esters: ii PET. [1]
i ethyl ethanoate [2]
ii propyl ethanoate. [2]

220

[Link] 220 24/02/21 10:11 PM