Teachers’ Copy

YISHUN JUNIOR COLLEGE

H2 CHEMISTRY 9729
Hydrocarbons – Alkanes

Content
1. Introduction
2. Nomenclature
3. Hybridisation of carbon
4. Isomerism
5. Physical properties
6. Preparation
7. Chemical properties
8. Environmental issues

Learning Outcomes
Candidates should be able to:
(a) recognise the general unreactivity of alkanes, including towards polar reagents
(b) describe the chemistry of alkanes as exemplified by the following of reactions of
ethane:
(i) combustion
(ii) free-radical substitution by chlorine and by bromine
(c) describe the mechanism of free-radical substitution with particular reference to the
initiation, propagation and termination reactions
(n) recognise the environmental consequences of:
(i) carbon monoxide, oxides of nitrogen and unburnt hydrocarbons arising from the
internal combustion engine and of their catalytic removal
(ii) gases that contribute to the enhanced greenhouse effect
(o) recognise that petroleum, a chemical feedstock, is a finite resource and the
importance of recycling

Reference Texts

o Understanding Advanced Organic and Analytical Chemistry: Kim Seng

Chan and Jeanne Tan
o Chemistry for Advanced Level: Peter Cannes and Peter Hughes

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1. INTRODUCTION

Organic chemistry is the chemistry of carbon compounds. The simplest

organic compounds are the hydrocarbons. Hydrocarbons are organic
compounds that contain only carbon and hydrogen. Although hydrocarbons
contain only two elements, these elements can be combined in many ways.
A saturated
Hydrocarbons hydrocarbon
contains only
C-C single
bonds while an
unsaturated
Saturated Unsaturated hydrocarbon
contains at
least one C=C
double or CC
triple bond.
Straight-chain Branched Cycloalkanes Alkenes Alkynes Arenes

Aliphatic Alicyclic
alkanes: alkanes
CnH2n+2 CnH2n

Alkanes are a homologous series of saturated hydrocarbons, which are

commonly found in crude oil (petroleum) and natural gas.
Alkanes form the backbone structure of organic compounds, where other
functional groups are appended and thereby imparting specific reactivity.

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2. NOMENCLATURE (Revision)
Learning outcome
Introduction to Organic Chemistry
(a) (i) interpret, and use the nomenclature, general formulae and
displayed formulae of alkanes

Alkanes have the suffix ‘–ane’.

Steps in naming alkanes
1. Locate the longest continuous carbon chain (parent chain)

Number of 1 2 3 4 5 6 7 8 9 10
C atoms

Prefix meth eth prop but pent hex hept oct non dec

2. Any other side chains or branches (alkyl groups, R groups) will be named
as prefixes
3. Number the parent carbon chain such that the smallest set of numbers
is used to identify the location of the branches
a) If the alkyl group occurs more than once, use the prefixes di-, tri-,
tetra- etc.
b) Arrange substituents in alphabetical order, ignoring prefixes such
as di-, tri-, tetra.
Exercise 1: Name the following compounds.
CH3

2-methylpropane

3,3-dimethylpentane

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3. HYBRIDISATION OF CARBON (Revision)

Learning outcomes
Introduction to Organic Chemistry
(d) describe sp3 hybridisation, as in ethane molecule
(e) explain the shape of, and bond angles in ethane in relation to σ
carbon-carbon bonds, as well as other analogous molecules.

The orbitals of an atom can mix and hybridise to form a new set of orbitals.
Hybrid orbitals have distinctive shapes and orientation, depending on the
number and type of atomic orbitals that have been mixed.

In alkanes, all the carbon atoms are sp3 hybridised.

Methane
As seen below, the three 2p orbitals of carbon combine with its 2s orbital to
form four sp3 hybrid orbitals. The resulting sp3 hybrid orbitals point towards the
corners of a regular tetrahedron. Hence the geometry with respect to each
carbon atom is tetrahedral (bond angle of 109.5°).

109.5°

2s
2px 2py 2pz Four sp3 hybrid orbitals

H
Each sp3 orbital then overlaps head-on with
the 1s orbital of the hydrogen atom to form
H
H 4 C-H  bonds.
H

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Ethane
Each carbon atom forms four sp3 hybrid orbitals, similar to that in methane.

One of the sp3 hybrid orbital overlaps head-on with the sp3 hybrid orbital of the
adjacent carbon atom to form a C-C  bond.

The remaining three sp3 hybrid orbitals will each overlap head-on with the 1s
orbital of hydrogen atom to form 3 C-H  bonds.

H H

H H
H H

4. ISOMERISM (Revision)
Learning outcome
Introduction to Organic Chemistry
(i) deduce the possible isomers for an organic molecule of known
molecular formula

4.1 Constitutional Isomerism

4.1.1 Chain isomerism
Chain isomerism exists in alkanes with more than 3 carbons.

Exercise 2: Draw the full structural formula and name all the isomers of C5H12.

pentane 2-methylbutane 2,2-dimethylpropane

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4.1.2 Positional isomerism

Positional isomerism exists in alkanes when the side chain is located at
different positions in the parent chain.

2-methylpentane 3-methylpentane

4.1.3 Functional group isomerism

Functional group isomerism exists in cycloalkanes since they have the same
molecular formula as alkenes.

Exercise 3: Draw the displayed formula and name all the isomers of C3H6.

cyclopropane propene

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4.2 Stereoisomerism
4.2.1 Enantiomerism
Alkanes can display enantiomerism if it contains a chiral centre i.e. the carbon
atom is bonded to 4 different groups, and there is no plane of symmetry within
the molecule.

Example:

3-methylhexane
Exercise 4: Draw the structures of the two enantiomers of 3-methylhexane.

4.2.2 Cis-trans isomerism

Cycloalkanes can exhibit cis-trans isomerism as a ring prevents rotation in a
similar manner as a double bond.

CH3

cis-1,2-dimethylcyclopropane trans-1,2-dimethylcyclopropane

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5. PHYSICAL PROPERTIES (Revision)

5.1 Melting and Boiling Points
At room temperature and atmospheric pressure, the first 4 alkanes (C1 to C4)
are gases; the next 13 alkanes (C5 to C17) are liquids while longer alkanes
(C18 and longer) are solids.

physical state at
alkane formula boiling point / oC
298 K
methane CH4 gas −162
ethane C2H6 gas −88.6
propane C3H8 gas −42.2
butane C4H10 gas −0.50
pentane C5H12 liquid 36.3
hexane C6H14 liquid 68.7
heptane C7H16 liquid 98.4
octane C8H18 liquid 126
nonane C9H20 liquid 151
decane C10H22 liquid 174
undecane C11H24 liquid 196
dodecane C12H26 liquid 216
pentadecane C15H32 liquid 271
eicosane C20H42 solid 344

Alkanes have simple molecular structure and are non-polar. Hence, The C-H bond is
considered non-
instantaneous dipole – induced dipole attractions exists between the alkanes polar as C and H
have similar
molecules. electronegativities
.
The melting and boiling points of alkanes only depend on the strength of the
instantaneous dipole-induced dipole attractions between the molecules, which
is dependent on:
 number of electrons in the molecule
The greater the number of electrons, the bigger the size of the electron
cloud, the more polarisable is the electron cloud, the stronger the
intermolecular instantaneous dipole-induced dipole attractions.
 surface area for contact of the molecule
The greater the surface area of contact possible between the molecules,
the greater the extent of instantaneous dipole-induced dipole. A straight-

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chain molecule will have a greater surface area of contact for

intermolecular forces to develop as compared to a branched molecule of
similar molecular size.

Exercise 5. The table below gives the boiling point of 3 molecules with the
molecular formula C6H14. Explain in terms of structure and bonding, the
differences in boiling point.
boiling
isomer structure
point / oC

hexane CH3CH2CH2CH2CH2CH3 68.7

3-methylpentane 60.3

2,2-dimethylbutane 49.7

All 3 compounds have simple molecular structure with weak instantaneous

dipole-induced dipole between molecules. The increase in branching of the
alkanes decreases the boiling point of the alkanes. All 3 compounds have the
same molecular formula, C6H14, which means they have the same number of
electrons. The decrease in the boiling point is due to the relative size of the
surface areas of the molecules. There is more extensive instantaneous dipole-
induced dipole between hexane molecules due to their greater surface area
of contact and hence the higher boiling point.

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5.2 Solubility
Alkanes, being non-polar, are insoluble in polar solvents such as water as they
cannot form hydrogen bonds with water. Thus the energy evolved when
instantaneous dipole-induced dipole attractions is formed between the alkane
and water molecules is insufficient to compensate the energy required to
overcome the instantaneous dipole-induced dipole attractions between the
alkane molecules and the hydrogen bonds between the water molecules.
However, they are soluble in non-polar solvents like tetrachloromethane, CCl4.

5.3 Density
As the size of the alkane increases, its molar mass increases and
consequently its density increases. However, the density tends towards
0.8 g cm−3. Because alkanes are less dense than water and insoluble in water,
alkanes in the liquid state floats on water.

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6. PREPARATION OF ALKANES

Learning Outcome
Hydrocarbons
(e) describe the chemistry of alkenes as exemplified, where relevant, by
the following reactions of ethene
(i) addition of hydrogen, steam, hydrogen halides and halogens

Addition of Hydrogen to Alkenes

Reagent: H2(g)
Conditions: nickel at high temperature or platinum at room
temperature
Type of reaction: addition reaction (or reduction)

heat

where R, R1, R2, R3 = H atoms or alkyl groups

Exercise 5:
Draw the structural formula of the alkane obtained in the following addition
reactions in the presence of nickel at high temperature.

(a)

+ H2(g) →

(b)

+ H2(g) →

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7. CHEMICAL PROPERTIES OF ALKANES

Learning outcome
Hydrocarbons
(a) recognise the general unreactivity of alkanes, including towards polar
reagents

7.1 Low Reactivity of Alkanes

Alkanes are organic compounds, which are very unreactive. Alkanes are
sometimes referred to as paraffins, a general name derived from the Latin
words param affinis meaning “little affinity”. Alkanes are chemically inert to
most reagents used in organic chemistry.

In general, alkanes show a relatively low reactivity as they are non-polar and
thus lack electron-deficient or electron-rich sites on the alkane molecules.
They are therefore inert towards polar molecules such as water, as well as
positive and negative ions such as OH− and H+.
In addition, the C−H and C−C bonds in alkanes are strong and they require a
large amount of energy to break.

7.2 Reactions of alkanes

Learning outcome
Hydrocarbons
(b) describe the chemistry of alkanes as exemplified by the following
reactions of ethane: (i) combustion; (ii) substitution by chlorine and by
bromine

7.2.1 Combustion (Revision)

Alkanes burn in excess oxygen to give carbon dioxide, water and heat.
The general equation for combustion of hydrocarbons applies:

y y
Cx Hy + (x + 4 ) O2 → xCO2 + 2
H2 O

When there is insufficient oxygen, incomplete combustion occurs and carbon

monoxide or even soot may be produced.

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7.2.2 Free-radical substitution with halogens

In the presence of ultraviolet radiation or strong heat, alkanes undergo free A substitution
reaction is one
radical substitution reaction with the halogens. that involves the
replacement of
an atom or a
Reagent: limited amount of Cl2 or Br2 group of atoms by
another atom or
Conditions: ultraviolet (uv) light or heat groups of atoms.

Type of reaction: free-radical substitution

Examples: CH4 + Cl2 → CH3Cl + HCl A free radical is an
atom or a group of
CH3CH3 + Br2 → CH3CH2Br + HBr atoms having an
unpaired electron.
Observation: X2 is decolourised and white fumes of HX is produced.

7.2.2.1 Mechanism of free-radical substitution

Learning outcome
Hydrocarbons
(c) describe the mechanism of free-radical substitution at methyl groups
with particular reference to the initiation, propagation and termination
reactions.

The mechanism of free-radical substitution, which is a chain reaction proceeds

homo- = same
through 3 stages – initiation, propagation and termination. The breaking -lytic = to break.
Homolytic = To
and forming of all the bonds in this mechanism are homolytic. break the
(covalent) bond
with the electron
equally split.
The mechanism below will explore the free-radical substitution mechanism in
the reaction between CH4 and Cl2.

Initiation A half arrow

denotes the
In the presence of UV light, chlorine molecules undergo homolytic fission to movement of a
single electron.
form chlorine radicals.

×× ••
× • •
× Cl × Cl •
×× ••

The C―C and C―H bonds in methane are not broken. The bond energy of
C―C and C―H are much higher, 350 kJ mol−1 and 435 kJ mol−1 respectively xx
x
−1 Cl x + Cl
(Cl―Cl bond energy is 244 kJ mol ). x xx

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Propagation
Free radicals are highly reactive. The chlorine radicals attack the methane Once a free
radical is
molecules to produce new radicals that will eventually lead to the formation of produced, a large
chlorinated products. number of
product
Cl + CH4 → CH3 + HCl molecules can be
formed before the
termination step.
CH3 + Cl2 → CH3Cl + Cl Hence a chain
reaction occurs.
Termination
Reaction terminates (ends) when two radicals combine to form a neutral
molecule. In actuality, there is
a low yield of
Cl + Cl → Cl2 termination
products.
In this example,
CH3+ CH3 → CH3CH3 CH3CH3 is produced
only in the
Cl + CH3 → CH3Cl termination step,
and has a very low
yield compared to
Key points to include when describing free radical substitution CH3Cl (which is
produced in
propagation).
 Name of mechanism: Free radical substitution
 Reaction conditions: UV light
 Label the 3 stages: initiation, propagation, termination
 Construct equations for each stage
o use of half arrows to denote movement of electrons in the initiation
stage
o write enough equations until the required product is formed in the
propagation stage
o at least 2 equations for termination stage

Note:
1. The chloromethane formed could undergo further substitution to give a
For e.g., for the
mixture of products.
first reaction:
CH3Cl + Cl2 → CH2Cl2 + HCl CH3Cl + Cl→

CH2Cl2 + Cl2 → CHCl3 + HCl CH2Cl + HCl

CH2Cl + Cl2 →
CHCl3 + Cl2 → CCl4 + HCl
CH2Cl2 + + Cl

2. Thus, free-radical substitution is not a highly reliable method to prepare

alkyl halides as the reaction can yield a mixture of products. The
proportions of the different products formed depend on the proportions of
halogen and alkane used.

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 If an excess of alkane is used, the mono-substituted product will

predominate.
CH3CH3 + Cl2 → CH3CH2Cl + HCl

 If an excess of halogen is used, the fully substituted product will

predominate.
CH3CH3 + 6Cl2 → CCl3CCl3 + 6HCl

Exercise 6
Propane was reacted with limited bromine in the presence of ultraviolet light.
Mono-brominated propanes were obtained.

(a) Draw the structures and name the 2 mono-brominated propanes that
can be formed.

1-bromopropane 2-bromopropane

(b) Write a balanced equation for the formation of one of the mono-
brominated propanes in (a).

CH3CH2CH3 + Br2 → CH3CHBrCH3 + HBr

OR CH3CH2CH3 + Br2 → CH3CH2CH2Br + HBr

(c) Describe the mechanism for the formation of the mono-brominated

propane in (b).
Using the formation of 2-bromopropane:
Free radical substitution

Initiation:
Propagation:

CH3CH2CH3 + Br CH3CHCH3 + HBr

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CH3CHCH3 + Br2 CH3CHBrCH3 + Br

Termination:

Br + Br Br2

(d) What is the approximate ratio of the yield of the mono-brominated

propanes in (a)?

The 6 circled H atoms have the same chemical environment. The 2 squared
H atoms have the same chemical environment but this environment is different
from the circled ones.
Assuming that substitution is fully random (the bromine radicals are non-
selective) and that there are no other considerations for the reaction, the ratio
of 1-bromopropane to 2-bromopropane = 6 : 2 = 3 : 1.

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7.2.2.2 Relative rates and reactivities of free radical substitution

For free radical substitution of alkanes by halogens, for example:

CH4(g) + X2(g) → CH3X(g) + HX(g)

rate of reaction is in the order: F2 > Cl2 > Br2 > I2

halogen reactivity ∆H / kJ mol−1

reaction is vigorous even in the dark

fluorine −479
and at room temperature.

reaction occurs only when reactants

chlorine −117
are exposed to UV light or heated.
reaction occurs only when reactants
bromine −43
are exposed to UV light or heated.

iodine no reaction occurs. +22

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Exercise 7
(a) Using the bond energy data below, calculate the enthalpy change of
reaction for the first and second steps in the propagation stage for the
free radical substitution of methane and the halogens.
CH4(g) + X2(g) → CH3X(g) + HX(g) for X = F, Cl, Br and I.

[F-F: 158 kJ mol−1, Cl-Cl: 244 kJ mol−1, Br-Br: 193 kJ mol−1, I-I: 151 kJ mol−1
C-F: 485 kJ mol−1, C-Cl: 340 kJ mol−1, C-Br: 280 kJ mol−1, C-I: 240 kJ mol−1,
H-F: 562 kJ mol−1, H-Cl: 431 kJ mol−1, H-Br: 366 kJ mol−1 , H-I: 299 kJ mol−1,
C-H: 410 kJ mol−1]

For each reaction:

enthalpy change / kJ mol−1

halogen, X step 1 step 2
X + CH4 → CH3 + HX CH3 + X2 → CH3X + X

fluorine +410 – 562 = −152 +158 – 485 = −327

chlorine +410 – 431 = −21 +244 – 340 = −96

bromine +410 – 366 = +44 +193 – 280 = −87

iodine +410 – 299 = +111 +151 – 240 = −89

(b) Hence, suggest why alkanes do not undergo free radical substitution
with iodine.

The first step of the propagation stage is endothermic. Thus reaction

with iodine does not occur (or occurs very slowly).

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8. EFFECTS OF HYDROCARBONS ON THE ENVIRONMENT (self-

reading)
Learning outcomes
Hydrocarbons
(n) recognise the environmental consequences of:
(i) carbon monoxide, oxides of nitrogen and unburnt hydrocarbons
arising from the internal combustion engine and of their catalytic
removal
(ii) gases that contribute to the enhanced greenhouse effect

Crude oil and its refined products are responsible for air pollution and water
pollution. The main components of crude oil are hydrocarbons. Crude oil also
has varying proportions of sulfur-, nitrogen- and oxygen-containing
compounds.

8.1 Consequences of combustion of fuels

The table on below shows the type of air pollutant present in a typical car
exhaust and their effects on health and the environment.

pollutant percentage by environmental effects & health issues

volume (%)
carbon dioxide 9 This causes the greenhouse effect,
which leads to global warming.
This is produced by the incomplete
combustion of fuels. It is very toxic and
carbon as it binds tightly to haemoglobin in
4 – 10 blood to form carboxyhaemoglobin.
monoxide
As a result, blood is not able to
transport oxygen, leading to oxygen
starvation
These are also produced by the
incomplete combustion of fuels. They
unburnt can cause liver damage and even
0.2 cancer. In strong sunlight, they
hydrocarbons
combine with nitrogen oxides to form
photochemical smog, which causes
respiratory problems.
oxides of They are soluble in rainwater and
0.4 contribute to the formation of acid rain.
nitrogen
Acid rain damages trees, aquatic life
sulfur dioxide 0.006 and buildings.
These are found in smoke. Smoke
carbon and lead 0.0001 attacks the lungs. The lead
particulates can cause brain damage.

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A catalytic converter is a device used to reduce the toxicity of emissions from

an internal combustion engine. It works by using a catalyst (platinum,
palladium or rhodium) to stimulate a chemical reaction in which toxic by-
products of combustion are converted to less toxic substances. The following
reactions occur:

 Reduction of nitrogen oxides to nitrogen and oxygen with rhodium

catalyst: 2NOx → xO2 + N2
 Oxidation of carbon monoxide to carbon dioxide with platinum and
palladium catalyst: 2CO + O2 → 2CO2
 Oxidation of unburnt hydrocarbons to carbon dioxide and water with
platinum and palladium catalyst.

8.2 Greenhouse Effect and Global Warming

Carbon dioxide and water vapour have important roles to play in maintaining
a fairly uniform temperature on the earth’s surface. These gases allow the
visible radiation from the sun to reach the earth’s surface, but trap some of the
infrared radiation (heat), which is emitted by the earth. Heat energy, thus
retained in the atmosphere produced a warming effect, called the greenhouse
effect. Gases such as carbon dioxide, methane and nitrous oxide (dinitrogen
oxide, N2O), which absorb infrared radiation given off by the earth and prevent
heat from escaping into outer space are called greenhouse gases.

Scientists are concerned that the earth is overheating. Human activities such
as burning fossil fuels and the large-scale cutting down of forests are causing
some greenhouse gases, especially carbon dioxide to build up rapidly in the
atmosphere at a faster rate than photosynthesis can remove the excess gas.

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The effect of carbon dioxide build-up is an increase in the earth’s average

temperature. This phenomenon is called global warming.

It has been estimated that unless action is taken to reduce carbon dioxide
emissions into the atmosphere, the earth’s temperature could rise by 2 °C to
4 °C by the year 2030. This could result in significant changes in climate.
Patterns of rainfall and snowfall worldwide are expected to change. Many
plants and animals may not be able to adjust to such changes in climate. Other
possible consequences of global warming include the melting of glaciers and
large quantities of ice in the North and South Poles. This will cause sea levels
to rise and the flooding of many low-lying coastal areas.

In recent years, along with political actions such as the ratification of the Paris
Agreement, there has been significant scientific research and development
performed towards reducing the rate of consumption of fuels, in particular
through the development of alternative renewable energy and hybrid and
electric vehicles.

9. PETROLEUM (self-reading)
Learning outcomes
Hydrocarbons
(o) recognise that petroleum, a chemical feedstock, is a finite resource
and the importance of recycling

9.1 Cracking
Due to the advancement of automobiles by the end of the 20th century, the
demand for petroleum (crude oil) has become much greater. Petroleum,
extracted from beneath the ground and sea are usually long-chain alkanes.
Thus, methods have been developed to convert the more abundant, longer
chain alkanes into shorter units.

Cracking is a process which longer chain molecules are broken down into
shorter ones.
Example: C22H46 → C10H22 + C12H24 OR C22H46 → C12H26 + 5C2H4

There are two different cracking methods:

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1. Thermal cracking
It involves heating the alkanes at temperatures of about 800 ⁰C. The high
temperature provides sufficient energy for the homolytic fission of the C-C
bonds in alkanes. The reaction proceeds by free radical substitution.
2. Catalytic cracking
The alkane is heated to about 500 ⁰C and passed over a catalyst (a
mixture of aluminium and silicon oxides).

9.2 Reforming
The demand for branched-chain, cyclic and aromatic hydrocarbons as
components of high octane petrol is further satisfied by reforming straight-
chain alkanes.

Reforming changes straight-chain alkanes into branched-chain alkanes and

cycloalkanes, without the loss of carbon atoms.

Example:

9.3 Non-renewability and the importance of recycling

Despite the continual search and drilling for petroleum, it is estimated that the
global oil reserves will run out in 50 years (by 2065) if consumption stays in
the current rate. The decline in oil reserves necessitates effort to both develop
alternative forms of energy and to reduce the rate of consumption.

In that respect, environmental efforts in everyday life can add up. Plastic
products, for example, is one of the major uses for oil. Despite the
convenience and low price, however, plastic wastes contribute greatly to
pollution, due to its non-biodegradable nature. There are, in fact, many simple
and affordable environmental practices to reduce the reliance on plastics.

 Usage of reusable bags rather than plastic bags in grocery shopping

 Reduce the amount of packaging used for gifts
 Dispose plastic bottles (and aluminium cans) in recycling bins.

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Similar recycling efforts exist for other products, such as paper and aluminium.

In summary, recycling can be a useful method to reduce the use of plastics.

However, despite the economic and environmental benefits, the significant
challenges remain to be in altering social behaviour, especially in relation to
the willingness for residents to properly dispose recyclable wastes, and to be
willing to create a greater market for recycled goods rather than virgin
materials (for example, to purchase recycled foolscap paper versus the non-
recycled version).

“Earth provides enough to satisfy every man’s needs, but not

every man’s greed.” – Mahatma Gandhi

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