H2 Chemistry 9647

Alkanes

NYJC 2014

Alkanes
Lecturers: Ms Joanne Low and Mrs Zhuo (Mdm Tan Shuyun)
Contents
Alkanes (exemplified by ethane)
(i) Free-radical reactions
Hydrocarbons as fuels
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 reactions of ethane:
(i) Combustion
(ii) Substitution by chlorine and by bromine
(c) Describe the mechanism of free-radical substitution at methyl groups with particular
reference to the initiation, propagation and termination reactions
(d) 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

1. Introduction
1.1 Alkanes

belong to a homologous series of hydrocarbons (contain C and H atoms only)

are saturated (only single bonds between atoms, hence they contain maximum
number of hydrogens per carbon atoms)
are combustible but unreactive
There are two homologous series of alkanes:

Aliphatic alkanes (open-chained alkanes)

General formula: CnH2n+2
E.g.

CH3CH2CH2CH2CH3
Pentane C5H12

Alicyclic alkanes (closed-chained alkanes)

General formula: CnH2n
E.g.

Cyclobutane C4H8

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Cyclopentane C5H10

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nclature
1.2 Nomen
No.
N of C
atoms

IUPAC Name/
N
Molecular formula

Conde
ensed
form
mula

Metha
ane
CH4

CH
H4

Displayed
d formula
H
H

Ethane
C2H6

CH3C
CH3

Propa
ane
C3H8

CH3CH
H2CH3

Butane
C4H10

CH3 (CH
H2)2CH3

182

164

183

88

190

42

138

0.5

Boiling
point /oC

H
C

Melting
point /oC

2-methylp
propane
C4H10

CH(C
CH3)3

160

12

2,2-dimethyylpropane
C5H12

C(CH
H3)4

17

10

94

49

81

cyclopen
ntane
C5H10

H2
C
CH2

H2C
H2C

H2
C

cyclohexan
ne C6H12

H
C

CH2

H
C

H
H

H
H

H
H

H2C

CH2

H2C

CH2

C
H2

H
H

H
H

1.3 Alkyl g
groups

formed
d when one of the hy
ydrogen of the alkane
es is remov
ved
named
d by replaccing ane by
b yl
Aliphatic Alkane
A
neral formula: CnH2n+2
Gen
CH3 H
Methane
CH3CH2 H
Ethan
ne

Alkyl grroup
Ge neral formu
ula: CnH2n+1
CH3
Methyl
CH3CH
H2
Ethy
yl

A
Abbreviatio
on
Genneral symbol: R
Me

CH3CH2CH
C 2 H
Propan
ne

CH3CH2CH
C 2
Propyl

Pr

C
CH3CH2CH2CH2 H
ne
Butan

CH3CH2CH
H2CH2
Buty
yl

Bu

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Et

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Alkanes

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2. Bondiing in Alkanes
Bonding a
and molec
cular struc
cture of allkanes

C has 4 valence electrons and

a it has electron co
onfiguration: 1s22s222p2.
C atom
ms share ellectrons by
y forming 4 covalent bonds to achieve
a
no ble gas ele
ectronic
configu
uration.
Shape of the mollecule with respect to
o carbon: Tetrahedra
T
al (4bp, 0lp
p)

o carbon in alkanes
s
2.1. Hybridization of
W
What is hyb
bridization
n?

The concept of hybridisatio

on is usefu
ul in explaiining the s hape of
ular orbitals
s for moleccules.
molecu

Hybridiisation des
scribes the bonding atoms
a
from
m an atomss point of
view. It involves mixing off atomic orbitals to form
f
new hybrid
orbitals.

All the carbons inn alkanes are

a sp3 hyb
bridised.
Hence alkanes have carbonn with tetraahedral arrrangementt of CC aand CH bonds.
Each ccarbon is able
a
to form four sp
p3 hybrid orbitals
o
(by
y mixing oone 2s and three 2p
p
atomic orbitals)

bridised state):
s
C* (hyb
1s

fo
our sp3 hyb
brid orbitals
s

How?
e electron in
i the 2s orbital first g
gets excite
ed and it is
s promotedd to the 2p orbital.
1. The
2. Durring hybridisation, on
ne 2s and tthree 2p atomic
a
orbittals are hyybridised (m
mixed) to
3
form
m four sp hybrid orrbitals.
3. The
e four sp3 hybrid
h
orbittals form a tetrahedrral arrange
ement. (Boond angle = 109o)
4. Bon
nding will then occur when the sp3 hybrid orbitals ov
verlap withh orbitals of
o other
atom
ms.

groundstate
g
eC

heat

excitedsttateC

heeat

hybrridisedstateC

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Recall: Ov
verlap of orbitals
o
to
o form bon
nds (Chem
mical bond
ding chaptter)
Sigma
a () bonds
s are formed by head
d-on overllap of orbitals
e formed by
y side-on overlap off orbitals.
Pi () bonds are
All single bonds
s are sigm
ma bonds.

Example: Methane (CH4)

During hybridisattion, one 2s

2 and thre
ee 2p atom
mic orbitals are hybriddised (mixe
ed) to form
m
3
four sp
p hybrid orbitals.
o
3
Each s
sp hybrid orbital
o
will overlap he
ead-on witth one of th
he 1s orbittals of four H atoms.
four CH bond
ds are form
med.

s orbitall of H

on
orbital of C
n
ne sp33 orbit

Example: Ethane (C
C2H6)

The C atom forms four sp3 hybrid orrbitals.

c
atom
ms form a CC bo
ond by hea
ad-on overrlapping of one sp3
The tettrahedral carbon
orbital from each C atom.
The rem
maining sp
p3 orbitals of carbon form CH bonds by
b head-o
on overlapp
ping with a
1s orbiital of hydrrogen atom
m.

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Alkanes

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3. Physical Properties
3.1 Boiling point and melting point

Alkanes have relatively low boiling and melting points.

Alkanes are non-polar: C H bond is considered non-polar as C and H only
differ slightly in electronegativity. [electronegativity of C(2.5) and H(2.1) are
similar]
Have a simple molecular structure consisting of alkane molecules held
together by weak van der Waals forces.
Boiling or melting involves overcoming the weak van der Waals forces between
the alkane molecules.

Boiling point generally increase with an increasing number of C atoms.

C1 C4: gas
-

C5 C17: liquid

*at room
temperature

>C18: solid

When Mr increases, number of electrons increases.

Larger electron cloud becomes more polarisable.
Strength of intermolecular van der Waals forces increases.
More energy is required to overcome the van der Waals forces.

The greater the degree of branching (with the same number of C atoms), the
lower the boiling point.
Name

pentane

2-methylbutane

2,2-dimethylpropane
CH3

Structure

CH3CH2CH2CH2CH3

CH3CHCH2CH3
CH3CCH3

CH3
CH3

Boiling point /oC

36

28

10

Melting point /oC

130

160

17

Highly branched alkanes are more spherical in shape.

Smaller surface area of contact between molecules.
Strength of intermolecular van der Waals forces decreases.
Less energy is required to overcome the weak intermolecular forces.

The trend for melting point less regular than that of boiling point
- Branched alkanes can have lower or higher melting points than the straight chain
alkanes depending on the packing of the molecules in the solid
- Highly symmetrical branched alkanes allow the molecules to be packed more
efficiently in the solid and hence have unusually high melting point.
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3.2 Solubility
Alkanes are:
soluble in non-polar (organic) solvents like CCl4, benzene and ether (R-O-R).
- They can form van der Waals interactions with the non-polar solvent.
- The energy released during the formation of van der Waals forces with the nonpolar solvent is enough to overcome the van der Waals forces between the
alkane molecules and the van der Waals forces between the solvent molecules.

insoluble in polar solvents like water.

- They can only interact with water molecules via weak van der Waals bonds
- the energy released during the formation of weak van der Waals forces with
water is not enough to overcome the strong hydrogen bonds between water
molecules.
weak van der Waals between alkane molecules

alkane layer
water
layer

weak van der Waals

interactions
between alkane
and water molecules

strong hydrogen bonding between water molecules

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H2 Chemistry 9647

Alkanes

NYJC 2014

4. Chemical Properties

Alkanes are saturated and are generally unreactive because:

(i) The C-H bond is non-polar
They have no centres of electrical charge to act as electrophiles or
nucleophiles to attract polar reagents like H+, OH- or MnO4-.
(ii) The C-C and C-H bonds are relatively strong
C C: 350 kJ mol-1
C H: 410 kJ mol-1

Alkanes do, however, react with oxygen and halogens under appropriate conditions,
like in the presence of ultraviolet light or heat.

Alkanes undergo two main types of reactions:

(i)
Combustion
(ii)
Free Radical Substitution

(i) Combustion
Complete combustion
Alkanes burn in excess oxygen to form carbon dioxide and water. This reaction is
very exothermic, which accounts for their use as fuels.

Alkanes burn with a non-luminous blue flame with little or no soot if combustion is

complete.
General equation:
y
y
H2O
CxHy + (x + ) O2 x CO2 +
2
4

e.g. Complete combustion of hexane:

19
C6H14 (l) +
O2 (g) 6CO2 (g) + 7H2O (l)
2
Incomplete combustion
In a limited supply of oxygen, alkanes burn to form carbon monoxide, water and
soot (C).
e.g.

Incomplete combustion of methane:

2CH4 + 3O2
CH4 + O2

4CH4 + 5O2

2CO + 4H2O
C
+ 2H2O
(soot)
2CO + 2C + 4H2O
(soot)
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(ii) Substitution

Alkanes react with halogen (e.g. Cl2 and Br2) to form halogenoalkanes (alkyl halides)
when irradiated with ultraviolet light or heated.
No reaction takes place in the dark.
The mechanism for the halogenation reactions of alkanes is known as free radical
substitution.
Type of
reaction
Equation
Reagents
Conditions

Product
Observations

free radical substitution

CxHy (g) + Cl2 (g) CxHy-1Cl (g) + HCl (g)
Cl2
Ultra-violet light
sunlight
Heat may be supplied to initiate the reaction. Reaction
proceeds very slowly at room temperature.
chloroalkanes
Yellowish-green colour of Cl2 decolourises.
White fumes of HCl produced.

Example:
Write a balanced equation for the reaction of propane with bromine. Indicate clearly the
conditions and observations in this reaction.
C3H8 (g) + Br2 (l) C3H9Br (l) + HBr (g)
Conditions: UV light or heat
Observations: Reddish-brown Br2 turns colourless. White fumes of HBr formed.
Note:
Solvent is CCl4 (used when alkane and halogen is present in different phases)
Example: C3H8 (g) + Br2 (l)
Bromination takes place less readily than chlorination
because weaker C-Br and H-Br bonds are formed. (Refer to Group VII)
Fluorination is dangerously exothermic while iodination is slow and reversible.

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5. Reaction mechanism

A cchemical reaction
r
ta
akes place
e when old
d bonds are
a brokenn and new
w ones are
e
crea
ated.
Bon
nd cleavag
ge or bond fission is tthe breakin
ng of chem
mical bondss.
The
ere are two
o types of bond
b
fissio
on required
d for organic chemistrry mechan
nisms:
i)
ii)

Homollytic fissio
on
Hetero
olytic fission

5.1 Homolytic Fissiion

Homolytic fission ten

nds to occu
ur when the two bond
ded atoms are identic
cal or have
e
ectronega
ativities.
similar ele
When the bond bre
eaks, each
h of the bo
onded ato
oms takes one of th
he bonding
g
electrons.
Half arrrow :

Depictss the move

ement
of a sin
ngle electrron.

cals are fo
ormed in ho
omolytic fis
ssion.
Free radic
[Recall: A free radica
al is an ato
om or mole
ecule with an
a unpaireed electron. E.g. Cl]
A free radical is extre
emely reacctive becau
use the unpaired elecctron has a strong
tendency to
t pair up with
w anothe
er electron
n from anotther speciees.

Notte: How yo
ou draw your half a
arrows matter!
Arro
ows mustt start from
m the bon
nd and end
d
at tthe atom to
t clearly show thaat a single
elec
ctron is tra
ansferred from bon
nd to atom
m.

5.2 Hetero
olytic fissiion

Heterolyticc fission te
ends to occcur when one of th
he two bonnded atom
ms is much
h
more elec
ctronegative than th e other. (e
e.g. polar bonds)
When the bond brea
aks, the m
more electrronegative atom takees both th
he bonding
g
electrons to
t form an anion. Th
he counterp
part becom
mes a catio
on.
+

Full arrow
w:
Depicts th
he movem
ment
of an elecctron pair..

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4

5.3 Free-Radical Substitution (FRS) Mechanis

sm
M
Mechanism

D
Description

Initiattion
Cl bond under UV radiation to form
f
free Cl rad
dicals.
Homolyytic fission of Cl

uv

Cl

u.v.

Cl

Cl

Cl

vourable?
Why is this step not fav
CH3CH
H3
CH
H3CH2 + H
C-H bo
onds in alkanes are
a not broken as
a the C-H bond is much stronge
er than the Cl-Cl bond.
-1
-1
Note: B
BE(Cl-Cl) = 242 kJmol , BE(C-H
H) = 435 kJmol

Propa
agation

Cl + CH3CH2H

CH3CH2 + HCl

CH3CH
C 2Cl + Cl

CH3CH2 + ClCl

The cchlorine radical removes

r
a hydro
ogen atom from a ethane molec
cule to form a hy
ydrogen
chlorid
de molecule.
A high
hly reactive ethy
yl radical is produ
uced.

Why is this step not fa

avourable?
Cl + CH3CH2H
CH3CH2Cl + H
The fformation of a C-Cl bond is le
ess exothermic and hence les
ss favourable th
han the
forma
ation of a H-Cl bo
ond in the above
e mechanism.
Note: BE(H-Cl) = 431 kJmol-1, BE(C-C
Cl) = 340 kJmol-1

The e
ethyl radical reacts with a chlorrine molecule to
o produce chloro
oethane and a chlorine
c
radica
al.
The tw
wo steps are re
epeated till all th
he reactants hav
ve been used up or when radic
cals are
destro
oyed i.e. termina
ation step.

Termiination
CH3CH2 +

CH3CH2Cl

Cl

Cl + Cl
CH3CH2 + CH3CH2

The cchain reaction terminates when two

t
free radicals
s collide with eac
ch other.

ClCl
H3
CH3CH2CH2CH

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4

Exam
mple
Exam
mple
The cchlorination of p
propane in the presence of a limited amoun
nt of Cl2 1-cho
olorocyclohexane can be made from cycloh
hexane. Descrribe the
formss 2-chloroprop
pane as a possible pro
oduct. Suggest the reaction mechanism
m of its formatio
on.
mech
hanism of the re
eaction.
Free radical substiitution

Free radical substitution

Initiation

Cl

Cl

In
nitiation

u.vv.

Cl

Cl

Cl

Cl

u.vv.

Cl

Cl

Prropagation

Cl

HCl
Cl

Cl

Cl2
Te
ermination

Cl

C
Cl

Cl2
Cl

Cl

Note: For initiation s

step uv light is
i to be written in your answers but sometim
mes conditions like sunlight/he
eat can be state
ed as a conditio
on as
of a question fo
or free radical substitution.
s
part o

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5.4. Problems with Free-Radical Substtitution

In reality, a pure sam
mple of the chloroalka
ane (or bro
omoalkane
e) is seldom
m obtained
d because
of the follo
owing problems:

5.4.1 Multti-substitu
ution
Depen
nding on th
he relative amounts o
of halogen and alkane present and the tim
me allowed
d
for rea
action, a mixture of products wi ll be obtain
ned.
The re
eaction of CH
C 4 and Cl
C 2 is able to
o yield a mixture
m
of CH
C 3Cl, CH2 Cl2, CHCl3 and CCl4:

CH3Cl predominates when

n there is e xcess CH4.
CCl4 p
predominattes when there is exccess Cl2.
To avo
oid multisu
ubstitution, use an ex
xcess of allkane or a limited am
mount of Cl
C 2.
(This m
maximisess the proba
ability that C
Cl attacks
s CH4.)

Examplle
A possible producct for the chlorinatio
c
n of ethan
ne in the presence
p
oof excess chlorine iss
1,1-dich
hloroethan
ne. Sugges
st the mecchanism of the reactio
on.
Mechan
nism: Free Radical Substitutio
S
on

Initiatio
on
uv/ heat

Cl
C
Cl
Propagation

C
Cl + Cl

Termina
ation

(**Write a
at least 3, in
ncluding forrmation of t he halogen, product an
nd one posssible side product)

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5.4.2 Isomeric Products

In the case of alkanes with 3C, isomeric products are formed depending upon which
H atom is replaced.

Expected Ratio:

10%

90%

A simplified way to obtain the expected ratios is to count the number of hydrogens that
have the same chemical environment which will lead to the formation of a specific
product. (probability)
Example:
Draw all the possible monosubstituted products when a mixture of 2-methylbutane and
bromine is allowed to react in the presence of sunlight. State the ratio in which they are
formed.

Hd

Hd

Ha

Hb

Hc

Hb

Hc

Hd
Hd

Hc

Hd

Hd

Br

Br

Br
Br

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Example:
Draw all the possible monosubstituted products when a mixture of pentane and bromine is
allowed to react in the presence of sunlight. State the ratio in which they are formed.

Br

=
=

6
3

Br

:
:

4
2

:
:

Br

2
1

a) Draw the displayed formula of another isomer of C5H12 which reacts with bromine to
form only one monobrominated product.

H
H
H

C
H

Ans:

C
H

C
H

H
C

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6. Environmental Concern (Refer to Heterogenous catalysis in Kinetics, Page 30)

There are several environmental concerns regarding the use of hydrocarbons as fuels.
(i) Pollutants such as carbon monoxide, oxides of nitrogen and unburnt hydrocarbons
(soot) found in car exhaust can be removed from the car engines using catalytic
converter.

Pollutants
Carbon
monoxide

Oxides of
nitrogen
(NO2, NO)

Formation in
car engine
Incomplete
combustion of
fuel

Reaction of N2
with O2 at high
temperatures

Incomplete
Unburnt
hydrocarbon combustion of
fuel

Environmental/
Health Impact
Combines irreversibly
with haemoglobin and
makes it ineffective
as oxygen carrier in
the human body
suffocation or
blood poisoning
Catalyzes formation
of acid rain
Forms smog

Forms smog

Reaction for removal in catalytic

converter
Conversion of CO to CO2
Pt
2CO(g) + O2(g) 2CO2(g)

Conversion of NO to N2
Pt
2NO(g) N2(g) + O2(g)
2NO(g) + 2CO(g)
N2(g) + 2CO2(g)
Oxidation of unburnt hydrocarbon to
CO2 and H2O
e.g. 2C8H18(l) + 25O2(g)
Pt
16CO2(g) + 18H2O(l)

Note:
- The catalyst in the converters would be poisoned by the lead present in petrol.
Therefore, cars fitted with catalytic converters must use unleaded petrol.
- A honeycomb structure is used to maximise the surface area on which catalysed
reactions can take place.
(ii) Carbon dioxide and methane are greenhouse gases responsible for global warming
and climate changes. One of the major sources of carbon dioxide comes from burning
of fossil fuels for energy production; hence there is a need to find alternative fuels for
mankind.

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Summary of important concepts in Alkanes

Physical Properties of Alkanes:

Non-polar
Consisting of molecules held together by weak intermolecular van der Waals forces.
Soluble in non-polar (organic) solvents
Insoluble in polar solvents
Boiling point increases with number of carbons
o Number of electrons in the molecule increases.
o Polarisability increases,
o Strength of intermolecular van der Waals forces increases.
o More energy is required.
Branching decreases the boiling point.
o More spherical in shape
o Smaller surface areas of contact between molecules
o Strength of intermolecular van der Waals forces decreases
o Less energy is required

Chemical Properties of Alkanes:

Alkanes are unreactive because the C-H bond is non polar and relatively strong.
Carbon atoms in alkanes form four sp3 hybrid orbitals from hybridization of one 2s and three 2p
orbitals.
They form 4 sigma bonds () via head-on overlap of orbitals.
Complete combustion of alkanes produces carbon dioxide(CO2) and water(H2O).
Alkanes undergo reactions by a mechanism called free-radical substitution in the presence of
ultraviolet light or heat.
o

In reaction of ethane with bromine, the 3 stages in the mechanism are

(1) Initiation
Equation: Cl

Cl

u.v.

(2) Propagation
Equations:1st step - Cl
2nd step - CH3CH2

Cl

2CH3 CHH
2

Cl

(3) Termination
CH 3CH2
Equations:
Cl
CH 3CH2

Cl

CH3CH2

Cl

Cl
Cl

Cl
CH 3CH2

CH 3CH2

Cl

Cl
CH 3CH2

CH2 CH 3

HCl
Cl

Cl

2 Types of
Bond Fission

Occurs between
atoms of _______
electronegativities

Electrons in bond broken

goes to

(1) Homolytic
fission

Similar

One to each atom

Radicals

Different

Both electrons go to
more EN atom

Cation + Anion

(2) Heterolytic
fission

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CH3CH2

Arrows

Products

H2 Chemistry 9647

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Annex (For additional reading)

A1. Cracking
Cracking is a process of breaking down large alkane molecules into smaller alkanes and
alkenes.
There are two processes we can split alkane chains:
By high temperature (about 800oC) and pressure, known as thermal cracking.
By catalyst (Al2O3 and SiO2, 450 oC), known as catalytic cracking.
For example,
C10H22 C4H8 + C6H14
C14H30 C2H4 + C12H26
[Note TYS Pg 118, Qn 5a (N2005/III/8 Either) is no longer in syllabus]
A2. Hydrocarbons as Crude Oil
Fractional Distillation
Petroleum is a mixture of a very large number of different hydrocarbons; the most
commonly found molecules are alkanes (linear or branched), cycloalkanes and aromatic
hydrocarbons.
Raw oil or unprocessed ("crude") oil is not useful in the form it comes in out of the ground.
To make it useful, it must be separated into its components by fractional distillation as
shown in Figure 1.

Figure 1. Fractional distillation of crude oil. The fractionating column is cooler at the top than
at the bottom because the fractions at the top have lower boiling points than the fractions at
the bottom.
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Crude oil is fractionally distilled to give the following fractions.

Fraction

Length of Carbon

Uses

chain
Refinery

C1-C4

Fuel; domestic heating, gas cookers

Gasoline

C5-C12

Fuel in internal combustion engines

Kerosene

C12-C18

Fuel for jet engines

Diesel Oil

C18-C25

Fuel for transport and industrial

gases

heating
Residue

> C25

paraffin wax, lubricating oil, petroleum

jelly, bitumen

A3. Octane number (octane rating)

In a cylinder of a motor car engine, a mixture of petrol vapour (mostly C5 to C10 alkanes)
and the air is ignited by an electric spark, producing an explosive reaction which drives
the piston down.
Petrol rich in straight-chain alkanes (e.g. heptane) ignites very readily and explodes
rapidly, causing knocking of the engine and inefficient combustion.
Combustion of branch-chain alkanes (e.g. 2,2,4-trimethylpentane) is much smoother and
more controlled. It is a more efficient fuel and less likely to cause knocking.
A numerical representation of the antiknock properties of motor fuel, compared with a
standard reference fuel.
Heptane is assigned an octane number of 0.
2,2,4-trimethylpentane (iso-octane) is assigned an octane number of 100.
The octane number of a petrol is found by comparing its performance with a mixture of
heptane and 2,2,4-trimethylpentane.
The octane number of a sample of fuel is determined by burning the gasoline in an
engine under controlled conditions, e.g., of spark timing, compression, engine speed,
and load, until a standard level of knock occurs.
Gasoline that have high octane numbers denotes that they have good anti-knock
properties

Reference texts
1. Understanding Chemistry for Advanced level, Ted Lester, Janet Renshaw,
Chapter 19 [540LIS]
2. Chemistry for Advanced Level. Peter Cann, Peter Hughes, Chapter 23 [540CAN]

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