HYDROCARBONS

ALKANES
 Learning objectives
• What are Alkanes?
• Sources of Alkanes: Petroleum
• Fractional Distillation of crude oil
• Global warming
• Reactions of Alkanes
• Combustion
• Substitution: Free radical
 Alkanes
• Alkanes are the name of a type of chemical that makes up the compounds in
crude oil.

• They are hydrocarbons (contain only hydrogen and carbon) and form a series of
increasing molecular weights.
 Alkanes: Saturated Hydrocarbons
• Alkanes are saturated hydrocarbon containing only carbon-carbon
single bond in their molecule. They are also called Paraffins. At high
temperatures and pressure do undergo some reaction. The Alkanes
may be divided as:

• Open chain
• Cycloalkanes
 Alkanes
We can work out a general formula for any alkane it is:

CnH2n+2
• where n is the number of carbon atoms
• and 2n+2 is the number of hydrogen atoms
Hybridisation : sp3
Petroleum – a source of hydrocarbons
• Petroleum, which is also called crude oil, or mineral
oil, is the main source of hydrocarbons.
• The conversion of crude oil into useful products is
called refining and is carried out at an oil refinery.
 Fractional Distillation of crude oil

1. Crude oil is heated

2. Hydrocarbons
evaporate
3. Fractionating
column is hotter at
the bottom / cooler
at the top
4. Vapours condense
at their boiling
points / at different
levels.
 Boiling points
Hydrocarbon Formula State / boiling
point(°C)
Methane CH4 Gas / -161

Ethane C2H6 Gas / -89

Propane C3H8 Gas / -42

Butane C4H10 Gas / -1

Cracking : Alkanes
 Types of cracking
• Steam/Thermal cracking
• High temperature and pressure

• Catalytic cracking
• (Relatively) Low temperature and pressure
• Used in the production of petrol
Chemical properties
• Alkanes are generally unreactive compounds. Non-polar – neither
attacked by electrophiles nor nucleophiles
• They do not react with acids or alkalis.
• But shows two important reactions:
i) Combustion
ii) Substitution reactions
 Combustion
• They burn with a clean blue flame if there is plenty of available
oxygen to react with.
This is known as complete combustion.
• With an adequate supply of air they react to form carbon dioxide
and water.

Methane + oxygen water + carbon dioxide

CH4 + 2O2 2H2O + CO2

 Incomplete combustion
• In the absence of an adequate supply of air, alkanes
may react to form carbon monoxide and water.
• Carbon monoxide is a toxic gas as it leads to
suffocation if inhaled as it combines with
haemoglobin to form a more stable compound than
oxy- haemoglobin.

Methane + oxygen water + carbon monoxide

2CH4 + 3O2 4H2O + 2CO

Combustion: General Equation
 Significance: Combustion
• To generate electricity in power stations
• To heat our homes and cook our food
• To provide energy needed in industrial processes
• To provide power for ships, aeroplanes,trains, cars etc
Catalytic Converter
 Reaction of Organic Compounds
• During the organic reaction, chemical bonds have to be broken in order
that new compounds may be formed.
- the breaking of chemical bonds is called fission.
 BREAKING COVALENT BONDS

There are 3 ways to split the shared electron pair in an unsymmetrical covalent bond.

UNEQUAL SPLITTING
produces IONS
known as HETEROLYSIS or
HETEROLYTIC FISSION

EQUAL SPLITTING
produces RADICALS
known as HOMOLYSIS or
HOMOLYTIC FISSION

• If several bonds are present the weakest bond is usually broken first
• Energy to break bonds can come from a variety of energy sources - heat / light
• In the reaction between methane and chlorine either can be used, however...
• In the laboratory a source of UV light (or sunlight) is favoured.
 HOMOLYTIC FISSION

• Homolytic fission: two shared electrons of the covalent

bond are split equally between the two atoms joined by
the bond.
• Also known as homolysis.
• One electrons goes to X and the others goes to Y.
• The resulting species is called free radicals.
• Free radicals: It has unpaired electron and is very reactive.
 WHAT ATTACKS ALKANES?
ALKANES ARE RELATIVELY UNREACTIVE ORGANIC COMPOUNDS

ALKANES CONTAIN TWO BOND TYPES

C-H and C-C

Both bonds are single – no electron rich areas like alkenes

Bonds are non-polar - no electron deficient areas

Free radicals are very reactive and attacks - substitution

FREE RADICAL SUBSTITUTION

Free radical - Substitution reaction
• This reaction takes place only in certain conditions.
• Alkanes doesn’t react with chlorine in the dark but
reacts with it in the presence of sunlight. This is a
photochemical reaction.
• This type of reaction is only for saturated
hydrocarbons.
• It involves the substituting of one atom with another ,
in this reaction chlorine replaces hydrogen atoms in
alkanes, this is known as a substitution reaction.
 CHLORINATION OF METHANE

Initiation Cl2 ——> 2Cl• RADICALS CREATED

The single dots represent UNPAIRED ELECTRONS

During initiation, the WEAKEST BOND IS BROKEN as it requires less energy.

There are three possible bonds in a mixture of alkanes and chlorine.

412 348 242

Average bond enthalpy kJ mol-1

The Cl-Cl bond is broken in preference to the others as it is the weakest and
requires requires less energy to separate the atoms.