Organic Chemistry
Crude oil is a complex mixture of hydrocarbons (compounds containing hydrogen and carbon
only). It forms a valuable resource, both as the origin of many types of fuel, and as the starting
point for petrochemicals (plastics, detergents, solvents etc).
However, it must first be separated into mixtures with a much narrower boiling range.
In industry, crude oil is separated by FRACTIONAL DISTILLATION in a continuous process, taking
off the samples at different levels from the fractionating column. The dissolved gases come out of
the top, and the boiling points rise as one goes down the column. Note that the process does not
produce single substances, but less complex mixtures than in crude oil. A simplified diagram is
shown below:
• The Crude oil is initially heated and evaporated.
• The small molecules have a low boiling point and rise to the top of the tower.
• As the tower is descended the molecules get longer and have a higher boiling point and so
condense at higher temperatures.
There is a problem with the fractional distillation of crude oil;
• it produces too many of the less useful long chained fractions.
The products obtained from oil are invaluable to society, providing transportation fuels (cars,
planes), plastics, pesticides, detergents — a huge range of petrochemicals.
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There is an environmental cost to this. Extraction of oil may pollute the environment (e.g. in
Alaska). Transport of oil by pipeline (leaks in Siberia) and tanker (routine spillages, major accidents
from Torrey Canyon to Esso Valdez) is hazardous, and is bound to result in problems.
Some substances obtained from oil have their own environmental problems:
Petrol, diesel: greenhouse effect, air pollution (nitrogen oxides, carbon monoxide, unburnt
hydrocarbons, particulates)
Plastics: most are not biodegradable (not broken down by bacteria in the environment), and so
last for very long periods in landfill sites. When burnt some give toxic fumes, so safe disposal,
especially of packaging, is difficult.
Carbon compounds
Carbon always forms four bonds and hydrogen forms one bond. For
example: H H H H H
H—C—C—C—C—C—H
H H H H H Pentane
The simplest carbon compounds are the hydrocarbons (defined as compounds which contain
carbon and hydrogen only).
The molecular formula of a compound shows how many of each type of atom there are in a
molecule. For pentane (above) this is C5H12.
The displayed formula of a compound shows all the bonds between the atoms in a molecule (as
shown for pentane and cyclobutane above).
ALKANES
Most of the hydrocarbons present in crude oil are alkanes.
The alkanes are said to form a homologous series, that is a series of organic compounds with the
same general formula and similar chemical properties.
The general formula for alkanes is CnH2n+2.
Each member (after the first) differs from the one before by addition of a –CH2– group.
The physical properties of a homologous series usually show a regular trend.
For example, their boiling points increase steadily along the series; this is because, as the
molecules get larger, the attractions between molecules increase and so take more energy to
break.
The alkanes may be defined as hydrocarbons of general formula CnH2n+2.
You should learn the names and structures of the first five members:
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H
H H H H H HH H H
H—C—H H—C—C—H H—C—C—C—H H—C—C—C—C—H
H H H HH H HH H H
methane CH4 ethane C2H6 propane C3H8 butane C4H10
Pentane, C5H12, is shown at the top of this page.
In alkanes the four bonds on each carbon are directed to the corners of a tetrahedron.
Isomers
Alkanes with four or more C atoms can show isomerism.
Isomerism: when two or more different compounds have the same molecular formula but
different
structural they are called isomers. For example there are two compounds of formula
formula, C4H
10:
H H H
H H H H H —C—C—C—H
H—C—C—C—C—H H H
HH H H H —C— H
H
butane methylpropane
The one on the right is a branched-chain compound (i.e. the carbon atoms are not all in a row).
For C5H12 there are three isomers, two of which are branched:
CH3 CH3
CH3–CH2–CH2–CH2–CH3 CH3–CH2–C–CH3 CH3–C–CH3
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H CH3 pentane methylbutane
dimethylbutane
Reactions of Alkanes
Alkanes are widely used as fuels.
When they burn in air they form waste gas (carbon dioxide and water vapour), and the reaction
gives out heat to the surroundings (exothermic).
e.g. CH4 + 2 O2 CO2 + 2H2O (combustion of natural gas)
C5H12 + 8 O2 5CO2 + 6H2O C8H18 +
12½O2 8CO2 + 9H2O
In a restricted supply of air, carbon monoxide is formed: this is highly toxic (and particularly
dangerous since it has no colour or smell). Carbon monoxide is poisonous because it reduces the
capacity of blood to carry oxygen by bonding to haemoglobin.
During the combustion of fuels such as petrol and diesel, sulphur dioxide and nitrogen oxides may
also be formed. These gases are pollutants which contribute to acid rain.
Apart from combustion, alkanes are very unreactive.
They will however react with chlorine and bromine in the presence of sunlight.
CH4 + Cl2 CH3Cl + HCl
C2H6 + Br2 C2H5Br + HBr
Catalytic Cracking
Cracking: this is an example of a thermal decomposition (a reaction in which a substance is
heated until it breaks down into other substances).
When an alkane is cracked, by passing its hot vapour over a catalyst, it splits into a shorter-chain
alkane and an alkene:
long-chain alkane shorter-chain alkane + alkene (or hydrogen)
e.g. C10H22 C8H18 + C2H4
or C3 H 8 C3 H 6 + H2
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Conditions for Catalytic Cracking – Temperature 600-700 oC
Catalyst SiO2 or Al2O3
Importance of Catalytic Cracking
Cracking is important because;
(a) it produces valuable alkenes, which are the starting point for
petrochemicals; (b) it also gives shorter alkanes, which are more useful as
fuels.
We can illustrate this using displayed formulae, for cracking pentane, the fifth alkane:
H H H H H H H H H H
H—C—C—C—C—C—H H—C—C—C—H + C C
HH HHH H H H H H pentane propane + ethene
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