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Hydrocarbons
Cracking and Isomers
Catalytic cracking
Large hydrocarbon molecules are broken down into smaller useful hydrocarbon molecules:
C10H22
decane
C8H18 + C2H4
octane ethene
Catalytic cracking
Catalysts used are:
Silica (silicon dioxide) Alumina (aluminium oxide)
Molecular formula
SiO2
Al2O3
H
H
H C
H
H C
H
H C
H
H C
H
H C
H
H C
H
C
H
C H
C H
C H
decane C10H22 H H C H H C H C H H C H H C H H C H H C H
Catalyst at high temperature: 650C Heat energy used to break carbon to carbon bonds
H C H H +
H C
H C H
H
Octane
Ethene
An unsaturated hydrocarbon
A saturated hydrocarbon
H H C H
H C H
H
C H
H
C H
H C H
H C H
H C H
H C H
H C H
H
C H H
decane C10H22 H
H
Heat This energy hydrogen used atom to break can move carbon here to carbon to form bonds a new C join H bond to produce Two electrons form a carbon C to H bond breaks octane to carbon double bond
H C
H
Octane
H C
H
H C
H
H C
H
H C
H
H H ++ C
H
C
H
C H
C H
C H
A saturated hydrocarbon
Isomers
Isomers are chemical substances which have the same molecular formula but have different structural formulae A structural formula shows the arrangement of different atoms or groups of a molecule in space Hydrocarbons such as members of the alkane series which have four or more carbon atoms form isomers
The number of possible isomers increase as the number of carbon atoms increase
Isomers may have different functional groups e.g. cyclobutane and butene are isomers
H
H C H H H H
H H H H H C C C C H
C
H
C C H
H
iso-butane
H H H H
n-butane
A straight chain hydrocarbon
A branched hydrocarbon
H C4 H H H
H C 1 C2 C3 H
H C5 H H H
H C4 C3 C2 C1 H
H
H H
H C5 H H
Carbon atom 2 is joined to carbon atoms 1, 3 and 5 by three carbon to carbon single bonds
C1
H
C2
H
C3
H
C4
H
C5
H
C6 H
H H H H
2
H H C
H
4
H H
C C C H
H H
2
Hydrocarbon A H H C
1
H C
C5 H C H H
H H
H H Hydrocarbon B
C HH
HH C H H H H H C H
1
H
H H
2
C C
H H
2
Hydrocarbon C
H
3
H H
3
C C H
H H
C C
C H H
H H
C H
H H
H C1 H
Hydrocarbon D Hydrocarbon E H H The correct answer is A and E as they are both the same straight chain molecule All the other molecules are different branched isomers
C1
C2
C3
C4
C5
C6 C
4
C C
Hydrocarbon A C5 C C C C
Hydrocarbon B
4
C
C C C C C C Hydrocarbon C C C
4
C1 Hydrocarbon D
Hydrocarbon E
The correct answer is A and E as they are both the same straight chain molecule All the other molecules are different branched isomers
Formula Number of
C4H10
C5H12 C6H14 C7H16
4
5 6 7
2
3 5 9
Octane
Nonane Decane Dodecane Pentadecane Icosane Triacontane
C8H18
C9H20 C10H22 C12H26 C15H32 C20H42 C30H62
8
9 10 12 15 20 30
18
35 75 355 4,347 366,319 4,111,846,763
Homologous series
H C H C
H C H Cycloalkanes
C3H6
Same molecular formula
H H
Propene
C3H6
C C C H H H
Alkenes
Key Websites
1. Catalytic cracking: http://bbc.net.uk/schools/gcsebitesize/chemistry/usefulproductsoil/oil_and_oilprod uctsrev7.shtml
http://www.chemguide.co.uk/physical/catalysis/petrochem.html http://en.wikipedia.org/wiki/Cracking_(chemistry) http://www.uyseg.org/catalysis/petrol/petrol2.htm
http://science.howstuffworks.com/oil-refining5.htm
Mr D. Shand 2006
Work address: Chemistry Department Harris Academy Dundee DD5 4HE Tel No. 01382 435700