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Topic 6

Hydrocarbons
Cracking and Isomers

Catalytic cracking
Large hydrocarbon molecules are broken down into smaller useful hydrocarbon molecules:

C10H22
decane

C8H18 + C2H4
octane ethene

Thermal cracking high temperature Catalytic cracking catalyst used

Catalytic cracking
Catalysts used are:
Silica (silicon dioxide) Alumina (aluminium oxide)
Molecular formula

SiO2

Al2O3

Zeolite (silicate compounds)

http://www.cybered.net/com merce.asp?CatId=311&ProdId =X5005108

Catalytic Cracking of Decane


Bond often breaks here

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

Catalytic Cracking of Decane showing bonds breaking


Bond often breaks here

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

Catalyst at high temperature: 650C

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

Ethene Single electron available to form a new bond An unsaturated 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

Drawing the isomers of butane


1. Draw carbon backbones of different isomers 2. Draw in four bonds for each carbon atom 3. Add a hydrogen atom to each of the remaining bonds

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

Differences in physical properties between the two isomers:

Melting point = -138C Boiling point = 0 C Density = 0.58 g cm-3

Melting point = -159C Boiling point = -12 C Density = 0.56 g cm-3

The isomers of pentane


H H H H H
H C1 C2 C3 C4 C5 H H H H H H
H H
Carbon Carbon atom atom 2 2 is is joined joined to to carbon carbon atoms by two to atoms 1 1,and 3, 43 and 5 bycarbon four carbon carbon single bonds to carbon single bonds

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

Which pair of hydrocarbon molecules are not isomers?


H H H H H H H

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

Which pair of hydrocarbon molecules are not isomers?


It is much easier to identify isomers if you look at the carbon backbone only:
C

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

Number of Alkane Isomers


Name
Butane
Pentane Hexane Heptane

Formula Number of
C4H10
C5H12 C6H14 C7H16

Number of carbon atoms Isomers

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

Isomers with different functional groups


Isomers exist for hydrocarbon compounds which have different functional groups e.g. cyclopropane and propene are isomers
Cyclopropane and propene are isomers with different functional groups as only propene has a carbon to carbon double bond

Name of alkane Cyclopropane

Full Structural formula

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