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28.02.2012
Stefan IglauerDavid Parks
27.3.2013
Tutorial 3 Petroleum Chemistry
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Exercise 1.1
Cyclopentane
naphthene
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Exercise 1.1
2,2-Dimethylbutane
paraffin
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Exercise 1.1
2,3-Dimethylbutane
paraffin
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Exercise 1.1
2-Methylpentane
paraffin
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Exercise 1.1
3-Methylpentane
paraffin
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Exercise 1.1
n-Hexane
paraffin
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Exercise 1.1
2,4-Dimethylpentane
paraffin
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Exercise 1.1
Cyclohexane
naphthene
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Exercise 1.1
1,1-Dimethylcyclopentane
naphthene
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Exercise 1.1
1,2-Dimethylcyclopentane
naphthene
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Exercise 1.1
3-Methylhexane
paraffin
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Exercise 1.1
n-Heptane
paraffin
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Exercise 1.1
Methylcyclohexane
naphthene
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Exercise 1.1
Benzene
aromatic
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Exercise 1.1
Toluene = Methylbenzene
aromatic
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Exercise 1.1
Ethylbenzene
aromatic
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Exercise 1.1
para-Xylene =
1,4-Dimethylbenzene
aromatic
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Exercise 1.1
meta-Xylene =
1,3-Dimethylbenzene
aromatic
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Exercise 1.1
ortho-Xylene =
1,2-Dimethylbenzene
aromatic
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Exercise 1.1
Isopropylbenzene =
(1-Methyl)Ethylbenzene
aromatic
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Exercise 1.1
n-Propylbenzene
aromatic
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Exercise 1.2
Conformation Isomerism
Because of the sp3 hybridization cycloalkanes are not planarrings but have a three-dimensional zig-zag structure.
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Exercise 1.2
Ethane
CC
H
H
HH
H
H
rotation by180 degree
CC
H
H
H
H
H
H
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Exercise 1.2
Structural Isomers
Structure of 2,3-Dimethylhexane (left) and 2,4-
Dimethylhexane (right).
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Exercise 1.2
Structural Isomers
The three structural isomers of xylene. Left: ortho-xylene (o-xylene); middle:
meta-xylene (m-xylene); right: para-xylene (p-xylene).
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Exercise 1.2
Cis/Trans Isomers
Trans-3-methyl-hept-5-ene Cis-3-methyl-hept-5-ene
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Exercise 1.2
Cis/Trans Isomers
Alkenes can have cis or trans configuration, depending on which side of
the planar C=C bond the functional groups are attached.
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Exercise 1.2
Optical Isomers
(+) and (-) 1-Amino-ethanol
A solution of one enantiomer rotates
the plane of polarisation in a
clockwise direction. This enantiomer
is known as the (+) form.
C
H
CH3 OH
NH2C
H
CH3 NH2
OH
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Exercise 1.2
Optical Isomers
Left: (S)-thalidomide
Right: (R)-thalidomide
The (R) enantiomeris effective against morning sickness, but the (S) is
teratogenic (causes physiological abnormalities, e.g. birth defects).
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Exercise 1.3
Prediction of boiling point
a) n-Pentane (36 C) versus n-Hexane (68 C)
Because n-Hexane has a higher cohesive force because of
stronger London forces.
The London forces are stronger because n-Hexane is larger than
n-Pentane.
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Exercise 1.3
Prediction of boiling point
a) 3-Methylpentane (63 C) versus n-Hexane (68 C)
Because n-Hexane has a higher cohesive force because of
stronger London forces.
The London forces are stronger because 3-Methylpentane
is branched which leads to lower London forces even though the
Molecules are both C6.
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Exercise 1.3
Prediction of boiling point
a) n-Pentane (36 C) versus 1-Pentene(30 C)
Because n-Pentane has a higher cohesive force because of
stronger London forces.
The London forces are stronger because 1-Pentene has a
double-bond which leads to lower London forces (as compared to
London forces induced by a single bond.
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Exercise 1.3
Prediction of boiling point
a) Cyclohexane (80.7 C) versus Benzene (80.1 C)
Because Cyclohexane has a higher cohesive force because of
stronger London forces.
The London forces are stronger because Benzene is an aromat
which leads to lower London forces.
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Tutorial Examination - Exercise
Plot all structural isomers of hexane
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Tutorial Examination - Exercise
Plot all structural isomers of hexane
Structure of 2,3-Dimethylhexane
2,4-Dimethylhexane
n-Hexane