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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).

http://en.wikipedia.org/wiki/Optical_isomerismhttp://en.wikipedia.org/wiki/Teratologyhttp://en.wikipedia.org/wiki/Teratologyhttp://en.wikipedia.org/wiki/Optical_isomerism

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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