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BKF1323
Chapter 2
2.1 Alkanes and Cycloalkanes
Topics
Cycloalkanes
Cycloalkanes have molecular formula CnH2n and contain
carbon atoms arranged in a ring.
Simple cycloalkanes are named by adding the cyclo- to
the name of the acyclic alkane having the same number
of carbons.
Introduction to Alkanes and Cycloalkanes
For rings with more than one substituent, begin numbering at one
substituent and proceed around the ring to give the second
substituent the lowest number.
Introduction to Alkanes and Cycloalkanes
Boiling Point
Boiling PointPhysical Properties of Alkanes
Physical Properties of Alkanes
Melting Point
2.2 Conformations of Cycloalkanes:
Substituted and Disubstituted
Conformations of Acyclic Alkanes
29
Conformations of Acyclic Alkanes
Rotating the atoms on one carbon by 60 converts an eclipsed
conformation into a staggered conformation, and vice versa.
The angle that separates a bond on one atom from a bond on an
adjacent atom is called a dihedral angle. For ethane in the
staggered conformation, the dihedral angle for the CH bonds
is 60. For eclipsed ethane, it is 0.
30
Alkanes
Conformations of Acyclic Alkanes
Figure 4.6
Newman projections for
the staggered and eclipsed
conformations of ethane
Conformations of Acyclic Alkanes
Figure 4.7
Newman
projections for
the staggered
and eclipsed
conformations
of propane
Introduction to CycloalkanesDisubstituted Cycloalkanes
Stereoisomers are isomers that differ only in the way the
atoms are oriented in space.
The prefixes cis and trans are used to distinguish these
isomers.
The cis isomer has two groups on the same side of the ring.
The trans isomer has two groups on opposite sides of the ring.
CH3
H Br
Cl
H
Br H
H
2.3 Synthesis of Alkanes and Cycloalkanes
Alkenes Hydrogenation
H2
CnH2n CnH2n+2
Pt, Pd, Ni
Ex:
H2
CH3CH2CH CH2 CH3CH2CH2CH3
Pt, Pd, Ni
Alkyl Halides Reduction
b) Reduction by Metal+Acid
Zn
R-X R-H
CH3COOH
2.4 Chemical reactions of Alkanes
Chemical Reactions of Alkanes
Oxidation of Alkanes
Since alkanes are the only family of organic molecules
that have no functional group, they undergo very few
reactions.
One reaction that alkanes undergo is combustion.
Combustion is an oxidation-reduction reaction
Recall that oxidation is the loss of electrons and
reduction is the gain of electrons.
To determine if an organic compound undergoes
oxidation or reduction, we concentrate on the carbon
atoms of the starting material and the product, and
compare the relative number of CH and CZ bonds,
where Z = an element more electronegative than carbon
(usually O, N, or X).
Chemical Reactions of Alkanes
41
2.5 Industrial Applications
Some industrial applications of alkanes
The applications of a certain alkane can be
determined quite well according to the
number of carbon atoms. The first four
alkanes are used mainly for heating and
cooking purposes, and in some countries
for electricity generation. Methane and
ethane are the main components of natural
gas; they are normally stored as gases
under pressure. It is, however, easier to
transport them as liquids: This requires
both compression and cooling of the gas.
Some industrial applications of alkanes:
Propane and butane can be liquefied at
fairly low pressures, and are well known as
liquified petroleum gas (LPG). Propane, for
example, is used in the propane gas
burner, butane in disposable cigarette
lighters. The two alkanes are used as
propellants in aerosol sprays.
From pentane to octane the alkanes are
reasonably volatile liquids. They are used
as fuels in internal combustion engines.
Alkanes from nonane to, for instance,
hexadecane (an alkane with sixteen carbon
atoms) are liquids of higher viscosity, less
and less suitable for use in gasoline. They
form instead the major part of diesel and
aviation fuel. Diesel fuels are characterised
by their cetane number, cetane being an old
name for hexadecane. However, the higher
melting points of these alkanes can cause
problems at low temperatures and in polar
regions, where the fuel becomes too thick to
flow correctly.
Some industrial applications of alkanes:
Alkanes from hexadecane upwards form the
most important components of fuel oil and
lubricating oil.
Alkanes with a chain length of approximately
35 or more carbon atoms are found in
bitumen, used, for example, in road surfacing.
However, the higher alkanes have little value
and are usually split into lower alkanes by
cracking.
Some industrial applications of alkanes:
Many solid alkanes find use as paraffin wax,
for example, in candles. This should not be
confused however with true wax, which
consists primarily of esters.
Some synthetic polymers such as
polyethylene and polypropylene are alkanes
with chains containing hundreds of
thousands of carbon atoms. These materials
are used in innumerable applications, and
billions of kilograms of these materials are
made and used each year.