Boiling Points - The boiling points shown are for the "straight chain" isomers of which there is more

than one. The first four alkanes are gases at room temperature, and solids do not begin to appear
until about C17H36C17H36, but this is imprecise because different isomers typically have different
melting and boiling points. By the time you get 17 carbons into an alkane, there are unbelievable
numbers of isomers!

Solubility - Alkanes (both alkanes and cycloalkanes) are virtually insoluble in water, but dissolve in
organic solvents. However, liquid alkanes are good solvents for many other non-ionic organic
compounds.

Solubility in Water - When a molecular substance dissolves in water, the following must occur:

a) break the intermolecular forces within the substance. In the case of the alkanes, these are
the Van der Waals dispersion forces.
b) break the intermolecular forces in the water so that the substance can fit between the water
molecules. In water, the primary intermolecular attractions are hydrogen bonds.

Breaking either of these attractions requires energy, although the amount of energy to break the
Van der Waals dispersion forces in something like methane is relatively negligible; this is not true of
the hydrogen bonds in water.

As something of a simplification, a substance will dissolve if there is enough energy released when
new bonds are made between the substance and the water to compensate for what is used in
breaking the original attractions. The only new attractions between the alkane and the water
molecules are Van der Waals forces. These forces do not release a sufficient amount of energy to
compensate for the energy required to break the hydrogen bonds in water.; the alkane does not
dissolve.

Solubility in organic solvents - In most organic solvents, the primary forces of attraction between
the solvent molecules are Van der Waals - either dispersion forces or dipole-dipole attractions.
Therefore, when an alkane dissolves in an organic solvent, the Van der Waals forces are broken and
are replaced by new Van der Waals forces. The two processes more or less cancel each other out
energetically; thus, there is no barrier to solubility.

Alkanes: Sources and Importance

Alkanes do not only occur naturally in crude oil and natural gas but can also be found in living
matter. Thus, methane, also called biogas, is generated from organic matter by fermentation.

Alkanes gained great technical importance through the various uses of crude oil. The diverse crude
oil products, particularly in the area of polymeric materials, are an indispensable part of daily life.
These three areas - crude oil, alkanes as natural products and polymers

Alkanes are found in nature mainly in natural gas and crude oil from which they are produced on a
technical scale in large amounts by distillation and extraction. Natural gas mainly consists of
methane, ethane and small amounts of propane. Propane is the main component of liquified gas
which, compressed in steel bottles, is being used as heating fuel. Crude oil is mainly composed of
alkanes and cycloalkanes which have been generated by decomposition of animal and plant matter.
Coal is an additional source of raw material. It consists of a complex mixture of mostly high-
molecular alicyclic, heterocyclic, saturated, unsaturated, and aromatic hydrocarbons formed from
the original residues of plant matter.

REACTIONS OF ALKANES

1. Combustion

The combustion of carbon compounds, especially hydrocarbons, has been the most important
source of heat energy for human civilizations throughout recorded history. The practical importance
of this reaction cannot be denied, but the massive and uncontrolled chemical changes that take
place in combustion make it difficult to deduce mechanistic paths. Using the combustion of propane
as an example, we see from the following equation that every covalent bond in the reactants has
been broken and an entirely new set of covalent bonds have formed in the products. No other
common reaction involves such a profound and pervasive change, and the mechanism of
combustion is so complex that chemists are just beginning to explore and understand some of its
elementary features.

2. Halogenation

Halogenation is the replacement of one or more hydrogen atoms in an organic compound by a

halogen (fluorine, chlorine, bromine or iodine). Unlike the complex transformations of combustion,
the halogenation of an alkane appears to be a simple substitution reaction in which a C-H bond is
broken and a new C-X bond is formed. The chlorination of methane, shown below, provides a simple
example of this reaction.

CH4 + Cl2 + energy ——> CH3Cl + HCl

Since only two covalent bonds are broken (C-H & Cl-Cl) and two covalent bonds are formed (C-Cl &
H-Cl), this reaction seems to be an ideal case for mechanistic investigation and speculation.
However, one complication is that all the hydrogen atoms of an alkane may undergo substitution,
resulting in a mixture of products, as shown in the following unbalanced equation. The relative
amounts of the various products depend on the proportion of the two reactants used. In the case of
methane, a large excess of the hydrocarbon favors formation of methyl chloride as the chief
product; whereas, an excess of chlorine favors formation of chloroform and carbon tetrachloride.

CH4 + Cl2 + energy ——> CH3Cl + CH2Cl2 + CHCl3 + CCl4 + HCl

USES OF ALKANES

Refining crude oil

Crude oil needs to be refined not only to remove the dark color and bad odor but also to remove
sulfur compounds which lower the response of gasoline to anti-knock agents like tetraethyl lead
(now not recommended). Crude oil is refined after fractional distillation. In these videos (below), you
can get an idea how crude oil is refined.

Common usage of alkanes in natural gas

Natural gas contains lighter alkanes (mainly methane, ethane, propane and butane) and produces
less pollutants compared to petroleum derived fuels. Some of the usage are listed below14:

 heating/cooling house (air conditioning)

 ovens

 fireplaces

 outdoor lights

 Fuel cells

 plastic products (from cracking of ethane, propane)

 fertilizer (in Haber-Bosch process for production of ammonia, hydrogen comes from
methane)

 fabric

 anti-freeze

 Motor fuel [used as compressed natural gas (CNG) or liquefied natural gas (LNG) less
pollution and cheaper]

Biogas

Biogas is a non-petroleum fuel produced via anaerobic digestion or fermentation of renewable

materials such as manure, crops, sewage, farm waste, municipal waste, etc. Biogas mainly comprises
of methane and carbon dioxide and also contains hydrogen, nitrogen, oxygen and hydrogen
sulfide15. In India, biogas fuel is being used in many rural households16.

Renewable diesel

Renewable diesel as opposed to petrodiesel is produced from renewable resources such as

vegetable oil, fat under elevated temperature, pressure and in the presence of catalyst.17 It is also
known as green diesel because it does not contain sulfur and other toxic materials. Renewable diesel
can contain alkanes of 9-18 carbon atoms

http://padakshep.org/otp/subjects/chemistry/organic-chemistry/alkanes-role-and-usage/
http://www.chemgapedia.de/vsengine/vlu/vsc/en/ch/2/vlu/alkane/alk_vorkommen.vlu/Page/vsc/e
n/ch/2/oc/stoffklassen/systematik_struktur/acyclische_verbindungen/gesaettigte_kohlenwasserstof
fe/erdoel/erdoel_entstehung.vscml.html