What are alkanes?

The Alkanes

Alkanes are saturated hydrocarbons; they only contain single bonds. They are called saturated because
they contain the maximum amount of hydrogen atoms possible.

The general formula for an alkane is CnH2n+2 where n is a positive integer.

Above is a table with the frst ten alkanes. Note that at the end of each name is -ane this is the
same for all alkanes. At the beginning of the word is the stem eth-, th-.. this relates to how
many carbons there are in the alkane.

A series of compounds that are all related, like alkanes, are called a homologous series.

All the series have the same general formula, but each member differs from the next by a CH2 unit.

All the compounds in the series have similar chemical properties, but different physical properties such
as boiling point and density. However the physical properties change gradually in the series as the
number of carbons increase.

Alkane structural Isomers

As well has just having a straight line chained carbons, it is often possible for branches of chains to
branch off the primary chain.

There are often many different structural formulas for a given molecular formula.

For Example:

C4H10 has two possible structural formulae:

These two compounds are isomers, because they have the same chemical formula, but different
structural formulae.

Notice that the branched alkane has a different name; it is considered to have been formed from a
propane group with an added methyl group. It is therefore called methyl propane.
To name branched alkanes:

1) Find the longest chain of carbons. This doesn't have to be a straight line - it can go around corners, as
long as it follows the carbon chain. This is the constituent chain and goes on the end of the name. In the
above example the longest possible chain is 3 (either a horizontal line or the one at the top, bottom
middle then either bottom left or right). This number then names the isomer: e.g. three carbons means
that the name of this ends with propane.

2) Using the longest chain, identify any branching out from it. In the above isomer there is just one
branch - this branches off the second carbon from either end (if the numbers from either end were
different, the lowest would be taken). The branch consists of just one carbon, or a methyl group.

3) The table below contains the names of the groups with more carbons in them:

As well open chained alkanes, it is also possible for alkane molecules to form rings.

These rings are called cyclo-alkanes, and have the same general formula as an alkene CnH2n. They have
two less hydrogens, because there are no CH3 groups at the end of the chains.

Every corner on the skeletal formula represents a CH2 group. Skeletal diagrams are very useful when
drawing cyclic hydrocarbons.

Skeletal diagrams can also be used to draw chained and branched isomers.

The above represents pentane, every kink in the line represents a CH2 group, and the ends represent a
CH3 group.

The above represents 4 methyl heptane.

Shapes of Alkanes

Representing three dimensional shapes in 2D on paper can give a misleading image of what the
molecule looks like.
The pairs of electrons in covalent bonds repeal each other and so arrange themselves around the carbon
atom as far apart as possible.

The C-H bonds in methane are directed so that they form a tetrahedron shape, with bond angles of 109o

The structure of ethane:

(Photo)

The structure of butane:

(Photo)

Hydrocarbon chains are not really straight, but are "Zig-Zaggged". All the bond angles are 109o

Alkane characteristics

What an alkane looks like at room temperature depends upon its size.

-Alkanes contain non-polar molecules and mix well with each other; however they do not mix well with
non-polar substances such as water.

-Alkanes are unreactive towards many laboratory reagents; they are unaffected by acids, alkalis, metals
and oxidising agents.

-When they do react, it is usually in the gas phase, and energy is needed to get the reaction started.

Melting and Boiling points of Alkanes

As the molecular number increases, the boiling and melting point of the alkane increases.

C1 to C4 are gases, C5 to C17 are liquids, C18 and higher are solids.

The increase in the boiling point is due to the stronger intermolecular forces.

In hydrocarbons the only intermolecular forces are instantaneous dipole, induced dipole interactions.
In a molecule, electrons are mobile, and at one point they may all fnd themselves at one end of the
molecule. This will form a temporary dipole, affecting neighbouring molecules, pulling the molecules
together.

At the next instant the electrons could end up at the other side reversing the polarity of the molecule.

This permanent moving around of the electrons causes rapidly fluctuating dipoles which hold together
the hydrocarbons.

The higher the molecular weight of the compound, the more electrons there are in the molecules,
meaning the stronger these Van der Waahl forces. This is why the melting points and boiling points of
the larger molecules are higher.

Branched alkanes have a lower Van der Waahl force than chains, due to their shape, which doesn
allow the molecules get close enough to each other.

Oxidation of Alkanes

Alkanes do not react readily with air, but if they are heated they can combust to form carbon dioxide and
water.

The reaction has a high activation energy; the energy must be supplied in order for the reaction to begin.

Alkanes must be vaporised before they can combust, thus more volatile hydrocarbons ignite easier.

Once ignited, the reaction is very exothermic, which is why alkanes are often used for fuels.

If the air supply is limited, the combustion may be incomplete, producing carbon dioxide and soot, along
with partially combusted hydrocarbons.

Molecular and Empirical Formula of Alkanes

A molecular formula shows how many atoms of each type are present in a given compound.

The empirical formula shows the smallest ratio of the different types of atom present.

The Molecular Formula = M x Empirical Formula (where M= a positive integer).

The empirical formula of a compound can be worked out from its percentage composition. For a
hydrocarbon this can be found out by burning a known mass in oxygen and working out the amounts of
carbon dioxide and water formed. This is called combustion analysis.
Example:

0.1g of a hydrocarbon x gave 0.309g CO2 and 0.142g H2O on combustion. What is the empirical formula
of x?

Calculate the mass of C and H in 0.1g of the compound (all of the compound goes to H2O and CO2, so
the mass of carbon and hydrogen in the compound can be worked out from the mass's of carbon dioxide
and water produced).

44g CO2 contains 12g of C (Mr of CO2 is 44, and Ar of C is 12).

so 0.309g contains 0.309 x 12/44 = 0.0843g

18g H2O contains 2g of H

so 0.142g contains 0.142 x 2/18 = 0.0158g

So the compound contains 0.0843g of Carbon and 0.0158g of Hydrogen.

Alkanes are saturated hydrocarbons, which means they are made of only carbon and hydrogen atoms
and the carbon atoms are connected by single bonds only.

Alkanes: Physical Properties

The alkanes can exist as gases, liquids, or solids at room temperature. The unbranched alkanes methane,
ethane, propane, and butane are gases; pentane through hexadecane are liquids; the homologues larger
than hexadecane are solids.Branched alkanes normally exhibit lower boiling points than unbranched
alkanes of the same carbon content. This occurs because of the greater van der Waals forces that exist
between molecules of the unbranched alkanes. These forces can be dipole-dipole, dipole-induced
dipole, or induced dipole-induced dipole in nature. The unbranched alkanes have greater van der Waals
forces of attraction because of their greater surface areas.

Solid alkanes are normally soft, with low melting points. These characteristics are due to strong repulsive
forces generated between electrons on neighboring atoms, which are in close proximity in crystalline
solids. The strong repulsive forces counterbalance the weak van der Waals forces of attraction.

Finally, alkanes are almost completely insoluble in water. For alkanes to dissolve in water, the van der
Waals forces of attraction between alkane molecules and water molecules would have to be greater than
the dipole-dipole forces that exist between water molecules. This is not the case.

Alkanes: Natural Sources

The alkanes are isolated from natural gas and petroleum. Natural gas contains mainly methane, with
smaller amounts of other low-molecular-weight alkanes. Petroleum, which is a complex mixture of many
compounds, is the main source of all other alkanes. The lighter fractions are distilled from the mixture to
produce the liquid alkanes, while the residue from the distillation produces the solid alkanes.

Major sources of alkanes are:

Petroleum. Petroleum is a complex mixture of alkanes and other hydrocarbons. It usually contains
alkanes having up to forty carbon atoms in their molecule. The natural wax found near petroleum wells
is a mixture of higher solid hydrocarbons.

Natural gas. Methane is the major constituent of the natural gas and occurs along with petroleum in the
earths sedimentary traps.

Destructive distillation of wood and coal. Methane is produced as one of the by-products in the
manufacture of wood charcoal by destructive distillation of wood and coke by destructive distillation of
coal.

Anaerobic decomposition of organic matter, in the presence of bacteria, liberates methane. For example,
bio-gas produced by anaerobic decomposition of animal dung, excreta and plant wastes is rich in
methane gas. Methane is produced in marshy lands by the bacterial decomposition of plant and animal
matter under water and is observed bubbling through the surface. Since methane gas is produced in
marshy lands, it is also known as marsh gas.

Decomposed wastes from rice felds and termites are other sources of methane.
Methane gas is also present in coal mines where it is known as damp fre. It is formed as a by-product
during the formation of coal.

Octane rating is the measure of a fuel's ability to resist "knocking" or "pinging" during combustion,
caused by the air/fuel mixture detonating prematurely in the engine. In the U.S., unleaded gasoline
typically has octane ratings of 87 (regular), 8890 (midgrade), and 9194 (premium).

What is octane rating?

Octane rating is the measure of a fuel's ability to resist "knocking" or "pinging" during combustion,
caused by the air/fuel mixture detonating prematurely in the engine.

In the U.S., unleaded gasoline typically has octane ratings of 87 (regular), 8890 (midgrade), and 9194
(premium). Gasoline with an octane rating of 85 is available in some high-elevation areas of the U.S.
(more about that below).

The octane rating is prominently displayed in large black numbers on a yellow background on gasoline
pumps.

What octane fuel should I use in my vehicle?

You should use the octane rating required for your vehicle by the manufacturer. So, check your owner's
manual. Most gasoline vehicles are designed to run on 87 octane, but others are designed to use higher
octane fuel.

Why do some manufacturers require or recommend the use of higher octane gasoline?

Higher octane fuels are often required or recommended for engines that use a higher compression ratio
and/or use supercharging or turbocharging to force more air into the engine. Increasing pressure in the
cylinder allows an engine to extract more mechanical energy from a given air/fuel mixture but requires
higher octane fuel to keep the mixture from pre-detonating. In these engines, high octane fuel will
improve performance and fuel economy.
What if I use a lower octane fuel than required for my vehicle?

Using a lower octane fuel than required can cause the engine to run poorly and can damage the engine
and emissions control system over time. It may also void your warranty. In older vehicles, the engine can
make an audible "knocking" or "pinging" sound. Many newer vehicles can adjust the spark timing to
reduce knock, but engine power and fuel economy will still suffer.

Will using a higher octane fuel than required improve fuel economy or performance?

It depends. For most vehicles, higher octane fuel may improve performance and gas mileage and reduce
carbon dioxide (CO2) emissions by a few percent during severe duty operation, such as towing a trailer
or carrying heavy loads, especially in hot weather. However, under normal driving conditions, you may
get little to no beneft.

Why does higher octane fuel cost more?

The fuel components that boost octane are generally more expensive to produce.

Is higher octane fuel worth the extra cost?

If your vehicle requires midgrade or premium fuel, absolutely. If your owner's manual says your vehicle
doesn't require premium but says that your vehicle will run better on higher octane fuel, it's really up to
you. The cost increase is typically higher than the fuel savings. However, lowering CO2 emissions and
decreasing petroleum usage by even a small amount may be more important than cost to some
consumers.

What is 85 octane, and is it safe to use in my vehicle?

The sale of 85 octane fuel was originally allowed in high-elevation regionswhere the barometric
pressure is lowerbecause it was cheaper and because most carbureted engines tolerated it fairly well.
This is not true for modern gasoline engines. So, unless you have an older vehicle with a carbureted
engine, you should use the manufacturer-recommended fuel for your vehicle, even where 85 octane fuel
is available.

Can ethanol boost gasoline's octane rating?

Yes. Ethanol has a much higher octane rating (about 109) than gasoline. Refners usually blend ethanol
with gasoline to help boost its octane ratingmost gasoline in the U.S. contains up to 10% ethanol.
Blends of up to 15% ethanol are available in some areas, and several manufacturers approve using this
blend in recent-model vehicles.

Octane ratings

Understanding octane ratings.

About octane ratings

Octane rating is a measure of a fuel's ability to resist knock. The octane requirement of an engine varies
with compression ratio, geometrical and mechanical considerations and operating conditions. The higher
the octane number the greater the fuels resistance to knocking or pinging during combustion.

The octane ratings of Exxon- and Mobil-branded Synergy gasoline

Exxon and Mobil Regular Unleaded Octane 87

Exxon Plus and Mobil Special Unleaded Octane 89

Exxon Supreme and Mobil Super+ Unleaded Octane 91-93

The right octane level for your vehicle

The recommended octane rating for most vehicles is usually octane 87, but be sure to check your vehicle
owners manual. Ordinarily, a vehicle will not beneft from using an octane higher than recommended in
the owners manual. However, some car models have high-compression engines and electronic controls,
which are designed to beneft from the greater power output and improved fuel economy of high octane
fuel. Since octane requirements can vary with operating and environmental conditions, your vehicle may
need a higher octane fuel than recommended to prevent knocking.

Shell:

91 - FuelSave

95 - V-Power Nitro+

97 - V-Power Nitro+ Racing

Caltex:

91 - Silver

95 - Gold

Total:

91 - Premier

95 - Excellium

Petron:

91 - Super Xtra

93 - Xtra Advance

95 - XCS

100 - Blaze

Seaoil:

91 - Extreme U

95 - Extreme 95

97 - Extreme 97
Unioil:

91 - Euro IV 91

95 - Euro IV 95

97 - Euro IV 97

Phoenix:

91 - Regular 91

95 - Premium 95

98 - Premium 98

Flying V:

91 - Volt

95 - Thunder

97 - Rush