SOURCES OF HYDROCARBONS

Hydrocarbons are the organic compounds that contain only carbon and hydrogen.
They have a carbon skeleton to which hydrogen atoms are attached.

When burnt hydrocarbons release carbon dioxide, water and heat energy. About 85%
of the world's electricity is generated by burning hydrocarbons.

Crude oil, natural gas, coal and tar sand are some of the sources of hydrocarbons.

As they are produced from decaying plants and animals, they are referred to as fossil
fuels. It takes millions of years to produce them and hence they are a nonrenewable
source of energy.

The remains of plants and animals (organic matter) are compressed under the
surface of the Earth at very high pressures and temperatures for a long time. The
high temperatures break down the carbon - carbon bonds in the organic matter. As
the depth increases, the temperature also increases.

Shallower deposits with low temperature and pressure produce crude oil or
petroleum. Deeper deposits with high temperature and pressure produce natural gas,
particularly pure methane. The methane produced in this manner is referred to as
thermogenic or abiogenic methane.

Commercial natural gas is usually a mixture of methane and ethane. Propane and
butane removed from natural gas are liquefied under pressure and sold as liquefied
petroleum gas (LPG).

Surface methane is produced by Methanogens in the solid, tiny methane producing

micro organisms. Methanogens chemically break down the organic matter to
produce methane. The methane thus produced is referred to as biogenic methane.
Using this method, the waste materials in landfill can be converted to methane.

Methane, ethane, propane, butane, benzene, naphthalene, cyclohexane, ethylene and

acetylene are some of the hydrocarbons found in crude oil.

Natural gas is a mixture of hydrocarbon gases that are combustible. In its pure form,
it is colourless and odourless. It contains about 70-90% methane, other hydrocarbons
like ethane, propane, butane, pentane and carbon dioxide, oxygen, nitrogen, hydrogen
sulphide and rare gases in small amounts. It burns well and emits lower amounts of
bye products into the air. It has low density. Hence it rises to the surface of the earth
through loose, shale type rocks. It is trapped under the porous, impermeable
sedimentary rocks. More dense oil is trapped under the less dense natural gas. It can
be brought to the surface by drilling a hole in the impermeable rock.

Coal is referred to as a combustible sedimentary rock. Plant and fossil remains are
pressurized over millions of earth by the layers of sediments. They break down to
form hydrocarbons and this process is referred to as coalification. Coal contains 50-
98% carbon. Black coal has high carbon content (about 71-91%).

Methane and other hydrocarbon gases can be extracted directly from underground
deposits of coal by pumping a mixture of water and chemicals under pressure into
the coal, thus making the coal release its gases. This is called Hydraulic Fracturing
or Fracking.

Tar sands or oil sands are loose sand that contain a mixture of clay, sand, water and
a dense extremely viscous form of petroleum known as bitumen.

It is estimated that coal makes up 64% of all fossil fuel resources and will last
another 148 years at the present rate of consumption, oil 19% and 43 years and gas
17% and 61 years.

Organic compounds in which one hydrogen atom of an alkane is replaced by an -OH

group (hydroxyl group) are called as alcohols. The simplest alcohol, methanol is
obtained by the replacement of one of the hydrogen atom in methane by the
functional group -OH: CH3OH. Depending upon the position of the -OH group on the
chain of carbon atoms, alcohols are classified as either primary, secondary or
tertiary alcohols.

Primary Alcohols

A carbon atom forms four bonds. If the carbon atom containing the -OH group is
directly attached to another one carbon atom and two hydrogen atoms, it is a
primary alcohol.

The hydroxyl group is always on the end of a chain in Primary Alcohols: -CH2OH.

Examples: ethanol and 2-methylpropan-1-ol.

In methanol the carbon atom containing the -OH group is not attached to any other
carbon atom and it is attached to three hydrogen atoms. But it is a primary alcohol.

Secondary Alcohols

If the carbon atom containing the -OH group is directly attached to two other carbon
atoms and one hydrogen atom, it is a secondary alcohol.

The hydroxyl group is attached in the middle of a chain in Secondary Alcohols.

Example: propan-2-ol

Tertiary Alcohols

If the carbon atom containing the -OH group is directly attached to three other
carbon atoms and no hydrogens, it is a tertiary alcohol.

The hydroxyl group is attached in the intersection of two chains in Tertiary Alcohols.

Example: 2-methylpropan-2-ol
 The terms primary, secondary and tertiary can be easily seen in the following
diagram.

Naming

1. Find the longest chain containing the -OH group.

2. If there are more carbon atoms other than the longest chain, they should be
taken as substituents.(side chain)

3. Number the carbon atoms of the longest chain in such a way that the
-OH group gets the lowest number.

4. The number of carbon atoms in the longest chain determines the root word.
Write the position of the substituent, a hypen, name of the substituent, root word,
the word ‘an’, a hypen, position of the -OH group and the suffix 'ol'.

Here there is no substituent or side chain. The carbon atoms are numbered from left
to right so that the -OH group gets the lowest number. Since there are 5 carbon
atoms, the root word is 'pent'. and its name is pentan-2-ol.

The naming of alcohols can be better understood by viewing the following examples.
The Secondary Alcohol 2-methylpropan-1-ol and the Tertiary Alcohol 2-methylpropan-
2-ol are shown above.

Organic compounds that contain a carbonyl functional group, a carbon atom

attached to an oxygen atom by a double bond, are said to be carbonyl compounds.
Either aldehydes and ketones

Aldehydes

The carbonyl group has a hydrogen atom attached to it and is on the end of a chain.
Hence the functional group of an aldehyde is -CHO group.

Aldehydes end in the suffix - al.

Examples: methanal, ethanal

In ketones

The carbonyl group has no hydrogen atoms attached to it and are in the middle of a
chain. Hence the functional group of a ketone is -C=O group.

Ketones end in the suffix - one.

Examples: propanone, butanone

Primary alcohols to Aldehydes

Primary alcohols can be first oxidised to aldehydes and then to carboxylic acids with
strong Oxidizing Agents.

In order to get an aldehyde, we have to use excess of alcohol and distilling the
aldehyde as soon as it is formed. If there is an excess of alcohol, there is shortage of
the oxidising agentand hence alcohols cannot be fully oxidised and if the aldehyde is
removed as soon as it is formed, it can’t be oxidised to carboxylic acid. In this
manner we get an aldehyde from a primary alcohol.

Potassium or sodium dichromate acidified with dilute sulphuric acid is used as the
oxidising agent.

For example ethanol is oxidised to ethanal. In the equation below [O] means oxygen
from the oxidising agent. The reaction can be better understood by the second
equation.

Secondary alcohols to Ketones

Secondary alcohols are oxidised to ketones if heated with potassium or sodium

dichromate acidified with dilute sulphuric acid.
 Naming Aldehydes and Ketones

1. The longest carbon chain containing the carbonyl group must be identified.

2. It should be numbered so that the carbonyl group gets the lowest number. In
the case of aldehyde, the carbonyl group is always at the first position.

3. The longest carbon chain determines the root word. Add ‘an’ to it. For the
aldehydes, the suffix ‘al’ should be added.

4. For the ketones, after the root word, add 'an', a hypen, position of the carbonyl
group, a hypen and suffix ‘one’.

Organic compounds that contain the -COOH functional group are said to be
carboxylic acids. They consist of two functional groups - a carbonyl group (-CO) and a
hydroxyl group(-OH). The -COOH group is attached either to a hydrogen atom or to an
alkyl group. Methanoic acid, HCOOH is the simplest carboxylic acid. The -COOH
group is always located at the end of a hydrocarbon chain.

While naming a carboxylic acid, the carbonyl carbon is given the number 1. The
longest chain with the -COOH group determines the root word. If there is a
substiutent, its position has to be given, and then add a hypen, the substituent, root
word, and then ‘an’ and ‘oic acid. Examples of some carboxylic acids are illustrated
in the diagram.
 Oxidation of aldehydes to form carboxylic acids

Aldehydes are oxidised to carboxylic acids using potassium or sodium dichromate

solution acidified with dilute sulfuric acid. It is usually uncommon to produce
carboxylic acids from aldehydes. We can start the reaction with a primary alcohol.
The alcohol is heated with a mixture of excess of potassium dichromate and dilute
sulfuric acid. The flask is fitted with a condenser placed vertically above it. This
condenser stops the aldehydes that are formed from escaping. Excess of the
catalyst helps in the oxidation of the formed aldehydes to carboxylic acids. After the
completion of oxidation, the acid can be distilled. The reagents should be thoroughly
mixed before heating in order to avoid any vigorous reaction.

Esters

In a carboxylic acid if the hydrogen in the -COOH group is replaced by an alkyl

(methyl, ethyl etc.,) or aryl (benzyl, phenyl etc.,) the resultant compound is said to be
an ester. Esters have a strong fruity smell. The structure of the ester is illustrated
below.

Ester formation

When carboxylic acids are heated with alcohols in presence of concentrated sulfuric
acid, esters are obtained. For example when ethanoic acid is heated with ethanol in
presence of concentrated sulfuric acid, ethyl ethanoate is formed. Esterification
process is always slow and reversible. The ester obtained should be distilled
immediately. Otherwise the reverse reaction will take place.

Naming of ester

1. Identify the alkyl group that replaces the hydrogen in the -COOH group.

2. Number the remaining carbon atoms to find the ‘root word’.

3. Write down the name of the alkyl group found in step 1.

4. Write the root word and then ‘an’ and then ‘oate’.

For example, in the diagram given below methyl (-CH3) is the alkyl group that
replaces the hydrogen in the -COOH group. There are 3 carbon atoms in the other
part. The carbonyl carbon should also be taken into account while numbering. Hence
the root word is ‘prop’. Adding ‘an’ and ‘oate’ to it, the name becomes methyl
propanoate.

Alicyclic hydrocarbons are aliphatic hydrocarbons that have a ring structure and may
be either saturated with single bonds or unsaturated with double or triple bonds.
They do not have a benzene ring which is the basis of aromatic hydrocarbons.

Alicyclic alkanes

Alicyclic alkanes or cycloalkanes are hydrocarbons that contain at least one ring of
carbon atoms linked together by single bonds. They are saturated, with the general
formula CnH2n. This general formula is shared with chain alkenes.

The simplest cycloalkane is cyclopropane that has three carbon atoms linked in a
ring. Its formula is C3H6.

In the IUPAC system the prefix ‘cyclo’ is added to the root word and the the suffix is
‘ane’. In the case of substituted cycloalkanes, the carbon atoms in the ring are
numbered in such a way that the substituents receive the lowest numbers. The
structure of cyclopropane, cyclobutane, cyclopentane and cyclohexane are
illustrated in the following diagram.

Alicyclic alkenes

Alicyclic alkenes or cycloalkenes are the hydrocarbons that contain at least one ring
of carbon atoms and a carbon-carbon double bond. They are unsaturated.
In the IUPAC system the prefix ‘cyclo’ is added to the root word and the suffix is
‘ene’. The structure of cyclopentene and cyclohexene are illustrated in the following
diagram.

Aromatic hydrocarbons

Aromatic hydrocarbons are unsaturated cyclic hydrocarbons with hybrid bonding

resulting from alternate single and double bonds. The word 'aromatic' originated
from the Greek word ‘aroma’ meaning fragrant smell.

They contain at least six carbon atoms that are connected by hybrid bonds, half-way
in strength between a single and double carbon-carbon bond.

These hybrid bonds are formed by the averaging of the alternate single and double
bonds forming the hexagonal ring known as the benzene ring. The simplest aromatic
hydrocarbon is benzene and its formula is C6H6. Its structure is illustrated in the
following diagram.

Another example of aromatic hydrocarbon is methyl benzene or toluene.