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 cant 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 (-CH 3) 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 C 3H6.
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.