Hydrocarbons

Hydrocarbons are organic compounds that contain carbon and

hydrogen atoms.

Crude Oil
Decaying the fossils of plants and animals in the earths crust and
subjecting the fossils under high temperature and pressure for
millions of years form crude oil.

Crude oil is a mixture of a large number of compounds with different

weight, size and boiling point. To convert it into usable components,
it must be separated into various fractions via fractional distillation.

Fractional Distillation
Fractional distillation is done to separate crude oil into useful
fractions based on the different molecular size and boiling point.
Each fraction is a mixture of hydrocarbons, which boil over a limited
range of temperature.

Combination with various other processes (e.g. cracking) can further

convert the fractions into thousands of starting materials for making
petrochemicals like plastics, paints, etc.

Physical Properties of Hydrocarbons

Hydrocarbons are non-polar and hence insoluble in water (which is
polar). Liquid hydrocarbons are also less dense than water and they
float on the water surface.

Smaller hydrocarbons are gases at room temperature due to the

weak intermolecular interactions (dependent on size of molecule).
Hence, the larger the molecule, the higher the melting and boiling
points.

Classification of Hydrocarbons
According to the chemical bonds between carbons, hydrocarbons
are classified into two basic groups: aliphatic and aromatic.

Aliphatic Hydrocarbons
Aliphatic hydrocarbons contain single, double and/or triple carbon-
carbon bonds. They can be straight chain, branched chain and/or
contain non-aromatic rings.

Aliphatic hydrocarbons can be further classified into saturated and

unsaturated compounds. Saturated hydrocarbons contain only
single carbon-carbon bonds (alkane) in the molecule. Unsaturated
hydrocarbons contain at least one carbon-carbon double (alkene) or
triple bond (alkyne) in the molecule.

Aromatic Hydrocarbons
Aromatic hydrocarbons contain one or more benzene rings in the
molecules.
Formula
Molecular formula describes the chemical composition of a
molecule, indicating the exact numbers of each atom (namely
carbon and hydrogen in a hydrocarbon molecule).

Structural formula represents the exact structure of the molecule. It

describes the number of different atoms, the skeletal structure of
carbons and the types and number of the chemical bonds in the
molecule. There are two types of structural formula that can be
drawn: full structural formula showing all the bonds in the molecule,
and the condensed structural formula showing some or no bonds in
the molecule.

IUPAC Nomenclature
International Union of Pure and Applied Chemistry nomenclature
system includes a main chains (parent chains) name and
substituents names with numbers to indicate their positions on the
main chain.

IUPAC Nomenclature of Alkanes

The parent chain is the longest continuous chain (need not be
straight) of carbon atoms. All names end with ane for members of
the alkane series. The general formula for non-cyclic alkanes is
CnH2n+2.
(methane, ethane, propane, butane, pentane, hexane, heptane,
octane, nonane, decane)

The substituent e.g. alkyl groups (R) have the general formula of
CnH2n+1 (one hydrogen fewer than alkanes). Alkyls are named by
having a suffix of yl and a prefix of meth-, eth-, etc.

To name an alkane, firstly select the longest continuous carbon

chain. Secondly, number that chain by giving the smallest number
to the first substituent. Thirdly, assign other numbers to other
substituents based on their point of attachment to the parent chain
and name the substituents. Fourthly, place the substituent names in
alphabetical order before the parent name (e.g. ethyl is written
before methyl). Fifthly, if two or more identical substituents are
present, use prefixes di-, tri-, tetra-, etc (prefixes do not affect the
alphabetical order). Note: commas are used to separate numbers
and hyphens are used to separate numbers and alphabets. The
name is written as a single word.

IUPAC Nomenclature of Alkenes

Use suffix ene in the parent name. Assign a number to both the
carbon-carbon double bond and the substituents.
Firstly, select the longest continuous carbon chain which includes
the double bond. Secondly, use the prefix of ene. Thirdly, number
the chain and give the smallest possible number to the double bond.
Fourthly, locate and name the substituents (same as for alkanes).

IUPAC Nomenclature of Aromatic Hydrocarbons

Benzene has a molecular formula of C6H6. Aromatic hydrocarbons
are a six membered ring with 3 conjugated double bonds (cyclic),
and they possess a regular hexagonal shape. They are chemically
stable and behave more like an alkane than an alkene. The structure
of benzene is a resonance hybrid.

Name Structure Name Structure

Phenol Benzaldehyde

Toluene Benzoic acid

Aniline Styrene

Benzene when named as a substituent group is phenyl.

Isomerism
Isomerism is a phenomenon whereby two or more different
compounds are represented by identical molecular formulas.
Isomers have the same molecular formulas but different structural
formulas.

Structural (Constitutional) Isomerism in Alkanes

Structural isomers differ in the bonding arrangement of atoms.
There are 3 steps to draw structural isomers. Firstly, draw the
straight chain isomer first (given the molecular formula). Secondly,
branch the carbon chain with 1 methyl group so that the parent
chain is left with n-1 carbons. Thirdly, further branch the carbon
chain as many times as possible until there are repeats.

Geometric Isomerism in Alkenes

Geometric isomerism is a type of stereoisomerism in which atoms or
substituents display different orientation due to restricted rotation
around a double bond (which is rigid).

Prioritise the two atoms directly bonded to a carbon atom in the

C=C bond. The priority order is based on the atomic number (higher
atomic number, higher priority).

(Z)-notation: substituents with higher priorities on each carbon atom

are on the same side of the bond (both top or both bottom).
(E)-notation: substituents with higher priorities on each carbon atom
are on opposite sides of the bond (top and bottom).