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Molecular and empirical formulae

There are many ways of representing organic compounds
by using different formulae.

The molecular formula of a

compound shows the number Molecular Empirical
of each type of atom present in formula formula
one molecule of the compound. C2H6 CH3
C6H12O6 CH2O
The empirical formula of a
compound shows the simplest C2H4O2 CH2O
ratio of the atoms present.

Neither the molecular nor empirical formula gives information

about the structure of a molecule.

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Displayed formula of organic compounds
The displayed formula of a compound shows the
arrangement of atoms in a molecule, as well as all the bonds.

Single bonds are represented

by a single line, double
bonds with two lines and
triple bonds by three lines.

The displayed formula can show the different structures of

compounds with the same molecular formulae.

ethanol (C2H6O) methoxymethane (C2H6O)

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Structural formula of organic compounds
The structural formula of a compound shows how the
atoms are arranged in a molecule and, in particular, shows
which functional groups are present.

Unlike displayed formulae, structural formulae do not show

single bonds, although double/triple bonds may be shown.

CH3CHClCH3 H2C=CH2 CH3C≡N

2-chloropropane ethene ethanenitrile

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Skeletal formula of organic compounds
The skeletal formula of a
compound shows the
bonds between carbon
atoms, but not the atoms
themselves. Hydrogen
atoms are also omitted, but
other atoms are shown.

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 Functional groups and homologous series
A functional group is an atom or group of atoms
responsible for the typical chemical reactions of a molecule.

A homologous series is a group of molecules with the same

functional group but a different number of –CH2 groups.

methanoic acid ethanoic acid propanoic acid

(HCOOH) (CH3COOH) (CH3CH2COOH)
Functional groups determine the pattern of reactivity of a
homologous series, whereas the carbon chain length
determines physical properties such as melting/boiling points.

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Homologous series and general formulae
The general formula of a homologous series can be used
to calculate the molecular formula of any member of the
series by substituting n for the number of carbon atoms.

For example, the general formula of a halogenoalkane is

CnH2n+1X, where X is a halogen.

Example: what is the molecular formula of chloroethane?

1. Write down the general formula: CnH2n+1X
2. Write down the value of n: n=2
3. Substitute n into the general formula: C2H5Cl

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What is isomerism?
Isomers are molecules with the same molecular formula
(i.e. the same number and type of atoms) but in which the
atoms are arranged in a different way.

There are two main categories of isomerism: structural

isomerism and stereoisomerism.

 Structural isomers have different structural formulae.

Three types of structural isomerism are chain isomerism,
positional isomerism and functional group isomerism.

 Stereoisomers have the same structural formula, but

the 3D arrangement of atoms is different. Two types
are cis–trans isomerism and optical isomerism.

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Chain isomerism in alkanes
In chain isomers, the carbon chain is arranged differently.
For example, hexane has several chain isomers, all with the
molecular formula C6H14:

hexane

2,3-dimethylbutane

3-methylpentane
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Positional isomerism
In positional isomers, the functional group is attached to
a different carbon atom.

For example, 1-chloropentane

chloropentane has
several positional
isomers, all with
the molecular
formula C5H11Cl: 2-chloropentane

3-chloropentane

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Positional isomerism in alkenes
Positional isomerism also exists in alkenes with four or more
carbon atoms.

hex-1-ene
For example,
hexene has
several positional
isomers, all with hex-2-ene
the molecular
formula C6H12:

hex-3-ene

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Functional group isomerism
Functional group isomers contain different functional groups
and so are members of different homologous series.

For example, both alcohols and ethers have the general

formula CnH2n+2O so they may be functional group isomers:

propanol (C3H8O) methoxyethane (C3H8O)

an alcohol an ether

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Rotation around the C=C bond in alkenes
Molecules can rotate freely around single C-C covalent bonds,
but not around C=C double bonds.

This leads to type of stereoisomerism called cis–trans

isomerism, in which isomers differ in the arrangement of
the groups attached to the carbons in the double bonds.

is not the
same as

These isomers cannot be superimposed on each other

because the arrangement of the methyl groups is different.

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Cis–trans isomerism
If an alkyl group or atom other than hydrogen is attached
to each carbon then the isomers can be named either
cis (‘on the same side’) or trans (‘on the opposite side’).

cis-but-2-ene trans-but-2-ene

cis-1,2-dichloroethene trans-1,2-dichloroethene
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Limitations of cis–trans isomerism
In more complex organic compounds, in which multiple
hydrogens have been substituted by different groups,
isomers cannot be defined using the cis–trans notation.

For example, is it possible to identify which of these

halogenoalkanes is the cis isomer and which is the
trans isomer?

Instead, a different system is used for these type of

molecules: E–Z notation.

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E–Z isomerism
The E–Z notation is used to identify stereoisomers that
cannot be called cis or trans.

Isomers are identified as either E or Z depending on what

‘priority’ is given to the groups attached to the carbon
atoms in the double bond. The priority of these groups is
determined by a complex series of rules.
 E represents the German word ‘entgegen’, and
corresponds to trans isomers. The highest priority groups
are on the opposite side of the double bond.
 Z represents the German word ‘zusammen’, and
corresponds to cis isomers. The highest priority
groups are on the same side of the double bond.

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Optical isomerism
Another form of stereoisomerism is optical isomerism, in
which a molecule can exist as two isomers that are non-
superimposable, mirror images of each other, just like a left
hand and right hand.

optical isomers of the

amino acid alanine

Optical isomers have the same physical properties, but they

rotate polarized light in opposite directions.

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