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Name: -


CMS ID: - 33722

Department: - BIOTECH (1st Semester)
Instructor: -

The phenomenon where certain compounds, with the same molecular formula, exist in different
forms owing to their different organizations of atoms. The concept of isomerism illustrates the
fundamental importance of molecular structure and the shape in organic chemistry.

Structural Isomerism:
Structural Isomers have different structural formulae because their atoms are linked together in
different ways.
It arises owing to:

of Carbon skeleton

e.g. The formula C4H10 represents two possible structural formulae, butane and methylpropane:


of Functional group

e.g. propan-1-ol and propan-2-ol


Functional groups

e.g. the molecular formula C2H60 represents both ethanol and methoxymethane.

Cyclic alkanes are isomeric with alkenes, e.g. cyclopropane and propene

Stereoisomers have the same structure and bond order but their atoms and groups of atoms are
arranged differently in space. They have different spatial arrangements and their molecules are
not superimposable. There are two types:


Involves a double bond, usually C=C, that does not allow free rotation about the double bond
(unlike a C-C single bond). They are not superimposable.
e.g. cis-but-2-ene and trans-but-2-ene

Stereoisomers may possess quite different physical properties, such as melting point, density and
solubility in water (look up those of maleic acid and fumaric acid). Ring structures and other steric
factors also result in geometric isomerism.

Geometric Isomers:
Geometric isomerism is actually a term that is strongly discouraged by IUPAC (the International Union of
Pure & Applied Chemistry), who prefer cis-trans, or E-Z in the specific case of alkenes. However,
geometric isomerism is still consistently used in many A Level courses to refer to both, so for that reason
Ive used that name here.
This type of isomerism most frequently involves carbon carbon double bonds (shown by two lines joining
each carbon instead of one). Rotation of these bonds is restricted, compared to single bonds, which can
rotate freely. This means that, if there are two different atoms, or groups of atoms, attached to each
carbon of the carbon carbon double bond, they can be arranged in different ways to give different
molecules. These atoms or groups can be given priorities, with atoms with higher atomic numbers given
higher priorities. If the highest priority groups for each carbon are on the same side of the molecule, that
molecule is denoted as the cis or Z isomer. If theyre on opposite sites, its denoted as the trans or E

The two different nomenclatures are a little confusing cis/trans is now less commonly used, with E/Z
instead being favoured. E stands for entgegen (opposite in german) whilst Z stands for zusammen
(together in german). The letter is simply added in brackets at the start of the molecules name in order
to indicate which isomer it is.

Optical isomerism:
Involves an atom, usually carbon, bonded to four different atoms or groups of atoms. They exist in
pairs, in which one isomer is the mirror image of the other.
e.g. butan-2-ol

These isomers are referred to as enantiomers. The central carbon atom to which four different
atoms or groups are attached, is called an asymmetrical carbon atom.
Enantiomers have identical physical constants, such as melting points and boiling points, but are
said to be optically active since they can be distinguished from each other by their ability to rotate
the plane of polarised light in opposite directions. A mixture of enantiomers in equal proportions is
optically inactive, and is called a racemic mixture. Use an organic chemistry textbook to find out
more about optical isomerism.