Define isomerism and the different types relevant to stereochemistry
Isomerism is the existence of two or more compounds having the same
molecular but exhibit difference in their chemical and physical properties.
The two compounds show different properties even if they have same
atoms or group present and have same covalent bonding .
The isomers that differ in their bond connectivity are called constitutional or
structural isomer.
• Bond connectivity ; it describes the sequence in which different atoms or
groups are bonded to each other in a molecule.
• The study of the three-dimensional nature (spatial arrangement) of
molecules in space is known as stereochemistry.
Constitutional or structural isomers
• Constitutional isomers have same molecular formula but different bond
connectivity, that is, the sequence in which atoms are bonded in a
molecule, is different.
• The different in structure is due to the difference in the arrangement of
atoms within the molecules, irrespective of their position in space.
Structural isomerism can be subdivided into 3 types
• Chain isomerism; the isomers differ in way the carbon atoms are bonded to
each other in a chain.
Position isomerism
• Two or more molecules those having same molecular formulae but having
difference in the position of functional group on the carbon chain are
called position isomers and the phenomenon is called position isomerism.
Functional isomerism
• Two or more than two molecules those having the same molecular
formulae but different functional groups are called functional isomers and
the phenomenon is termed as functional isomerism.
Configurational isomerism
• The carbon is tetravalent in the nature and non-polar tetrahedral geometry
in carbon compounds gave arise concept stereochemistry . The
arrangement of different groups or atoms in space is termed as
configuration.
Stereoisomers
These differ from structural isomers, in that structural isomers have different
structural formulae, where as stereoisomers have the same general
structural formula but different orientation in space.
Kinds of stereoisomerism
Optical isomerism
Geometrical isomerism
• Optical isomerism is the phenomenon when the isomer have a unique
ability to rotate the plane polarized light either towards the left hand /
clockwise direction called dextrorotary (+) or right / anticlockwise
direction called levorotatory (-)
Enantiomers
They are optical isomers, with two stereoisomers that are related to each
other by reflection they are mirror image if each other that are non-
superimposable .
They have the same physical properties, except for the direction in which
they rotate polarized light (optical activity)
Diastereomers
• The stereoisomers of a compound, which are not mirror images of each
other are termed as Diastereomers. They exist only when a compound has
two or more stereogenic centres.
• The pair of stereoisomers that differs in the arrangement of atoms or
groups bonded with at least one stereocenters .
Geometrical isomerism
• Geometrical isomerism contain double bonds, which cannot rotate,
however they can also arise from ring structures, wherein the rotation of
bonds is greatly restricted.
Cis-trans isomers
• The term cis and trans are derived from Latin, in which cis means ’’on the
other side’’ or “ across”
• If the total number of different substituents on a double bond is 2, then
geometric isomers may be classified as cis- or trans-
