13.

4 Isomerism: structural and stereoisomerism

Organic chemistry
CONTENTS

• Classification of isomers

• (E) And (Z) nomenclature

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Classification of isomers
Isomers are different compounds that have the same molecular formula

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Classification of isomers
1. Structural isomers: compounds with the same number of atoms and bonds but with
different arrangement

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Classification of isomers
2. Stereoisomer: Compound with the same molecular formula and structural formula but
different arrangement of their bond in space
If both groups are located on the same side of the double bond – CIS
If both groups are located on opposite sides of the doble bond – Trans

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Classification of isomers
3. Configurational Isomers:
• Unlike conformational isomers that interconvert simple bond rotation, configurational
isomers can only change from one form to another by breaking and reforming covalent
bonds
• The two categories of configurational isomers are enantiomers and diastereomers
• Both of these can also be considered as optical isomers because the different special
arrangement of groups in these molecules affect the rotation of the plane of polarization
of plane polarized light
• An object is considered chiral if its mirror image can not be superimposed on the original
object
• This implies that the molecule lacks an internal plane of symmetry

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Classification of isomers
• Two molecules that are non-superimposed mirror images of each other are called
enantiomers
• Molecules may also be related as diastereomers
• These are chiral and share the same connectivity but are not mirror images of each
other
• This is because they differ at some (n=but not all) of their multiple chiral centers

diastereomer

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Classification of isomers
Polarised and optical activity
• Optical activity refers to h=the rotation of this plane-
polarize light by a chiral molecule
• At molecular level, 1 enantiomer will rotate plane-
polarized light to the same magnitude but in the
opposite direction of its mirror image
• A compound that rotates the plane of polarized light to
the right or clockwise is dextrorotatory (d-) and is
labelled (+)
• A compound that rotates the plane of polarized light to
the left or anticlockwise is levorotatory (l-) and is labelled
(-)

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(E) and (Z) nomenclature
• This nomenclature is used for compounds with polysubstituted double bonds
• Priority is assigned based on the atom bound to the double bonded carbons
• The alkane is named (Z) if two of the highest priority substituents on each carbon
atom are on the same side of the double bond
• (E) if they are on the opposite sides

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(E) and (Z) nomenclature
Rules:
• The higher atomic number, the higher the priority
• If the atomic numbers are equal, priority is determined by the next atom outwards
• If a tie, the atoms in this group are compared one-by-one in descending atomic
number order unitil the tie is broken

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