3.6.6
Isomerism
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Structural Isomerism
Structural isomers are molecules which have the same molecular formula but a different arrangement of atoms in space.
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Chain isomers
- Chain isomers are molecules that have the same molecular formula but one is linear and one is branched. For example:
- Butane is a linear molecule with the molecular formula C4H10.
- Methylpropane is a branched molecule with the molecular formula C4H10.
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Position isomers
- Position isomers are molecules that have the same molecular formula but have their functional group in different places. For example:
- Butan-1-ol has a hydroxyl group attached to carbon-1.
- Butan-2-ol has a hydroxyl group attached to carbon-2.

Functional group isomers
- Functional group isomers are isomers that have had their structures changed so that they have different functional groups. For example:
- Propanoic acid.
- Methyl ethanoate.
Stereoisomerism
Stereoisomers are molecules that have the same molecular formula, same functional groups and same functional group positions but different arrangements of atoms in space.

Alkene stereoisomerism
- Stereoisomerism can be seen in alkenes.
- It is possible in alkenes because of the presence of double bonds:
- Unlike single bonds, double bonds are rigid and you cannot rotate around them.
- So alkenes can display stereoisomerism at the double bond.

An example
- The simplest way to understand what this means is with an example.
- Above are the two different alkenes, (E)-but-2-ene and (Z)-but-2-ene.
- The molecules are the same in every way, except for the atoms' position in space.
- Above are the two different alkenes, (E)-but-2-ene and (Z)-but-2-ene.

What do E and Z mean?
- E and Z come from the German words 'entgegen' and 'zusammen' for 'opposite' and 'together'.
- An E-alkene has the larger groups on opposite sides.
- A Z-alkene has the larger groups on the same side.
- A good way to remember this is that Z alkenes have large groups on the 'zame zide'.
Cahn-Ingold Prelog Rules
The Cahn-Ingold Prelog rules help us assign E/Z isomerism to more complicated molecules.

The Cahn-Ingold Prelog rules
- They help to distinguish between E and Z isomers for more complicated cases.
- The rules work by numbering the four directly connecting atoms in order of their atomic mass number. From this, we give them a 'priority'.
- The highest atomic number gets priority 1.
- The second highest atomic number gets priority 2, and so on.

E vs Z
- E:
- Priority 1 and 2 are on different sides of the double bond.
- I.e. The two atoms with the highest atomic mass number are on different sides.
- Priority 1 and 2 are on different sides of the double bond.
- Z:
- Priority 1 and 2 are on the same side of the double bond.
- I.e. The two atoms with the highest atomic mass number are on the same side.
- Priority 1 and 2 are on the same side of the double bond.

An example: E
- The shown but-2-ene is an E geometry because the two methyl groups are on opposite sides of the double bond.

An example: Z
- The shown but-2-ene is a Z geometry because the two methyl groups are on the same side of the double bond.
1Structure - Models of the Particulate of Matter
1.1Introduction to the Particulate Model of Matter
1.2The Nuclear Atom
1.3Electron Configuration
1.4Counting Particles by Mass: The Mole
1.6Elements, Compounds & Mixtures
1.7States of Matter & Changes of State
1.8Reacting Masses &. Volumes
1.9Solutions
2Structure - Models of Bonding & Structure
2.1The Ionic Model
2.2The Covalent Model
2.3Covalent Structures
2.4The Metallic Model
2.5From Models to Materials
2.6Valence Electrons & Ionic Compounds
2.7Molecular Shape
3Structure - Classification of Matter
3.1The Periodic Table: Classification of Elements
3.2Periodic Trends
3.3Group 1 Alkali Metals
3.4Halogens
3.5Noble gases, group 18
3.6Functional Groups: Classification of Organic
3.7Functional Group Chemistry
3.8Alkanes
3.9Alcohols
4Reactivity - What Drives Chemical Reaction?
4.1Endothermic & Exothermic Reactions
4.2Enthalpy of Reaction, Formation, & Hess' Law
5Reactivity - How Much, How Fast & How Far?
5.1Kinetics
5.2Rates of Reaction
5.3Stoichometry
5.4Le Châtelier’s Principle
5.5Introduction to Equilibrium
5.6Equilibrium Constant
5.7Reaction Quotient & Equilibrium Constant
6Reactivity - The Mechanisms of Chemical Change
6.1Proton Transfer Reactions
6.2The pH Scale
6.3Strong & Weak Acids and Bases
6.4Acid Deposition
6.5Types of Organic Reactions
6.6Oxidation & Reduction
6.7Electrochemical Cells
6.9Acid-Base Titrations
6.9.1Titration Calculation Weak Acid & Strong Base6.9.2Titration Experimental Detail6.9.3Extended Response - Titration6.9.4Titration Calculations6.9.5Titration Curves6.9.6Titration Calculation Strong Acid & Weak Base6.9.7IB Multiple Choice - Titrations6.9.8Polyprotic Acids6.9.9Titration Calculations Strong Acid & Strong Base6.9.10Titrations Curves 2
7Measurement, Data Processing & Analysis
7.1Uncertainties & Errors in Measurements & Results
7.2Graphical Techniques
7.3Spectroscopic Identification of Organic Compounds
7.4Infrared Spectroscpy
Jump to other topics
1Structure - Models of the Particulate of Matter
1.1Introduction to the Particulate Model of Matter
1.2The Nuclear Atom
1.3Electron Configuration
1.4Counting Particles by Mass: The Mole
1.6Elements, Compounds & Mixtures
1.7States of Matter & Changes of State
1.8Reacting Masses &. Volumes
1.9Solutions
2Structure - Models of Bonding & Structure
2.1The Ionic Model
2.2The Covalent Model
2.3Covalent Structures
2.4The Metallic Model
2.5From Models to Materials
2.6Valence Electrons & Ionic Compounds
2.7Molecular Shape
3Structure - Classification of Matter
3.1The Periodic Table: Classification of Elements
3.2Periodic Trends
3.3Group 1 Alkali Metals
3.4Halogens
3.5Noble gases, group 18
3.6Functional Groups: Classification of Organic
3.7Functional Group Chemistry
3.8Alkanes
3.9Alcohols
4Reactivity - What Drives Chemical Reaction?
4.1Endothermic & Exothermic Reactions
4.2Enthalpy of Reaction, Formation, & Hess' Law
5Reactivity - How Much, How Fast & How Far?
5.1Kinetics
5.2Rates of Reaction
5.3Stoichometry
5.4Le Châtelier’s Principle
5.5Introduction to Equilibrium
5.6Equilibrium Constant
5.7Reaction Quotient & Equilibrium Constant
6Reactivity - The Mechanisms of Chemical Change
6.1Proton Transfer Reactions
6.2The pH Scale
6.3Strong & Weak Acids and Bases
6.4Acid Deposition
6.5Types of Organic Reactions
6.6Oxidation & Reduction
6.7Electrochemical Cells
6.9Acid-Base Titrations
6.9.1Titration Calculation Weak Acid & Strong Base6.9.2Titration Experimental Detail6.9.3Extended Response - Titration6.9.4Titration Calculations6.9.5Titration Curves6.9.6Titration Calculation Strong Acid & Weak Base6.9.7IB Multiple Choice - Titrations6.9.8Polyprotic Acids6.9.9Titration Calculations Strong Acid & Strong Base6.9.10Titrations Curves 2
7Measurement, Data Processing & Analysis
7.1Uncertainties & Errors in Measurements & Results
7.2Graphical Techniques
7.3Spectroscopic Identification of Organic Compounds
7.4Infrared Spectroscpy
Practice questions on Isomerism
Can you answer these? Test yourself with free interactive practice on Seneca — used by over 10 million students.
- 1Three types of structural isomerism:Fill in the list
- 2What do position isomers have?Multiple choice
- 3Which of the following is NOT a chain isomer of pentane?Multiple choice
- 4What do stereoisomers NOT have in common?Multiple choice
- 5E-alkene isomers are identified by which of the following?Multiple choice
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