Geometric Isomerism
A concise revision guide to stereoisomerism in alkenes, restricted rotation around C=C bonds, E-Z naming, priority groups and the link between E-Z and cis-trans isomerism.
How Cambridge Names This Isomerism
The Cambridge syllabus divides stereoisomerism into geometrical (cis/trans) isomerism and optical isomerism. Geometrical isomerism is the type shown by alkenes, and it arises from restricted rotation about the C=C bond caused by the π bond.
Cambridge uses the cis/trans names as the standard system. The E/Z system is acceptable but not required, so you may use either in an answer. This page teaches both, with cis/trans as the naming you should be able to use for every example.
Exam focus: Describe geometrical isomerism as a form of stereoisomerism, and explain its origin in terms of restricted rotation due to the presence of the π bond. Cambridge also expects you to identify geometrical isomerism in cyclic compounds, not only in alkenes.
What Are Stereoisomers?
Stereoisomers are compounds with the same structural formula but a different three-dimensional arrangement of atoms in space.
In alkenes, this matters because the C=C double bond restricts rotation. The atoms or groups attached to the double bond cannot freely rotate into a new arrangement without breaking the pi bond.
This produces a type of stereoisomerism called E-Z stereoisomerism, also called geometric isomerism.
Key idea: E-Z isomers are not structural isomers. They have the same connectivity, but different spatial arrangement around the carbon-carbon double bond.
Quick Check: Structural Isomer or Stereoisomer?
Complete a comparison of three alkenes that are not on this page.
Why E-Z Isomerism Occurs
E-Z isomerism occurs because the carbon-carbon double bond contains a pi bond. Rotation around the C=C bond is restricted because rotating one carbon would break the sideways overlap of the p orbitals.
By contrast, a carbon-carbon single bond can rotate freely. This is why simple alkanes do not usually produce this type of fixed geometric arrangement.
Exam focus: Always link E-Z isomerism to restricted rotation around the C=C double bond.
Quick Check: Explain Two Forms Against One
Write a short explanation, then compare it with the mark points and the model answer.
Chloroethane: rotation around the C-C single bond
The C-C single bond is a σ bond. In this model, the CH₃ side remains fixed while the CH₂Cl side rotates slowly around the C-C bond axis.
Conditions for E-Z Stereoisomerism
For an alkene to show E-Z stereoisomerism, two conditions must both be met:
- There must be restricted rotation about the carbon-carbon double bond.
- Each carbon atom of the C=C bond must be attached to two different atoms or groups.
If either carbon in the C=C bond has two identical groups attached, E-Z isomerism is not possible.
Quick Check: Which Alkenes Show E-Z Isomerism?
Sketch each alkene, then click every one that has E and Z isomers.
1,2-Dichloroethene: restricted rotation around the C=C bond
The C=C double bond contains a π bond. When one side tries to rotate, the sideways overlap needed for the π bond would be disrupted, so the molecule is knocked back instead of rotating freely.
Assigning E and Z
To name an alkene with E-Z stereoisomerism, first identify the priority group on each carbon atom of the double bond.
The priority group is found by comparing the atoms directly attached to each double-bond carbon. The atom with the higher atomic number has higher priority.
| Arrangement of priority groups | Name used | Memory aid |
|---|---|---|
| Priority groups on the same side of the C=C bond | Z | Z comes from zusammen, meaning together. |
| Priority groups on opposite sides of the C=C bond | E | E comes from entgegen, meaning opposite. |
Quick Check: E, Z or Neither?
Find the priority group on each carbon atom, then decide quickly.
Cis-Trans Isomerism
Cis-trans isomerism is a simpler special case of E-Z isomerism. It can be used when two of the substituent groups attached to the double bond are identical.
For but-2-ene, the two CH3 groups can be on the same side or on opposite sides of the double bond.
Z-but-2-ene
The two CH3 groups are on the same side, so this can also be called cis-but-2-ene.
E-but-2-ene
The two CH3 groups are on opposite sides, so this can also be called trans-but-2-ene.
Important: E-Z notation is the more general and accurate naming system, especially when the groups attached to the C=C bond are not identical.
Quick Check: Pick the Accurate Statement
Each round puts a common mistake next to the correct idea, in a molecule you have not met on this page.
Common Exam Mistakes
- Do not call E-Z isomers structural isomers. They have the same structural formula.
- Do not assign E or Z by only looking at the largest group visually. Use atomic number priority. For Cambridge, cis/trans names are accepted wherever two of the substituents are the same.
- Do not assume every alkene shows E-Z isomerism. Each carbon in the C=C bond must have two different groups attached.
- Do not say the molecule rotates around the double bond. The whole point is that rotation around C=C is restricted.
Master Alkenes for Cambridge International AS & A Level Chemistry
Continue from these free revision notes into the full Topic 14.2 Alkenes course. The guided video lessons are ready now; the Cambridge International MCQ bank, teacher-marked short-answer questions and KASP spec-point report are being written, and the course opens for enrolment as soon as they are complete.
Guided video teaching
Learn the chemistry and exam technique through structured video lessons with worked examples and walkthroughs.
Instant MCQ feedback
Auto-marked MCQ quizzes provide immediate diagnostic feedback for every answer choice.
Teacher-marked SAQs
Submit written exam responses and receive chemistry specialist feedback with improvement guidance.
Progress tracking
Identify strengths and weaknesses across the full Topic 14.2 specification with targeted reporting.
See how the course works
Click play to start the course preview animation.
Some ionic radii are shown.
| Ion | Ionic radius / nm |
|---|---|
| Na+ | 0.102 |
| K+ | 0.138 |
| F− | 0.133 |
| Cl− | 0.180 |
Which compound has the strongest ionic bonding?
Explain why the metallic bonding in magnesium is much stronger than that in sodium.
Copyright notice: This OLS revision content, including the explanations, layout, diagrams, tables and embedded learning structure, is authored for Online Learning System by Dr. Mohammed Al-Fatah. It may not be copied, reproduced, redistributed or adapted without written permission.
Keep this note — free
Save your progress across every Cambridge topic. A free account remembers which topics you have covered, saves your question scores, and syncs across your phone and laptop.
- Track every topic you have finished
- Keep your practice-question scores
- No payment, no card, free forever
Already registered? Log in