Isomerism
A concise revision guide to structural isomerism in organic chemistry, including chain isomerism, position isomerism and functional group isomerism.
- 4.10-a
- 4.10-b
- 4.11-a
- 4.11-b
What these spec points say
- 4.10-a understand the term 'structural isomerism'
- 4.10-b be able to draw structural isomers of organic molecules given their molecular formula
- 4.11-a be able to draw structural isomers of alkanes with up to six carbon atoms
- 4.11-b be able to name structural isomers of alkanes with up to six carbon atoms
Isomers of C₅H₁₂ and Surface Contact
Choose a step to compare the three chain isomers of C₅H₁₂, see how branching cuts surface contact, and watch their boiling points appear. Drag to rotate.
© Dr. Mohammed Al-Fatah – onlinelearningsystem.net
GCSE Recap: Molecular and Structural Formulae
Check that you can count atoms in a structural formula and know what a molecular formula leaves out.
What Are Structural Isomers?
Structural isomers are compounds that have the same molecular formula but different structural formulae.
This means the compounds contain the same number of each type of atom, but the atoms are connected in a different order. In organic chemistry, this usually changes the carbon skeleton, the position of a functional group or the functional group itself.
Definition: Structural isomers have the same molecular formula but different structural formulae. The difference is in how the atoms are arranged and bonded together.
Exam focus: To decide whether two compounds are structural isomers, compare the molecular formula first, then compare how the atoms are connected.
Quick Check: Same Molecular Formula?
Work out each molecular formula to find the one true isomer of hexane.
Quick Check: Isomers from Skeletal Formulae
Work out the molecular formula of each skeletal structure, then pick the pair of isomers.
Chain Isomerism
Chain isomerism occurs when compounds have the same molecular formula but different structures of the carbon skeleton.
The carbon chain may be straight or branched. For example, pentane, 2-methylbutane and 2,2-dimethylpropane all have the molecular formula C5H12, but their carbon skeletons are different.
Pentane
A straight-chain alkane with five carbon atoms.
2-methylbutane
A branched isomer with the same molecular formula as pentane.
2,2-dimethylpropane
A more highly branched isomer of C5H12.
Quick Check: Isomers or the Same Compound?
Decide whether each pair shows chain isomers, one compound drawn twice, or two compounds that are not isomers.
Position Isomerism
Position isomerism occurs when compounds have the same molecular formula but different structures because the same functional group is in a different position on the same carbon skeleton.
For example, 1-bromopropane and 2-bromopropane both have the formula C3H7Br, but the bromine atom is attached to a different carbon atom.
1-bromopropane
The bromine atom is attached to carbon 1 of the propane chain.
2-bromopropane
The bromine atom is attached to carbon 2 of the propane chain.
Halogenoalkanes are useful examples for practising position isomerism because the halogen can occupy different positions on the carbon chain.
Shorten the chain one carbon at a time, move the branch or group along, and throw out any repeats.
Quick Check: Spot the Position Isomer
Only one of these four structures is a position isomer of pentan-1-ol.
Quick Check: Counting Isomers
Draw the isomers on paper and count them before you flip each card.
Functional Group Isomerism
Functional group isomerism occurs when compounds have the same molecular formula but the atoms are arranged to give different functional groups.
This is more than a change in the position of the same group. The compounds belong to different homologous series, so they may have different chemical reactions and physical properties.
Butan-1-ol
An alcohol, C4H10O. Its functional group isomer is the ether ethoxyethane, C2H5OC2H5, which has the same formula.
Cyclohexane
A cycloalkane, C6H12. It is a functional group isomer of hex-1-ene, C6H12: the same atoms form a ring with no C=C bond in one and a chain with a C=C bond in the other.
Important: Butan-1-ol and cyclohexane are not isomers of each other, because their molecular formulae differ. Two structures are only isomers if they have the same molecular formula. Do not classify compounds as isomers simply because their structures look similar or contain related atoms.
Quick Check: Every Isomer of Pent-1-ene
Click all the compounds that share the molecular formula of pent-1-ene.
Comparing the Types of Structural Isomerism
The table below summarises the difference between the three common types of structural isomerism used in this topic.
| Type of isomerism | What changes? | Typical example |
|---|---|---|
| Chain isomerism | The arrangement of the carbon skeleton changes. | Pentane, 2-methylbutane and 2,2-dimethylpropane. |
| Position isomerism | The same functional group is attached at a different position on the same carbon skeleton. | 1-bromopropane and 2-bromopropane. |
| Functional group isomerism | The atoms are arranged to give different functional groups. | Cyclohexane and hex-1-ene, both C6H12. |
Exam focus: Always check the molecular formula before naming the type of isomerism. Same formula first, then decide what structural feature has changed.
Check the molecular formula first, then the functional group, then the carbon skeleton.
Quick Check: Which Type of Isomerism?
Pick the accurate statement about each new pair of compounds.
Common Exam Mistakes
- Do not say structural isomers have the same structural formula. They have the same molecular formula but different structural formulae.
- Do not confuse chain isomerism with position isomerism. Chain isomerism changes the carbon skeleton.
- Do not describe position isomerism as a different functional group. It is the same functional group in a different position.
- Do not ignore the molecular formula. If the molecular formula is different, the compounds are not isomers.
Isomerism Summary
Structural isomers
Same molecular formula, different structural formulae.
Chain isomerism
The carbon skeleton changes from straight-chain to branched.
Position isomerism
The same functional group is in a different position on the carbon skeleton.
Functional group isomerism
The same atoms are arranged to give different functional groups.
Isomerism FAQs
These questions check how to decide whether two structures are isomers and which type.
Are butane and 2-methylpropane isomers?
Yes. Both are C4H10, but one has a straight chain and the other a branched chain, so they are chain isomers.
Is 3-bromopropane a different isomer from 1-bromopropane?
No. It is the same molecule numbered from the other end, so the correct name is 1-bromopropane. Always use the lowest number.
Which pair shows functional group isomerism?
Cyclohexane and hex-1-ene. Both are C6H12, but one is a cycloalkane and the other an alkene.
Why are butan-1-ol and cyclohexane not isomers?
Butan-1-ol is C4H10O and cyclohexane is C6H12. Different molecular formulae mean they cannot be isomers.
Is drawing the same chain bent a new isomer?
No. A chain drawn with a bend is the same molecule. Count the longest continuous chain before deciding that two drawings are isomers.
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.
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