3.1.4Organic Chemistry
Structural Isomerism — Edexcel AS Chemistry Revision Notes & Topical Questions
5 min read 4 parts Lesson 17 of 42
Curriculum Equation Key معادلة تفاعل تكوين الإستر (الأسترة) - Esterification Reaction EquationFast Exam Solution
R-COOH + R2-OH ⇌ (conc. H₂SO₄) R-COO-R2 + H₂O
Word Equation & Conditions: حمض كربوكسيلي + كحول (في وجود حمض الكبريتيك المركز كعامل حفاز ونازع للماء) ⇌ إستر + ماء
Location & Specifications: الكيمياء العضوية للثانوية العامة والتحصيلي و Edexcel Chemistry.
Part 1 of 4What Structural Isomers Are
Definition
- Definition Structural isomers have the same molecular formula but different arrangements of atoms joined together.
Properties
- Properties They often have different physical properties, such as boiling points, and may have different chemical properties.
Chain
- Chain Chain isomers have different carbon skeletons, for example straight-chain and branched forms.
Position
- Position Positional isomers keep the same skeleton and functional group but place the group at different positions.
Functional group
- Functional group Functional group isomers have the same molecular formula but different functional groups.
Part 2 of 4Examples to Know
Examples to Know
C₄H₁₀
- C₄H₁₀ Butane and 2-methylpropane are chain isomers with different carbon skeletons.
C₅H₁₂
- C₅H₁₂ Pentane, 2-methylbutane and 2,2-dimethylpropane are the three chain isomers of this formula.
C₄H₈
- C₄H₈ But-1-ene and but-2-ene are positional isomers because the double bond moves along the chain.
C₃H₈O
- C₃H₈O Propan-1-ol and propan-2-ol are positional isomers, while methoxyethane is a functional group isomer.
Strategy
- Strategy Work systematically: start with the longest chain, then shorten it and move the groups to each position.
| Type | Same | Different | Example |
|---|---|---|---|
| Chain | Molecular formula | Carbon skeleton | Butane / 2-methylpropane |
| Position | Skeleton and group | Group position | Propan-1-ol / propan-2-ol |
| Functional group | Molecular formula | Functional group | Propan-1-ol / methoxyethane |
Part 3 of 4Effect of Branching on Boiling Point
1
Straight-chain molecules lie side by side and have a large surface area in contact with their neighbours.
2
This gives stronger London forces between molecules and therefore higher boiling points.
3
Branched isomers are more compact, so molecules touch over a smaller area.
4
The London forces are weaker, so less energy is needed to separate the molecules.
5
For example, pentane boils at about 36 °C whereas 2,2-dimethylpropane boils at about 10 °C.
Part 4 of 4Exam Checklist & Tips
3.1.4 – Key Points for the Exam
- Isomers Compounds with the same molecular formula but different structures.
- Structural isomers Isomers with the same molecular formula but different structural formulae.
- Chain isomerism Isomerism caused by different arrangements of the carbon skeleton.
- Positional isomerism Isomerism caused by the functional group occupying different positions.
- Functional group isomerism Isomerism in which isomers have different functional groups.
Common Mistakes
- Drawing the same molecule twice in a different orientation and counting it as two isomers.
- Missing isomers by not working systematically from the longest chain.
- Thinking that isomers have the same boiling point, when branching generally lowers it.
- Calling propan-1-ol and methoxyethane positional isomers, when they have different functional groups.
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