IB ChemistryStructure 33.23.2.6
3.2.6

Structural Isomerism

Same molecular formula, different connectivity. Three types of structural isomers.

Type What Changes Example (C₄H₁₀)
Chain Arrangement of the carbon skeleton (straight vs branched) Butane vs 2-methylpropane
Positional Position of the functional group on the same chain Butan-1-ol vs Butan-2-ol
Functional group The functional group itself is different Ethanol (C₂H₅OH) vs Methoxymethane (CH₃OCH₃)

🔑 Consequences

Structural isomers have the same molecular formula but different physical properties (different BPs, solubilities) and may have different chemical properties (if the functional group changes). Branched isomers typically have lower boiling points due to smaller surface area and weaker LDFs.

⚠️ "Bending" Is Not Isomerism

Drawing a straight-chain molecule with a bend at 90° does not create an isomer. Test: name both structures using IUPAC rules. If they have the same name, they are the same molecule, not isomers.

⚠️ 1° / 2° / 3° Classification

Alcohols & halogenoalkanes: classify by how many carbons are attached to the alpha-carbon (the C bonded to –OH or –X).

Amines & amides: classify by how many carbons are attached directly to the nitrogen atom.

Don't mix these rules up. The IB tests this distinction!

← 3.2.5 Nomenclature3.2.7 Stereoisomerism (HL) →