IB ChemistryStructure 33.23.2.6

Structural Isomerism

Same molecular formula, different connectivity: three types of structural isomers.

Structure 3.2 SL & HL ⏱️ ~4 min revision
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)
Key Concept

Consequences of Structural Isomerism

Structural isomers share the exact same molecular formula but have different physical properties (different boiling points due to surface contact area) and different chemical reactivity (especially functional group isomers like ethanol vs methoxymethane).

Examiner Trap

Chain Conformation vs True Isomerism

Drawing a straight carbon chain with a bend or 90° angle does NOT create an isomer! Because single C–C sigma bonds rotate freely, conformational rotation produces identical molecules. To form a true isomer, you must disconnect and reconnect atoms in a different order.

Classification

Primary (1°), Secondary (2°), and Tertiary (3°) Compounds

Alcohols & Halogenoalkanes: Classified by the number of carbon atoms bonded to the carbon bearing the functional group:

  • Primary (1°): Carbon attached to 1 (or 0) other carbon (e.g. CH₃CH₂OH)
  • Secondary (2°): Carbon attached to 2 other carbons (e.g. CH₃CH(OH)CH₃)
  • Tertiary (3°): Carbon attached to 3 other carbons (e.g. (CH₃)₃COH)

Amines: Classified by the number of carbons bonded directly to the nitrogen atom.

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