3.1.10 Structural Isomerism

• Structural isomers are compounds that have the same molecular formula but different structural formulae
  • Eg. propene and cyclopropane

Both propene and cyclopropane are made up of 3 carbon and 6 hydrogen atoms but the structure of the two molecules differs

• There are three different types of structural isomerism:
  • Chain isomerism
  • Positional isomerism
  • Functional group isomerism

Chain isomerism

• Chain isomerism is when compounds have the same molecular formula, but their longest hydrocarbon chain is not the same
• This is caused by branching
  • Eg. pentane and 2,2-dimethylpropane

Both compounds are made up of the same atoms however the longest carbon chain in pentane is 5 and in 2,2-dimethylpropane 3 (with two methyl branches)

Positional isomerism

• Positional isomers arise from differences in the position of a functional group in each isomer
  • The functional group can be located on different carbons
  • For example, butanol and 2-butanol

Both compounds have an alcohol group and are made up of 4 carbon, 10 hydrogen and one oxygen atom however in butanol the functional group is located on the first carbon and in 2-butanol on the second carbon

Functional group isomerism

• When different functional groups result in the same molecular formula, functional group isomers arise
• The isomers have very different chemical properties as they have different functional groups
  • For example, butanol and ethoxyethane

Both compounds have the same molecular formula however butanol contains an alcohol functional group and ethoxyethane an ether functional group