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Isomerism

Isomers are compounds that have the same molecular formula but possess a different chemical structure, potentially leading to vastly different physical, chemical, and biological properties.
Constitutional isomers possess a different connectivity from one another. This means while the molecular formulae are the same, there can be many possibilities for different functional groups or bonding patterns.

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Stereoisomers possess the same molecular formula in the same connectivity, but have the arrangement of atoms or bonds in 3D space being different.

Conformational isomers are a type of stereoisomer where the difference in spatial arrangement is due to rotation or twisting about a single bond.

Note: conformational isomers are identical molecules!



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Stereoisomers possess the same molecular formula in the same connectivity, but have the arrangement of atoms or bonds in 3D space being different.

Configurational isomers are a type of stereoisomer where the difference in spatial arrangement is not due to rotation or twisting about a single bond.
  • Geometric isomers (cis-trans or E/Z isomers) are a type of configurational isomer where the difference in spatial position is around a bond where rotation is not possible (e.g. a double bond).

Watch Out!
Geometric isomers are not possible if two groups on one carbon are the same!

  • Optical isomers are a type of configurational isomer where the difference is in the three-dimensional relationship between the substituents. Chiral carbons give rise to optical isomers.




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Example: Isomerism

Complete the table below, by filling each row. If something is not possible write N/A. If one or more of the isomers are not possible please explain your reasoning for each.


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