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Chirality

  • A molecule is described as being chiral if has a non-superimposable mirror images.
  • One way for a molecule to be chiral is through the presence of an asymmetric center (sometimes referred to as a chiral center), a tetrahedral center with four unique substituents.
  • We use the R and S stereochemical identifiers to distinguish between the two chiral forms, called enantiomers.
  • Enantiomers have the same physical properties (melting points, boiling points, etc.) but different chemical properties when they interact with other chiral molecules. This is especially common in biological systems which are full of chiral molecules.


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Very Important in Pharmaceuticals!!
  • Different enantiomers of the same drug can have wildly different properties.
  • It was found that the R isomer actually converts into the S isomer in the body.



Example: Locate Chiral Centres

Locate the asymmetric centers (chiral centers) in the molecule below
Find asymmetric centers by looking for atoms with four unique groups attached.


Practice: Molecules That Display Chirality

Which of the following molecules would display chirality?