text: Two compounds are said to be enantiomers if their molecules are mirror images of each other, that cannot be made to coincide only by rotations or translations – like a left hand and a right hand. The two shapes are said to be chiral.
  A classical example is bromochlorofluoromethane (). The two enantiomers can be distinguished, for example, by whether the path  turns clockwise or counterclockwise as seen from the hydrogen atom. In order to change one conformation to the other, at some point those four atoms would have to lie on the same plane – which would require severely straining or breaking their bonds to the carbon atom.  The corresponding energy barrier between the two conformations is so high that there is practically no conversion between them at room temperature, and they can be regarded as different configurations.
  The compound chlorofluoromethane , in contrast, is not chiral: the mirror image of its molecule is also obtained by a half-turn about a suitable axis.
  Another example of a chiral compound is 2,3-pentadiene  a hydrocarbon that contains two overlapping double bonds. The double bonds are such that the three middle carbons are in a straight line, while the first three and last three lie on perpendicular planes. The molecule and its mirror image are not superimposable, even though the molecule has an axis of symmetry.  The two enantiomers can be distinguished, for example, by the right-hand rule. This type of isomerism is called axial isomerism.
  Enantiomers behave identically in chemical reactions, except when reacted with chiral compounds or in the presence of chiral catalysts, such as most enzymes. For this latter reason, the two enantiomers of most chiral compounds usually have markedly different effects and roles in living organisms. In biochemistry and food science, the two enantiomers of a chiral molecule – such as glucose – are usually identified, and treated as very different substances.
  Each enantiomer of a chiral compound typically rotates the plane of polarized light that passes through it. The rotation has the same magnitude but opposite senses for the two isomers, and can be a useful way of distinguishing and measuring their concentration in a solution. For this reason, enantiomers were formerly called "optical isomers". However, this term is ambiguous and is discouraged by the IUPAC.
  Stereoisomers that are not enantiomers are called diastereomers. Some diastereomers may contain chiral center, some not.
  Some enantiomer pairs (such as those of trans-cyclooctene) can be interconverted by internal motions that change bond lengths and angles only slightly. Other pairs (such as CHFClBr) cannot be interconverted without breaking bonds, and therefore are different configurations.