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Introduction to Enantiomorphism

A consideration of the chirality of molecular configurations defines the curious stereoisomerism that is observed for carvone, lactic acid and a multitude of another organic compound. Tetravalent carbons have a tetrahedral configuration. If all four substituent groups are identical, like in tetrachloromethane or methane, the configuration is that of a highly symmetric "regular tetrahedron". Regular tetrahedron has six planes of symmetry and seven symmetry axes (four C3& three C2) and is, obviously, achiral. 

 If one of the carbon substituents is distinct from the other three, the degree of symmetry is lowered to a C3 axis and three planes of symmetry, although the configurations stay achiral. The tetrahedral configuration in such type of compounds is no longer regular, since bond angles and bond lengths vary as the bonded atoms or groups vary. Additional substitution may get reduced the symmetry even more, but as long as two of the four substituents are similar there is always a plane of symmetry that bisects the angle linking those substituents, these configurations so, are also achiral.

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A carbon atom which is bonded to four different atoms or groups loses all symmetry, and is frequently considered as an asymmetric carbon. The configuration of this type of a molecular unit is chiral and the structure may present in either a left-handed configuration or a right-handed configuration. This kind of configurational stereoisomerism is termedenantiomorphism and non-identical, mirror-image pair of stereoisomers that result are known as enantiomers. The structural formulas of carvone and lactic acid are displayed in the diagram with the asymmetric carbon that is red in color. Subsequently, we suppose and find these compounds to present as pairs of enantiomers. The existence of a single asymmetrically substituted carbon atom in a molecule is adequate to render the whole configuration chiral and modern terminology consider to such asymmetric (or dissymmetric) groupings as chiral centers. Most of the chiral centers we shall consider are asymmetric carbon atoms, although it should be recognized that other pyramidal or tetrahedral atoms may become chiral centers if correctly substituted. When more than one chiral center is present in a molecular structure, care have to be taken to analyze their relationship before concluding that a particular molecular configuration is chiral or achiral. This feature of stereoisomerism will be treated later.

In examining structural formulas to decide whether stereoisomers may exist, a useful first step is to identify all stereogenic elements. A stereogenic element is an axis, center, or plane that is a focus of stereoisomerism, like that an interchange of two groups attached to this characteristic leads to a stereoisomer. Stereogenic elements may be achiral or chiral. An asymmetric carbon is frequently a chiral stereogenic center, because interchanging any two substituent groups converts one enantiomer to the other. Though, care must be taken when evaluating bridged structures where bridgehead carbons are asymmetric.

Alkenes having two different groups on each double bond carbon (for example abC=Cab) comprise an achiral stereogenic element, because interchanging substituents at one of the carbons modifies the cis/trans configuration of the double bond. Chiral stereogenic planes or axes may be exists in a molecular configuration, as in the example of allenes.

Structural formulas for eight organic compounds are shown in the diagram below. Few of these structures are chiral and few are achiral. First, try to recognize all chiral stereogenic centers. Formulas having no chiral centers are essentially achiral. Formulas having one chiral center are all the time chiral and if two or more chiral centers are exist in a given structure it is probably to be chiral, but in unique cases, may be achiral.

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Structures F and G are achiral. The former has a plane of symmetry passing from the chlorine atom and bisecting the opposite carbon-carbon bond. The identical structure of compound E does not have this type of a symmetry plane and the carbon bonded to the chlorine is a chiral center (the two ring segments connecting this carbon are not same). Structure G is must be flat. All the carbons apart from that of the methyl group are sp2 hybridized, and so trigonal-planar in configuration. The Compounds C, D & H have more than one chiral center, and are also chiral. Keep in mind that all chiral structures may exist as a pair of enantiomers. Another configurational stereoisomers are possible if more than one stereogenic center is exists in a structure.

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