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Introduction of Configurational Stereoisomers of Cycloalkanes

Stereoisomers are also observed in certain disubstituted and higher substituted cyclic compounds. Different from the relatively flat molecules of alkenes, substituted cycloalkanes have to be viewed as 3-d configurations in order to appreciate the spatial orientations of the substituents. By agreement, chemists make use of heavy, wedge-shaped bonds to point out a substituent located above the average plane of the ring (note: cycloalkanes that are larger than three carbons are not planar) and a hatched line for bonds to groups or atoms located below the ring. Like in the case of the 2-butene stereoisomers, the disubstituted cycloalkane stereoisomers can be designated by nomenclature prefixes like Trans and cis. The stereoisomeric 1,2-dibromocyclopentanes displayed in the diagram, are an example.
Generally, stereoisomerism is possible if any two sp3 carbons in a ring have two different substituent groups (not counting other ring atoms). This is identical to the substitution pattern that gives rise to stereoisomers in alkenes; certainly, one might view a double bond as a two-membered ring. Four other illustrations of this type of stereoisomerism in cyclic compounds are shown below in the diagram.

 

If more than the two ring carbons have different substituents (not counting other ring atoms) the stereo chemical notation differentiate the various isomers becomes more complex.

Examples of the IUPAC Rules in Practice

When one hydrogen atom and one substituent are attached at each of more than two positions of a monocycle, steric relations of the substituents can be expressed by first recognizing a reference substituent (labeled r) that is followed by a hyphen and the substituent locator name and number. Relative configuration of other substituents are then reported as cis (c) or trans (t) to the reference substituent.

 

At the same position of a monocycle, when the two different substituents are attached, then as reference group the lowest-numbered substituent named as a suffix is selected, and If none of substituents is named like a suffix then that substituent of pair of substituents which are having the lowest number and which is preferred by sequence rule is selected as the reference group. The relationship of sequence-rule-preferred substituent at geminally substituted positions, relative to reference group is referred as the c- or t-, as appropriate.

A Cahn-Ingold-Prelog rule is an Alternative system that describes the absolute configuration of substituted carbon atoms may also be used, which elaborates and uses the priority rules developed earlier.

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