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Cycloalkane Stereoisomer

Configurational Stereoisomers of Cycloalkanes

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Stereoisomers are also observed in certain disubstituted (and higher substituted) cyclic compounds. Unlike the relatively flat molecules of alkenes, substituted cycloalkanes must be viewed as three-dimensional configurations in order to appreciate the spatial orientations of the substituents. By agreement, chemists use heavy, wedge-shaped bonds to indicate a substituent located above the average plane of the ring (note that cycloalkanes larger than three carbons are not planar), and a hatched line for bonds to atoms or groups located below the ring. As in the case of the 2-butene stereoisomers, disubstituted cycloalkane stereoisomers may be designated by nomenclature prefixes such as cis and trans. The stereoisomeric 1,2-dibromocyclopentanes shown to the right are an example.

In general, if any two sp3 carbons in a ring have two different substituent groups (not counting other ring atoms) stereoisomerism is possible. This is similar to the substitution pattern that gives rise to stereoisomers in alkenes; indeed, one might view a double bond as a two-membered ring. Four other examples of this kind of stereoisomerism in cyclic compounds are shown below.

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

Examples of the IUPAC Rules in Practice

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

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

An alternative system which specifies the absolute configuration of substituted carbon atoms may also be used. This system, known as the Cahn-Ingold-Prelog rules, uses and elaborates the priority rules developed earlier.

Practice Problems

Three problems concerning the naming of alkene stereoisomers.