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Cycloalkanes nomenclature

By German Fernandez, 25 May, 2024

Naming Construction
Cycloalkanes are named by prefixing the alkane name with cyclo- (e.g., cyclopropane, cyclobutane, cyclopentane, etc.). They can also be named as cycloalkyl radicals (e.g., cyclopropyl, cyclobutyl).

Chain Numbering
Number the chain so that the substituents get the lowest possible locants. If there is a tie, the alphabetical order of the substituents is considered.

[1] 1,2-Dimethylcyclopropane
[2] 1-Bromo-3-chloro-2-methylcyclopentane

Molecular model of cis-1,2-dimethylcyclopropane. The cis- isomer has substituents on the same side of the ring.

Molecular model of trans-1,2-dimethylcyclopropane. The trans- isomer has substituents on opposite sides of the ring.

Cycloalkanes as Substituents
In some cases, it is convenient to consider the cycloalkane as a substituent and the carbon chain as the principal structure.

[3] 2-Cyclobutyl-5-cyclopropylhexane
[4] 4-Cyclopentylpentanol

cis/trans Isomerism
Cycloalkanes exhibit stereoisomerism, and depending on the spatial position of the groups, we can have cis or trans isomers. When substituents are on the same side of the ring, the stereoisomer is called cis, and if they are on opposite sides, it is called trans.

[5] cis-1,2-Dimethylcyclohexane
[6] trans-1,2-Dimethylcyclohexane

Molecular model of cis-1,4-dimethylcyclohexane. Note that the methyl groups are on the same side of the ring.

Molecular model of trans-1,4-dimethylcyclohexane. Note that the methyl groups are on opposite sides of the ring.

 

Book traversal links for Nomenclatura Cicloalcanos

  • CYCLOALKANES
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  • Ring Strain in Cycloalkanes

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