IUPAC Rules for Nomenclature of substituted Cycloalkanes

The naming of substituted cycloalkanes follows the same basic steps used in naming alkanes.

1. Determine the parent chain.
2. Number the substituents of the ring so that the sum of the numbers is the lowest possible.
3. Name the substituents and place them in alphabetical order.

More specific rules for naming substituted cycloalkanes with examples are given below.

1. Determine the cycloalkane to use as the parent. If there is an alkyl straight chain that has a greater number of carbons than the cycloalkane, then the alkyl chain must be used as the primary parent chain. Cycloalkanes substituents have an ending "-yl". If there are two cycloalkanes in the molecule, use the cycloalkane with the higher number of carbons as the parent.

2) When there is only one substituent on the ring, the ring carbon attached to the substituent is automatically carbon #1.  Indicating the number of the carbon with the substituent in the name is optional.

Example 1.2

1-chlorocyclobutane or cholorocyclobutane	1-propylcyclohexane or propylcyclohexane

If there are multiple substituents on the ring, number the carbons of the cycloalkane so that the carbons with substituents have the lowest possible number. A carbon with multiple substituents should have a lower number than a carbon with only one substituent or functional group. One way to make sure that the lowest number possible is assigned is to number the carbons so that when the numbers corresponding to the substituents are added, their sum is the lowest possible. 

3) When naming the cycloalkane, the substituents must be placed in alphabetical order.  Remember the prefixes di-, tri-, etc. , are not used for alphabetization.

Hydrocarbons having more than one ring are common, and are referred to as bicyclic (two rings), tricyclic (three rings) and in general, polycyclic compounds. The molecular formulas of such compounds have H/C ratios that decrease with the number of rings. In general, for a hydrocarbon composed of n carbon atoms associated with m rings the formula is: C_nH_{(2n + 2 - 2m)}. The structural relationship of rings in a polycyclic compound can vary. They may be separate and independent, or they may share one or two common atoms. Some examples of these possible arrangements are shown in the following table.

Table 1.1: Examples of Isomeric  Bicycloalkanes

Isolated Rings	Spiro Rings	Fused Rings	Bridged Rings
No common atoms	One common atom	One common bond	Two common atoms

Polycyclic compounds, like cholesterol shown below, are biologically important and typically have common names accepted by IUPAC. However, the common names do not generally follow the basic IUPAC nomenclature rules, and will not be covered here.

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