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Ball-and-stick model of In, the cycloalkanes (also called naphthenes, but distinct from ) are the. In other words, a cycloalkane consists only of and atoms arranged in a structure containing a single ring (possibly with ), and all of the carbon-carbon bonds are. Cycloalkanes are named analogously to their normal counterparts of the same carbon count:,,,, etc. The larger cycloalkanes, with more than 20 carbon atoms are typically called cycloparaffins. The cycloalkanes without side chains are classified as small (cyclopropane and cyclobutane), common (cyclopentane, cyclohexane, and ), medium ( through ), and large (all the rest). Each is an of its counterpart—for example, cyclopropane has the same chemical formula (C 3H 6) as.
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Besides this standard definition by (IUPAC), in some authors' usage the term cycloalkane includes also those saturated hydrocarbons that are polycyclic. In any case, the general form of the for cycloalkanes is C nH 2( n+1− r), where n is the number of carbon atoms and r is the number of rings. The simpler form, when working without focusing on rings is C nH 2( n). (also called bicyclo[2.2.1]heptane) The naming of polycyclic alkanes such as alkanes and alkanes is more complex, with the base name indicating the number of carbons in the ring system, a prefix indicating the number of rings (e.g., 'bicyclo-'), and a numeric prefix before that indicating the number of carbons in each part of each ring, exclusive of junctions. For instance, a bicyclooctane that consists of a six-membered ring and a four-membered ring, which share two adjacent carbon atoms that form a shared edge, is [4.2.0]-bicyclooctane. That part of the six-membered ring, exclusive of the shared edge has 4 carbons. That part of the four-membered ring, exclusive of the shared edge, has 2 carbons.
The edge itself, exclusive of the two vertices that define it, has 0 carbons. There is more than one convention (method or nomenclature) for the naming of compounds, which can be confusing for those who are just learning, and inconvenient for those who are well rehearsed in the older ways.
For beginners it is best to learn IUPAC nomenclature from a source that is up to date, because this system is constantly being revised. In the above example [4.2.0]-bicyclooctane would be written bicyclo[4.2.0]octane to fit the conventions for IUPAC naming. It then has room for an additional numerical prefix if there is the need to include details of other attachments to the molecule such as chlorine or a methyl group. Another convention for the naming of compounds is the common name, which is a shorter name and it gives less information about the compound. An example of a common name is, the name of which can tell us only that it is an alcohol (because the suffix '-ol' is in the name) and it should then have a (–OH) group attached to it. An example of the IUPAC method is given in the adjacent image.
In this example the base name is listed first, which indicates the total number of carbons in both rings including the carbons making up the shared edge (e.g., 'heptane', which means 'hepta-' or 7 carbons, and '-ane', which indicates only single bonding between carbons). Then in front of the base name is the numerical prefix, which lists the number of carbons in each ring, excluding the carbons that are shared by each ring, plus the number of carbons on the bridge between the rings.