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In organic chemistry, a cycloalkene or cycloolefin is a type of alkene hydrocarbon which contains a closed ring of carbon atoms and either one or more double bonds, but has no aromatic character. Some cycloalkenes, such as cyclobutene and cyclopentene, can be used as monomers to produce polymer chains. Due to geometrical considerations, smaller cycloalkenes are almost always the cis isomers, and the term cis tends to be omitted from the names. Cycloalkenes require considerable p-orbital overlap in the form of a bridge between the carbon-carbon double bond; however, this is not feasible in smaller molecules due to the increase of strain that could break the molecule apart. In greater carbon number cycloalkenes, the addition of substituents decreases strain. trans-Cycloalkenes with 7 or fewer carbons in the ring will not occur under normal conditions because of the large amount of ring strain needed. In larger rings (8 or more atoms), cis–trans isomerism of the double bond may occur. This stability pattern forms part of the origin of Bredt's rule, the observation that alkenes do not form at the bridgehead of many types of bridged ring systems because the alkene would necessarily be trans in one of the rings. File:Cyclopropene 2D skeletal.svg|[[Cyclopropene]] File:Cyclobutene.svg|[[Cyclobutene]] File:Cyclopentene.svg|[[Cyclopentene]] File:Cyclohexene.svg|[[Cyclohexene]] File:Cycloheptene.svg|[[Cycloheptene]] File:1,3-cyclohexadiene.svg|[[1,3-Cyclohexadiene]] File:1,4-cyclohexadiene.svg|[[1,4-Cyclohexadiene]] File:1,5-Cyclooctadiene.svg|[[1,5-Cyclooctadiene]] File:Cis-cyclooctene.png|[[Cis-Cyclooctene|cis-cyclooctene]] File:(S)-(+)-trans-Cyclooctene Structural Formula V.1.svg|[[Trans-Cyclooctene|trans-cyclooctene]] Cycloalkenes follow a similar nomenclature system to alkenes, but the carbons are numbered starting at a carbon on the double bond and then through the double bond and around the ring. This method is used to keep the index numbers small. File:Cycloalkene nomenclature.svg|1-methylcyclohexene File:3-methylcyclohexene nomenclature.

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Ring strain

In organic chemistry, ring strain is a type of instability that exists when bonds in a molecule form angles that are abnormal. Strain is most commonly discussed for small rings such as cyclopropanes and cyclobutanes, whose internal angles are substantially smaller than the idealized value of approximately 109°. Because of their high strain, the heat of combustion for these small rings is elevated. Ring strain results from a combination of angle strain, conformational strain or Pitzer strain (torsional eclipsing interactions), and transannular strain, also known as van der Waals strain or Prelog strain.

Alicyclic compound

In organic chemistry, an alicyclic compound contains one or more all-carbon rings which may be either saturated or unsaturated, but do not have aromatic character. Alicyclic compounds may have one or more aliphatic side chains attached. The simplest alicyclic compounds are the monocyclic cycloalkanes: cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, and so on. Bicyclic alkanes include bicycloundecane, decalin, and housane. Polycyclic alkanes include cubane, basketane, and tetrahedrane.

Cycloalkane

In organic chemistry, the cycloalkanes (also called naphthenes, but distinct from naphthalene) are the monocyclic saturated hydrocarbons. In other words, a cycloalkane consists only of hydrogen and carbon atoms arranged in a structure containing a single ring (possibly with side chains), and all of the carbon-carbon bonds are single. The larger cycloalkanes, with more than 20 carbon atoms are typically called cycloparaffins. All cycloalkanes are isomers of alkenes.