Editing Alkene (section)

===''Cis''–''trans'' isomerism===
If the double bond of an acyclic mono-ene is not the first bond of the chain, the name as constructed above still does not completely identify the compound, because of [[cis–trans isomerism|''cis''–''trans'' isomerism]].  Then one must specify whether the two single C–C bonds adjacent to the double bond are on the same side of its plane, or on opposite sides. For monoalkenes, the configuration is often indicated by the prefixes ''cis''- (from [[Latin]] "on this side of") or ''trans''- ("across", "on the other side of") before the name, respectively; as in ''cis''-2-pentene or ''trans''-2-butene.
[[Image:Cis-trans example.svg|thumb|300px|center|The difference between ''cis-'' and ''trans-'' isomers]]

More generally, ''cis''–''trans'' isomerism will exist if each of the two carbons of in the double bond has two different atoms or groups attached to it.  Accounting for these cases, the IUPAC recommends the more general [[E–Z notation]], instead of the ''cis'' and ''trans'' prefixes.  This notation considers the group with highest [[Cahn-Ingold-Prelog priority rule|CIP priority]] in each of the two carbons. If these two groups are on opposite sides of the double bond's plane, the configuration is labeled ''E'' (from the [[German language|German]] ''entgegen'' meaning "opposite"); if they are on the same side, it is labeled ''Z'' (from German ''zusammen'', "together").  This labeling may be taught with mnemonic  "''Z'' means 'on ze zame zide'".<ref name=murr2014>{{cite book |first=John E. |last=McMurry |date=2014 |page=[https://books.google.com/books?id=KDIeCgAAQBAJ&pg=PA189 189] |title=Organic Chemistry with Biological Applications |publisher=Cengage Learning |edition=3rd |isbn=978-1-285-84291-2}}</ref>

[[Image:EZalkenes2.png|400px|center|thumb|The difference between ''E'' and ''Z'' isomers]]