Cyclooctene

Cyclooctene is the cycloalkene with a

formula C8H14. Its molecule has a ring of 8
carbon atoms, connected by seven single
bonds and one double bond.

Possible isomers of cyclooctene.

Cyclooctene is notable because it is the

smallest cycloalkene that can exist stably
as either the cis or trans stereoisomer,
with cis-cyclooctene being the most
common. Theoretical analysis implies a
total of 16 conformational and
configurational isomers, all chiral, forming
8 enantiomeric pairs.[1] The cis isomer can
adopt various conformations, the most
stable one being shaped like a ribbon.[1]
The most stable conformation of trans-
cyclooctene is shaped like the 8-carbon
equivalent of the chair conformation of
cyclohexane.

Longer cycloalkene rings such as the ten-

carbon cyclodecene also occur as cis and
trans isomers.