Alkene

A 3D model of ethylene, the simplest alkene.

In organic chemistry, an alkene, olefin, or olefine is an unsaturated chemical compound

containing at least one carbon-to-carbon double bond.[1] The simplest acyclic alkenes, with
only one double bond and no other functional groups, form an homologous series of
hydrocarbons with the general formula CnH2n.[2]

The simplest alkene is ethylene (C2H4), which has the International Union of Pure and
Applied Chemistry (IUPAC) name ethene. Alkenes are also called olefins (an archaic
synonym, widely used in the petrochemical industry). For bridged alkenes, the Bredt's rule
states that a double bond cannot be placed at the bridgehead of a bridged ring system, unless
the rings are large enough. Aromatic compounds are often drawn as cyclic alkenes, but their
structure and properties are different and they are not considered to be alkenes.

Structure
Bonding

Ethylene (ethene), showing the pi bond in green.

Like single covalent bonds, double bonds can be described in terms of overlapping atomic
orbitals, except that, unlike a single bond (which consists of a single sigma bond), a carbon-
carbon double bond consists of one sigma bond and one pi bond. This double bond is stronger
than a single covalent bond (611 kJ/mol for C=C vs. 347 kJ/mol for CC)[1] and also shorter
with an average bond length of 1.33 Angstroms (133 pm).

Each carbon of the double bond uses its three sp hybrid orbitals to form sigma bonds to three
atoms. The unhybridized 2p atomic orbitals, which lie perpendicular to the plane created by
the axes of the three sp hybrid orbitals, combine to form the pi bond. This bond lies outside
the main CC axis, with half of the bond on one side and half on the other.

Rotation about the carbon-carbon double bond is restricted because it involves breaking the pi
bond, which requires a large amount of energy (264 kJ/mol in ethylene). As a consequence,
substituted alkenes may exist as one of two isomers, called cis or trans isomers. More
complex alkenes may be named using the E-Z notation, used to describe molecules having
three or four different substituents (side groups). For example, of the isomers of butene, the
two methyl groups of (Z)-but-2-ene (aka cis-2-butene) face the same side of the double bond,
and in (E)-but2-ene (aka trans-2-butene) the methyl groups face the opposite side. These two
isomers of butene are slightly different in their chemical and physical properties.

It is certainly not impossible to twist a double bond. In fact, a 90 twist requires an energy
approximately equal to half the strength of a pi bond. The misalignment of the p orbitals is
less than expected because pyramidalization takes place (See: pyramidal alkene). trans-
Cyclooctene is a stable strained alkene and the orbital misalignment is only 19 with a
dihedral angle of 137 (normal 120) and a degree of pyramidalization of 18. This explains
the dipole moment of 0.8 D for this compound (cis-isomer 0.4 D) where a value of zero is
expected.[3] The trans isomer of cycloheptene is only stable at low temperatures.

Physical properties
The physical properties of alkenes are comparable with those of alkanes. The main differences
between the two are that the acidity levels of alkenes are much higher than the ones in
alkanes. The physical state depends on molecular mass (gases from ethene to butene - liquids
from pentene onwards). The simplest alkenes, ethene, propene and butene are gases. Linear
alkenes of approximately five to sixteen carbons are liquids, and higher alkenes are waxy
solids.

Reactions
Alkenes are relatively stable compounds, but are more reactive than alkanes due to the
presence of a carbon-carbon pi-bond. It is also attributed to the presence of pi-electrons in the
molecule. The majority of the reactions of alkenes involve the rupture of this pi bond, forming
new single bonds.

Alkenes serve as a feedstock for the petrochemical industry because they can participate in a
wide variety of reactions.