The Alkene reference article from the English Wikipedia on 24-Jul-2004
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Alkene

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An alkene is a hydrocarbon that has a double bond between two carbon atoms.

Alkenes are unsaturated substances.

The generic formula is CnH2n. The simplest alkene is ethene (also known as ethylene):

image:ethene.png

Table of contents
1 Physical properties
2 Chemical properties
3 Reactions
4 See also:

Physical properties

Chemical properties

Alkenes are relatively stable compounds, but are more reactive than alkanes.

Reactions

Synthesis

  1. The most common industrial synthesis path for alkenes is cracking of petroleum.
  2. Alkenes can be synthesized from alcohols via an elimination reaction that removes one water molecule:
    H3C-CH2-OH + H2SO4 → H3C-CH2-O-SO3H + H2O → H2C=CH2 + H2SO4
  3. Catalytic synthesis of higher α-alkenes can be achieved by a reaction of ethene with triethylaluminium, an organometallic compound in the presence of nickel, cobalt or platinum.

Addition reactions

Catalytic addition of hydrogen

Catalytic hydrogenation of alkenes produce the corresponding alkanes. The reaction is carried out under pressure in the presence of a metallic catalyst. Common industrial catalysts are based on platinum, nickel or palladium, for laboratory syntheses, Raney's nickel is often employed. This is an alloy of nickel and aluminium.

This is the catalytic hydrogenation of ethylene to yield ethane:

CH2=CH2 + H2 → CH3-CH3

Electrophilic addition

Most addition reactions to alkenes follow the mechanism of electrophilic addition.

  1. Halogenation: Addition of elementary bromine or chlorine to alkenes yield vicinal Dibromo- and dichloroalkenes, respectively. The decoloration of a solution of bromine in water is an analytical test for the presence of alkenes:
    CH2=CH2 + Br2 → BrCH2-CH2Br
  2. Hydrohalogenation: Addition of hydrohalic acids like HCl or HBr to alkenes yield the corresponding haloalkanes.
    CH3-CH=CH2 + HBr --> CH3-CHBr-CH3
    If the two carbon atoms at the double bond are linked to a different number of hydrogen atoms, the halogen is found preferentially at the carbon with less hydrogen substituents (Markovnikov's rule).

Oxidation

  1. In the presence of oxygen, alkenes burn with a bright flame to carbon dioxide and water.
  2. Catalytic oxidation with oxygen or the reaction with percarboxylic acids yields epoxides
  3. Reaction with ozone leads to the breaking of the double bond, yielding two aldehydes or ketones
    R1-CH=CH-R2 + O3 → R1-CHO + R2-CHO + H2O
    This reaction can be used to determine the position of a double bond in an unknown alkene.

Polymerisation

Polymerization of alkenes is an economically important reaction which yields polymers of high industrial value, such as the plastics polyethylene and polypropylene. Polymerization can either proceed via a free-radical or an ionic mechanism. For detail regarding the reaction mechanisms, see the polymerization article.

See also:

alkane, alkyl.