Alkene

From Wikipedia, the free encyclopedia

This article is about the chemical compound. For the material, see Olefin fiber.
Not to be confused with Alkane or Alkyne.

A 3D model ofethylene, the simplest alkene.

In organic chemistry, an alkene is an unsaturated hydrocarbon that contains at least one carbon
carbon double bond.[1] Alkene, olefin, and olefine are used often interchangeably (see nomenclature
section below). Acyclic alkenes, with only one double bond and no other functional groups, known as
mono-enes, form a homologous series of hydrocarbons with the general formula CnH2n.[2] Alkenes
have two hydrogen atoms less than the corresponding alkane (with the same number of carbon
atoms). The simplest alkene, ethylene (C2H4), which has theInternational Union of Pure and Applied
Chemistry (IUPAC) name ethene is the organic compound produced on the largest scale industrially.
[3]
Aromatic compounds are often drawn as cyclic alkenes, but their structure and properties are
different and they are not considered to be alkenes.[2]
Contents
[hide]

1Structure
1.1Bonding
1.2Shape
2Physical properties
3Reactions
3.1Addition reactions
3.1.1Hydrogenation
3.1.2Hydration
3.1.3Halogenation
3.1.4Hydrohalogenation
3.1.5Halohydrin formation
3.1.6Oxidation
3.1.7Photooxygenation

3.2Polymerization
3.3Metal complexation
3.4Reaction overview
4Synthesis
4.1Industrial methods
4.2Elimination reactions
4.3Synthesis from carbonyl compounds
4.4Synthesis from alkenes: olefin metathesis and hydrovinylation
4.5From alkynes
4.6Rearrangements and related reactions
5Nomenclature
5.1IUPAC names
5.2Cis-trans notation
5.3E,Z notation
5.4Groups containing C=C double bonds
6See also
7Nomenclature links
8References

Structure[edit]
Bonding[edit]

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

Like a single covalent bond, 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 carboncarbon 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 carboncarbon double bond is restricted because it involves an energetic cost to
break the alignment of the p orbitals on the two carbon atoms. 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 (a.k.a. cis-2-butene) face the same side of the double bond, and in (E)-but-2-ene
(a.k.a. trans-2-butene) the methyl groups face the opposite side. These two isomers of butene are
slightly different in their chemical and physical properties.
A 90 twist of the C=C bond, as determined by the positions of the groups attached to the carbons,
requires less energy than the strength of a pi bond, which means that that there is still some bonding
present. This contradicts the simple and common textbook explanation of bond twisting, which
usually says that this sort of molecular rotation would cause the p orbitals on the two carbons to be
twisted 90 to each other and thus be unable to have a bonding effect. Instead, 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. [4] The trans isomer
of cycloheptene is only stable at low temperatures.

Shape[edit]
As predicted by the VSEPR model of electron pair repulsion, the molecular geometry of alkenes
includes bond angles about each carbon in a double bond of about 120. The angle may vary
because of steric strainintroduced by nonbonded interactions created by functional groups attached
to the carbons of the double bond. For example, the C-C-C bond angle in propylene is 123.9.
For bridged alkenes, 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 (8 or more atoms).

Physical properties[edit]
The physical properties of alkenes and alkanes are similar. They are colourless, nonpolar,
combustable, and almost odorless. The physical state depends on molecular mass: like the
corresponding saturated hydrocarbons, the simplest alkenes, ethene, propene, and butene are
gases at room temperature. Linear alkenes of approximately five to sixteen carbons are liquids, and
higher alkenes are waxy solids.

Reactions[edit]
Alkenes are relatively stable compounds, but are more reactive than alkanes, either because of the
reactivity of the carboncarbon pi-bond or the presence of allylic CH centers. Most reactions of
alkenes involve additions to 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, prominently,
polymerization and alkylation.

Addition reactions[edit]
Alkenes react in many addition reactions, which occur by opening up the double-bond. Most addition
reactions to alkenes follow the mechanism of electrophilic addition. Examples of addition
reactions arehydrohalogenation, halogenation, halohydrin
formation, oxymercuration, hydroboration, dichlorocarbene addition, SimmonsSmith
reaction, catalytic hydrogenation, epoxidation, radical polymerization andhydroxylation.

Hydrogenation[edit]
Hydrogenation of alkenes produces the corresponding alkanes. The reaction is carried out under
pressure at a temperature of 200 C in the presence of a metallic catalyst. Common industrial
catalysts are based onplatinum, nickel or palladium. For laboratory syntheses, Raney
nickel (an alloy of nickel and aluminium) is often employed. The simplest example of this reaction is
the catalytic hydrogenation of ethylene to yieldethane:
CH2=CH2 + H2 CH3-CH3
Hydration[edit]
Hydration, the addition of water across the double bond of alkenes, yields alcohols. The reaction is
catalyzed by strong acids such as sulfuric acid. This reaction is carried out on an industrial scale to
produceethanol.
CH2=CH2 + H2O CH3-CH2OH
Alkenes can also be converted into alcohols via the oxymercurationdemercuration
reaction or hydroborationoxidation reaction.
Halogenation[edit]
In electrophilic halogenation the addition of elemental bromine or chlorine to alkenes
yields vicinal dibromo- and dichloroalkanes (1,2-dihalides or ethylene dihalides), respectively. The
decoloration of a solution of bromine in water is an analytical test for the presence of alkenes:
CH2=CH2 + Br2 BrCH2-CH2Br
Related reactions are also used as quantitative measures of unsaturation, expressed as the bromine
number and iodine number of a compound or mixture.
Hydrohalogenation[edit]
Hydrohalogenation is the addition of hydrogen halides such as HCl or HI to alkenes to yield the
corresponding haloalkanes:
CH3-CH=CH2 + HI CH3-CHI-CH2-H

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 fewer hydrogen substituents. This patterns is
known asMarkovnikov's rule. The use of radical initiators or other compounds can lead to the
opposite product result. Hydrobromic acid in particular is prone to forming radicals in the presence of
various impurities or even atmospheric oxygen, leading to the reversal of the Markovnikov result: [5]
CH3-CH=CH2 + HBr CH3-CHH-CH2-Br
Halohydrin formation[edit]
Alkenes react with water and halogens to form halohydrins by an addition reaction. Markovnikov
regiochemistry and anti stereochemistry occur.
CH2=CH2 + X2 + H2O XCH2-CH2OH + HX
Oxidation[edit]
Alkenes are oxidized with a large number of oxidizing agents. In the presence of oxygen, alkenes
burn with a bright flame to produce carbon dioxide and water. Catalytic oxidation with oxygen or the
reaction withpercarboxylic acids yields epoxides. Reaction with ozone in ozonolysis leads to the
breaking of the double bond, yielding two aldehydes or ketones. Reaction with concentrated, hot
KMnO4 (or other oxidizing salts) in an acidic solution will yield ketones or carboxylic acids.
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.
The oxidation can be stopped at the vicinal diol rather than full cleavage of the alkene by using
milder (dilute,lower temperature) KMnO4 or with osmium tetroxide or other oxidants.
Photooxygenation[edit]
In the presence of an appropriate photosensitiser, such as methylene blue and light, alkenes can
undergo reactions with reactive oxygen species generated by the photosensitiser, such as hydroxyl
radicals, singlet oxygen or superoxide ion. These reactive photochemical intermediates are
generated in what are known as Type I, Type II, and Type III processes, respectively.[citation needed] These
various alternative processes and reactions can be controlled by choice of specific reaction
conditions, leading to a wide range of different products. A common example is the
[4+2] cycloaddition of singlet oxygen with a diene such as cyclopentadieneto yield an endoperoxide:

Another example is the Schenck ene reaction, in which singlet oxygen reacts with an allylic structure
to give a transposed allyl peroxide:

Polymerization[edit]
Main article: polyolefin
Polymerization of alkenes is a reaction that yields polymers of high industrial value at great
economy, such as the plastics polyethylene and polypropylene. Polymers from
alkene monomers are referred to in a general way as polyolefins or in rare instances as polyalkenes.
A polymer from alpha-olefins is called a polyalphaolefin (PAO). Polymerization can proceed via either
a free-radical or an ionic mechanism, converting the double to a single bond and forming single
bonds to join the other monomers. Polymerization of conjugated dienes such as buta-1,3diene or isoprene (2-methylbuta-1,3-diene) results in largely 1,4-addition with possibly some 1,2addition of the diene monomer to a growing polymer chain.

Metal complexation[edit]

Structure ofbis(cyclooctadiene)nickel(0), a metalalkene complex

Alkenes are ligands in transition metal alkene complexes. The two carbon centres bond to the metal
using the C-C pi- and pi* orbitals. Mono- and diolefins are often used as ligands in stable
complexes. Cyclooctadiene and norbornadiene are popular chelating agents, and
even ethylene itself is sometimes used as a ligand, for example, in Zeise's salt. In addition, metal
alkene complexes are intermediates in many metal-catalyzed reactions including hydrogenation,
hydroformylation, and polymerization.

Reaction overview[edit]
Reaction name

Product

Hydrogenation

alkanes

Hydroalkenylation

alkenes

Halogen addition reaction

1,2-dihalide

Reaction name

Product

Hydrohalogenation (Markovnikov)

haloalkanes

Antimarkovnikovhydrohalogenation

haloalkanes

Hydroamination

amines

Hydroformylation

aldehydes

Sharpless bishydroxylation

diols

Woodward cis-hydroxylation

diols

Ozonolysis

aldehydes or
ketones

Olefin metathesis

alkenes

Diels-Alder reaction

cyclohexenes

Pauson-Khand reaction

cyclopentenones

Hydroborationoxidation

alcohols

Oxymercuration-reduction

alcohols

Prins reaction

1,3-diols

Reaction name

Product

PaternoBchi reaction

oxetanes

Epoxidation

epoxide

Cyclopropanation

cyclopropanes

Hydroacylation

ketones

Synthesis[edit]
Industrial methods[edit]
Alkenes are produced by hydrocarbon cracking. Raw materials are mostly natural gas
condensate components (principally ethane and propane) in the US and Mideast and naphtha in
Europe and Asia. Alkanes are broken apart at high temperatures, often in the presence of
a zeolite catalyst, to produce a mixture of primarily aliphatic alkenes and lower molecular weight
alkanes. The mixture is feedstock and temperature dependent, and separated by fractional
distillation. This is mainly used for the manufacture of small alkenes (up to six carbons). [6]

Related to this is catalytic dehydrogenation, where an alkane loses hydrogen at high temperatures to
produce a corresponding alkene.[1] This is the reverse of the catalytic hydrogenation of alkenes.

This process is also known as reforming. Both processes are endothermic and are driven towards
the alkene at high temperatures by entropy.
Catalytic synthesis of higher -alkenes (of the type RCH=CH2) can also be achieved by a reaction of
ethylene with the organometallic compound triethylaluminium in the presence of nickel, cobalt,
or platinum.

Elimination reactions[edit]
One of the principal methods for alkene synthesis in the laboratory is the elimination of alkyl halides,
alcohols, and similar compounds. Most common is the -elimination via the E2 or E1 mechanism,
[7]
but -eliminations are also known.
The E2 mechanism provides a more reliable -elimination method than E1 for most alkene
syntheses. Most E2 eliminations start with an alkyl halide or alkyl sulfonate ester (such as
a tosylate or triflate). When an alkyl halide is used, the reaction is called a dehydrohalogenation. For
unsymmetrical products, the more substituted alkenes (those with fewer hydrogens attached to the
C=C) tend to predominate (see Zaitsev's rule). Two common methods of elimination reactions are
dehydrohalogenation of alkyl halides and dehydration of alcohols. A typical example is shown below;
note that if possible, the H is anti to the leaving group, even though this leads to the less stable Zisomer.[8]

Alkenes can be synthesized from alcohols via dehydration, in which case water is lost via the E1
mechanism. For example, the dehydration of ethanol produces ethene:
CH3CH2OH + H2SO4 H2C=CH2 + H3O+ + HSO4
An alcohol may also be converted to a better leaving group (e.g., xanthate), so as to allow a
milder syn-elimination such as the Chugaev elimination and the Grieco elimination. Related
reactions include eliminations by -haloethers (the Boord olefin synthesis) and esters (ester
pyrolysis).
Alkenes can be prepared indirectly from alkyl amines. The amine or ammonia is not a suitable
leaving group, so the amine is first either alkylated (as in the Hofmann elimination) or oxidized to
an amine oxide (theCope reaction) to render a smooth elimination possible. The Cope reaction is
a syn-elimination that occurs at or below 150 C, for example:[9]

The Hofmann elimination is unusual in that the less substituted (non-Saytseff) alkene is usually the
major product.
Alkenes are generated from -halo sulfones in the Ramberg-Bcklund reaction, via a threemembered ring sulfone intermediate.

Synthesis from carbonyl compounds[edit]

Another important method for alkene synthesis involves construction of a new carboncarbon double
bond by coupling of a carbonyl compound (such as an aldehyde or ketone) to

a carbanion equivalent. Such reactions are sometimes called olefinations. The most well-known of
these methods is the Wittig reaction, but other related methods are known.
The Wittig reaction involves reaction of an aldehyde or ketone with a Wittig reagent (or
phosphorane) of the type Ph3P=CHR to produce an alkene and Ph3P=O. The Wittig reagent is itself
prepared easily fromtriphenylphosphine and an alkyl halide. The reaction is quite general and many
functional groups are tolerated, even esters, as in this example:[10]

Related to the Wittig reaction is the Peterson olefination. This uses a less accessible silicon-based
reagent in place of the phosphorane, but it allows for the selection of E or Z products. If an E-product
is desired, another alternative is the Julia olefination, which uses the carbanion generated from
a phenyl sulfone. The Takai olefination based on an organochromium intermediate also delivers Eproducts. A titanium compound, Tebbe's reagent, is useful for the synthesis of methylene
compounds; in this case, even esters and amides react.
A pair of carbonyl compounds can also be reductively coupled together (with reduction) to generate
an alkene. Symmetrical alkenes can be prepared from a single aldehyde or ketone coupling with
itself, using Ti metal reduction (the McMurry reaction). If two different ketones are to be coupled, a
more complex, indirect method such as the BartonKellogg reaction may be used.
A single ketone can also be converted to the corresponding alkene via its tosylhydrazone,
using sodium methoxide (the BamfordStevens reaction) or an alkyllithium (the Shapiro reaction).

Synthesis from alkenes: olefin metathesis and hydrovinylation [edit]

Main article: Olefin metathesis
Alkenes can be prepared by exchange with other alkenes, in a reaction known as olefin metathesis.
Frequently, loss of ethene gas is used to drive the reaction towards a desired product. In many
cases, a mixture of geometric isomers is obtained, but the reaction tolerates many functional groups.
The method is particularly effective for the preparation of cyclic alkenes, as in this synthesis
of muscone:

Transition metal catalyzed hydrovinylation is another important alkene synthesis process starting
from alkene itself.[11] In general, it involves the addition of a hydrogen and a vinyl group (or an alkenyl
group) across a double bond. The hydrovinylation reaction was first reported by Alderson, Jenner,
and Lindsey by using rhodium and ruthenium salts, other metal catalysts commonly employed
nowadays included iron, cobalt, nickel, and palladium. The addition can be done highly regio- and

stereo-selectively, the choices of metal centers, ligands, substrates and counterions often play very
important role.[12][13][14] Recent studies showed that the use of N-heterocyclic carbene with Ni can be
useful for the selective preparations of functionalized geminal olefins or 1,1-disubstituted alkenes. [15]
[16]

From alkynes[edit]
Reduction of alkynes is a useful method for the stereoselective synthesis of disubstituted alkenes. If
the cis-alkene is desired, hydrogenation in the presence of Lindlar's catalyst (a heterogeneous
catalyst that consists of palladium deposited on calcium carbonate and treated with various forms of
lead) is commonly used, though hydroboration followed by hydrolysis provides an alternative
approach. Reduction of the alkyne by sodium metal in liquid ammonia gives the trans-alkene.[17]

For the preparation multisubstituted alkenes, carbometalation of alkynes can give rise to a large
variety of alkene derivatives.

Rearrangements and related reactions[edit]

Alkenes can be synthesized from other alkenes via rearrangement reactions. Besides olefin
metathesis (described above), a large number of pericyclic reactions can be used such as the ene
reaction and the Cope rearrangement.

In the Diels-Alder reaction, a cyclohexene derivative is prepared from a diene and a reactive or
electron-deficient alkene.

Nomenclature[edit]
Although the nomenclature is not followed widely, according to IUPAC, alkenes are acyclic
hydrocarbons with one double bond between carbon centers. Olefins comprise a larger collection of
cyclic and acyclic alkenes as well as di- and polyenes.[18]

IUPAC names[edit]
To form the root of the IUPAC names for alkenes, simply change the -an- infix of the parent to -en-.
For example, CH3-CH3 is the alkane ethANe. The name of CH2=CH2 is therefore ethENe.
In higher alkenes, where isomers exist that differ in location of the double bond, the following
numbering system is used:
Number the longest carbon chain that contains the double bond in the direction that gives the carbon
atoms of the double bond the lowest possible numbers.
Indicate the location of the double bond by the location of its first carbon.

Name branched or substituted alkenes in a manner similar to alkanes.

Number the carbon atoms, locate and name substituent groups, locate the double bond, and name
the main chain.

Naming substituted hex-1-enes

Cis-trans notation[edit]
Main article: Cis-trans isomerism
In the specific case of disubstituted alkenes where the two carbons have one substituent each, Cistrans notation may be used. If both substituents are on the same side of the bond, it is defined as
(cis-). If the substituents are on either side of the bond, it is defined as (trans-).

The difference between cis- and trans- isomers

E,Z notation[edit]
Main article: E-Z notation
When an alkene has more than one substituent (especially necessary with 3 or 4 substituents), the
double bond geometry is described using the labels E and Z. These labels come from the German
words "entgegen," meaning "opposite," and "zusammen," meaning "together." Alkenes with the
higher priority groups (as determined by CIP rules) on the same side of the double bond have these
groups together and are designated Z. Alkenes with the higher priority groups on opposite sides are
designated E. A mnemonic to remember this: Z notation has the higher priority groups on "ze zame
zide."

The difference between E and Z isomers

Groups containing C=C double bonds[edit]

IUPAC recognizes two names for hydrocarbon groups containing carboncarbon double bonds,
the vinyl group and the allyl group. .[2]

See also[edit]
Look up alkene in
Wiktionary, the free
dictionary.
Wikiquote has
quotations related
to: Alkene

Alpha-olefin
Cycloalkene
Arenes
Diene
Dendralene
Radialene
Annulene
Polyene
Nitroalkene

Nomenclature links[edit]
Rule A-3. Unsaturated Compounds and Univalent Radicals [1] IUPAC Blue Book.
Rule A-4. Bivalent and Multivalent Radicals [2] IUPAC Blue Book.
Rules A-11.3, A-11.4, A-11.5 Unsaturated monocyclic hydrocarbons and substituents [3] IUPAC Blue
Book.
Rule A-23. Hydrogenated Compounds of Fused Polycyclic Hydrocarbons [4] IUPAC Blue Book.

References[edit]
^ Jump up to:a b c Wade, L.G. (2006). Organic Chemistry (6th ed.). Pearson Prentice Hall. p. 279. ISBN 1-40585345-X.

^ Jump up to:a b c Moss, G. P.; Smith, P. A. S.; Tavernier, D. (1995). "Glossary of Class Names of Organic
Compounds and Reactive Intermediates Based on Structure (IUPAC Recommendations 1995)". Pure and
Applied Chemistry 67 (89): 13071375. doi:10.1351/pac199567081307.
Jump up^ "Production: Growth is the Norm". Chemical and Engineering News 84 (28): 59. July 10,
2006. doi:10.1021/cen-v084n034.p059.
Jump up^ Barrows, Susan E.; Eberlein, Thomas H. (2005). "Understanding Rotation about a C=C Double
Bond". J. Chem. Educ. 82 (9): 1329. Bibcode:2005JChEd..82.1329B. doi:10.1021/ed082p1329.
Jump up^ Streiwieser, A.; Heathcock, C.H.; Kosower, E.M. (1992). "11.6.G. Alkenes: Reacttions: Free Radical
Additions". Introduction to Organic Chemistry (4th ed.). New York: Macmillan. p. 288.
Jump up^ Wade. p. 309. Missing or empty |title= (help)
Jump up^ Saunders, W. H. (1964). Patai, Saul, ed. The Chemistry of Alkenes. Wiley Interscience. pp. 149
150.
Jump up^ Cram, D.J.; Greene, Frederick D.; Depuy, C. H. (1956). "Studies in Stereochemistry. XXV. Eclipsing
Effects in the E2 Reaction1". Journal of the American Chemical Society 78 (4): 790
796. doi:10.1021/ja01585a024.
Jump up^ Bach, R.D.; Andrzejewski, Denis; Dusold, Laurence R. (1973). "Mechanism of the Cope
elimination". J. Org. Chem. 38 (9): 17423. doi:10.1021/jo00949a029.
Jump up^ Snider, Barry B.; Matsuo, Y; Snider, BB (2006). "Synthesis of ent-Thallusin". Org. Lett. 8 (10): 2123
6. doi:10.1021/ol0605777. PMC 2518398. PMID 16671797.
Jump up^ Vogt, D. (2010). "Cobalt-Catalyzed Asymmetric Hydrovinylation". Angew. Chem. Int. Ed. 49 (40):
71668. doi:10.1002/anie.201003133. PMID 20672269.
Jump up^ Grutters, M. M. P. Muller, C. Vogt, D. (2006). "Highly Selective Cobalt-Catalyzed Hydrovinylation of
Styrene". J. Am. Chem. Soc. 128 (23): 74145. doi:10.1021/ja058095y. PMID 16756275.
Jump up^ Hilt, G. Danz, M. Treutwein, J. (2009). "Cobalt-Catalyzed 1,4-Hydrovinylation of Styrenes and 1Aryl-1,3-butadienes". Org. Lett. 11 (15): 33225. doi:10.1021/ol901064p. PMID 19583205.
Jump up^ Sharma, R. K. RajanBabu, T. V. (2010). "Asymmetric Hydrovinylation of Unactivated Linear 1,3Dienes". J. Am. Chem. Soc. 132 (10): 32957. doi:10.1021/ja1004703. PMC 2836389. PMID 20163120.
Jump up^ Ho, C.-Y., He, L. (2010). "Catalytic Intermolecular Tail-to-Tail Hydroalkenylation of Styrenes with
alpha-Olefins: Regioselective Migratory Insertion Controlled by a Nickel/N-Heterocyclic Carbene". Angew.
Chem. Int. Ed. 49 (48): 91829186. doi:10.1002/anie.201001849. PMID 20853303.
Jump up^ Ho, C.-Y., He, L. (2012). "Shuffle Off the Classic Beta-Si Elimination by Ni-NHC Cooperation:
Implication for CC Forming Reactions Involving Ni-Alkyl-Beta-Silanes". Chem. Commun. 48 (10): 1481
1483.doi:10.1039/c1cc14593b. PMID 22116100.
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York: W. H. Freeman & Co. p. 366. ISBN 0-7167-7266-3.
Jump up^ http://goldbook.iupac.org/O04281.html
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