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Hydrocarbon compound containing one or more C=C bonds
In organic chemistry, an alkene, or olefin, is a hydrocarbon containing one or more carbon–carbon double bonds. The double bond may be internal or at the
Alkene
Hydrocarbon compounds with a C=C bond at the alpha carbon
organic chemistry, terminal alkenes (alpha-olefins, α-olefins, or 1-alkenes) are a family of organic compounds which are alkenes (also known as olefins) with
Terminal_alkene
Pyramidal alkenes are alkenes in which the two carbon atoms making up the double bond are not coplanar with their four substituents. This deformation
Pyramidal_alkene
Alkene carboamination is the simultaneous formation of C–N and C–C bonds across an alkene. This method represents a powerful strategy to build molecular
Alkene_carboamination
Chemical reaction
organic chemistry, enone–alkene cycloadditions are a version of the [2+2] cycloaddition. This reaction involves an enone and alkene as substrates. Although
Enone–alkene_cycloadditions
Class of enzymes
Alkene monooxygenase (EC 1.14.13.69) is an enzyme that catalyzes the chemical reaction propylene + NADH + H+ O2 H2O propylene oxide + NAD+
Alkene_monooxygenase
Catalyst for synthesis of polymers of 1-alkenes
and Giulio Natta, is a catalyst used in the synthesis of polymers of 1-alkenes (alpha-olefins). Two broad classes of Ziegler–Natta catalysts are employed
Ziegler–Natta_catalyst
Cleavage of C=C, C≡C, or N=N bonds with ozone
ketones, and carboxylic acids. The reaction is predominantly applied to alkenes, but alkynes and azo compounds are also susceptible to cleavage. The outcome
Ozonolysis
Chemical coupling reaction
Wittig reactions are most commonly used to convert aldehydes and ketones to alkenes. Most often, the Wittig reaction is used to introduce a methylene group
Wittig_reaction
Pairs of molecules with same chemical formula showing different spatial orientations
temperature. Thus, trans alkenes, which are less polar and more symmetrical, have lower boiling points and higher melting points, and cis alkenes, which are generally
Cis–trans_isomerism
Transformation of the chemical structure of a molecule or ion
better with straight-chain hydrocarbons. Trans-alkenes are about 1 kcal/mol more stable than cis-alkenes. An example of this effect is cis- vs trans-2-butene
Isomerization
Alkenes with CnH2n
Straight-chain terminal alkenes, also called linear alpha olefins (LAO) or normal alpha olefins (NAO), are alkenes (olefins) having a chemical formula
Straight-chain terminal alkene
Straight-chain_terminal_alkene
Coordination compound
organometallic chemistry, a transition metal alkene complex is a coordination compound containing one or more alkene ligands. The inventory is large. Such compounds
Transition metal alkene complex
Transition_metal_alkene_complex
Variation on the Wittig chemical reaction
oxaphosphetanes 4a and 4b yield (E)-alkene 5 and (Z)-alkene 6, with the by-product being a dialkyl-phosphate. The ratio of alkene isomers 5 and 6 is not dependent
Horner–Wadsworth–Emmons reaction
Horner–Wadsworth–Emmons_reaction
Organic reaction involving the breakup and reassembly of alkene double bonds
chemistry, olefin metathesis or alkene metathesis is an organic reaction that entails the redistribution of fragments of alkenes (olefins) by the breaking and
Olefin_metathesis
Type of molecule
preferentially at the disubstituted alkene, whereas epoxidation with m-CPBA occurs at the trisubstituted alkene. In another synthetic method Markovnikov
Limonene
Empirical rule in organic chemistry
Saytzeff's rule, Saytzev's rule) is an empirical rule for predicting the favored alkene product(s) in elimination reactions. While at the University of Kazan, Russian
Zaytsev's_rule
Notation in organic chemistry for double bonds
6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoic acid, indicating that the alkenes starting at positions 2, 4, and 8 are E while the one starting at position
E–Z_notation
Chemical reaction in organic chemistry
elimination is an elimination reaction of an amine to form alkenes. The least stable alkene (the one with the fewest substituents on the carbons of the
Hofmann_elimination
Formation of a thioether (–S–) compound from a thiol (–SH) and an alkene ( >C=C< )
chemistry, the thiol-ene reaction (also alkene hydrothiolation) is an organic reaction between a thiol (R−SH) and an alkene (R2C=CR2) to form a thioether (R−S−R')
Thiol-ene_reaction
Functional group of organic compounds
group is conjugated with an alkene (hence the adjective unsaturated). Unlike the case for carbonyls without a flanking alkene group, α,β-unsaturated carbonyl
Α,β-Unsaturated carbonyl compound
Α,β-Unsaturated_carbonyl_compound
Class of chemical compounds
with aliphatic monounsaturated n- and iso-alkenes was described as early as 1936 in a patent. The alkenes are obtained from the "cracked distillate"
Alkenylsuccinic_anhydrides
Chemical reaction that converts an alkene to an alcohol
Hydroboration–oxidation reaction is a two-step hydration reaction that converts an alkene into an alcohol. The process results in the syn addition of a hydrogen and
Hydroboration–oxidation reaction
Hydroboration–oxidation_reaction
Form of interaction between two atoms
backbonding can be broken into three groups: carbonyls and nitrogen analogs, alkenes and alkynes, and phosphines. Compounds where π backbonding is prominent
Pi_backbonding
Chemical process of converting alkenes to nitriles
conversion of alkenes to nitriles. The reaction involves the addition of hydrogen cyanide and requires a catalyst if the substrate alkene is unactivated
Hydrocyanation
Terms for the placement of chemical substituents relative to a double or triple bond
anti-addition are different ways in which substituent molecules can be added to an alkene (R2C=CR2) or alkyne (RC≡CR). The concepts of syn and anti addition are used
Syn_and_anti_addition
Chemical reaction between molecular hydrogen and another compound or element
constitutes the addition of pairs of hydrogen atoms to a molecule, often an alkene. Catalysts are required for the reaction to be usable; non-catalytic hydrogenation
Hydrogenation
Chemical reaction
(or aldehydes) to form a β-hydroxysilane (2) which eliminates to form alkenes (3). Several reviews have been published. One attractive feature of the
Peterson_olefination
Model in organometallic chemistry
organometallic chemistry that explains the chemical bonding in transition metal alkene complexes. The model is named after Michael J. S. Dewar, Joseph Chatt and
Dewar–Chatt–Duncanson_model
Chemical reaction which removes a hydrogen halide from a substrate
a substrate. The reaction is usually associated with the synthesis of alkenes, but it has wider applications. Traditionally, alkyl halides are substrates
Dehydrohalogenation
Psychoactive species of plant
Some chemical groups that are essential for biofuel properties, such as alkene groups and O-H bonds have been found in Khat waste. In 2009, the University
Khat
Chemical compound
2-Butene is an acyclic alkene with four carbon atoms. It is the simplest alkene exhibiting cis/trans-isomerism (also known as (E/Z)-isomerism); that is
2-Butene
Chemical compound
Fp–alkene and Fp–alkyne complexes. The exchange process is facilitated by the loss of gaseous and bulky isobutene. Generally, less substituted alkenes bind
Cyclopentadienyliron dicarbonyl dimer
Cyclopentadienyliron_dicarbonyl_dimer
Chemical reaction
reaction described as a formal cycloaddition between an aromatic imine and an alkene. The imine in this organic reaction is a condensation reaction product from
Povarov_reaction
Chemical process for converting alkenes to aldehydes
is an industrial process for the production of aldehydes (R−CH=O) from alkenes (R2C=CR2). This chemical reaction entails the net addition of a formyl
Hydroformylation
Group of chemical compounds derived from alkanes containing one or more halogens
versatile methods included the addition of halogens to alkenes, hydrohalogenation of alkenes, and the conversion of alcohols to alkyl halides. These
Haloalkane
Electrophilic addition of hydrogen halides to alkenes
addition of hydrogen halides like hydrogen chloride or hydrogen bromide to alkenes to yield the corresponding haloalkanes. If the two carbon atoms at the
Hydrohalogenation
Hydrocarbon compounds without aromatic rings
(single carbon-carbon bonds), or unsaturated, with carbon-carbon double (alkenes) or triple bonds (alkynes). It may also be cyclic (as long as it is not
Aliphatic_compound
Addition of a hydrogen-boron bond to C=C, C=N, C=O, or C≡C bonds
known reaction of the organoboranes is oxidation to produce alcohols from alkenes. The development of this technology and the underlying concepts were recognized
Hydroboration
Chemical reaction in which a substance combines with water
chemistry, water is added to an unsaturated substrate, which is usually an alkene or an alkyne. This type of reaction is employed industrially to produce
Hydration_reaction
Addition of Si-H bonds across unsaturated bonds
catalytically and usually the substrates are unsaturated organic compounds. Alkenes and alkynes give alkyl and vinyl silanes; aldehydes and ketones give silyl
Hydrosilylation
Organic reaction
is an organic reaction in which a ketone or aldehyde is converted to an alkene through an intermediate hydrazone in the presence of 2 equivalents of organolithium
Shapiro_reaction
Modular approach to chemical synthesis
partners may interact specifically with the strained alkene, staying bioorthogonal to endogenous alkenes found in lipids, fatty acids, cofactors, and other
Click_chemistry
Chemical bond involving four bonding electrons; has one sigma plus one pi bond
Double bonds occur most commonly between two carbon atoms, for example in alkenes. Many double bonds exist between two different elements: for example, in
Double_bond
Chemical compound made of only carbon and nitrogen
Carbon nitrides are organic compounds consisting only of carbon and nitrogen atoms. These materials are organic semiconductors. Due to its hydrogen-bonding
Carbon_nitride
Organic reaction in which 2+ molecules combine to form a larger one
bonds. Examples include a molecule with a carbon–carbon double bond (an alkene) or a triple bond (an alkyne). Another example is a compound that has rings
Addition_reaction
Coupling reaction
unsaturated halide (or triflate) with an alkene in the presence of a base and a palladium catalyst to form a substituted alkene. It is named after Tsutomu Mizoroki
Heck_reaction
Chemical reaction involving organic compounds
consisting of an electrophilic addition of an aldehyde or ketone to an alkene or alkyne followed by capture of a nucleophile or elimination of an H+ ion
Prins_reaction
Chemical reaction in which water is produced as a byproduct
heating acetic acid and trapping the product: CH3C(O)OH → CH2=C=O + H2O Alkenes can be made from alcohols by dehydration. This conversion, among others
Dehydration_reaction
Chemical reaction of an alkene with mercuric acetate to form an alcohol
chemical reaction that uses mercury salts to transform an alkene (R2C=CR2) into an alcohol. The alkene reacts with mercuric acetate (AcO−Hg−OAc), an electrophile
Oxymercuration_reaction
Organic compounds with a carbon-carbon-oxygen ring
transfers an O center to the alkene. Vanadium(II) oxide catalyzes the epoxidation at specifically less-substituted alkenes. Electron-deficient olefins
Epoxide
Hydrocarbon compound containing one or more C≡C bonds
of 118 picometers (for C2H2) is much shorter than the C=C distance in alkenes (132 pm, for C2H4) or the C–C bond in alkanes (153 pm). The triple bond
Alkyne
Chemical compound
triacetate has been used as an oxidant in radical cyclizations. It can oxidize alkenes via addition of acetic acid to form lactones. This process is thought to
Manganese(III)_acetate
Rule for predicting outcomes of some addition reactions
the addition of a protic acid HX or other polar reagent to an asymmetric alkene, the acid hydrogen (H) or electropositive part gets attached to the carbon
Markovnikov's_rule
Organic chemical reaction
organic chemistry of phenyl sulfones (1) with aldehydes (or ketones) to give alkenes (olefins)(3) after alcohol functionalization and reductive elimination
Julia_olefination
Chemical reaction
of an alkene with osmium tetroxide in the presence of a chiral quinine ligand to form a vicinal diol. The reaction has been applied to alkenes of virtually
Sharpless asymmetric dihydroxylation
Sharpless_asymmetric_dihydroxylation
Chemical reaction in which two ligands of a metal complex combine
migrate is called their migratory aptitude. The neutral ligand can be CO, alkene, alkyne, or in some cases, even carbene. Diverse reactions apply to the
Migratory_insertion
Chemical reaction
cheletropic reaction involving an organozinc carbenoid that reacts with an alkene (or alkyne) to form a cyclopropane. It is named after Howard Ensign Simmons
Simmons–Smith_reaction
Organic compounds with a saturated carbon-carbon-sulfur ring
episulfides: RC2H3OSCO → RC2H3S + CO2 The metal-catalyzed reaction of sulfur with alkenes has been demonstrated but is of little preparative value. Tertiary episulfonium
Episulfide
Chemical compound
enantioselectively transform prochiral alkenes into epoxides. Before its development, catalysts for the asymmetric epoxidation of alkenes required the substrate to
Jacobsen's_catalyst
Group of atoms introduced into a compound to prevent subsequent reactions
of an alkene with a diene leads to a cyclic alkene, which is nevertheless similarly endangered by electrophilic attack as the original alkene. The cleavage
Protecting_group
Chemical reaction
Prileschajew reaction or Prilezhaev epoxidation, is the chemical reaction of an alkene with a peroxy acid to form epoxides. It is named after Nikolai Prilezhaev
Prilezhaev_reaction
Chemical reaction in which a ring is formed/broken by adding/removing a single atom
stereospecifically to alkenes, and alkene stereochemistry is retained in the cyclopropane product. The mechanism for addition of a carbene to an alkene is a concerted
Cheletropic_reaction
Chemical compound
acetone and isobutyraldehyde followed by hydrogenation of the resulting alkene. Siegel H, Eggersdorfer M (2000). "Ketones". Ullmann's Encyclopedia of Industrial
5-Methyl-2-hexanone
Chemical compound
dichloromethane. The compound is widely used as a catalyst for hydrogenation of alkenes. It is named after chemist and Nobel laureate Sir Geoffrey Wilkinson, who
Wilkinson's_catalyst
Chemical compounds and groups containing nitrogen with a lone pair (:N)
to prepare aryl amines is the Buchwald-Hartwig reaction. Disubstituted alkenes react with HCN in the presence of strong acids to give formamides, which
Amine
Class of chemical compounds
ozonolysis of alkenes or the Griesbaum coozonolysis of O-methyl oximes. They are sometimes called ozonides or secondary ozonides in the context of alkene-ozonolysis
1,2,4-Trioxolanes
Chemical reaction
enantioselective epoxidation of unfunctionalized alkyl- and aryl- substituted alkenes. It is complementary to the Sharpless epoxidation (used to form epoxides
Jacobsen_epoxidation
compounds (X = Cl, Br, H) to alkenes. The reaction is used to append trichloromethyl or dichloromethyl groups to terminal alkenes. The method has attracted
Kharasch_addition
Class of organic compounds
alcohols are produced by hydroformylation of alkenes followed by hydrogenation. When applied to a terminal alkene, as is common, one typically obtains a linear
Alcohol_(chemistry)
(PH3). Although most of this article concerns addition of P–H bonds to alkenes, an important variant is the hydrophosphination of formaldehyde.
Hydrophosphination
Chemical compound
organometallic chemistry as one of the first examples of a transition metal alkene complex and is named for its discoverer, William Christopher Zeise. This
Zeise's_salt
Pharmaceutical compound
Deuterated testosterone (developmental code name AVA-291), also known as d3-testosterone (d3-T), is an androgen or androgen receptor agonist which is under
Deuterated_testosterone
Class of heterocycles
3-imidazolines contain an imine center, whereas the 4-imidazolines contain an alkene group. The 2-imidazoline group occurs in several drugs. Imidazoline receptor
Imidazoline
Unsaturated hydrocarbon compound (H2C=C(CH3)2)
hydrocarbon with the chemical formula (CH3)2C=CH2. It is a four-carbon branched alkene (olefin), one of the four isomers of butylene. It is a colorless flammable
Isobutylene
Chemical compound
with a methyl group substituent attached to carbon most distant from the alkene group. Two other structural isomers are known: 1-methylcyclohexene and 3-methylcyclohexene
4-Methylcyclohexene
Hydrocarbon compound (H2C=CH2)
gas with a faint "sweet and musky" odour when pure. It is the simplest alkene (a hydrocarbon with carbon–carbon double bonds). Ethylene is widely used
Ethylene
Reaction which adds a halogen molecule
where a halogen molecule is added to the carbon–carbon double bond of an alkene functional group. The general chemical formula of the halogen addition reaction
Halogen_addition_reaction
Chemical compound
alcohol and glycidol via an ether linkage. Because it contains both an alkene and an epoxide group, either group can be reacted selectively to yield a
Allyl_glycidyl_ether
Chemical reaction to produce organic compounds
(IMHR) in chemistry is the coupling of an aryl or alkenyl halide with an alkene in the same molecule. The reaction may be used to produce carbocyclic or
Intramolecular_Heck_reaction
Hydrocarbon compound containing a non-aromatic ring with a C=C bond
In organic chemistry, a cycloalkene or cycloolefin is a type of alkene hydrocarbon which contains a closed ring of carbon atoms and either one or more
Cycloalkene
Chemical compound
consisting of cyclohexene with a methyl group substituent attached to the alkene group. Two other structural isomers are known: 3-methylcyclohexene and 4-methylcyclohexene
1-Methylcyclohexene
Chemical compound
alkenes in the thiol-ene reaction to form polymeric networks. Being functionalized with four thiol groups, it can react with multifunctional alkenes to
Pentaerythritol tetrakis(3-mercaptopropionate)
Pentaerythritol_tetrakis(3-mercaptopropionate)
Reaction of N-oxide to alkene and hydroxylamine
developed by Arthur C. Cope, is the elimination reaction of an N-oxide to an alkene and a hydroxylamine. Typically, the amine oxide is prepared from the corresponding
Cope_reaction
Chemical compound
several fragrances. A less-common isomeric form, having one of the three alkene units in a different position, is α-myrcene. Myrcene is often produced commercially
Myrcene
Addition of an N–H group across a C=C or C≡C bond
addition of an N−H bond of an amine across a carbon-carbon multiple bond of an alkene, alkyne, diene, or allene. In the ideal case, hydroamination is atom economical
Hydroamination
Catalyst enabling the hydrogenation of alkynes to alkenes
forms of lead or sulfur. It is used for the hydrogenation of alkynes to alkenes (i.e. without further reduction into alkanes), specifically the syn product
Lindlar_catalyst
Chemical compound
(predicted) NhH NhH3 Nh2H6 NhH5 Group 14 hydrides Hydrocarbons alkanes alkenes alkynes Cycloalkanes Cycloalkenes Cycloalkynes Annulenes CH CH2 CH3 C2H
Tetraoxidane
Chemical process
the reduction of alkyne by one equivalent of hydrogen gas (H2) to give alkene rather than the fully reduced alkane. This process is a valuable transformation
Semi-hydrogenation_of_alkynes
Chemical compound
the basicity of the molecule, which does exhibit properties of a typical alkene. TDAE reacts with oxygen in a chemiluminescent reaction to give tetramethylurea
Tetrakis(dimethylamino)ethylene
Tetrakis(dimethylamino)ethylene
Chemical compound
reaction, the byproducts include 12,12,13,13-tetramethyltetracosane and some alkenes. Adding hydrogen to 13-bromo-2-methyldecan-2-ol can produce some 2-methyltridecane
2-Methyltridecane
Mass of bromine absorbed by 100 grams of a given substance
chemistry techniques. The qualitative bromine test detects the presence of alkenes and alkynes and of aromatic rings with certain substituent groups. The
Bromine_number
Chemical compound
aliphatic hydrocarbons Alkenes CnH2n Linear alkenes Ethene Propene Butene Pentene Hexene Heptene Octene Nonene Decene Branched alkenes Isobutene Isopentene
Octacene
functionality of its constituent parts, an alkene and nitro group, while displaying its own chemical properties through alkene activation, making the functional
Nitroalkene
Atom, molecule, or ion that has an unpaired valence electron; typically highly reactive
free-radical additions, a radical adds to an alkene. This addition generates a new radical, which can add to yet another alkene, etc. This behavior underpins radical
Radical_(chemistry)
Chemical reaction involving the removal of hydrogen
are relatively inert and thus low-valued, to alkenes, which are reactive and thus more valuable. Alkenes are precursors to aldehydes (R−CH=O), alcohols
Dehydrogenation
Interaction of an organic molecule's reaction center with unconjugated electrons
alkene is more remote from the reacting center the alkene can still act in this way. For instance in the following alkyl benzenesulfonate the alkene is
Neighbouring group participation
Neighbouring_group_participation
Branch of organometallic chemistry
nickel coordinated to an alkene. Practical applications of this theme include polymerization or oligomerization of alkenes, as in the Shell Higher Olefin
Organonickel_chemistry
Chemical compound
(predicted) NhH NhH3 Nh2H6 NhH5 Group 14 hydrides Hydrocarbons alkanes alkenes alkynes Cycloalkanes Cycloalkenes Cycloalkynes Annulenes CH CH2 CH3 C2H
Americium_trihydride
Organic compound containing the functional group R–CH=O
a very large scale for diverse aldehydes. It involves treatment of the alkene with a mixture of hydrogen gas and carbon monoxide in the presence of a
Aldehyde
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