1461:
1611:
1603:
1649:
2891:
3189:
3100:
3438:
3624:
2982:
3643:
3662:
2868:
3383:
3685:
3893:
9040:
633:
645:
3947:
9064:
3490:
621:
661:
3513:
51:
1540:
9076:
4045:
3539:
9052:
2422:
405:
4013:
3565:
2408:
2397:
1356:
2112:
1998:
ion. Reactions of the excited sensitizer can involve electron or hydrogen transfer, usually with a reducing substrate (Type I reaction) or interaction with oxygen (Type II reaction). These various alternative processes and reactions can be controlled by choice of specific reaction conditions, leading
451:
to form sigma bonds to three atoms (the other carbon atom and two hydrogen 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 C–C axis, with half of the
2086:, allylic C-H bonds can be halogenated. The presence of two C=C bonds flanking one methylene, i.e., doubly allylic, results in particularly weak HC-H bonds. The high reactivity of these situations is the basis for certain free radical reactions, manifested in the chemistry of
2863:
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).
3711:
Although the nomenclature is not followed widely, according to IUPAC, an alkene is an acyclic hydrocarbon with just one double bond between carbon atoms. Olefins comprise a larger collection of cyclic and acyclic alkenes as well as dienes and polyenes.
4777:
Baptista, Maurício S.; Cadet, Jean; Mascio, Paolo Di; Ghogare, Ashwini A.; Greer, Alexander; Hamblin, Michael R.; Lorente, Carolina; Nunez, Silvia
Cristina; Ribeiro, Martha Simões; Thomas, Andrés H.; Vignoni, Mariana; Yoshimura, Tania Mateus (2017).
365:: 13 isomers: 1-hexene, 2-hexene, 3-hexene, 2-methyl-1-pentene, 3-methyl-1-pentene, 4-methyl-1-pentene, 2-methyl-2-pentene, 3-methyl-2-pentene, 4-methyl-2-pentene, 2,3-dimethyl-1-butene, 3,3-dimethyl-1-butene, 2,3-dimethyl-2-butene, 2-ethyl-1-butene
3367:(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
2392:{\displaystyle {\overset {\text{diisobutene}}{{\ce {(CH3)3C-CH=C(CH3)2}}}}+{\color {red}{\ce {CH2=CH2}}}\longrightarrow {\overset {\text{neohexane}}{{\ce {(CH3)3C-CH=}}{\color {red}{\ce {CH2}}}}}+{\ce {(CH3)2C=}}{\color {red}{\ce {CH2}}}}
1482:
is defined as gram of bromine able to react with 100g of product. Similar as hydrogenation, the halogenation of bromine is also depend on the number of π bond. A higher bromine number indicates higher degree of unsaturation.
1966:
743:) are gases at room temperature. Linear alkenes of approximately five to sixteen carbon atoms are liquids, and higher alkenes are waxy solids. The melting point of the solids also increases with increase in molecular mass.
3923:. Then one must specify whether the two single C–C bonds adjacent to the double bond are on the same side of its plane, or on opposite sides. For monoalkenes, the configuration is often indicated by the prefixes
1342:
because they can participate in a wide variety of reactions, prominently polymerization and alkylation. Except for ethylene, alkenes have two sites of reactivity: the carbon–carbon pi-bond and the presence of
226:
compounds are often drawn as cyclic alkenes, however their structure and properties are sufficiently distinct that they are not classified as alkenes or olefins. Hydrocarbons with two overlapping double bonds
4620:
1629:. Such reaction proceed with retention of stereochemistry. The rates are sensitive to electron-withdrawing or electron-donating substituents. When irradiated by UV-light, alkenes dimerize to give
4540:
3763:
For straight-chain alkenes with 4 or more carbon atoms, that name does not completely identify the compound. For those cases, and for branched acyclic alkenes, the following rules apply:
3970:
isomerism will exist if each of the two carbons of in the double bond has two different atoms or groups attached to it. Accounting for these cases, the IUPAC recommends the more general
2970:). 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
2954:
The E2 mechanism provides a more reliable β-elimination method than E1 for most alkene syntheses. Most E2 eliminations start with an alkyl halide or alkyl sulfonate ester (such as a
1035:
In their C NMR spectra of alkenes, double bonds also deshield the carbons, making them have low field shift. C=C double bonds usually have chemical shift of about 100–170 ppm.
683:
can be used instead in a more general case where all four functional groups attached to carbon atoms in a double bond are different. E- and Z- are abbreviations of German words
3339:
is another important alkene synthesis process starting from alkene itself. It involves the addition of a hydrogen and a vinyl group (or an alkenyl group) across a double bond.
3134:
Another important class of methods for alkene synthesis involves construction of a new carbon–carbon double bond by coupling or condensation of a carbonyl compound (such as an
1801:. The stoichiometry of the reaction is sensitive to conditions. This reaction and the ozonolysis can be used to determine the position of a double bond in an unknown alkene.
1554:
involves addition of H−X to unsaturated hydrocarbons. This reaction results in new C−H and C−X σ bonds. The formation of the intermediate carbocation is selective and follows
606:
mean "on this side of" and "on the other side of" respectively. Therefore, if the functional groups are both on the same side of the carbon chain, the bond is said to have
2947:
of alkyl halides, alcohols, and similar compounds. Most common is the β-elimination via the E2 or E1 mechanism. A commercially significant example is the production of
3912:
If the double bond of an acyclic mono-ene is not the first bond of the chain, the name as constructed above still does not completely identify the compound, because of
3800:
The positions need not be indicated if they are unique. Note that the double bond may imply a different chain numbering than that used for the corresponding alkane:
746:
Alkenes generally have stronger smells than their corresponding alkanes. Ethylene has a sweet and musty odor. Strained alkenes, in particular, like norbornene and
3767:
Find the longest carbon chain in the molecule. If that chain does not contain the double bond, name the compound according to the alkane naming rules. Otherwise:
5999:
5581:
5520:
2439:, alkenes serve as ligands for metals. In this case, the π electron density is donated to the metal d orbitals. The stronger the donation is, the stronger the
197:
compounds, somewhat similar to alkanes but more reactive. The first few members of the series are gases or liquids at room temperature. The simplest alkene,
5989:
5984:
5505:
2498:
5971:
5492:
467:
isomers interconvert so slowly that they can be freely handled at ambient conditions without isomerization. More complex alkenes may be named with the
5563:
4215:
4181:
3661:
94:
553:
states that a double bond cannot occur at the bridgehead of a bridged ring system unless the rings are large enough. Following
Fawcett and defining
452:
bond on one side of the molecule and a half on the other. With a strength of 65 kcal/mol, the pi bond is significantly weaker than the sigma bond.
2890:
8135:
6011:
5532:
3797:
The position of the double bond is often inserted before the name of the chain (e.g. "2-pentene"), rather than before the suffix ("pent-2-ene").
6057:
3300:
Olefin metathesis is also used commercially for the interconversion of ethylene and 2-butene to propylene. Rhenium- and molybdenum-containing
6072:
6067:
6052:
5637:
8236:
6141:
6110:
5889:
5879:
5764:
1821:
8241:
7176:
6146:
6125:
6120:
5904:
5899:
5894:
5884:
5779:
5774:
5769:
5759:
5425:
2443:
from the metal d orbital to π* anti-bonding orbital of the alkene. This effect lowers the bond order of the alkene and increases the C-C
753:
are known to have strong, unpleasant odors, a fact consistent with the stronger π complexes they form with metal ions including copper.
3684:
4480:
Duan, Xufang; Block, Eric; Li, Zhen; Connelly, Timothy; Zhang, Jian; Huang, Zhimin; Su, Xubo; Pan, Yi; Wu, Lifang (28 February 2012).
3437:
699:
configuration, otherwise (i.e. the two groups with higher priority are on the opposite side of the double bond), the bond is assigned
8095:
4330:
2966:. For unsymmetrical products, the more substituted alkenes (those with fewer hydrogens attached to the C=C) tend to predominate (see
692:
6987:
3159:
8219:
8100:
4980:
Cram, D.J.; Greene, Frederick D.; Depuy, C. H. (1956). "Studies in
Stereochemistry. XXV. Eclipsing Effects in the E2 Reaction1".
3150:. Knoevenagel condensations are a related class of reactions that convert carbonyls into alkenes.Well-known methods are called
8263:
5266:
3986:
in each of the two carbons. If these two groups are on opposite sides of the double bond's plane, the configuration is labeled
3099:
5232:
5152:
5084:
5051:
4964:
4931:
4868:
4762:
4464:
4395:
4360:
4163:
610:
configuration, otherwise (i.e. the functional groups are on the opposite side of the carbon chain), the bond is said to have
455:
Rotation about the carbon–carbon double bond is restricted because it incurs an energetic cost to break the alignment of the
3277:(the smallest alkene) is both inexpensive and readily available, with hundreds of millions of tonnes produced annually. The
8275:
8214:
3188:
3382:
2867:
761:
Below is a list of the boiling and melting points of various alkenes with the corresponding alkane and alkyne analogues.
432:
for C=C vs. 347 kJ/mol for C–C), but not twice as strong. Double bonds are shorter than single bonds with an average
8128:
4252:"Glossary of Class Names of Organic Compounds and Reactive Intermediates Based on Structure (IUPAC Recommendations 1995)"
3238:
to generate an alkene. Symmetrical alkenes can be prepared from a single aldehyde or ketone coupling with itself, using
6972:
6733:
4680:
2883:, where an alkane loses hydrogen at high temperatures to produce a corresponding alkene. This is the reverse of the
3983:
7017:
3123:
9080:
7169:
6191:
2436:
8959:
8121:
2981:
1986:
and light, alkenes can undergo reaction with reactive oxygen species generated by the photosensitiser, such as
8402:
8156:
7999:
506:-2-butene) the methyl groups appear on opposite sides. These two isomers of butene have distinct properties.
3200:, which uses silicon-based reagents in place of the phosphorane. This reaction allows for the selection of
2772:
1460:
6947:
3258:
2426:
2463:. These complexes are related to the mechanisms of metal-catalyzed reactions of unsaturated hydrocarbons.
1474:
is used to test the saturation of hydrocarbons. The bromine test can also be used as an indication of the
8679:
8166:
6952:
4752:
4350:
3294:
3247:
2733:
2412:
3642:
3623:
1698:
is conducted on a very large scale industrially using oxygen in the presence of silver-based catalysts:
9056:
8605:
8576:
8556:
8509:
7572:
7162:
5259:
4256:
2664:
2651:
1634:
695:. If the two groups with higher priority are on the same side of the double bond, the bond is assigned
3464:
Unsaturated hydrocarbons are widely used to produce plastics, medicines, and other useful materials.
8194:
7143:
3278:
2720:
2511:
2079:
1013:
4646:
4592:
632:
8949:
8865:
8504:
7609:
7123:
4923:
4155:
3607:
3446:
3174:
3062:
3058:
2746:
2707:
5007:
Bach, R.D.; Andrzejewski, Denis; Dusold, Laurence R. (1973). "Mechanism of the Cope elimination".
3273:
The formation of longer alkenes via the step-wise polymerisation of smaller ones is appealing, as
3231:, is useful for the synthesis of methylene compounds; in this case, even esters and amides react.
86:. The double bond may be internal or in the terminal position. Terminal alkenes are also known as
8887:
8798:
8761:
8645:
8571:
8392:
8375:
8318:
8082:
7083:
5651:
3913:
3301:
2917:
2884:
574:
370:
187:
17:
3253:
A single ketone can also be converted to the corresponding alkene via its tosylhydrazone, using
2074:
The presence of a C=C π bond in unsaturated hydrocarbons weakens the dissociation energy of the
620:
8805:
8793:
8684:
8549:
8323:
8189:
7982:
7078:
6957:
6601:
5415:
5144:
4566:
4098:
3411:
3042:
2852:
1786:
1602:
1475:
1420:
1419:. The total number of hydrogens that can be added to an unsaturated hydrocarbon depends on its
1339:
1059:
535:
5224:
4722:
3590:
Alkenes are prevalent in nature. Plants are the main natural source of alkenes in the form of
3246:). If different ketones are to be coupled, a more complicated method is required, such as the
2859:
in Europe and Asia. Alkanes are broken apart at high temperatures, often in the presence of a
1058:
of saturated ones with same number of carbons. This trend can be clearly seen in the list of
675:
For there to be cis- and trans- configurations, there must be a carbon chain, or at least one
8954:
8851:
8836:
8766:
8689:
8521:
8471:
8380:
8305:
8204:
8089:
7977:
7002:
6726:
6662:
6596:
5252:
4780:"Type I and Type II Photosensitized Oxidation Reactions: Guidelines and Mechanistic Pathways"
4387:
4379:
4033:
IUPAC recognizes two names for hydrocarbon groups containing carbon–carbon double bonds, the
3364:
2528:
1732:
Alkenes react with ozone, leading to the scission of the double bond. The process is called
1555:
691:(opposite). In E- and Z-isomerism, each functional group is assigned a priority based on the
448:
381:
131:
ones; and "olefin" for the general class – cyclic or acyclic, with one or more double bonds.
5136:
4911:
4696:
4411:
Fawcett, Frank S. (1950). "Bredt's Rule of Double Bonds in Atomic-Bridged-Ring
Structures".
4143:
2902:. Both processes are endothermic and are driven towards the alkene at high temperatures by
8944:
8899:
8674:
8494:
8424:
8181:
8161:
8058:
7503:
7012:
6992:
6929:
6180:
5979:
4493:
4067:
3783:
Define the position of each side group as the number of the chain carbon it is attached to.
3197:
2990:
2944:
2848:
1626:
194:
98:
5034:
Crowell, Thomas I. (1964). "Alkene-Forming
Condensation Reactions". In Patai, Saul (ed.).
4116:
4110:
4104:
4095:
3770:
Number the carbons in that chain starting from the end that is closest to the double bond.
8:
8967:
8921:
8846:
8819:
8717:
8699:
8652:
8590:
8486:
8466:
8335:
8330:
8231:
7364:
6982:
6962:
6933:
6920:
6508:
4912:
4144:
3423:
3081:
3034:
2963:
2899:
2643:
2037:. Some polymerizations are of great economic significance, as they generate the plastics
1805:
1610:
1503:
1025:
591:
102:
4497:
2102:, which cleaves and interchanges the substituents of the alkene. A related reaction is
9044:
9010:
8872:
8841:
8722:
8664:
8362:
8345:
8340:
8295:
8258:
8248:
8209:
7073:
7047:
6977:
6695:
6652:
5510:
5500:
5196:
5169:
4806:
4779:
4516:
4481:
4275:
3716:
3611:
3431:
3228:
3227:
based on an organochromium intermediate also delivers E-products. A titanium compound,
3182:
3147:
3038:
2824:
2596:
1487:
644:
523:
2082:
at these C-H sites as well as addition reactions at the C=C site. In the presence of
542:
attached to the carbon atoms of the double bond. For example, the C–C–C bond angle in
9063:
9025:
8990:
8973:
8911:
8829:
8824:
8752:
8737:
8707:
8628:
8595:
8566:
8561:
8536:
8526:
8446:
8434:
8313:
8226:
8048:
8018:
7776:
7398:
7113:
7037:
7027:
6997:
6938:
6586:
6558:
6401:
6161:
6156:
5994:
5515:
5228:
5201:
5148:
5137:
5117:
5080:
5047:
4960:
4927:
4864:
4811:
4758:
4676:
4521:
4460:
4429:
4391:
4356:
4159:
3415:
3352:
3290:
3224:
3213:
3112:
3076:. The amine or ammonia is not a suitable leaving group, so the amine is first either
2967:
2920:
2694:
2621:
2543:
2524:
2099:
2083:
2052:
2051:
although they contain no olefins. Polymerization can proceed via diverse mechanisms.
1551:
1009:
747:
660:
584:
530:
about each carbon atom in a double bond of about 120°. The angle may vary because of
350:
266:
143:
63:
5076:
4279:
4225:
4191:
2993:, in which case water is lost via the E1 mechanism. For example, the dehydration of
1736:. Often the reaction procedure includes a mild reductant, such as dimethylsulfide (
703:
configuration. Cis- and trans- configurations do not have a fixed relationship with
9102:
9068:
8985:
8640:
8499:
8476:
8429:
8370:
7753:
7247:
7185:
7093:
7022:
7007:
6719:
6550:
5191:
5181:
5109:
5072:
5039:
5016:
4989:
4952:
4947:
Saunders, W. H. (1964). "Elimination
Reactions in Solution". In Patai, Saul (ed.).
4838:
4801:
4791:
4511:
4501:
4456:
4452:
4421:
4302:
4265:
4229:
4220:
4195:
4186:
3971:
3789:
Write the names of the alkane with the same chain, replacing the "-ane" suffix by "
3523:
3262:
3254:
3243:
2798:
2577:
1987:
1812:
1544:
680:
676:
578:
557:
as the total number of non-bridgehead atoms in the rings, bicyclic systems require
539:
391:). The number of potential isomers increases rapidly with additional carbon atoms.
217:
135:
2066:(2-methylbuta-1,3-diene) also produce polymers, one example being natural rubber.
8926:
8882:
8877:
8771:
8747:
8581:
8544:
8397:
8387:
8270:
7972:
7731:
7726:
7709:
7692:
7493:
7242:
7133:
7103:
7032:
6700:
6657:
6566:
6440:
5405:
5395:
4671:
Shriner, R.L.; Hermann, C.K.F.; Morrill, T.C.; Curtin, D.Y.; Fuson, R.C. (1997).
4325:"Sequence A000631 (Number of ethylene derivatives with n carbon atoms)"
4111:
Rules A-11.3, A-11.4, A-11.5 Unsaturated monocyclic hydrocarbons and substituents
3991:
3453:
derivative is prepared from a diene and a reactive or electron-deficient alkene.
3399:
3336:
3155:
3054:
3046:
2880:
2008:
1979:
1972:
1798:
1016:
the hydrogen attached to the carbons adjacent to sp carbons, and this generates δ
985:, while the bending of C=C bond absorbs between 1000 and 650 cm wavelength.
550:
128:
5038:. PATAI'S Chemistry of Functional Groups. Wiley Interscience. pp. 241–270.
4951:. PATAI'S Chemistry of Functional Groups. Wiley Interscience. pp. 149–201.
4829:
Oda, Masaji; Kawase, Takeshi; Kurata, Hiroyuki (1996). "1,3,5-Cyclooctatriene".
8810:
8788:
8783:
8778:
8733:
8729:
8712:
8669:
8600:
8461:
8456:
8441:
8253:
8171:
8043:
8038:
7914:
7909:
7904:
7697:
7664:
7448:
7430:
7420:
7128:
7118:
6631:
6626:
6591:
6542:
6448:
5420:
5410:
4486:
Proceedings of the
National Academy of Sciences of the United States of America
3532:
3166:
2948:
2811:
2759:
2556:
2059:
2034:
1991:
1983:
1479:
1020:=1.6–2. ppm peaks. Cis/trans isomers are distinguishable due to different
1002:
728:
724:
5043:
4306:
3780:
Name the side groups (other than hydrogen) according to the appropriate rules.
9096:
9015:
8904:
8860:
8585:
8419:
8414:
8407:
8285:
8063:
8011:
7942:
7828:
7818:
7813:
7803:
7798:
7748:
7743:
7659:
7654:
7644:
7498:
7453:
7415:
7403:
7374:
7252:
7088:
7063:
6967:
6308:
6115:
6105:
5601:
4919:
4842:
4224:, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "
4190:, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "
4151:
3652:
3360:
3235:
3089:
2600:
2485:
2042:
2000:
1597:
1465:
1416:
1366:
531:
437:
421:
4885:
4506:
4270:
4251:
4233:
4199:
8892:
8742:
8657:
8633:
8623:
8615:
8516:
8451:
8350:
8199:
7994:
7881:
7876:
7853:
7604:
7443:
7369:
7306:
7301:
7279:
7235:
7220:
7210:
7138:
7068:
7042:
6414:
6378:
6274:
6047:
6037:
5946:
5936:
5926:
5467:
5457:
5447:
5205:
5121:
5113:
4815:
4525:
4433:
4057:
3427:
3282:
2943:
One of the principal methods for alkene synthesis in the laboratory is the
2440:
2038:
2012:
1471:
1454:
1347:
CH centers. The former dominates but the allylic sites are important too.
1334:. Most reactions of alkenes involve additions to this pi bond, forming new
515:
468:
87:
42:
4956:
3935:- ("across", "on the other side of") before the name, respectively; as in
3281:
allows for the formation of very long chains, for instance those used for
8290:
8053:
8006:
7967:
7848:
7736:
7721:
7716:
7704:
7269:
7264:
7230:
7225:
7215:
7193:
7098:
6462:
6419:
6392:
6326:
6289:
6208:
6062:
6042:
6029:
5961:
5956:
5951:
5941:
5931:
5918:
5749:
5482:
5477:
5472:
5462:
5452:
5439:
5275:
5186:
4748:
4346:
4320:
4078:
4034:
3886:
3633:
3603:
3575:
3450:
3085:
2785:
2444:
2103:
1695:
1661:
1630:
1622:
1575:
1499:
1491:
1044:
982:
479:
433:
429:
330:
270:
147:
83:
75:
8113:
5020:
4993:
4425:
8916:
7962:
7953:
7833:
7788:
7684:
7649:
7639:
7579:
7515:
7438:
7386:
7108:
6924:
6521:
6409:
6213:
6100:
6090:
6019:
5754:
5576:
5571:
5546:
5400:
5390:
4413:
4073:
3694:
3286:
3077:
3050:
2681:
2634:
2087:
2047:
2024:
1995:
1733:
1648:
1559:
1335:
1048:
1021:
731:: like the corresponding saturated hydrocarbons, the simplest alkenes (
527:
483:
413:
237:
213:
4796:
3892:
3165:
The Wittig reaction involves reaction of an aldehyde or ketone with a
2855:
components (principally ethane and propane) in the US and
Mideast and
1961:{\displaystyle {\ce {R'CH=CR2 + 1/2 O2 + H2O -> R'CH(OH)-C(OH)R2}}}
273:. Acyclic alkene structural isomers with only one double bond follow:
8978:
8280:
8145:
7929:
7843:
7808:
7793:
7781:
7624:
7599:
7408:
6526:
6264:
6233:
6223:
6218:
6095:
5823:
5611:
5606:
5385:
4083:
3671:
3667:
3506:
3143:
2909:
1144:
736:
543:
456:
441:
305:
7154:
5168:
Ninkuu, Vincent; Zhang, Lin; Yan, Jianpei; et al. (June 2021).
4482:"Crucial role of copper in detection of metal-coordinating odorants"
3946:
3489:
3158:
is illustrative, but other related methods are known, including the
1330:
Alkenes are relatively stable compounds, but are more reactive than
594:
are used to describe the positions of functional groups attached to
9000:
7937:
7891:
7858:
7554:
7460:
7334:
7289:
7274:
6756:
6690:
6685:
6495:
6487:
6479:
6359:
6351:
6343:
6294:
6279:
6269:
6259:
6254:
6228:
6151:
5863:
5843:
5693:
5621:
5616:
5596:
4062:
3690:
3648:
3629:
3599:
3595:
3483:
3402:
of alkynes can give rise to a large variety of alkene derivatives.
3274:
3239:
3135:
3026:
2959:
2955:
2932:
2063:
1642:
1495:
1412:
1377:
1370:
1360:
1301:
1274:
1121:
1055:
1032:, whereas the trans will have coupling constants of 11–18 Hz.
998:
978:
732:
519:
326:
322:
288:
250:
223:
198:
171:
55:
5170:"Biochemistry of Terpenes and Recent Advances in Plant Protection"
4117:
Rule A-23. Hydrogenated
Compounds of Fused Polycyclic Hydrocarbons
3092:) to render a smooth elimination possible. The Cope reaction is a
3025:
An alcohol may also be converted to a better leaving group (e.g.,
50:
9020:
7899:
7823:
7674:
7669:
7634:
7619:
7614:
7584:
7567:
7391:
7318:
7284:
6841:
6807:
6773:
6647:
6621:
6471:
6316:
6249:
5848:
5838:
5828:
5718:
5708:
5698:
5586:
5552:
5540:
5354:
5344:
5334:
5324:
3997:
meaning "opposite"); if they are on the same side, it is labeled
3698:
3591:
3558:
3372:
3285:. Where shorter chains are wanted, as they for the production of
3220:
3119:
2994:
2903:
2894:
Dehydrogenation of butane to give butadiene and isomers of butene
2860:
2856:
2506:
hydrometalation / insertion / beta-elimination by metal catalyst
2075:
2030:
1665:
1523:
1344:
1220:
1197:
1170:
1028:
hydrogens will have coupling constants in the range of 6–14
766:
723:
are similar: they are colorless, nonpolar, and combustible. The
417:
346:
232:
115:
5100:
Vogt, D. (2010). "Cobalt-Catalyzed
Asymmetric Hydrovinylation".
4754:
Advanced Organic Chemistry: Reactions, Mechanisms, and Structure
4352:
Advanced Organic Chemistry: Reactions, Mechanisms, and Structure
4044:
3538:
3512:
2974:
to the leaving group, even though this leads to the less stable
1054:
The combustion of alkenes release less energy than burning same
7987:
7919:
7763:
7472:
7465:
7359:
7340:
7329:
7313:
6942:
6892:
6875:
6858:
6824:
6790:
6516:
6435:
6335:
6284:
5858:
5853:
5833:
5793:
5733:
5728:
5723:
5713:
5703:
5591:
5369:
5364:
5359:
5349:
5339:
5329:
5294:
5244:
3739:
3368:
3348:
3217:
3139:
3096:-elimination that occurs at or below 150 °C, for example:
3066:
2928:
2924:
1794:
1539:
1381:
1331:
1243:
1098:
740:
720:
595:
588:
498:-2-butene) appear on the same side of the double bond, and in (
262:
183:
175:
79:
35:
31:
3041:. Related reactions include eliminations by β-haloethers (the
1457:
are intermediates. These reactions do not require catalysts.
404:
7868:
7838:
7771:
7629:
7594:
7589:
7562:
7510:
7477:
7381:
7205:
6200:
6166:
6082:
4746:
4344:
4038:
4012:
3928:
3675:
3594:. Many of the most vivid natural pigments are terpenes; e.g.
3073:
2819:
oxidative addition / reductive elimination by metal catalyst
2055:
2004:
1638:
1618:
425:
4005:, "together"). This labeling may be taught with mnemonic "
1784:
When treated with a hot concentrated, acidified solution of
1498:. The first step in hydration often involves formation of a
1486:
The π bonds of alkenes hydrocarbons are also susceptible to
384:
carbon atoms particularly within the larger molecules (from
8995:
7296:
4861:
Organotransition Metal Chemistry: From Bonding to Catalysis
4670:
4324:
3777:
of the double bond as being the number of its first carbon.
2754:
electrophilic addition of mercuric acetate, then reduction
2642:
industrial process: alkene alkylating carboxylic acid with
2470:
2421:
2407:
1808:
561: ≥ 7 for stability and tricyclic systems require
491:
6711:
4776:
4723:"The Mechanism for the Acid Catalysed Hydration of Ethene"
4355:(6th ed.), New York: Wiley-Interscience, p. 23,
3982:
prefixes. This notation considers the group with highest
3564:
3441:
Cope rearrangement of divinylcyclobutane to cyclooctadiene
2962:). When an alkyl halide is used, the reaction is called a
2916:) can also be achieved by a reaction of ethylene with the
1001:
bonded to the carbon adjacent to double bonds will give a
9005:
3549:
2383:
2358:
2345:
2314:
2281:
2268:
2240:
2222:
2197:
2184:
2147:
2134:
1954:
1894:
1878:
1852:
1376:
resulting in an alkane. The equation of hydrogenation of
994:
5067:
Delaude, Lionel; Noels, Alfred F. (2005). "Metathesis".
1562:. The reaction equation of HBr addition to ethylene is:
134:
Acyclic alkenes, with only one double bond and no other
119:
for acyclic hydrocarbons with two or more double bonds;
3405:
1029:
5006:
4319:
4096:
Rule A-3. Unsaturated Compounds and Univalent Radicals
1999:
to a wide range of products. A common example is the -
1858:
1506:. The reaction equation for hydration of ethylene is:
1426:
Similar to hydrogen, halogens added to double bonds.
1355:
447:
Each carbon atom of the double bond uses its three sp
4647:"Organic Compounds: Physical and Thermochemical Data"
4028:
2115:
1824:
27:
Hydrocarbon compound containing one or more C=C bonds
4863:. New York: University Science Books. p. 1160.
4250:
Moss, G. P.; Smith, P. A. S.; Tavernier, D. (1995).
3181:. The Wittig reagent is itself prepared easily from
3129:
2659:
oxidation, reagent: osmium tetroxide, chiral ligand
2551:
free radicals mediated addition of hydrohalic acids
2078:
C−H bonds. Thus, these groupings are susceptible to
1350:
5000:
4479:
3606:(yellow in egg yolk). The simplest of all alkenes,
349:, 2-pentene, 2-methyl-1-butene, 3-methyl-1-butene,
4673:The Systematic Identification of Organic Compounds
4249:
3410:Alkenes can be synthesized from other alkenes via
3126:, via a three-membered ring sulfone intermediate.
2391:
2045:. Polymers from alkene are usually referred to as
1960:
4615:
4613:
4532:
4449:Comprehensive Organic Name Reactions and Reagents
4211:
4209:
4207:
4177:
4175:
2912:synthesis of higher α-alkenes (of the type RCH=CH
1811:rather than full cleavage of the alkene by using
1558:. The hydrohalogenation of alkene will result in
241:—and those with three or more overlapping bonds (
95:International Union of Pure and Applied Chemistry
9094:
5167:
3212:-product is desired, another alternative is the
2629:industrial process, addition of CO and alcohol.
186:are possible, distinguished by the position and
5293:
5069:Kirk-Othmer Encyclopedia of Chemical Technology
4979:
4828:
4567:"Boiling Points and Structures of Hydrocarbons"
3786:Write the position and name of each side group.
3107:The Hofmann elimination is unusual in that the
2780:photochemical reaction with aldehyde or ketone
2767:electrophilic addition with aldehyde or ketone
719:Many of the physical properties of alkenes and
408:Ethylene (ethene), showing the pi bond in green
41:"Olefin" redirects here. For the material, see
5221:Organic Chemistry with Biological Applications
5135:Zweifel, George S.; Nantz, Michael H. (2007).
5071:. Weinheim: Wiley-VCH. pp. metanoel.a01.
4757:(6th ed.), New York: Wiley-Interscience,
4610:
4204:
4172:
3398:For the preparation multisubstituted alkenes,
3072:Alkenes can be prepared indirectly from alkyl
2702:two alkenes rearrange to form two new alkenes
679:attached to each carbon is the same for both.
8129:
7170:
6727:
5260:
4940:
4621:"Nuclear Magnetic Resonance (NMR) of Alkenes"
3103:Synthesis of cyclooctene via Cope elimination
2989:Alkenes can be synthesized from alcohols via
756:
420:. This double bond is stronger than a single
235:—the simplest such compound is itself called
5134:
5128:
5066:
3563:
3537:
3511:
3488:
3216:, which uses the carbanion generated from a
2676:oxidation, reagents: iodine, silver acetate
1502:. The net result of the reaction will be an
1066:Combustion energies of various hydrocarbons
220:produced on the largest scale industrially.
5174:International Journal of Molecular Sciences
5161:
4539:Nguyen, Trung; Clark, Jim (23 April 2019).
4538:
4105:Rule A-4. Bivalent and Multivalent Radicals
3419:
3355:synthesis of disubstituted alkenes. If the
1359:typical electrophilic addition reaction of
478:for molecules with three or four different
444:) vs 1.53 Å for a typical C-C single bond.
170:being a >1 natural number (which is two
8136:
8122:
7177:
7163:
6734:
6720:
5267:
5253:
5223:(3rd ed.). Cengage Learning. p.
3885:More complex rules apply for polyenes and
1543:Example of hydrohalogenation: addition of
412:A carbon–carbon double bond consists of a
8143:
5195:
5185:
5139:Modern Organic Synthesis: An Introduction
4805:
4795:
4515:
4505:
4331:On-Line Encyclopedia of Integer Sequences
4269:
4245:
4243:
4241:
3268:
1637:, in which singlet oxygen reacts with an
598:atoms joined by a double bond. In Latin,
5212:
5093:
4982:Journal of the American Chemical Society
4973:
4946:
4373:
4371:
4011:
3945:
3891:
3618:Selected unsaturated compounds in nature
3614:that influences the ripening of plants.
3192:A typical example of the Wittig reaction
2938:
2420:
2406:
1601:
1538:
1459:
1411:Hydrogenation reactions usually require
1354:
1338:. Alkenes serve as a feedstock for the
977:The stretching of C=C bond will give an
972:
403:
394:
105:hydrocarbons with just one double bond;
49:
5218:
5033:
4858:
4564:
4451:. Vol. 116. 2010. pp. 525–8.
4410:
3719:for straight-chain alkenes, change the
3146:or its equivalent. Pre-eminent is the
3115:) alkene is usually the major product.
2608:industrial process, addition of CO and
2585:industrial process, addition of CO and
2069:
256:
14:
9095:
4883:
4854:
4852:
4593:"Overview of Chemical Shifts in H-NMR"
4377:
4238:
4137:
4135:
4133:
3900:
3499:Monomers for synthesizing polyethylene
3234:A pair of ketones or aldehydes can be
3196:Related to the Wittig reaction is the
714:
459:on the two carbon atoms. Consequently
8117:
7184:
7158:
6715:
5248:
4903:
4720:
4368:
4286:
4089:
3706:
3585:
2842:
2793:electrophilic addition of a peroxide
2402:
1641:structure to give a transposed allyl
1625:. This conversion is an example of a
9051:
5099:
4909:
4141:
3406:Rearrangements and related reactions
2847:Alkenes are produced by hydrocarbon
2728:cycloaddition with an alkyne and CO
2466:
1804:The oxidation can be stopped at the
1664:and even hydrogen peroxide to yield
9075:
4849:
4130:
3845:is "2,2-dimethyl pentane", whereas
3697:and universal precursor to natural
2875:-octane to give pentane and propene
2806:addition of carbenes or carbenoids
2519:electrophilic addition of halogens
2029:Terminal alkenes are precursors to
988:
482:(side groups). For example, of the
269:. Most alkenes are also isomers of
24:
5060:
4590:
4293:"Production: Growth is the Norm".
4221:Compendium of Chemical Terminology
4187:Compendium of Chemical Terminology
4043:
4029:Groups containing C=C double bonds
3436:
3381:
3187:
3098:
2980:
2889:
2866:
2741:reagents: borane, then a peroxide
1978:In the presence of an appropriate
1647:
1609:
1051:to give carbon dioxide and water.
981:absorption peak at 1670–1600
25:
9114:
3289:, then processes incorporating a
3130:Synthesis from carbonyl compounds
3118:Alkenes are generated from α-halo
2437:transition metal alkene complexes
2371:
2302:
2210:
2018:
1351:Addition to the unsaturated bonds
693:Cahn–Ingold–Prelog priority rules
9074:
9062:
9050:
9039:
9038:
6988:Horner–Wadsworth–Emmons reaction
5274:
4541:"Physical Properties of Alkenes"
3683:
3660:
3641:
3622:
3160:Horner–Wadsworth–Emmons reaction
1591:
1490:. The reaction usually involves
659:
643:
631:
619:
369:Many of these molecules exhibit
193:Alkenes are generally colorless
5077:10.1002/0471238961.metanoel.a01
5027:
4877:
4822:
4784:Photochemistry and Photobiology
4770:
4740:
4714:
4689:
4664:
4639:
4584:
4558:
4473:
4440:
3674:, precursor to the diterpenoid
3342:
3173:P=CHR to produce an alkene and
3169:(or phosphorane) of the type Ph
2985:An example of an E2 Elimination
1060:standard enthalpy of combustion
4457:10.1002/9780470638859.conrr116
4404:
4338:
4313:
3459:
2898:This process is also known as
2348:
2332:
2271:
2255:
2246:
2187:
2171:
2137:
2121:
1940:
1934:
1921:
1915:
1900:
1793:, alkenes are cleaved to form
1478:for unsaturated hydrocarbons.
765:Melting and boiling points in
13:
1:
8403:Interface and colloid science
8157:Glossary of chemical formulae
6973:Corey–Winter olefin synthesis
4884:Toreki, Rob (31 March 2015).
4295:Chemical and Engineering News
4123:
3896:Naming substituted hex-1-enes
3882:is "3,3-dimethyl 1-pentene".
2879:Related to this is catalytic
2537:addition of hydrohalic acids
2447:. One example is the complex
2093:
1038:
4890:Organometallic HyperTextbook
4721:Clark, Jim (November 2007).
4301:(28): 59–236. 10 July 2006.
2837:
2427:bis(cyclooctadiene)nickel(0)
1655:
1325:
1012:. The double bond will also
568:
486:, the two methyl groups of (
261:Alkenes having four or more
174:less than the corresponding
7:
8680:Bioorganometallic chemistry
8167:List of inorganic compounds
6741:
4384:Organic Reaction Mechanisms
4051:
3351:is a useful method for the
3335:Transition metal catalyzed
3295:Shell higher olefin process
3029:), so as to allow a milder
2851:. Raw materials are mostly
2715:cycloaddition with a diene
2473:
2413:Dewar-Chatt-Duncanson model
1756:→ RCHO + R'CHO + O=SMe
638:structure of trans-2-butene
101:the name "alkene" only for
10:
9119:
8606:Dynamic covalent chemistry
8577:Enantioselective synthesis
8557:Physical organic chemistry
8510:Organolanthanide chemistry
5143:. W. H. Freeman. pp.
4321:Sloane, N. J. A.
4257:Pure and Applied Chemistry
4009:means 'on ze zame zide'".
3304:are used in this process:
3261:) or an alkyllithium (the
2685:
2680:
2672:
2663:
2655:
2652:Sharpless bishydroxylation
2650:
2638:
2633:
2625:
2620:
2604:
2595:
2581:
2576:
2560:
2555:
2547:
2541:
2533:
2523:
2515:
2510:
2489:
2484:
2022:
1595:
757:Boiling and melting points
572:
399:
40:
29:
9034:
8937:
8698:
8614:
8535:
8485:
8361:
8304:
8195:Electroanalytical methods
8180:
8152:
8072:
8031:
7951:
7928:
7890:
7867:
7762:
7683:
7553:
7530:
7486:
7429:
7352:
7327:
7192:
7144:Friedel-Crafts Alkylation
7056:
7018:Ramberg–Bäcklund reaction
6913:
6749:
6678:
6640:
6614:
6579:
6535:
6507:
6470:
6461:
6428:
6400:
6391:
6371:
6334:
6325:
6307:
6242:
6199:
6190:
6179:
6134:
6081:
6028:
6010:
5970:
5917:
5872:
5816:
5792:
5742:
5686:
5663:
5650:
5630:
5562:
5531:
5491:
5438:
5378:
5317:
5282:
5219:McMurry, John E. (2014).
5044:10.1002/9780470771044.ch4
4565:Ophardt, Charles (2003).
4307:10.1021/cen-v084n034.p059
3602:(orange in carrots), and
3124:Ramberg–Bäcklund reaction
3033:-elimination such as the
2512:Halogen addition reaction
2415:for alkene-metal bonding.
2080:free radical substitution
2003:of singlet oxygen with a
1633:. Another example is the
1369:involves the addition of
1239:
1166:
1094:
925:
880:
835:
790:
626:structure of cis-2-butene
150:with the general formula
8950:Nobel Prize in Chemistry
8866:Supramolecular chemistry
8505:Organometallic chemistry
6948:Bamford–Stevens reaction
5036:The Chemistry of Alkenes
4949:The Chemistry of Alkenes
4918:(6th ed.). Pearson
4843:10.15227/orgsyn.073.0240
4150:(6th ed.). Pearson
3715:To form the root of the
3426:can be used such as the
3259:Bamford–Stevens reaction
3063:diphosphorus tetraiodide
3059:Corey-Winter olefination
2747:Oxymercuration-reduction
2429:, a metal–alkene complex
1971:This reaction is called
509:
30:Not to be confused with
8888:Combinatorial chemistry
8799:Food physical chemistry
8762:Environmental chemistry
8646:Bioorthogonal chemistry
8572:Retrosynthetic analysis
8393:Chemical thermodynamics
8376:Spectroelectrochemistry
8319:Computational chemistry
8083:chemical classification
7084:Oxymercuration reaction
6953:Barton–Kellogg reaction
4507:10.1073/pnas.1111297109
4378:Bansal, Raj K. (1998).
4271:10.1351/pac199567081307
4234:10.1351/goldbook.O04281
4200:10.1351/goldbook.A00224
4016:The difference between
3950:The difference between
3723:infix of the parent to
3412:rearrangement reactions
3302:heterogeneous catalysis
3248:Barton–Kellogg reaction
2918:organometallic compound
2885:catalytic hydrogenation
2734:Hydroboration–oxidation
1776:CHO + R'CHO + O=SMe
681:E- and Z- configuration
265:atoms can form diverse
8960:of element discoveries
8806:Agricultural chemistry
8794:Carbohydrate chemistry
8685:Bioinorganic chemistry
8550:Alkane stereochemistry
8495:Coordination chemistry
8324:Mathematical chemistry
8190:Instrumental chemistry
7079:Electrophilic addition
6958:Boord olefin synthesis
6602:1,3,5-Triheptylbenzene
5114:10.1002/anie.201003133
4859:Hartwig, John (2010).
4048:
4025:
3959:
3931:"on this side of") or
3897:
3678:, an anticancer agent.
3568:
3542:
3516:
3493:
3442:
3395:
3269:Synthesis from alkenes
3193:
3104:
3043:Boord olefin synthesis
2986:
2895:
2876:
2853:natural-gas condensate
2773:Paterno–Büchi reaction
2430:
2416:
2393:
1962:
1652:
1614:
1607:
1606:a Diels-Alder reaction
1548:
1476:degree of unsaturation
1468:
1421:degree of unsaturation
1363:
1340:petrochemical industry
536:nonbonded interactions
409:
212:) (or "ethene" in the
59:
8955:Timeline of chemistry
8852:Post-mortem chemistry
8837:Clandestine chemistry
8767:Atmospheric chemistry
8690:Biophysical chemistry
8522:Solid-state chemistry
8472:Equilibrium chemistry
8381:Photoelectrochemistry
8090:chemical nomenclature
7003:Kauffmann olefination
6597:1,3,5-Triethylbenzene
4957:10.1002/9780470771044
4388:McGraw-Hill Education
4047:
4015:
3949:
3895:
3567:
3541:
3515:
3492:
3440:
3394:-alkenes from alkynes
3385:
3279:Ziegler–Natta process
3242:metal reduction (the
3191:
3185:and an alkyl halide.
3102:
2984:
2939:Elimination reactions
2893:
2870:
2721:Pauson–Khand reaction
2686:aldehydes or ketones
2493:addition of hydrogen
2424:
2410:
2394:
2033:via processes termed
1963:
1651:
1613:
1605:
1542:
1463:
1358:
973:Infrared spectroscopy
549:For bridged alkenes,
407:
395:Structure and bonding
58:, the simplest alkene
53:
8945:History of chemistry
8900:Chemical engineering
8675:Bioorganic chemistry
8425:Structural chemistry
8162:List of biomolecules
7124:Diels–Alder reaction
7013:Peterson olefination
6993:Hydrazone iodination
6930:Dehydration reaction
6000:Isopropylcyclohexene
5582:Perhydrophenanthrene
5521:Isopropylcyclohexane
5187:10.3390/ijms22115710
5102:Angew. Chem. Int. Ed
4625:Chemistry LibreTexts
4545:Chemistry LibreTexts
4068:Aromatic hydrocarbon
3773:Define the location
3447:Diels–Alder reaction
3424:pericyclic reactions
3359:-alkene is desired,
3198:Peterson olefination
3084:) or oxidized to an
2945:elimination reaction
2708:Diels–Alder reaction
2113:
2070:Allylic substitution
1822:
1635:Schenck ene reaction
1627:Diels-Alder reaction
526:of alkenes includes
522:pair repulsion, the
514:As predicted by the
502:)-but-2-ene (a.k.a.
380:. There may also be
257:Structural isomerism
190:of the double bond.
8968:The central science
8922:Ceramic engineering
8847:Forensic toxicology
8820:Chemistry education
8718:Radiation chemistry
8700:Interdisciplinarity
8653:Medicinal chemistry
8591:Fullerene chemistry
8467:Microwave chemistry
8336:Molecular mechanics
8331:Molecular modelling
7546:not C, H or O)
6983:Hofmann elimination
6963:Chugaev elimination
6921:Dehydrohalogenation
6696:Alicyclic compounds
6509:Tetramethylbenzenes
5021:10.1021/jo00949a029
4994:10.1021/ja01585a024
4910:Wade, L.G. (2006).
4747:Smith, Michael B.;
4498:2012PNAS..109.3492D
4426:10.1021/cr60147a003
4345:Smith, Michael B.;
4142:Wade, L.G. (2006).
3598:(red in tomatoes),
3468:
3363:in the presence of
3082:Hofmann elimination
3035:Chugaev elimination
2997:produces ethylene:
2964:dehydrohalogenation
2923:in the presence of
2644:silicotungstic acid
2385:
2360:
2347:
2316:
2283:
2270:
2242:
2224:
2199:
2186:
2149:
2136:
1956:
1896:
1880:
1854:
1815:or other oxidants:
1662:percarboxylic acids
1660:Alkenes react with
1067:
769:
715:Physical properties
575:Cis–trans isomerism
249:, etc.) are called
9011:Chemical substance
8873:Chemical synthesis
8842:Forensic chemistry
8723:Actinide chemistry
8665:Clinical chemistry
8346:Molecular geometry
8341:Molecular dynamics
8296:Elemental analysis
8249:Separation process
7988:Hypervalent iodine
7048:Cope rearrangement
6978:Grieco elimination
6653:Cyclopropenylidene
5990:Methylcyclopentene
5980:Methylcyclopropene
5511:Methylcyclopentane
5501:Methylcyclopropane
4886:"Alkene Complexes"
4390:. pp. 14–16.
4334:. OEIS Foundation.
4090:Nomenclature links
4049:
4026:
3960:
3898:
3707:IUPAC Nomenclature
3612:signaling molecule
3586:Natural occurrence
3569:
3543:
3522:For manufacturing
3517:
3494:
3467:
3443:
3432:Cope rearrangement
3396:
3365:Lindlar's catalyst
3293:step, such as the
3194:
3183:triphenylphosphine
3148:aldol condensation
3105:
3039:Grieco elimination
2987:
2896:
2877:
2843:Industrial methods
2825:Hydrophosphination
2597:Hydrocarboxylation
2431:
2417:
2403:Metal complexation
2389:
2387:
2373:
2335:
2330:
2318:
2304:
2258:
2253:
2244:
2230:
2212:
2174:
2169:
2124:
2119:
2084:radical initiators
1958:
1944:
1884:
1868:
1867:
1842:
1694:For ethylene, the
1653:
1615:
1608:
1556:Markovnikov's rule
1549:
1469:
1415:to increase their
1364:
1065:
997:spectroscopy, the
764:
524:molecular geometry
410:
267:structural isomers
214:IUPAC nomenclature
60:
9090:
9089:
9026:Quantum mechanics
8991:Chemical compound
8974:Chemical reaction
8912:Materials science
8830:General chemistry
8825:Amateur chemistry
8753:Photogeochemistry
8738:Stellar chemistry
8708:Nuclear chemistry
8629:Molecular biology
8596:Polymer chemistry
8567:Organic synthesis
8562:Organic reactions
8527:Ceramic chemistry
8517:Cluster chemistry
8447:Chemical kinetics
8435:Molecular physics
8314:Quantum chemistry
8227:Mass spectrometry
8111:
8110:
8049:Sulfenyl chloride
8027:
8026:
7526:
7525:
7345:(only C, H and O)
7186:Functional groups
7152:
7151:
7114:Hydrohalogenation
7038:Olefin metathesis
7028:Takai olefination
6998:Julia olefination
6939:Semihydrogenation
6709:
6708:
6674:
6673:
6610:
6609:
6587:Hexamethylbenzene
6575:
6574:
6457:
6456:
6402:Trimethylbenzenes
6387:
6386:
6303:
6302:
6175:
6174:
6162:Cyclododecatriene
6157:Cyclooctatetraene
5995:Methylcyclohexene
5985:Methylcyclobutene
5972:Alkylcycloalkenes
5913:
5912:
5788:
5787:
5646:
5645:
5516:Methylcyclohexane
5506:Methylcyclobutane
5493:Alkylcycloalkanes
5434:
5433:
5234:978-1-285-84291-2
5154:978-0-7167-7266-8
5086:978-0-471-23896-6
5053:978-0-470-77104-4
4966:978-0-470-77104-4
4933:978-1-4058-5345-3
4914:Organic Chemistry
4870:978-1-938787-15-7
4831:Organic Syntheses
4797:10.1111/php.12716
4764:978-0-471-72091-1
4466:978-0-470-63885-9
4397:978-0-07-462083-0
4362:978-0-471-72091-1
4165:978-1-4058-5345-3
4146:Organic Chemistry
3974:, instead of the
3583:
3582:
3416:olefin metathesis
3291:olefin metathesis
3225:Takai olefination
3214:Julia olefination
3208:-products. If an
3111:substituted (non-
3065:will deoxygenate
2921:triethylaluminium
2835:
2834:
2695:Olefin metathesis
2622:Carboalkoxylation
2544:hydrohalogenation
2542:Anti-Markovnikov
2525:Hydrohalogenation
2499:Hydroalkenylation
2467:Reaction overview
2376:
2363:
2338:
2324:
2323:
2307:
2294:
2286:
2261:
2233:
2215:
2204:
2203:
2177:
2168:
2160:
2152:
2127:
2100:olefin metathesis
1988:hydroxyl radicals
1947:
1939:
1932:
1920:
1913:
1906:
1899:
1887:
1871:
1866:
1845:
1836:
1829:
1552:Hydrohalogenation
1323:
1322:
1062:of hydrocarbons.
970:
969:
711:-configurations.
585:organic chemistry
565: ≥ 11.
540:functional groups
484:isomers of butene
351:2-methyl-2-butene
182:is four or more,
144:homologous series
136:functional groups
64:organic chemistry
16:(Redirected from
9110:
9078:
9077:
9066:
9054:
9053:
9042:
9041:
8986:Chemical element
8641:Chemical biology
8500:Magnetochemistry
8477:Mechanochemistry
8430:Chemical physics
8371:Electrochemistry
8276:Characterization
8138:
8131:
8124:
8115:
8114:
8078:
7983:Trifluoromethoxy
7551:
7550:
7547:
7350:
7349:
7346:
7199:
7179:
7172:
7165:
7156:
7155:
7094:Cyclopropanation
7023:Shapiro reaction
7008:McMurry reaction
6905:
6888:
6871:
6854:
6837:
6820:
6803:
6786:
6769:
6736:
6729:
6722:
6713:
6712:
6666:-Propenylbenzene
6468:
6467:
6398:
6397:
6332:
6331:
6323:
6322:
6197:
6196:
6188:
6187:
5873:Branched alkynes
5814:
5813:
5743:Branched alkenes
5684:
5683:
5661:
5660:
5564:Polycycloalkanes
5549:(bicycloheptane)
5543:(bicyclopentane)
5379:Branched alkanes
5315:
5314:
5291:
5290:
5269:
5262:
5255:
5246:
5245:
5239:
5238:
5216:
5210:
5209:
5199:
5189:
5165:
5159:
5158:
5142:
5132:
5126:
5125:
5097:
5091:
5090:
5064:
5058:
5057:
5031:
5025:
5024:
5004:
4998:
4997:
4977:
4971:
4970:
4944:
4938:
4937:
4917:
4907:
4901:
4900:
4898:
4896:
4881:
4875:
4874:
4856:
4847:
4846:
4826:
4820:
4819:
4809:
4799:
4774:
4768:
4767:
4744:
4738:
4737:
4735:
4733:
4718:
4712:
4711:
4709:
4707:
4697:"Bromine Number"
4693:
4687:
4686:
4668:
4662:
4661:
4659:
4657:
4643:
4637:
4636:
4634:
4632:
4617:
4608:
4607:
4605:
4603:
4588:
4582:
4581:
4579:
4577:
4571:Virtual Chembook
4562:
4556:
4555:
4553:
4551:
4536:
4530:
4529:
4519:
4509:
4477:
4471:
4470:
4447:"Bredt's Rule".
4444:
4438:
4437:
4408:
4402:
4401:
4386:(3rd ed.).
4375:
4366:
4365:
4342:
4336:
4335:
4317:
4311:
4310:
4290:
4284:
4283:
4273:
4264:(8–9): 1307–75.
4247:
4236:
4213:
4202:
4179:
4170:
4169:
4149:
4139:
4119:IUPAC Blue Book.
4113:IUPAC Blue Book.
4107:IUPAC Blue Book.
3962:More generally,
3881:
3880:
3879:
3869:
3865:
3864:
3863:
3855:
3854:
3844:
3843:
3842:
3832:
3831:
3830:
3820:
3819:
3818:
3810:
3809:
3687:
3664:
3645:
3626:
3524:synthetic rubber
3469:
3466:
3371:metal in liquid
3297:are important.
3263:Shapiro reaction
3255:sodium methoxide
3244:McMurry reaction
2799:Cyclopropanation
2725:cyclopentenones
2615:
2605:carboxylic acid
2591:
2578:Hydroformylation
2571:
2567:
2471:
2462:
2398:
2396:
2395:
2390:
2388:
2386:
2384:
2381:
2374:
2369:
2368:
2361:
2359:
2356:
2351:
2346:
2343:
2336:
2325:
2321:
2320:
2319:
2317:
2315:
2312:
2305:
2300:
2299:
2292:
2291:
2284:
2282:
2279:
2274:
2269:
2266:
2259:
2250:
2245:
2243:
2241:
2238:
2231:
2229:
2223:
2220:
2213:
2205:
2201:
2200:
2198:
2195:
2190:
2185:
2182:
2175:
2166:
2165:
2158:
2157:
2150:
2148:
2145:
2140:
2135:
2132:
2125:
2117:
2098:Alkenes undergo
1967:
1965:
1964:
1959:
1957:
1955:
1952:
1945:
1943:
1937:
1930:
1929:
1924:
1918:
1911:
1910:
1904:
1897:
1895:
1892:
1885:
1879:
1876:
1869:
1859:
1853:
1850:
1843:
1841:
1834:
1833:
1827:
1813:osmium tetroxide
1799:carboxylic acids
1792:
1780:
1760:
1742:
1728:
1690:
1586:
1534:
1068:
1064:
1043:Like most other
1008:of 4.5–6.5
989:NMR spectroscopy
770:
763:
677:functional group
663:
647:
635:
623:
390:
364:
344:
320:
303:
286:
248:
244:
230:
218:organic compound
211:
165:
99:recommends using
21:
9118:
9117:
9113:
9112:
9111:
9109:
9108:
9107:
9093:
9092:
9091:
9086:
9030:
8933:
8927:Polymer science
8883:Click chemistry
8878:Green chemistry
8772:Ocean chemistry
8748:Biogeochemistry
8694:
8610:
8582:Total synthesis
8545:Stereochemistry
8531:
8481:
8398:Surface science
8388:Thermochemistry
8357:
8300:
8271:Crystallography
8176:
8148:
8142:
8112:
8107:
8076:
8068:
8023:
7978:Trichloromethyl
7973:Trifluoromethyl
7947:
7924:
7886:
7863:
7758:
7727:Phosphine oxide
7679:
7545:
7543:
7542:
7540:
7538:
7536:
7534:
7532:
7522:
7482:
7425:
7344:
7343:
7338:
7333:
7323:
7197:
7196:
7188:
7183:
7153:
7148:
7134:Dehydrogenation
7104:Dihydroxylation
7052:
7033:Wittig reaction
6909:
6904:
6900:
6896:
6887:
6883:
6879:
6870:
6866:
6862:
6853:
6849:
6845:
6836:
6832:
6828:
6819:
6815:
6811:
6802:
6798:
6794:
6785:
6781:
6777:
6768:
6764:
6760:
6745:
6740:
6710:
6705:
6701:Petroleum jelly
6670:
6658:Phenylacetylene
6636:
6606:
6571:
6567:Isobutylbenzene
6531:
6503:
6453:
6424:
6383:
6367:
6321:
6299:
6238:
6182:
6171:
6130:
6077:
6024:
6006:
5966:
5909:
5868:
5810:
5802:
5796:
5784:
5738:
5680:
5673:
5667:
5656:
5654:
5642:
5626:
5558:
5555:(bicyclodecane)
5527:
5487:
5430:
5396:3-Methylpentane
5374:
5311:
5303:
5297:
5286:
5284:
5278:
5273:
5243:
5242:
5235:
5217:
5213:
5166:
5162:
5155:
5133:
5129:
5098:
5094:
5087:
5065:
5061:
5054:
5032:
5028:
5005:
5001:
4978:
4974:
4967:
4945:
4941:
4934:
4908:
4904:
4894:
4892:
4882:
4878:
4871:
4857:
4850:
4827:
4823:
4775:
4771:
4765:
4745:
4741:
4731:
4729:
4719:
4715:
4705:
4703:
4695:
4694:
4690:
4683:
4669:
4665:
4655:
4653:
4645:
4644:
4640:
4630:
4628:
4627:. 23 April 2019
4619:
4618:
4611:
4601:
4599:
4589:
4585:
4575:
4573:
4563:
4559:
4549:
4547:
4537:
4533:
4478:
4474:
4467:
4446:
4445:
4441:
4409:
4405:
4398:
4376:
4369:
4363:
4343:
4339:
4318:
4314:
4292:
4291:
4287:
4248:
4239:
4214:
4205:
4180:
4173:
4166:
4140:
4131:
4126:
4099:IUPAC Blue Book
4092:
4054:
4031:
3910:
3878:
3875:
3874:
3873:
3871:
3867:
3862:
3859:
3858:
3857:
3853:
3850:
3849:
3848:
3846:
3841:
3838:
3837:
3836:
3834:
3829:
3826:
3825:
3824:
3822:
3817:
3814:
3813:
3812:
3808:
3805:
3804:
3803:
3801:
3754:
3750:
3736:
3732:
3727:. For example,
3709:
3702:
3688:
3679:
3665:
3656:
3646:
3637:
3627:
3588:
3462:
3456:
3408:
3400:carbometalation
3353:stereoselective
3345:
3337:hydrovinylation
3331:
3327:
3323:
3319:
3315:
3311:
3271:
3229:Tebbe's reagent
3178:
3172:
3156:Wittig reaction
3132:
3055:phosphite ester
3047:ester pyrolysis
3020:
3016:
3012:
3008:
3004:
2941:
2915:
2881:dehydrogenation
2845:
2840:
2689:reagent: ozone
2613:
2609:
2590:
2586:
2569:
2565:
2469:
2460:
2456:
2452:
2448:
2405:
2382:
2377:
2372:
2370:
2364:
2357:
2352:
2344:
2339:
2331:
2329:
2313:
2308:
2303:
2301:
2295:
2287:
2280:
2275:
2267:
2262:
2254:
2252:
2251:
2249:
2239:
2234:
2225:
2221:
2216:
2211:
2209:
2196:
2191:
2183:
2178:
2170:
2161:
2153:
2146:
2141:
2133:
2128:
2120:
2118:
2116:
2114:
2111:
2110:
2096:
2072:
2027:
2021:
2009:cyclopentadiene
1980:photosensitiser
1973:dihydroxylation
1953:
1948:
1933:
1925:
1914:
1903:
1893:
1888:
1877:
1872:
1851:
1846:
1837:
1826:
1825:
1823:
1820:
1819:
1790:
1785:
1779:
1775:
1771:
1767:
1763:
1759:
1755:
1751:
1747:
1741:
1737:
1726:
1722:
1718:
1714:
1710:
1706:
1702:
1688:
1684:
1680:
1676:
1672:
1658:
1617:Alkenes add to
1600:
1594:
1584:
1580:
1576:
1573:
1569:
1532:
1528:
1524:
1521:
1517:
1513:
1464:Structure of a
1449:
1445:
1441:
1437:
1433:
1407:
1403:
1399:
1395:
1391:
1374:
1353:
1328:
1316:
1312:
1293:
1289:
1285:
1266:
1262:
1258:
1254:
1231:
1212:
1208:
1189:
1185:
1181:
1159:
1155:
1136:
1132:
1113:
1109:
1089:
1088:
1072:
1041:
1019:
1006:
991:
975:
774:
759:
717:
687:(together) and
671:
664:
655:
648:
639:
636:
627:
624:
614:configuration.
592:cis- and trans-
581:
573:Main articles:
571:
512:
449:hybrid orbitals
402:
397:
389:
385:
363:
359:
355:
343:
339:
335:
319:
315:
311:
302:
298:
294:
285:
281:
277:
259:
246:
242:
228:
210:
206:
202:
164:
157:
151:
138:(also known as
46:
39:
28:
23:
22:
15:
12:
11:
5:
9116:
9106:
9105:
9088:
9087:
9085:
9084:
9072:
9060:
9048:
9035:
9032:
9031:
9029:
9028:
9023:
9018:
9013:
9008:
9003:
8998:
8993:
8988:
8983:
8982:
8981:
8971:
8964:
8963:
8962:
8952:
8947:
8941:
8939:
8935:
8934:
8932:
8931:
8930:
8929:
8924:
8919:
8909:
8908:
8907:
8897:
8896:
8895:
8890:
8885:
8880:
8870:
8869:
8868:
8857:
8856:
8855:
8854:
8849:
8839:
8834:
8833:
8832:
8827:
8816:
8815:
8814:
8813:
8811:Soil chemistry
8803:
8802:
8801:
8796:
8789:Food chemistry
8786:
8784:Carbochemistry
8781:
8779:Clay chemistry
8776:
8775:
8774:
8769:
8758:
8757:
8756:
8755:
8750:
8740:
8734:Astrochemistry
8730:Cosmochemistry
8727:
8726:
8725:
8720:
8715:
8713:Radiochemistry
8704:
8702:
8696:
8695:
8693:
8692:
8687:
8682:
8677:
8672:
8670:Neurochemistry
8667:
8662:
8661:
8660:
8650:
8649:
8648:
8638:
8637:
8636:
8631:
8620:
8618:
8612:
8611:
8609:
8608:
8603:
8601:Petrochemistry
8598:
8593:
8588:
8579:
8574:
8569:
8564:
8559:
8554:
8553:
8552:
8541:
8539:
8533:
8532:
8530:
8529:
8524:
8519:
8514:
8513:
8512:
8502:
8497:
8491:
8489:
8483:
8482:
8480:
8479:
8474:
8469:
8464:
8462:Spin chemistry
8459:
8457:Photochemistry
8454:
8449:
8444:
8442:Femtochemistry
8439:
8438:
8437:
8427:
8422:
8417:
8412:
8411:
8410:
8400:
8395:
8390:
8385:
8384:
8383:
8378:
8367:
8365:
8359:
8358:
8356:
8355:
8354:
8353:
8343:
8338:
8333:
8328:
8327:
8326:
8316:
8310:
8308:
8302:
8301:
8299:
8298:
8293:
8288:
8283:
8278:
8273:
8268:
8267:
8266:
8261:
8254:Chromatography
8251:
8246:
8245:
8244:
8239:
8234:
8224:
8223:
8222:
8217:
8212:
8207:
8197:
8192:
8186:
8184:
8178:
8177:
8175:
8174:
8172:Periodic table
8169:
8164:
8159:
8153:
8150:
8149:
8141:
8140:
8133:
8126:
8118:
8109:
8108:
8106:
8105:
8104:
8103:
8098:
8086:
8079:
8073:
8070:
8069:
8067:
8066:
8064:Sulfinylamines
8061:
8056:
8051:
8046:
8044:Phosphoramides
8041:
8039:Isothiocyanate
8035:
8033:
8029:
8028:
8025:
8024:
8022:
8021:
8016:
8015:
8014:
8004:
8003:
8002:
7992:
7991:
7990:
7985:
7980:
7975:
7970:
7959:
7957:
7949:
7948:
7946:
7945:
7940:
7934:
7932:
7926:
7925:
7923:
7922:
7917:
7915:Selenenic acid
7912:
7910:Seleninic acid
7907:
7905:Selenonic acid
7902:
7896:
7894:
7888:
7887:
7885:
7884:
7879:
7873:
7871:
7865:
7864:
7862:
7861:
7856:
7851:
7846:
7841:
7836:
7831:
7826:
7821:
7816:
7811:
7806:
7801:
7796:
7791:
7786:
7785:
7784:
7774:
7768:
7766:
7760:
7759:
7757:
7756:
7751:
7746:
7741:
7740:
7739:
7729:
7724:
7719:
7714:
7713:
7712:
7702:
7701:
7700:
7698:Phosphodiester
7689:
7687:
7681:
7680:
7678:
7677:
7672:
7667:
7662:
7657:
7652:
7647:
7642:
7637:
7632:
7627:
7622:
7617:
7612:
7607:
7602:
7597:
7592:
7587:
7582:
7577:
7576:
7575:
7570:
7559:
7557:
7548:
7544:(one element,
7528:
7527:
7524:
7523:
7521:
7520:
7519:
7518:
7508:
7507:
7506:
7501:
7490:
7488:
7484:
7483:
7481:
7480:
7475:
7470:
7469:
7468:
7458:
7457:
7456:
7451:
7446:
7435:
7433:
7427:
7426:
7424:
7423:
7421:Methylenedioxy
7418:
7413:
7412:
7411:
7406:
7396:
7395:
7394:
7389:
7379:
7378:
7377:
7367:
7362:
7356:
7354:
7347:
7325:
7324:
7322:
7321:
7316:
7311:
7310:
7309:
7304:
7294:
7293:
7292:
7287:
7282:
7277:
7272:
7267:
7257:
7256:
7255:
7250:
7240:
7239:
7238:
7233:
7228:
7223:
7218:
7213:
7202:
7200:
7198:(only C and H)
7190:
7189:
7182:
7181:
7174:
7167:
7159:
7150:
7149:
7147:
7146:
7141:
7136:
7131:
7129:Wacker process
7126:
7121:
7119:Polymerization
7116:
7111:
7106:
7101:
7096:
7091:
7086:
7081:
7076:
7071:
7066:
7060:
7058:
7054:
7053:
7051:
7050:
7045:
7040:
7035:
7030:
7025:
7020:
7015:
7010:
7005:
7000:
6995:
6990:
6985:
6980:
6975:
6970:
6965:
6960:
6955:
6950:
6945:
6936:
6927:
6917:
6915:
6911:
6910:
6908:
6907:
6902:
6898:
6890:
6885:
6881:
6873:
6868:
6864:
6856:
6851:
6847:
6839:
6834:
6830:
6822:
6817:
6813:
6805:
6800:
6796:
6788:
6783:
6779:
6771:
6766:
6762:
6753:
6751:
6747:
6746:
6739:
6738:
6731:
6724:
6716:
6707:
6706:
6704:
6703:
6698:
6693:
6688:
6682:
6680:
6676:
6675:
6672:
6671:
6669:
6668:
6660:
6655:
6650:
6644:
6642:
6638:
6637:
6635:
6634:
6632:4-Vinyltoluene
6629:
6627:Divinylbenzene
6624:
6618:
6616:
6612:
6611:
6608:
6607:
6605:
6604:
6599:
6594:
6592:2-Phenylhexane
6589:
6583:
6581:
6577:
6576:
6573:
6572:
6570:
6569:
6564:
6556:
6548:
6539:
6537:
6533:
6532:
6530:
6529:
6524:
6519:
6513:
6511:
6505:
6504:
6502:
6501:
6493:
6485:
6476:
6474:
6465:
6459:
6458:
6455:
6454:
6452:
6451:
6449:4-Ethyltoluene
6446:
6444:-Propylbenzene
6438:
6432:
6430:
6426:
6425:
6423:
6422:
6417:
6412:
6406:
6404:
6395:
6389:
6388:
6385:
6384:
6382:
6381:
6375:
6373:
6369:
6368:
6366:
6365:
6357:
6349:
6340:
6338:
6329:
6320:
6319:
6313:
6311:
6305:
6304:
6301:
6300:
6298:
6297:
6292:
6287:
6282:
6277:
6272:
6267:
6262:
6257:
6252:
6246:
6244:
6240:
6239:
6237:
6236:
6231:
6226:
6221:
6216:
6211:
6205:
6203:
6194:
6185:
6177:
6176:
6173:
6172:
6170:
6169:
6164:
6159:
6154:
6149:
6144:
6138:
6136:
6132:
6131:
6129:
6128:
6123:
6118:
6113:
6108:
6103:
6098:
6093:
6087:
6085:
6079:
6078:
6076:
6075:
6070:
6065:
6060:
6055:
6050:
6045:
6040:
6034:
6032:
6026:
6025:
6023:
6022:
6016:
6014:
6012:Bicycloalkenes
6008:
6007:
6005:
6004:
6002:
5997:
5992:
5987:
5982:
5976:
5974:
5968:
5967:
5965:
5964:
5959:
5954:
5949:
5944:
5939:
5934:
5929:
5923:
5921:
5915:
5914:
5911:
5910:
5908:
5907:
5902:
5897:
5892:
5887:
5882:
5876:
5874:
5870:
5869:
5867:
5866:
5861:
5856:
5851:
5846:
5841:
5836:
5831:
5826:
5820:
5818:
5817:Linear alkynes
5811:
5804:
5798:
5790:
5789:
5786:
5785:
5783:
5782:
5777:
5772:
5767:
5762:
5757:
5752:
5746:
5744:
5740:
5739:
5737:
5736:
5731:
5726:
5721:
5716:
5711:
5706:
5701:
5696:
5690:
5688:
5687:Linear alkenes
5681:
5675:
5669:
5658:
5648:
5647:
5644:
5643:
5641:
5640:
5634:
5632:
5628:
5627:
5625:
5624:
5619:
5614:
5609:
5604:
5599:
5594:
5589:
5584:
5579:
5574:
5568:
5566:
5560:
5559:
5557:
5556:
5550:
5544:
5537:
5535:
5533:Bicycloalkanes
5529:
5528:
5526:
5525:
5523:
5518:
5513:
5508:
5503:
5497:
5495:
5489:
5488:
5486:
5485:
5480:
5475:
5470:
5465:
5460:
5455:
5450:
5444:
5442:
5436:
5435:
5432:
5431:
5429:
5428:
5423:
5418:
5413:
5408:
5403:
5398:
5393:
5388:
5382:
5380:
5376:
5375:
5373:
5372:
5367:
5362:
5357:
5352:
5347:
5342:
5337:
5332:
5327:
5321:
5319:
5318:Linear alkanes
5312:
5305:
5299:
5288:
5280:
5279:
5272:
5271:
5264:
5257:
5249:
5241:
5240:
5233:
5211:
5160:
5153:
5127:
5108:(40): 7166–8.
5092:
5085:
5059:
5052:
5026:
4999:
4972:
4965:
4939:
4932:
4902:
4876:
4869:
4848:
4821:
4769:
4763:
4739:
4713:
4688:
4681:
4663:
4638:
4609:
4591:Hanson, John.
4583:
4557:
4531:
4472:
4465:
4439:
4420:(2): 219–274.
4403:
4396:
4380:"Bredt's Rule"
4367:
4361:
4337:
4312:
4285:
4237:
4203:
4171:
4164:
4128:
4127:
4125:
4122:
4121:
4120:
4114:
4108:
4102:
4091:
4088:
4087:
4086:
4081:
4076:
4071:
4065:
4060:
4053:
4050:
4030:
4027:
3939:-2-pentene or
3909:
3899:
3876:
3860:
3851:
3839:
3827:
3815:
3806:
3795:
3794:
3787:
3784:
3781:
3778:
3771:
3768:
3752:
3748:
3745:. The name of
3734:
3730:
3708:
3705:
3704:
3703:
3689:
3682:
3680:
3666:
3659:
3657:
3647:
3640:
3638:
3628:
3621:
3619:
3587:
3584:
3581:
3580:
3579:
3578:
3570:
3561:
3555:
3554:
3553:
3552:
3544:
3535:
3533:vinyl chloride
3529:
3528:
3527:
3526:
3518:
3509:
3503:
3502:
3501:
3500:
3495:
3486:
3480:
3479:
3476:
3473:
3461:
3458:
3407:
3404:
3344:
3341:
3333:
3332:
3329:
3325:
3321:
3317:
3313:
3309:
3270:
3267:
3176:
3170:
3167:Wittig reagent
3131:
3128:
3069:to alkenes.
3057:combined (the
3045:) and esters (
3023:
3022:
3018:
3014:
3010:
3006:
3002:
2968:Zaitsev's rule
2949:vinyl chloride
2940:
2937:
2913:
2844:
2841:
2839:
2836:
2833:
2832:
2830:
2827:
2821:
2820:
2817:
2814:
2812:Hydroacylation
2808:
2807:
2804:
2803:cyclopropanes
2801:
2795:
2794:
2791:
2788:
2782:
2781:
2778:
2775:
2769:
2768:
2765:
2762:
2760:Prins reaction
2756:
2755:
2752:
2749:
2743:
2742:
2739:
2736:
2730:
2729:
2726:
2723:
2717:
2716:
2713:
2710:
2704:
2703:
2700:
2697:
2691:
2690:
2687:
2684:
2678:
2677:
2674:
2671:
2669:-hydroxylation
2661:
2660:
2657:
2654:
2648:
2647:
2646:the catalyst.
2640:
2637:
2631:
2630:
2627:
2624:
2618:
2617:
2611:
2606:
2603:
2593:
2592:
2588:
2583:
2580:
2574:
2573:
2562:
2559:
2557:Hydroamination
2553:
2552:
2549:
2546:
2539:
2538:
2535:
2532:
2521:
2520:
2517:
2514:
2508:
2507:
2504:
2501:
2495:
2494:
2491:
2488:
2482:
2481:
2478:
2475:
2468:
2465:
2458:
2454:
2450:
2433:
2432:
2404:
2401:
2400:
2399:
2380:
2367:
2355:
2350:
2342:
2334:
2328:
2311:
2298:
2290:
2278:
2273:
2265:
2257:
2248:
2237:
2228:
2219:
2208:
2194:
2189:
2181:
2173:
2164:
2156:
2144:
2139:
2131:
2123:
2095:
2092:
2071:
2068:
2060:buta-1,3-diene
2035:polymerization
2023:Main article:
2020:
2019:Polymerization
2017:
1992:singlet oxygen
1984:methylene blue
1969:
1968:
1951:
1942:
1936:
1928:
1923:
1917:
1909:
1902:
1891:
1883:
1875:
1865:
1862:
1857:
1849:
1840:
1832:
1788:
1782:
1781:
1777:
1773:
1769:
1765:
1761:
1757:
1753:
1749:
1748:RCH=CHR' + O
1739:
1730:
1729:
1724:
1720:
1716:
1712:
1708:
1704:
1692:
1691:
1686:
1682:
1681:H → RCHOCH
1678:
1674:
1657:
1654:
1596:Main article:
1593:
1590:
1589:
1588:
1582:
1578:
1571:
1567:
1537:
1536:
1530:
1526:
1519:
1515:
1511:
1480:Bromine number
1452:
1451:
1447:
1443:
1439:
1435:
1431:
1409:
1408:
1405:
1401:
1397:
1393:
1389:
1372:
1352:
1349:
1327:
1324:
1321:
1320:
1317:
1314:
1310:
1307:
1304:
1298:
1297:
1294:
1291:
1287:
1283:
1280:
1277:
1271:
1270:
1267:
1264:
1260:
1256:
1252:
1249:
1246:
1241:
1237:
1236:
1233:
1229:
1226:
1223:
1217:
1216:
1213:
1210:
1206:
1203:
1200:
1194:
1193:
1190:
1187:
1183:
1179:
1176:
1173:
1168:
1164:
1163:
1160:
1157:
1153:
1150:
1147:
1141:
1140:
1137:
1134:
1130:
1127:
1124:
1118:
1117:
1114:
1111:
1107:
1104:
1101:
1096:
1092:
1091:
1086:
1083:
1080:
1077:
1074:
1040:
1037:
1017:
1004:
990:
987:
974:
971:
968:
967:
964:
961:
958:
954:
953:
950:
947:
944:
940:
939:
936:
933:
930:
927:
923:
922:
919:
916:
913:
909:
908:
905:
902:
899:
895:
894:
891:
888:
885:
882:
878:
877:
874:
871:
868:
864:
863:
860:
857:
854:
850:
849:
846:
843:
840:
837:
833:
832:
829:
826:
823:
819:
818:
815:
812:
809:
805:
804:
801:
798:
795:
792:
788:
787:
784:
781:
778:
776:
758:
755:
729:molecular mass
725:physical state
716:
713:
673:
672:
665:
658:
656:
649:
642:
640:
637:
630:
628:
625:
618:
570:
567:
534:introduced by
511:
508:
401:
398:
396:
393:
387:
367:
366:
361:
357:
353:
341:
337:
333:
317:
313:
309:
300:
296:
292:
283:
279:
258:
255:
208:
204:
159:
153:
125:cycloalkadiene
54:A 3D model of
26:
9:
6:
4:
3:
2:
9115:
9104:
9101:
9100:
9098:
9083:
9082:
9073:
9071:
9070:
9065:
9061:
9059:
9058:
9049:
9047:
9046:
9037:
9036:
9033:
9027:
9024:
9022:
9019:
9017:
9016:Chemical bond
9014:
9012:
9009:
9007:
9004:
9002:
8999:
8997:
8994:
8992:
8989:
8987:
8984:
8980:
8977:
8976:
8975:
8972:
8969:
8965:
8961:
8958:
8957:
8956:
8953:
8951:
8948:
8946:
8943:
8942:
8940:
8936:
8928:
8925:
8923:
8920:
8918:
8915:
8914:
8913:
8910:
8906:
8905:Stoichiometry
8903:
8902:
8901:
8898:
8894:
8891:
8889:
8886:
8884:
8881:
8879:
8876:
8875:
8874:
8871:
8867:
8864:
8863:
8862:
8861:Nanochemistry
8859:
8858:
8853:
8850:
8848:
8845:
8844:
8843:
8840:
8838:
8835:
8831:
8828:
8826:
8823:
8822:
8821:
8818:
8817:
8812:
8809:
8808:
8807:
8804:
8800:
8797:
8795:
8792:
8791:
8790:
8787:
8785:
8782:
8780:
8777:
8773:
8770:
8768:
8765:
8764:
8763:
8760:
8759:
8754:
8751:
8749:
8746:
8745:
8744:
8741:
8739:
8735:
8731:
8728:
8724:
8721:
8719:
8716:
8714:
8711:
8710:
8709:
8706:
8705:
8703:
8701:
8697:
8691:
8688:
8686:
8683:
8681:
8678:
8676:
8673:
8671:
8668:
8666:
8663:
8659:
8656:
8655:
8654:
8651:
8647:
8644:
8643:
8642:
8639:
8635:
8632:
8630:
8627:
8626:
8625:
8622:
8621:
8619:
8617:
8613:
8607:
8604:
8602:
8599:
8597:
8594:
8592:
8589:
8587:
8586:Semisynthesis
8583:
8580:
8578:
8575:
8573:
8570:
8568:
8565:
8563:
8560:
8558:
8555:
8551:
8548:
8547:
8546:
8543:
8542:
8540:
8538:
8534:
8528:
8525:
8523:
8520:
8518:
8515:
8511:
8508:
8507:
8506:
8503:
8501:
8498:
8496:
8493:
8492:
8490:
8488:
8484:
8478:
8475:
8473:
8470:
8468:
8465:
8463:
8460:
8458:
8455:
8453:
8450:
8448:
8445:
8443:
8440:
8436:
8433:
8432:
8431:
8428:
8426:
8423:
8421:
8420:Sonochemistry
8418:
8416:
8415:Cryochemistry
8413:
8409:
8408:Micromeritics
8406:
8405:
8404:
8401:
8399:
8396:
8394:
8391:
8389:
8386:
8382:
8379:
8377:
8374:
8373:
8372:
8369:
8368:
8366:
8364:
8360:
8352:
8349:
8348:
8347:
8344:
8342:
8339:
8337:
8334:
8332:
8329:
8325:
8322:
8321:
8320:
8317:
8315:
8312:
8311:
8309:
8307:
8303:
8297:
8294:
8292:
8289:
8287:
8286:Wet chemistry
8284:
8282:
8279:
8277:
8274:
8272:
8269:
8265:
8262:
8260:
8257:
8256:
8255:
8252:
8250:
8247:
8243:
8240:
8238:
8235:
8233:
8230:
8229:
8228:
8225:
8221:
8218:
8216:
8213:
8211:
8208:
8206:
8203:
8202:
8201:
8198:
8196:
8193:
8191:
8188:
8187:
8185:
8183:
8179:
8173:
8170:
8168:
8165:
8163:
8160:
8158:
8155:
8154:
8151:
8147:
8139:
8134:
8132:
8127:
8125:
8120:
8119:
8116:
8102:
8099:
8097:
8094:
8093:
8092:
8091:
8087:
8085:
8084:
8080:
8075:
8074:
8071:
8065:
8062:
8060:
8057:
8055:
8052:
8050:
8047:
8045:
8042:
8040:
8037:
8036:
8034:
8030:
8020:
8017:
8013:
8010:
8009:
8008:
8005:
8001:
7998:
7997:
7996:
7993:
7989:
7986:
7984:
7981:
7979:
7976:
7974:
7971:
7969:
7966:
7965:
7964:
7961:
7960:
7958:
7956:
7955:
7950:
7944:
7943:Telluroketone
7941:
7939:
7936:
7935:
7933:
7931:
7927:
7921:
7918:
7916:
7913:
7911:
7908:
7906:
7903:
7901:
7898:
7897:
7895:
7893:
7889:
7883:
7880:
7878:
7875:
7874:
7872:
7870:
7866:
7860:
7857:
7855:
7852:
7850:
7847:
7845:
7842:
7840:
7837:
7835:
7832:
7830:
7829:Sulfonic acid
7827:
7825:
7822:
7820:
7819:Sulfinic acid
7817:
7815:
7814:Thiosulfonate
7812:
7810:
7807:
7805:
7804:Thiosulfinate
7802:
7800:
7799:Sulfenic acid
7797:
7795:
7792:
7790:
7787:
7783:
7780:
7779:
7778:
7775:
7773:
7770:
7769:
7767:
7765:
7761:
7755:
7754:Phosphaallene
7752:
7750:
7749:Phosphaalkyne
7747:
7745:
7744:Phosphaalkene
7742:
7738:
7735:
7734:
7733:
7730:
7728:
7725:
7723:
7720:
7718:
7715:
7711:
7708:
7707:
7706:
7703:
7699:
7696:
7695:
7694:
7691:
7690:
7688:
7686:
7682:
7676:
7673:
7671:
7668:
7666:
7663:
7661:
7658:
7656:
7653:
7651:
7648:
7646:
7643:
7641:
7638:
7636:
7633:
7631:
7628:
7626:
7623:
7621:
7618:
7616:
7613:
7611:
7608:
7606:
7603:
7601:
7598:
7596:
7593:
7591:
7588:
7586:
7583:
7581:
7578:
7574:
7571:
7569:
7566:
7565:
7564:
7561:
7560:
7558:
7556:
7552:
7549:
7529:
7517:
7514:
7513:
7512:
7509:
7505:
7502:
7500:
7497:
7496:
7495:
7492:
7491:
7489:
7485:
7479:
7476:
7474:
7471:
7467:
7464:
7463:
7462:
7459:
7455:
7452:
7450:
7447:
7445:
7442:
7441:
7440:
7437:
7436:
7434:
7432:
7428:
7422:
7419:
7417:
7416:Ethylenedioxy
7414:
7410:
7407:
7405:
7402:
7401:
7400:
7397:
7393:
7390:
7388:
7385:
7384:
7383:
7380:
7376:
7373:
7372:
7371:
7368:
7366:
7363:
7361:
7358:
7357:
7355:
7351:
7348:
7342:
7336:
7331:
7326:
7320:
7317:
7315:
7312:
7308:
7305:
7303:
7300:
7299:
7298:
7295:
7291:
7288:
7286:
7283:
7281:
7278:
7276:
7273:
7271:
7268:
7266:
7263:
7262:
7261:
7258:
7254:
7251:
7249:
7246:
7245:
7244:
7241:
7237:
7234:
7232:
7229:
7227:
7224:
7222:
7219:
7217:
7214:
7212:
7209:
7208:
7207:
7204:
7203:
7201:
7195:
7191:
7187:
7180:
7175:
7173:
7168:
7166:
7161:
7160:
7157:
7145:
7142:
7140:
7137:
7135:
7132:
7130:
7127:
7125:
7122:
7120:
7117:
7115:
7112:
7110:
7107:
7105:
7102:
7100:
7097:
7095:
7092:
7090:
7089:Hydroboration
7087:
7085:
7082:
7080:
7077:
7075:
7072:
7070:
7067:
7065:
7064:Hydrogenation
7062:
7061:
7059:
7055:
7049:
7046:
7044:
7041:
7039:
7036:
7034:
7031:
7029:
7026:
7024:
7021:
7019:
7016:
7014:
7011:
7009:
7006:
7004:
7001:
6999:
6996:
6994:
6991:
6989:
6986:
6984:
6981:
6979:
6976:
6974:
6971:
6969:
6968:Cope reaction
6966:
6964:
6961:
6959:
6956:
6954:
6951:
6949:
6946:
6944:
6940:
6937:
6935:
6931:
6928:
6926:
6922:
6919:
6918:
6916:
6912:
6894:
6891:
6877:
6874:
6860:
6857:
6843:
6840:
6826:
6823:
6809:
6806:
6792:
6789:
6775:
6772:
6758:
6755:
6754:
6752:
6748:
6744:
6737:
6732:
6730:
6725:
6723:
6718:
6717:
6714:
6702:
6699:
6697:
6694:
6692:
6689:
6687:
6684:
6683:
6681:
6677:
6667:
6665:
6661:
6659:
6656:
6654:
6651:
6649:
6646:
6645:
6643:
6639:
6633:
6630:
6628:
6625:
6623:
6620:
6619:
6617:
6615:Vinylbenzenes
6613:
6603:
6600:
6598:
6595:
6593:
6590:
6588:
6585:
6584:
6582:
6578:
6568:
6565:
6563:
6562:-Butylbenzene
6561:
6557:
6555:
6554:-Butylbenzene
6553:
6549:
6547:
6546:-Butylbenzene
6545:
6541:
6540:
6538:
6534:
6528:
6525:
6523:
6520:
6518:
6515:
6514:
6512:
6510:
6506:
6500:
6498:
6494:
6492:
6490:
6486:
6484:
6482:
6478:
6477:
6475:
6473:
6469:
6466:
6464:
6460:
6450:
6447:
6445:
6443:
6439:
6437:
6434:
6433:
6431:
6427:
6421:
6418:
6416:
6413:
6411:
6408:
6407:
6405:
6403:
6399:
6396:
6394:
6390:
6380:
6377:
6376:
6374:
6370:
6364:
6362:
6358:
6356:
6354:
6350:
6348:
6346:
6342:
6341:
6339:
6337:
6333:
6330:
6328:
6324:
6318:
6315:
6314:
6312:
6310:
6309:Alkylbenzenes
6306:
6296:
6293:
6291:
6288:
6286:
6283:
6281:
6278:
6276:
6273:
6271:
6268:
6266:
6263:
6261:
6258:
6256:
6253:
6251:
6248:
6247:
6245:
6241:
6235:
6232:
6230:
6227:
6225:
6222:
6220:
6217:
6215:
6212:
6210:
6207:
6206:
6204:
6202:
6198:
6195:
6193:
6189:
6186:
6184:
6178:
6168:
6165:
6163:
6160:
6158:
6155:
6153:
6150:
6148:
6145:
6143:
6140:
6139:
6137:
6133:
6127:
6124:
6122:
6119:
6117:
6114:
6112:
6109:
6107:
6104:
6102:
6099:
6097:
6094:
6092:
6089:
6088:
6086:
6084:
6080:
6074:
6071:
6069:
6066:
6064:
6061:
6059:
6056:
6054:
6051:
6049:
6046:
6044:
6041:
6039:
6036:
6035:
6033:
6031:
6027:
6021:
6018:
6017:
6015:
6013:
6009:
6003:
6001:
5998:
5996:
5993:
5991:
5988:
5986:
5983:
5981:
5978:
5977:
5975:
5973:
5969:
5963:
5960:
5958:
5955:
5953:
5950:
5948:
5945:
5943:
5940:
5938:
5935:
5933:
5930:
5928:
5925:
5924:
5922:
5920:
5916:
5906:
5903:
5901:
5898:
5896:
5893:
5891:
5888:
5886:
5883:
5881:
5878:
5877:
5875:
5871:
5865:
5862:
5860:
5857:
5855:
5852:
5850:
5847:
5845:
5842:
5840:
5837:
5835:
5832:
5830:
5827:
5825:
5822:
5821:
5819:
5815:
5812:
5808:
5801:
5795:
5791:
5781:
5778:
5776:
5773:
5771:
5768:
5766:
5763:
5761:
5758:
5756:
5753:
5751:
5748:
5747:
5745:
5741:
5735:
5732:
5730:
5727:
5725:
5722:
5720:
5717:
5715:
5712:
5710:
5707:
5705:
5702:
5700:
5697:
5695:
5692:
5691:
5689:
5685:
5682:
5679:
5672:
5666:
5662:
5659:
5653:
5649:
5639:
5636:
5635:
5633:
5629:
5623:
5620:
5618:
5615:
5613:
5610:
5608:
5605:
5603:
5602:Dodecahedrane
5600:
5598:
5595:
5593:
5590:
5588:
5585:
5583:
5580:
5578:
5575:
5573:
5570:
5569:
5567:
5565:
5561:
5554:
5551:
5548:
5545:
5542:
5539:
5538:
5536:
5534:
5530:
5524:
5522:
5519:
5517:
5514:
5512:
5509:
5507:
5504:
5502:
5499:
5498:
5496:
5494:
5490:
5484:
5481:
5479:
5476:
5474:
5471:
5469:
5466:
5464:
5461:
5459:
5456:
5454:
5451:
5449:
5446:
5445:
5443:
5441:
5437:
5427:
5424:
5422:
5419:
5417:
5414:
5412:
5409:
5407:
5404:
5402:
5399:
5397:
5394:
5392:
5389:
5387:
5384:
5383:
5381:
5377:
5371:
5368:
5366:
5363:
5361:
5358:
5356:
5353:
5351:
5348:
5346:
5343:
5341:
5338:
5336:
5333:
5331:
5328:
5326:
5323:
5322:
5320:
5316:
5313:
5309:
5302:
5296:
5292:
5289:
5281:
5277:
5270:
5265:
5263:
5258:
5256:
5251:
5250:
5247:
5236:
5230:
5226:
5222:
5215:
5207:
5203:
5198:
5193:
5188:
5183:
5179:
5175:
5171:
5164:
5156:
5150:
5146:
5141:
5140:
5131:
5123:
5119:
5115:
5111:
5107:
5103:
5096:
5088:
5082:
5078:
5074:
5070:
5063:
5055:
5049:
5045:
5041:
5037:
5030:
5022:
5018:
5015:(9): 1742–3.
5014:
5010:
5003:
4995:
4991:
4987:
4983:
4976:
4968:
4962:
4958:
4954:
4950:
4943:
4935:
4929:
4925:
4921:
4920:Prentice Hall
4916:
4915:
4906:
4891:
4887:
4880:
4872:
4866:
4862:
4855:
4853:
4844:
4840:
4836:
4832:
4825:
4817:
4813:
4808:
4803:
4798:
4793:
4789:
4785:
4781:
4773:
4766:
4760:
4756:
4755:
4750:
4743:
4728:
4724:
4717:
4702:
4698:
4692:
4684:
4682:0-471-59748-1
4678:
4674:
4667:
4652:
4648:
4642:
4626:
4622:
4616:
4614:
4598:
4594:
4587:
4572:
4568:
4561:
4546:
4542:
4535:
4527:
4523:
4518:
4513:
4508:
4503:
4499:
4495:
4492:(9): 3492–7.
4491:
4487:
4483:
4476:
4468:
4462:
4458:
4454:
4450:
4443:
4435:
4431:
4427:
4423:
4419:
4416:
4415:
4407:
4399:
4393:
4389:
4385:
4381:
4374:
4372:
4364:
4358:
4354:
4353:
4348:
4341:
4333:
4332:
4326:
4322:
4316:
4308:
4304:
4300:
4296:
4289:
4281:
4277:
4272:
4267:
4263:
4259:
4258:
4253:
4246:
4244:
4242:
4235:
4231:
4227:
4223:
4222:
4217:
4212:
4210:
4208:
4201:
4197:
4193:
4189:
4188:
4183:
4178:
4176:
4167:
4161:
4157:
4153:
4152:Prentice Hall
4148:
4147:
4138:
4136:
4134:
4129:
4118:
4115:
4112:
4109:
4106:
4103:
4100:
4097:
4094:
4093:
4085:
4082:
4080:
4077:
4075:
4072:
4069:
4066:
4064:
4061:
4059:
4056:
4055:
4046:
4042:
4040:
4036:
4023:
4019:
4014:
4010:
4008:
4004:
4001:(from German
4000:
3996:
3993:
3989:
3985:
3981:
3977:
3973:
3969:
3965:
3957:
3953:
3948:
3944:
3942:
3938:
3934:
3930:
3926:
3922:
3920:
3916:
3907:
3903:
3894:
3890:
3888:
3883:
3798:
3792:
3788:
3785:
3782:
3779:
3776:
3772:
3769:
3766:
3765:
3764:
3761:
3759:
3756:is therefore
3755:
3744:
3741:
3737:
3726:
3722:
3718:
3713:
3700:
3696:
3692:
3686:
3681:
3677:
3673:
3669:
3663:
3658:
3654:
3653:sesquiterpene
3650:
3644:
3639:
3635:
3631:
3625:
3620:
3617:
3616:
3615:
3613:
3609:
3605:
3601:
3597:
3593:
3577:
3574:precursor to
3573:
3572:
3571:
3566:
3562:
3560:
3557:
3556:
3551:
3548:Precursor to
3547:
3546:
3545:
3540:
3536:
3534:
3531:
3530:
3525:
3521:
3520:
3519:
3514:
3510:
3508:
3507:1,3-butadiene
3505:
3504:
3498:
3497:
3496:
3491:
3487:
3485:
3482:
3481:
3477:
3474:
3471:
3470:
3465:
3457:
3454:
3452:
3448:
3439:
3435:
3433:
3429:
3425:
3421:
3417:
3413:
3403:
3401:
3393:
3389:
3386:Synthesis of
3384:
3380:
3378:
3374:
3370:
3366:
3362:
3361:hydrogenation
3358:
3354:
3350:
3347:Reduction of
3340:
3338:
3307:
3306:
3305:
3303:
3298:
3296:
3292:
3288:
3284:
3280:
3276:
3266:
3264:
3260:
3256:
3251:
3249:
3245:
3241:
3237:
3232:
3230:
3226:
3222:
3219:
3215:
3211:
3207:
3203:
3199:
3190:
3186:
3184:
3180:
3168:
3163:
3161:
3157:
3153:
3149:
3145:
3141:
3137:
3127:
3125:
3121:
3116:
3114:
3110:
3101:
3097:
3095:
3091:
3090:Cope reaction
3087:
3083:
3079:
3075:
3070:
3068:
3064:
3060:
3056:
3052:
3048:
3044:
3040:
3036:
3032:
3028:
3000:
2999:
2998:
2996:
2992:
2983:
2979:
2977:
2973:
2969:
2965:
2961:
2957:
2952:
2950:
2946:
2936:
2934:
2930:
2926:
2922:
2919:
2911:
2907:
2905:
2901:
2892:
2888:
2886:
2882:
2874:
2869:
2865:
2862:
2858:
2854:
2850:
2831:
2828:
2826:
2823:
2822:
2818:
2815:
2813:
2810:
2809:
2805:
2802:
2800:
2797:
2796:
2792:
2789:
2787:
2784:
2783:
2779:
2776:
2774:
2771:
2770:
2766:
2763:
2761:
2758:
2757:
2753:
2750:
2748:
2745:
2744:
2740:
2737:
2735:
2732:
2731:
2727:
2724:
2722:
2719:
2718:
2714:
2712:cyclohexenes
2711:
2709:
2706:
2705:
2701:
2698:
2696:
2693:
2692:
2688:
2683:
2679:
2675:
2670:
2668:
2662:
2658:
2653:
2649:
2645:
2641:
2636:
2632:
2628:
2623:
2619:
2607:
2602:
2601:Koch reaction
2598:
2594:
2584:
2579:
2575:
2563:
2558:
2554:
2550:
2545:
2540:
2536:
2530:
2526:
2522:
2518:
2516:1,2-dihalide
2513:
2509:
2505:
2502:
2500:
2497:
2496:
2492:
2487:
2486:Hydrogenation
2483:
2479:
2476:
2474:Reaction name
2472:
2464:
2446:
2442:
2438:
2428:
2425:Structure of
2423:
2419:
2418:
2414:
2409:
2378:
2365:
2353:
2340:
2326:
2309:
2296:
2288:
2276:
2263:
2235:
2226:
2217:
2206:
2192:
2179:
2162:
2154:
2142:
2129:
2109:
2108:
2107:
2105:
2101:
2091:
2089:
2085:
2081:
2077:
2067:
2065:
2061:
2057:
2054:
2050:
2049:
2044:
2043:polypropylene
2040:
2036:
2032:
2026:
2016:
2014:
2010:
2006:
2002:
2001:cycloaddition
1997:
1993:
1989:
1985:
1981:
1976:
1974:
1949:
1926:
1907:
1889:
1881:
1873:
1863:
1860:
1855:
1847:
1838:
1830:
1818:
1817:
1816:
1814:
1810:
1807:
1802:
1800:
1796:
1791:
1762:
1746:
1745:
1744:
1735:
1701:
1700:
1699:
1697:
1671:
1670:
1669:
1667:
1663:
1650:
1646:
1644:
1640:
1636:
1632:
1628:
1624:
1620:
1612:
1604:
1599:
1598:cycloaddition
1592:Cycloaddition
1587:
1565:
1564:
1563:
1561:
1557:
1553:
1546:
1541:
1535:
1509:
1508:
1507:
1505:
1501:
1497:
1493:
1489:
1484:
1481:
1477:
1473:
1467:
1466:bromonium ion
1462:
1458:
1456:
1455:Halonium ions
1429:
1428:
1427:
1424:
1422:
1418:
1417:reaction rate
1414:
1387:
1386:
1385:
1383:
1379:
1375:
1368:
1367:Hydrogenation
1362:
1357:
1348:
1346:
1341:
1337:
1333:
1318:
1308:
1305:
1303:
1300:
1299:
1295:
1281:
1278:
1276:
1273:
1272:
1268:
1250:
1247:
1245:
1242:
1238:
1234:
1227:
1224:
1222:
1219:
1218:
1214:
1204:
1201:
1199:
1196:
1195:
1191:
1177:
1174:
1172:
1169:
1165:
1161:
1151:
1148:
1146:
1143:
1142:
1138:
1128:
1125:
1123:
1120:
1119:
1115:
1105:
1102:
1100:
1097:
1093:
1084:
1081:
1078:
1075:
1070:
1069:
1063:
1061:
1057:
1052:
1050:
1046:
1036:
1033:
1031:
1027:
1023:
1015:
1011:
1007:
1000:
996:
986:
984:
980:
965:
962:
959:
957:Boiling point
956:
955:
951:
948:
945:
943:Melting point
942:
941:
937:
934:
931:
928:
924:
920:
917:
914:
912:Boiling point
911:
910:
906:
903:
900:
898:Melting point
897:
896:
892:
889:
886:
883:
879:
875:
872:
869:
867:Boiling point
866:
865:
861:
858:
855:
853:Melting point
852:
851:
847:
844:
841:
838:
834:
830:
827:
824:
822:Boiling point
821:
820:
816:
813:
810:
808:Melting point
807:
806:
802:
799:
796:
793:
789:
785:
782:
779:
777:
772:
771:
768:
762:
754:
752:
750:
744:
742:
738:
734:
730:
726:
722:
712:
710:
706:
702:
698:
694:
690:
686:
682:
678:
669:
662:
657:
653:
646:
641:
634:
629:
622:
617:
616:
615:
613:
609:
605:
601:
597:
593:
590:
586:
580:
576:
566:
564:
560:
556:
552:
547:
545:
541:
537:
533:
532:steric strain
529:
525:
521:
517:
507:
505:
501:
497:
493:
489:
485:
481:
477:
475:
471:
466:
462:
458:
453:
450:
445:
443:
439:
435:
431:
427:
423:
422:covalent bond
419:
415:
406:
392:
383:
379:
377:
373:
354:
352:
348:
345:: 5 isomers:
334:
332:
328:
324:
321:: 3 isomers:
310:
307:
293:
290:
276:
275:
274:
272:
268:
264:
254:
252:
240:
239:
234:
231:) are called
225:
221:
219:
215:
200:
196:
191:
189:
185:
181:
177:
173:
169:
163:
156:
149:
145:
141:
137:
132:
130:
126:
122:
118:
117:
112:
108:
104:
100:
96:
91:
89:
85:
81:
78:containing a
77:
73:
69:
65:
57:
52:
48:
44:
37:
33:
19:
9079:
9067:
9055:
9043:
8893:Biosynthesis
8743:Geochemistry
8658:Pharmacology
8634:Cell biology
8624:Biochemistry
8452:Spectroscopy
8351:VSEPR theory
8200:Spectroscopy
8144:Branches of
8088:
8081:
7995:Vinyl halide
7952:
7882:Borinic acid
7877:Boronic acid
7854:Thioxanthate
7259:
7194:Hydrocarbons
7139:Ene reaction
7069:Halogenation
7043:Ene reaction
6914:Preparations
6742:
6663:
6559:
6551:
6543:
6496:
6488:
6480:
6441:
6415:Pseudocumene
6379:Ethylbenzene
6360:
6352:
6344:
6275:Phenanthrene
6183:hydrocarbons
6058:Cycloheptyne
6048:Cyclopentyne
6038:Cyclopropyne
6030:Cycloalkynes
5947:Cycloheptene
5937:Cyclopentene
5927:Cyclopropene
5919:Cycloalkenes
5806:
5799:
5677:
5670:
5664:
5657:hydrocarbons
5638:Spiroalkanes
5468:Cycloheptane
5458:Cyclopentane
5448:Cyclopropane
5440:Cycloalkanes
5307:
5300:
5287:hydrocarbons
5276:Hydrocarbons
5220:
5214:
5180:(11): 5710.
5177:
5173:
5163:
5138:
5130:
5105:
5101:
5095:
5068:
5062:
5035:
5029:
5012:
5009:J. Org. Chem
5008:
5002:
4988:(4): 790–6.
4985:
4981:
4975:
4948:
4942:
4913:
4905:
4893:. Retrieved
4889:
4879:
4860:
4834:
4830:
4824:
4790:(4): 912–9.
4787:
4783:
4772:
4753:
4749:March, Jerry
4742:
4730:. Retrieved
4726:
4716:
4704:. Retrieved
4701:Hach company
4700:
4691:
4672:
4666:
4654:. Retrieved
4650:
4641:
4629:. Retrieved
4624:
4600:. Retrieved
4596:
4586:
4574:. Retrieved
4570:
4560:
4548:. Retrieved
4544:
4534:
4489:
4485:
4475:
4448:
4442:
4417:
4412:
4406:
4383:
4351:
4347:March, Jerry
4340:
4328:
4315:
4298:
4294:
4288:
4261:
4255:
4219:
4185:
4145:
4058:Alpha-olefin
4032:
4021:
4017:
4006:
4002:
3998:
3994:
3987:
3984:CIP priority
3979:
3975:
3972:E–Z notation
3967:
3963:
3961:
3955:
3951:
3940:
3936:
3932:
3924:
3918:
3914:
3911:
3905:
3901:
3887:cycloalkenes
3884:
3799:
3796:
3790:
3774:
3762:
3757:
3746:
3742:
3728:
3724:
3720:
3714:
3710:
3604:xanthophylls
3589:
3463:
3455:
3444:
3428:ene reaction
3409:
3397:
3391:
3387:
3376:
3356:
3346:
3343:From alkynes
3334:
3299:
3283:polyethylene
3272:
3252:
3236:deoxygenated
3233:
3209:
3205:
3201:
3195:
3164:
3152:olefinations
3151:
3133:
3117:
3108:
3106:
3093:
3071:
3030:
3024:
2988:
2975:
2971:
2953:
2942:
2908:
2897:
2887:of alkenes.
2878:
2872:
2871:Cracking of
2846:
2666:
2572:double bond
2568:bond across
2564:addition of
2548:haloalkanes
2534:haloalkanes
2441:back bonding
2434:
2097:
2073:
2046:
2039:polyethylene
2028:
2013:endoperoxide
2011:to yield an
1977:
1970:
1803:
1783:
1768:C=CHR' + O
1731:
1693:
1659:
1631:cyclobutanes
1623:cyclohexenes
1616:
1550:
1547:to an alkene
1485:
1472:Bromine test
1470:
1453:
1425:
1410:
1365:
1336:single bonds
1329:
1306:unsaturated
1279:unsaturated
1225:unsaturated
1202:unsaturated
1149:unsaturated
1126:unsaturated
1053:
1045:hydrocarbons
1042:
1034:
1024:effect. Cis
992:
976:
760:
751:-cyclooctene
748:
745:
718:
708:
704:
700:
696:
688:
684:
674:
667:
651:
611:
607:
603:
599:
582:
579:E–Z notation
562:
558:
554:
551:Bredt's rule
548:
513:
503:
499:
495:
487:
480:substituents
473:
469:
464:
460:
454:
446:
411:
375:
371:
368:
271:cycloalkanes
260:
236:
222:
192:
188:conformation
179:
167:
161:
154:
148:hydrocarbons
139:
133:
124:
120:
114:
110:
106:
92:
71:
67:
61:
47:
43:olefin fiber
9081:WikiProject
8306:Theoretical
8291:Calorimetry
8059:Thiocyanate
8054:Sulfonamide
8019:Perchlorate
8007:Acyl halide
7968:Fluoroethyl
7849:Thionoester
7737:Phosphonium
7722:Phosphinate
7717:Phosphonous
7705:Phosphonate
7404:Hydroperoxy
7226:Cyclopropyl
7099:Epoxidation
6463:C4-Benzenes
6420:Hemellitene
6393:C3-Benzenes
6327:C2-Benzenes
6290:Corannulene
6209:Naphthalene
6073:Cyclodecyne
6068:Cyclononyne
6063:Cyclooctyne
6053:Cyclohexyne
6043:Cyclobutyne
5962:Cyclodecene
5957:Cyclononene
5952:Cyclooctene
5942:Cyclohexene
5932:Cyclobutene
5652:Unsaturated
5483:Cyclodecane
5478:Cyclononane
5473:Cyclooctane
5463:Cyclohexane
5453:Cyclobutane
4922:. pp.
4651:ucdsb.on.ca
4154:. pp.
4079:Nitroalkene
4035:vinyl group
3943:-2-butene.
3717:IUPAC names
3634:monoterpene
3576:polystyrene
3460:Application
3451:cyclohexene
3418:(described
3287:surfactants
3086:amine oxide
3080:(as in the
2991:dehydration
2829:phosphines
2786:Epoxidation
2529:Markovnikov
2445:bond length
2202:diisobutene
2104:ethenolysis
2088:drying oils
2048:polyolefins
1696:epoxidation
1500:carbocation
1492:strong acid
727:depends on
670:)-But-2-ene
654:)-But-2-ene
546:is 123.9°.
528:bond angles
434:bond length
331:isobutylene
127:, etc. for
121:cycloalkene
113:, etc., or
84:double bond
76:hydrocarbon
8917:Metallurgy
8616:Biological
8182:Analytical
7963:Haloalkane
7834:Thioketone
7789:Persulfide
7685:Phosphorus
7650:Isocyanate
7640:Isonitrile
7541:or oxygen
7539:hydrogen,
7535:not being
7516:Orthoester
7409:Dioxiranes
7387:Enol ether
7275:1-Propenyl
7109:Ozonolysis
6925:haloalkane
6522:Prehnitene
6410:Mesitylene
6265:Circulenes
6214:Anthracene
6142:Alkatriene
6111:Heptadiene
6101:Pentadiene
6091:Propadiene
6020:Norbornene
5890:Isoheptyne
5880:Isopentyne
5765:Isoheptene
5755:Isopentene
5577:Diamondoid
5572:Adamantane
5547:Norbornane
5411:Isoheptane
5401:Neopentane
5391:Isopentane
4414:Chem. Rev.
4124:References
4074:Dendralene
3990:(from the
3695:triterpene
3475:Structure
3414:. Besides
3375:gives the
3051:thioketone
2764:1,3-diols
2682:Ozonolysis
2635:alkylation
2582:aldehydes
2094:Metathesis
2053:Conjugated
2025:polyolefin
1996:superoxide
1982:, such as
1734:ozonolysis
1560:haloalkane
1248:saturated
1175:saturated
1103:saturated
1076:Substance
1047:, alkenes
1039:Combustion
1022:J-coupling
938:1-pentyne
803:acetylene
457:p orbitals
424:(611
414:sigma bond
111:alkatriene
8979:Catalysis
8487:Inorganic
8281:Titration
8146:chemistry
8096:inorganic
7930:Tellurium
7844:Thioester
7809:Sulfoxide
7794:Disulfide
7782:Sulfonium
7732:Phosphine
7710:Phosphite
7693:Phosphate
7625:Carbamate
7600:Hydrazone
7533:element,
7531:Only one
7504:Anhydride
7243:Methylene
7074:Hydration
7057:Reactions
6691:Annulynes
6686:Annulenes
6527:Isodurene
6260:Helicenes
6234:Heptacene
6224:Pentacene
6219:Tetracene
6147:Alkadiyne
6126:Decadiene
6121:Nonadiene
6116:Octadiene
6106:Hexadiene
6096:Butadiene
5905:Isodecyne
5900:Isononyne
5895:Isooctyne
5885:Isohexyne
5780:Isodecene
5775:Isononene
5770:Isooctene
5760:Isohexene
5750:Isobutene
5655:aliphatic
5612:Churchane
5607:Basketane
5426:Isodecane
5421:Isononane
5416:Isooctane
5406:Isohexane
5386:Isobutane
5285:aliphatic
5283:Saturated
4727:Chemguide
4675:. Wiley.
4084:Radialene
4070:("Arene")
3921:isomerism
3908:isomerism
3672:diterpene
3668:Taxadiene
3379:-alkene.
3144:carbanion
3078:alkylated
3009:OH → H
2978:-isomer.
2910:Catalytic
2900:reforming
2838:Synthesis
2777:oxetanes
2751:alcohols
2738:alcohols
2665:Woodward
2322:neohexane
2289:−
2247:⟶
2155:−
1927:−
1901:⟶
1656:Oxidation
1574:+ HBr →
1488:hydration
1413:catalysts
1326:Reactions
1145:acetylene
1090:(kJ/mol)
1071:Number of
935:1-pentene
893:1-butyne
845:propylene
773:Number of
737:propylene
569:Isomerism
544:propylene
518:model of
378:isomerism
347:1-pentene
306:propylene
251:cumulenes
247:C=C=C=C=C
216:) is the
195:non-polar
172:hydrogens
142:) form a
140:mono-enes
107:alkadiene
88:α-olefins
9097:Category
9045:Category
9001:Molecule
8938:See also
8363:Physical
8077:See also
8012:Chloride
7938:Tellurol
7892:Selenium
7859:Xanthate
7573:Ammonium
7555:Nitrogen
7537:carbon,
7494:Carboxyl
7461:Aldehyde
7449:Acryloyl
7431:carbonyl
7335:hydrogen
7290:Cumulene
6295:Kekulene
6280:Chrysene
6270:Butalene
6255:Fluorene
6229:Hexacene
6181:Aromatic
6152:Cumulene
5622:Twistane
5617:Pagodane
5597:Prismane
5206:34071919
5122:20672269
4816:28084040
4751:(2007),
4526:22328155
4434:24538877
4349:(2007),
4280:95004254
4063:Annulene
4052:See also
4037:and the
4003:zusammen
3995:entgegen
3927:- (from
3699:steroids
3691:Squalene
3649:Humulene
3630:Limonene
3608:ethylene
3600:carotene
3596:lycopene
3592:terpenes
3484:Ethylene
3430:and the
3422:), many
3324:→ 2 CH
3275:ethylene
3240:titanium
3136:aldehyde
3120:sulfones
3037:and the
3027:xanthate
2960:triflate
2956:tosylate
2933:platinum
2849:cracking
2816:ketones
2790:epoxide
2699:alkenes
2503:alkenes
2490:alkanes
2480:Comment
2064:isoprene
2058:such as
2031:polymers
2007:such as
1908:′
1831:′
1666:epoxides
1643:peroxide
1621:to give
1496:catalyst
1380:to form
1378:ethylene
1361:ethylene
1319:−2596.6
1302:1-butyne
1296:−2716.8
1275:1-butene
1269:−2876.5
1235:−1938.7
1215:−2058.1
1192:−2219.2
1162:−1300.8
1139:−1410.8
1122:ethylene
1116:−1559.7
1082:Formula
1073:carbons
1056:molarity
1014:deshield
999:hydrogen
890:1-butene
848:propyne
800:ethylene
775:carbons
733:ethylene
689:entgegen
685:zusammen
589:prefixes
538:between
520:electron
494:(a.k.a.
476:notation
436:of 1.33
327:2-butene
323:1-butene
289:ethylene
224:Aromatic
199:ethylene
178:). When
97:(IUPAC)
82:–carbon
56:ethylene
9103:Alkenes
9057:Commons
9021:Alchemy
8537:Organic
8101:organic
7900:Selenol
7824:Sulfone
7777:Sulfide
7675:NONOate
7670:Nitroso
7660:Nitrite
7655:Nitrate
7645:Cyanate
7635:Nitrile
7620:Amidine
7615:Imidate
7585:Nitrene
7580:Hydrazo
7568:Enamine
7499:Acetoxy
7487:carboxy
7454:Benzoyl
7392:Epoxide
7375:Methoxy
7365:Alcohol
7319:Carbene
7253:Methine
6934:alcohol
6842:Heptene
6808:Pentene
6774:Propene
6750:Alkenes
6743:Alkenes
6648:Benzene
6622:Styrene
6499:-Cymene
6491:-Cymene
6483:-Cymene
6472:Cymenes
6363:-Xylene
6355:-Xylene
6347:-Xylene
6336:Xylenes
6317:Toluene
6250:Azulene
5849:Heptyne
5839:Pentyne
5829:Propyne
5794:Alkynes
5719:Heptene
5709:Pentene
5699:Propene
5665:Alkenes
5587:Sterane
5553:Decalin
5541:Housane
5355:Heptane
5345:Pentane
5335:Propane
5325:Methane
5295:Alkanes
5197:8199371
4837:: 240.
4807:5500392
4597:ups.edu
4517:3295281
4494:Bibcode
4323:(ed.).
4226:olefins
4192:alkenes
4041:group.
4024:isomers
3958:isomers
3738:is the
3559:styrene
3445:In the
3373:ammonia
3349:alkynes
3320:CH=CHCH
3221:sulfone
3154:. The
3142:) to a
3122:in the
3113:Zaitsev
3067:glycols
2995:ethanol
2904:entropy
2861:zeolite
2857:naphtha
2561:amines
2477:Product
2076:allylic
1806:vicinal
1797:and/or
1795:ketones
1639:allylic
1504:alcohol
1345:allylic
1332:alkanes
1309:CH≡C-CH
1221:propyne
1198:propene
1171:propane
1049:combust
1026:vicinal
932:pentane
907:−125.7
862:−102.7
842:propane
786:Alkyne
783:Alkene
780:Alkane
721:alkanes
490:)-but-2
418:pi bond
400:Bonding
243:C=C=C=C
233:allenes
184:isomers
116:polyene
103:acyclic
74:, is a
18:Olefins
9069:Portal
8215:UV-Vis
8000:Iodide
7920:Selone
7764:Sulfur
7473:Ketone
7466:Ketene
7444:Acetyl
7399:Peroxy
7370:Alkoxy
7360:Acetal
7341:oxygen
7330:carbon
7314:Alkyne
7307:Benzyl
7302:Phenyl
7285:Allene
7280:Crotyl
7260:Alkene
7248:Bridge
7236:Pentyl
7221:Propyl
7211:Methyl
6943:alkyne
6893:Decene
6876:Nonene
6859:Octene
6825:Hexene
6791:Butene
6757:Ethene
6517:Durene
6436:Cumene
6285:Pyrene
6201:Acenes
6083:Dienes
5864:Decyne
5859:Nonyne
5854:Octyne
5844:Hexyne
5834:Butyne
5824:Ethyne
5734:Decene
5729:Nonene
5724:Octene
5714:Hexene
5704:Butene
5694:Ethene
5592:Cubane
5370:Decane
5365:Nonane
5360:Octane
5350:Hexane
5340:Butane
5330:Ethane
5231:
5204:
5194:
5151:
5120:
5083:
5050:
4963:
4930:
4895:29 May
4867:
4814:
4804:
4761:
4679:
4576:27 May
4550:27 May
4524:
4514:
4463:
4432:
4394:
4359:
4278:
4162:
3992:German
3956:trans-
3793:-ene".
3758:ethENe
3743:ethANe
3740:alkane
3390:- and
3369:sodium
3223:. The
3218:phenyl
3140:ketone
3074:amines
3053:and a
3049:). A
2929:cobalt
2925:nickel
2673:diols
2656:diols
2639:ester
2626:ester
2056:dienes
1752:+ SMe
1677:+ RCO
1673:RCH=CH
1619:dienes
1446:CBr−CH
1382:ethane
1286:=CH−CH
1244:butane
1099:ethane
952:−90.0
949:−165.2
904:−185.3
887:butane
876:−23.2
831:−84.7
817:−80.7
797:ethane
741:butene
739:, and
707:- and
612:trans-
596:carbon
416:and a
382:chiral
329:, and
263:carbon
238:allene
176:alkane
129:cyclic
80:carbon
72:olefin
68:alkene
36:alkyne
32:alkane
8242:MALDI
8210:Raman
8032:Other
7869:Boron
7839:Thial
7772:Thiol
7665:Nitro
7630:Imide
7610:Amide
7595:Oxime
7590:Imine
7563:Amine
7511:Ester
7478:Ynone
7382:Ether
7353:R-O-R
7328:Only
7270:Allyl
7265:Vinyl
7231:Butyl
7216:Ethyl
7206:Alkyl
6941:from
6932:from
6923:from
6679:Other
6664:trans
6641:Other
6580:Other
6536:Other
6429:Other
6372:Other
6243:Other
6167:Enyne
6135:Other
5631:Other
4732:6 May
4706:5 May
4656:5 May
4631:5 May
4602:5 May
4276:S2CID
4216:IUPAC
4182:IUPAC
4039:allyl
3980:trans
3968:trans
3941:trans
3933:trans
3929:Latin
3919:trans
3906:trans
3676:taxol
3610:is a
3472:Name
3420:above
3392:trans
3377:trans
3328:=CHCH
3316:+ CH
3257:(the
3204:- or
3088:(the
3061:) or
2931:, or
2005:diene
1772:→ R
1719:→ C
1685:+ RCO
1232:C≡CH
1209:CH=CH
1079:Type
993:In H
966:40.1
749:trans
604:trans
587:,the
516:VSEPR
510:Shape
504:trans
465:trans
440:(133
376:trans
229:C=C=C
166:with
70:, or
66:, an
8996:Atom
8264:HPLC
7954:Halo
7439:Acyl
7339:and
7297:Aryl
6560:tert
6192:PAHs
5229:ISBN
5202:PMID
5149:ISBN
5118:PMID
5081:ISBN
5048:ISBN
4961:ISBN
4928:ISBN
4897:2019
4865:ISBN
4812:PMID
4759:ISBN
4734:2019
4708:2019
4677:ISBN
4658:2019
4633:2019
4604:2019
4578:2019
4552:2019
4522:PMID
4461:ISBN
4430:PMID
4392:ISBN
4357:ISBN
4329:The
4160:ISBN
4020:and
3978:and
3954:and
3952:cis-
3725:-en-
3721:-an-
3693:, a
3670:, a
3651:, a
3632:, a
3478:Use
3449:, a
3109:less
3017:+ H
3013:C=CH
2972:anti
2599:and
2449:PtCl
2411:The
2062:and
2041:and
1809:diol
1787:KMnO
1711:+ 1/
1581:C−CH
1570:C=CH
1529:C-CH
1514:C=CH
1438:+ Br
1434:C=CH
1404:C−CH
1392:C=CH
1384:is:
963:29.9
946:−130
929:Name
921:8.0
918:−6.2
915:−0.5
901:−138
884:Name
859:−185
856:−190
839:Name
828:−104
814:−169
811:−183
794:Name
608:cis-
602:and
577:and
492:-ene
308:only
291:only
93:The
9006:Ion
8237:ICP
8220:NMR
7605:Azo
6552:sec
5809:− 2
5310:+ 2
5225:189
5192:PMC
5182:doi
5145:366
5110:doi
5073:doi
5040:doi
5017:doi
4990:doi
4953:doi
4924:309
4839:doi
4802:PMC
4792:doi
4512:PMC
4502:doi
4490:109
4453:doi
4422:doi
4303:doi
4266:doi
4230:doi
4228:".
4196:doi
4194:".
4156:279
3976:cis
3964:cis
3937:cis
3925:cis
3915:cis
3902:Cis
3751:=CH
3733:-CH
3550:PVC
3388:cis
3357:cis
3312:=CH
3265:).
3179:P=O
3138:or
3094:syn
3031:syn
2958:or
2667:cis
2570:C−C
2566:N−H
2435:In
1994:or
1743:):
1738:SMe
1545:HBr
1518:+ H
1494:as
1396:+ H
1010:ppm
995:NMR
873:−47
870:−42
825:−89
600:cis
583:In
496:cis
463:or
461:cis
430:mol
372:cis
146:of
62:In
34:or
9099::
8736:/
8732:/
8584:/
8259:GC
8232:EI
8205:IR
7337:,
7332:,
6903:20
6899:10
6886:18
6869:16
6852:14
6835:12
6818:10
5227:.
5200:.
5190:.
5178:22
5176:.
5172:.
5147:.
5116:.
5106:49
5104:.
5079:.
5046:.
5013:38
5011:.
4986:78
4984:.
4959:.
4926:.
4888:.
4851:^
4835:73
4833:.
4810:.
4800:.
4788:93
4786:.
4782:.
4725:.
4699:.
4649:.
4623:.
4612:^
4595:.
4569:.
4543:.
4520:.
4510:.
4500:.
4488:.
4484:.
4459:.
4428:.
4418:47
4382:.
4370:^
4327:.
4299:84
4297:.
4274:.
4262:67
4260:.
4254:.
4240:^
4218:,
4206:^
4184:,
4174:^
4158:.
4132:^
3889:.
3872:CH
3868:CH
3866:C–
3856:C)
3847:(H
3835:CH
3823:CH
3821:C–
3811:C)
3802:(H
3760:.
3747:CH
3729:CH
3434:.
3308:CH
3250:.
3175:Ph
3162:.
3005:CH
3001:CH
2951:.
2935:.
2927:,
2906:.
2616:.
2531:)
2461:)]
2453:(C
2375:CH
2337:CH
2306:CH
2293:CH
2260:CH
2232:CH
2214:CH
2176:CH
2159:CH
2126:CH
2106::
2090:.
2015::
1990:,
1975:.
1938:OH
1919:OH
1912:CH
1844:CR
1835:CH
1668::
1645::
1585:Br
1533:OH
1522:O→
1450:Br
1442:→H
1423:.
1400:→H
1313:CH
1290:CH
1282:CH
1263:CH
1259:CH
1255:CH
1251:CH
1240:4
1228:CH
1205:CH
1186:CH
1182:CH
1178:CH
1167:3
1095:2
1030:Hz
983:cm
979:IR
960:36
926:5
881:4
836:3
791:2
767:°C
735:,
701:E-
697:Z-
442:pm
426:kJ
362:12
342:10
325:,
304::
287::
253:.
245:,
123:,
109:,
90:.
8970:"
8966:"
8137:e
8130:t
8123:v
7178:e
7171:t
7164:v
6906:)
6901:H
6897:C
6895:(
6889:)
6884:H
6882:9
6880:C
6878:(
6872:)
6867:H
6865:8
6863:C
6861:(
6855:)
6850:H
6848:7
6846:C
6844:(
6838:)
6833:H
6831:6
6829:C
6827:(
6821:)
6816:H
6814:5
6812:C
6810:(
6804:)
6801:8
6799:H
6797:4
6795:C
6793:(
6787:)
6784:6
6782:H
6780:3
6778:C
6776:(
6770:)
6767:4
6765:H
6763:2
6761:C
6759:(
6735:e
6728:t
6721:v
6544:n
6497:p
6489:m
6481:o
6442:n
6361:p
6353:m
6345:o
5807:n
5805:2
5803:H
5800:n
5797:C
5678:n
5676:2
5674:H
5671:n
5668:C
5308:n
5306:2
5304:H
5301:n
5298:C
5268:e
5261:t
5254:v
5237:.
5208:.
5184::
5157:.
5124:.
5112::
5089:.
5075::
5056:.
5042::
5023:.
5019::
4996:.
4992::
4969:.
4955::
4936:.
4899:.
4873:.
4845:.
4841::
4818:.
4794::
4736:.
4710:.
4685:.
4660:.
4635:.
4606:.
4580:.
4554:.
4528:.
4504::
4496::
4469:.
4455::
4436:.
4424::
4400:.
4309:.
4305::
4282:.
4268::
4232::
4198::
4168:.
4101:.
4022:Z
4018:E
4007:Z
3999:Z
3988:E
3966:–
3917:–
3904:–
3877:2
3870:=
3861:3
3852:3
3840:3
3833:–
3828:2
3816:3
3807:3
3791:k
3775:k
3753:2
3749:2
3735:3
3731:3
3701:.
3655:.
3636:.
3330:3
3326:2
3322:3
3318:3
3314:2
3310:2
3210:E
3206:Z
3202:E
3177:3
3171:3
3021:O
3019:2
3015:2
3011:2
3007:2
3003:3
2976:Z
2914:2
2873:n
2614:O
2612:2
2610:H
2589:2
2587:H
2527:(
2459:4
2457:H
2455:2
2451:3
2379:2
2366:=
2362:C
2354:2
2349:)
2341:3
2333:(
2327:+
2310:2
2297:=
2285:C
2277:3
2272:)
2264:3
2256:(
2236:2
2227:=
2218:2
2207:+
2193:2
2188:)
2180:3
2172:(
2167:C
2163:=
2151:C
2143:3
2138:)
2130:3
2122:(
1950:2
1946:R
1941:)
1935:(
1931:C
1922:)
1916:(
1905:R
1898:O
1890:2
1886:H
1882:+
1874:2
1870:O
1864:2
1861:1
1856:+
1848:2
1839:=
1828:R
1789:4
1778:2
1774:2
1770:3
1766:2
1764:R
1758:2
1754:2
1750:3
1740:2
1727:O
1725:4
1723:H
1721:2
1717:2
1715:O
1713:2
1709:4
1707:H
1705:2
1703:C
1689:H
1687:2
1683:2
1679:3
1675:2
1583:2
1579:3
1577:H
1572:2
1568:2
1566:H
1531:2
1527:3
1525:H
1520:2
1516:2
1512:2
1510:H
1448:2
1444:2
1440:2
1436:2
1432:2
1430:H
1406:3
1402:3
1398:2
1394:2
1390:2
1388:H
1373:2
1371:H
1315:3
1311:2
1292:3
1288:2
1284:2
1265:3
1261:2
1257:2
1253:3
1230:3
1211:2
1207:3
1188:3
1184:2
1180:3
1158:2
1156:H
1154:2
1152:C
1135:4
1133:H
1131:2
1129:C
1112:6
1110:H
1108:2
1106:C
1087:c
1085:H
1018:H
1005:H
1003:δ
709:Z
705:E
668:Z
666:(
652:E
650:(
563:S
559:S
555:S
500:E
488:Z
474:Z
472:–
470:E
438:Å
428:/
388:5
386:C
374:–
360:H
358:6
356:C
340:H
338:5
336:C
318:8
316:H
314:4
312:C
301:6
299:H
297:3
295:C
284:4
282:H
280:2
278:C
227:(
209:4
207:H
205:2
203:C
201:(
180:n
168:n
162:n
160:2
158:H
155:n
152:C
45:.
38:.
20:)
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
