2210:
457:
997:
7047:
7071:
321:
7083:
7059:
1088:
310:
540:. Each p orbital on one atom overlaps one on the other atom, forming two pi bonds, giving a total of three bonds. The remaining sp orbital on each atom can form a sigma bond to another atom, for example to hydrogen atoms in the parent acetylene. The two sp orbitals project on opposite sides of the carbon atom.
183:
172:
665:
immediately preceding the "-yne" suffix, or 'locants' in the case of multiple triple bonds. Locants are chosen so that the numbers are low as possible. "-yne" is also used as a suffix to name substituent groups that are triply bound to the parent compound.
1200:
1094:
The largest scale application of this technology is the conversion of acetylene to ethylene in refineries (the steam cracking of alkanes yields a few percent acetylene, which is selectively hydrogenated in the presence of a
625:. When no superior functional groups are present, the parent chain must include the triple bond even if it is not the longest possible carbon chain in the molecule. Ethyne is commonly called by its trivial name acetylene.
2478:
617:, alkynes are named with the Greek prefix system without any additional letters. Examples include ethyne or octyne. In parent chains with four or more carbons, it is necessary to say where the triple bond is located. For
305:{\displaystyle {\ce {H-C#C}}{-}{\ce {\overset {\displaystyle {H} \atop |}{\underset {| \atop \displaystyle {H}}{C}}}}{-}{\ce {\overset {\displaystyle {H} \atop |}{\underset {| \atop \displaystyle {H}}{C}}}}{\ce {-H}}}
2084:
1738:
1409:
3197:
Chemistry and biology of naturally-occurring acetylenes and related compounds (NOARC): proceedings of a
Conference on the Chemistry and Biology of Naturally-Occurring Acetylenes and Related Compounds (NOARC)
1292:
3060:
Peter Pässler; Werner Hefner; Klaus Buckl; Helmut
Meinass; Andreas Meiswinkel; Hans-Jßrgen Wernicke; Gßnter Ebersberg; Richard Mßller; Jßrgen Bässler; Hartmut Behringer; Dieter Mayer (2008). "Acetylene".
938:
2802:
Gräfje, Heinz; KĂśrnig, Wolfgang; Weitz, Hans-Martin; ReiĂ, Wolfgang; Steffan, Guido; Diehl, Herbert; Bosche, Horst; Schneider, Kurt; Kieczka, Heinz (2000). "Butanediols, Butenediol, and
Butynediol".
2195:
653:
in the form of triple bonds may be denoted by substitutive nomenclature with the same methods used with alkynes (i.e. the name of the corresponding saturated compound is modified by replacing the "
87:
1884:
2291:
1562:
693:
by having the triple bond in different positions or having some of the carbon atoms be substituents rather than part of the parent chain. Other non-alkyne structural isomers are also possible.
2517:. Terminal alkynes, including acetylene itself, react with water to give aldehydes. The transformation typically requires metal catalysts to give this anti-Markovnikov addition result.
1567:
2539:, a subset of this class of natural products, have been isolated from a wide variety of plant species, cultures of higher fungi, bacteria, marine sponges, and corals. Some acids like
76:
2610:, are some of the most aggressive antitumor drugs known, so much so that the ene-diyne subunit is sometimes referred to as a "warhead". Ene-diynes undergo rearrangement via the
2105:
Terminal alkynes are readily converted to many derivatives, e.g. by coupling reactions and condensations. Via the condensation with formaldehyde and acetylene is produced
597:
values of around 40 and 50, respectively. The acidic hydrogen on terminal alkynes can be replaced by a variety of groups resulting in halo-, silyl-, and alkoxoalkynes. The
810:
4030:
3612:
3551:
4020:
806:
802:
798:
1069:
than alkenes, alkynes characteristically undergo reactions that show that they are "doubly unsaturated". Alkynes are capable of adding two equivalents of
4015:
3536:
980:
770:
2535:
species in 1826. In the nearly two centuries that have followed, well over a thousand naturally occurring acetylenes have been discovered and reported.
4002:
3523:
5049:
3594:
3063:
2973:
2804:
1004:
2360:
6142:
4042:
3563:
4088:
4103:
4098:
4083:
3668:
2338:) reacts with terminal alkynes signaled by formation of a white precipitate of the silver acetylide. This reactivity is the basis of alkyne
1076:, whereas an alkene adds only one equivalent. Depending on catalysts and conditions, alkynes add one or two equivalents of hydrogen. Partial
1125:
6243:
4172:
4141:
3920:
3910:
3795:
2543:
contain an alkyne group. Diynes and triynes, species with the linkage RCâĄCâCâĄCRⲠand RCâĄCâCâĄCâCâĄCRⲠrespectively, occur in certain plants (
6248:
5183:
4177:
4156:
4151:
3935:
3930:
3925:
3915:
3810:
3805:
3800:
3790:
3456:
1585:
790:
6102:
3006:
Fukuda, Y.; Utimoto, K. (1991). "Effective transformation of unactivated alkynes into ketones or acetals with a gold(III) catalyst".
2606:. Molecules called ene-diynes feature a ring containing an alkene ("ene") between two alkyne groups ("diyne"). These compounds, e.g.
673:
is inserted before it to state which atoms the triple bond is between. This suffix arose as a collapsed form of the end of the word "
621:, one can either write 3-octyne or oct-3-yne when the bond starts at the third carbon. The lowest number possible is given to the
6226:
6107:
404:
167:{\displaystyle {\ce {H-C#C}}{-}{\ce {\overset {\displaystyle {H} \atop |}{\underset {| \atop \displaystyle {H}}{C}}}}{\ce {-H}}}
6270:
3297:
2866:
A. Le Coq and A. Gorgues (1979). "Alkyness via Phase
Transfer-Catalyzed Dehydrohalogenatiion: Propiolaldehyde Diethyl Acetal".
844:
1972:
2758:
2115:
1322:
6282:
6221:
1206:
6135:
2513:
Alkynes form complexes with transition metals. Such complexes occur also in metal catalyzed reactions of alkynes such as
1762:
1066:
826:
Commercially, the dominant alkyne is acetylene itself, which is used as a fuel and a precursor to other compounds, e.g.,
650:
341:
2240:
5130:
3080:
2990:
2821:
1947:
1502:
5059:
4764:
3204:
2783:
2702:
2669:
1024:
516:
contributes 268 kJ/mol. and the second pi bond 202 kJ/mol. Bonding is usually discussed in the context of
2209:
1423:
7087:
5176:
5140:
4222:
2508:
2343:
6966:
6128:
3125:
Hintermann, Lukas; Labonne, AurĂŠlie (2007). "Catalytic
Hydration of Alkynes and Its Application in Synthesis".
2927:
2971:
Dreher, Eberhard-Ludwig; Torkelson, Theodore R.; Beutel, Klaus K. (2011). "Chlorethanes and
Chloroethylenes".
6409:
6163:
6006:
661:
is used when there are two triple bonds, and so on. The position of unsaturation is indicated by a numerical
2894:
33:
6686:
6173:
1477:
to form the aldehyde. This reaction was once a major industrial process but it has been displaced by the
423:
are 180°. By virtue of this bond angle, alkynes are rod-like. Correspondingly, cyclic alkynes are rare.
7063:
6612:
6583:
6563:
6516:
5579:
5169:
3290:
2217:
1910:. This general reaction has been extensively developed. Electrophilic alkynes are especially effective
6201:
5125:
1943:
1474:
548:
Internal alkynes feature carbon substituents on each acetylenic carbon. Symmetrical examples include
1453:. While this method has been abandoned in the West, it remains the main production method in China.
6956:
6872:
6511:
5616:
5120:
5054:
2529:, the first naturally occurring acetylenic compound, dehydromatricaria ester, was isolated from an
1899:
1016:
520:, which recognizes the triple bond as arising from overlap of s and p orbitals. In the language of
517:
6894:
6805:
6768:
6652:
6578:
6399:
6382:
6325:
6089:
3682:
3160:
Annabelle L. K. Shi Shun; Rik R. Tykwinski (2006). "Synthesis of
Naturally Occurring Polyynes".
6812:
6800:
6691:
6556:
6330:
6196:
5989:
4632:
3446:
2090:
6961:
6858:
6843:
6773:
6696:
6528:
6478:
6387:
6312:
6211:
6096:
5984:
4757:
4693:
4627:
3283:
642:
614:
533:
6951:
6906:
6681:
6501:
6431:
6188:
6168:
6065:
5510:
5135:
5115:
5013:
4211:
4010:
3233:
2598:. A carbonâcarbon triple bond is also present in marketed drugs such as the antiretroviral
2514:
2201:
1927:
677:". The final "-e" disappears if it is followed by another suffix that starts with a vowel.
576:
2647:
8:
6974:
6928:
6853:
6826:
6724:
6706:
6659:
6597:
6493:
6473:
6342:
6337:
6238:
5371:
5040:
4539:
2611:
2089:
Oxidative cleavage of alkynes proceeds via cycloaddition to metal oxides. Most famously,
1907:
1482:
1107:
is widely recommended to avoid formation of the alkane, for example in the conversion of
960:
521:
356:
3237:
7051:
7017:
6879:
6848:
6729:
6671:
6369:
6352:
6347:
6302:
6265:
6255:
6216:
5150:
5110:
5090:
4726:
4683:
3541:
3531:
3142:
2773:
2526:
2484:
1462:
1431:
646:
2216:
This reactivity exploits the fact that terminal alkynes are weak acids, whose typical
7070:
7032:
6997:
6980:
6918:
6836:
6831:
6759:
6744:
6714:
6635:
6602:
6573:
6568:
6543:
6533:
6453:
6441:
6320:
6233:
6055:
6025:
5783:
5405:
5100:
4617:
4589:
4432:
4192:
4187:
4025:
3546:
3261:
3256:
3221:
3200:
3177:
3098:
3076:
3040:
2986:
2949:
2923:
2900:
2839:
2817:
2779:
2754:
2698:
2665:
2614:, generating highly reactive radical intermediates that attack DNA within the tumor.
2531:
2351:
2339:
1959:
1446:
1438:
1054:
831:
690:
638:
549:
364:
333:
3146:
1926:
compound. Other specialized cycloadditions include multicomponent reactions such as
1053:, who in 1955 wrote the first book describing their versatility as intermediates in
590:
values of around 25. They are far more acidic than alkenes and alkanes, which have p
7109:
7075:
6992:
6647:
6506:
6483:
6436:
6377:
5760:
5254:
5192:
4750:
4581:
3251:
3241:
3169:
3134:
3107:
3068:
3059:
3016:
2978:
2875:
2848:
2809:
2731:
2690:
2563:
2308:
1955:
1104:
1046:
1042:
944:
360:
3072:
963:. The reaction provides a means to generate alkynes from alkenes, which are first
6933:
6889:
6884:
6778:
6754:
6588:
6551:
6404:
6394:
6277:
5979:
5738:
5733:
5716:
5699:
5500:
5249:
5145:
5018:
4731:
4688:
4597:
4471:
3436:
3426:
2347:
2323:
2094:
1939:
1489:
1108:
968:
572:
3035:
3033:
2944:
1954:. Cycloaddition processes involving alkynes are often catalyzed by metals, e.g.
6817:
6795:
6790:
6785:
6740:
6736:
6719:
6676:
6607:
6468:
6463:
6448:
6260:
6178:
6050:
6045:
5921:
5916:
5911:
5704:
5671:
5455:
5437:
5427:
4662:
4657:
4622:
4573:
4479:
3451:
3441:
2304:
2106:
1919:
1478:
1450:
2591:. 1-Phenylhepta-1,3,5-triyne is illustrative of a naturally occurring triyne.
2473:{\displaystyle {\ce {2R-\!{\equiv }\!-H->R-\!{\equiv }\!-\!{\equiv }\!-R}}}
575:(propyne using IUPAC nomenclature). They are often prepared by alkylation of
456:
7103:
7022:
6911:
6867:
6592:
6426:
6421:
6414:
6292:
6070:
6018:
5949:
5835:
5825:
5820:
5810:
5805:
5755:
5750:
5666:
5661:
5651:
5505:
5460:
5422:
5410:
5381:
5259:
5095:
5080:
4339:
4146:
4136:
3632:
3111:
3008:
2982:
2879:
2852:
2813:
2735:
2607:
2580:
2551:
2496:
1895:
1470:
1077:
1050:
1008:
525:
505:
3246:
6899:
6749:
6664:
6640:
6630:
6622:
6523:
6458:
6357:
6206:
6001:
5888:
5883:
5860:
5611:
5450:
5376:
5313:
5308:
5286:
5242:
5227:
5217:
5105:
5085:
5044:
4445:
4409:
4305:
4078:
4068:
3977:
3967:
3957:
3498:
3488:
3478:
3219:
3181:
3173:
3034:
Mizushima, E.; Cui, D.-M.; Nath, D. C. D.; Hayashi, T.; Tanaka, M. (2005).
2904:
2595:
2545:
2540:
2488:
2297:
1493:
1466:
1437:
Addition of hydrogen halides has long been of interest. In the presence of
1116:
1030:
984:
956:
3265:
3138:
6297:
6060:
6013:
5974:
5855:
5743:
5728:
5723:
5711:
5276:
5271:
5237:
5232:
5222:
5200:
4493:
4450:
4423:
4357:
4320:
4239:
4093:
4073:
4060:
3992:
3987:
3982:
3972:
3962:
3949:
3780:
3513:
3508:
3503:
3493:
3483:
3470:
3306:
2628:
2603:
976:
964:
835:
622:
501:
408:
352:
344:
6120:
3159:
3020:
2836:
2687:
March's
Advanced Organic Chemistry: Reactions, Mechanisms, and Structure
996:
6923:
5969:
5960:
5840:
5795:
5691:
5656:
5646:
5586:
5522:
5445:
5393:
5031:
4552:
4440:
4244:
4131:
4121:
4050:
3785:
3607:
3602:
3577:
3431:
3421:
2694:
2588:
2584:
2568:
1911:
1753:
1195:{\displaystyle {\ce {RC#CR' + H2 ->}}{\text{ cis-}}{\ce {RCH=CR'H}}}
537:
509:
420:
6985:
6287:
6152:
5936:
5850:
5815:
5800:
5788:
5631:
5606:
5415:
5075:
5035:
4869:
4864:
4784:
4557:
4295:
4264:
4254:
4249:
4126:
3854:
3642:
3637:
3416:
2599:
2576:
2397:
1096:
766:
762:
708:
674:
602:
598:
580:
557:
529:
428:
325:
80:
5161:
3220:
S. Walker; R. Landovitz; W.D. Ding; G.A. Ellestad; D. Kahne (1992).
2837:
Kenneth N. Campbell, Barbara K. Campbell (1950). "Phenylacetylene".
2404:
1733:{\displaystyle {\ce {HC#C(CH2)5C#CH + 2H2O -> CH3CO(CH2)5COCH3}}}
1426:
of alkynes gives vinylic boranes which oxidize to the corresponding
1312:
Alkynes characteristically are capable of adding two equivalents of
7007:
5944:
5898:
5865:
5561:
5467:
5341:
5296:
5281:
4995:
4990:
4949:
4944:
4903:
4898:
4893:
4840:
4835:
4721:
4716:
4526:
4518:
4510:
4390:
4382:
4374:
4325:
4310:
4300:
4290:
4285:
4259:
4182:
3894:
3874:
3724:
3652:
3647:
3627:
2594:
Alkynes occur in some pharmaceuticals, including the contraceptive
2572:
2492:
1951:
1931:
1923:
1915:
1442:
1427:
1012:
827:
794:
786:
746:
742:
553:
477:
384:. Alkynes are traditionally known as acetylenes, although the name
320:
314:
7027:
5906:
5830:
5681:
5676:
5641:
5626:
5621:
5591:
5574:
5398:
5325:
5291:
4910:
4847:
4801:
4678:
4652:
4502:
4347:
4280:
3879:
3869:
3859:
3749:
3739:
3729:
3617:
3583:
3571:
3385:
3375:
3365:
3355:
2774:
The
Commission on the Nomenclature of Organic Chemistry (1971) .
2536:
2231:
2227:
1963:
1749:
1313:
1112:
1080:, stopping after the addition of only one equivalent to give the
988:
972:
725:
658:
513:
424:
176:
3222:"Cleavage behavior of calicheamicin gamma 1 and calicheamicin T"
5994:
5926:
5770:
5479:
5472:
5366:
5347:
5336:
5266:
5026:
5022:
4973:
4956:
4927:
4876:
4818:
4547:
4466:
4366:
4315:
3889:
3884:
3864:
3764:
3759:
3754:
3744:
3734:
3695:
3622:
3400:
3395:
3390:
3380:
3370:
3360:
3325:
3275:
2557:
1935:
1100:
1081:
1020:
686:
670:
662:
618:
440:
400:
348:
24:
20:
2717:
5875:
5845:
5778:
5636:
5601:
5596:
5569:
5517:
5484:
5388:
5212:
4231:
4197:
4113:
1903:
1119:
of alkynes gives the alkene dihalides or alkyl tetrahalides:
830:. Hundreds of millions of kilograms are produced annually by
629:
3095:
1914:. The "cycloadduct" derived from the addition of alkynes to
1307:
950:
7002:
5303:
2623:
2204:, terminal alkynes are coupled with aryl or vinyl halides:
1422:
is general for silanes, boranes, and related hydrides. The
1084:, is usually more desirable since alkanes are less useful:
654:
633:
4742:
2314:
The reactions of alkynes with certain metal cations, e.g.
2100:
1087:
933:{\displaystyle {\ce {2 CH4 + 3/2 O2 -> HC#CH + 3 H2O}}}
601:
generated by deprotonation of terminal alkynes are called
536:. Overlap of an sp orbital from each atom forms one spâsp
488:, the strained cycloheptyne. Triple bonds are highlighted
484:, the naturally occurring 1-phenylhepta-1,3,5-triyne, and
7012:
3036:"Au(I)-Catalyzed hydratation of alkynes: 2,8-nonanedione"
2427:
2180:
2167:
2134:
2079:{\displaystyle {\ce {RC#CR + R'C#CR' <=> 2RC#CR'}}}
1872:
1846:
1793:
1726:
1713:
1700:
1679:
1660:
1629:
1616:
1579:
catalyzes hydration of 1,8-nonadiyne to 2,8-nonanedione:
1550:
1531:
1397:
1376:
1360:
1280:
1259:
1243:
1159:
923:
889:
863:
2945:"Palladium catalyst for partial reduction of acetylenes"
2892:
2865:
2190:{\displaystyle {\ce {2CH2O + HC#CH -> HOCH2CCCH2OH}}}
1404:{\displaystyle {\ce {RC#CR' + 2 Br2 -> RCBr2CR'Br2}}}
943:
Propyne, also industrially useful, is also prepared by
2036:
1817:
869:
3005:
2970:
2801:
2363:
2243:
2118:
1975:
1946:. Non-carbon reagents also undergo cyclization, e.g.
1765:
1588:
1505:
1481:. This reaction occurs in nature, the catalyst being
1325:
1287:{\displaystyle {\ce {RCH=CR'H + H2 -> RCH2CR'H2}}}
1209:
1128:
847:
277:
267:
235:
225:
186:
139:
129:
90:
36:
16:
Hydrocarbon compound containing one or more CâĄC bonds
1879:{\displaystyle {\ce {HC#C-CH3 <=> CH2=C=CH2}}}
1036:
637:
is used to denote the presence of a triple bond. In
2942:
2286:{\displaystyle {\ce {RC#CH + MX -> RC#CM + HX}}}
2472:
2285:
2189:
2078:
1878:
1732:
1557:{\displaystyle {\ce {PhC#CH + H2O -> PhCOCH3}}}
1556:
1403:
1286:
1194:
932:
304:
166:
70:
3124:
3096:K. StĂśckel and F. Sondheimer (1974). "Annulene".
2520:
2460:
2454:
2448:
2442:
2383:
2377:
2044:
2043:
2026:
2025:
1825:
1824:
1807:
1806:
427:cannot be isolated. The CâĄC bond distance of 118
407:. Like other hydrocarbons, alkynes are generally
7101:
2899:. London: Butterworths Scientific Publications.
2587:. These compounds are highly bioactive, e.g. as
543:
3324:
1934:compounds and the -cycloaddition of an alkyne,
1889:
359:alkynes with only one triple bond and no other
3064:Ullmann's Encyclopedia of Industrial Chemistry
2974:Ullmann's Encyclopedia of Industrial Chemistry
2917:
2805:Ullmann's Encyclopedia of Industrial Chemistry
6136:
5177:
4758:
3291:
1748:Terminal alkyl alkynes exhibit tautomerism.
2226:values around 25 place them between that of
1086:
556:. They may also be asymmetrical, such as in
451:) or the CâC bond in alkanes (153 pm).
3194:
439:) is much shorter than the C=C distance in
6143:
6129:
5184:
5170:
4765:
4751:
3298:
3284:
2684:
2659:
2322:also gives acetylides. Thus, few drops of
979:followed by treatment of the resulting of
967:and then dehydrohalogenated. For example,
6150:
5050:FritschâButtenbergâWiechell rearrangement
3255:
3245:
3053:
2964:
2896:Acetylenic compounds in organic synthesis
2797:
2795:
2753:(2nd ed.). McGraw-Hill. p. 57.
2368:
2123:
2058:
1649:
1469:. The reaction proceeds by formation of
1349:
1308:Addition of halogens and related reagents
1103:catalyst). For more complex alkynes, the
1005:FritschâButtenbergâWiechell rearrangement
951:Dehydrohalogenation and related reactions
912:
852:
524:, the carbon atoms in an alkyne bond are
2718:K. N. Campbell, B. K. Campbell (1950). "
2685:Smith, Michael B.; March, Jerry (2006).
1033:are susceptible to dehydrohalogenation.
455:
414:
319:
2101:Reactions specific for terminal alkynes
2019:
1800:
1304:to internal alkynes gives cis-alkenes.
955:Alkynes are prepared from 1,1- and 1,2-
680:
512:contributes 369 kJ/mol, the first
71:{\displaystyle {\ce {H-C#C}}{\ce {-H}}}
7102:
2922:. Great Britain: Collins. p. 82.
2792:
2778:(3rd ed.). London: Butterworths.
2664:. Vol. 1. John Wiley & Sons.
6124:
5191:
5165:
4746:
3279:
2748:
7058:
2920:Modern Organic Chemistry for A-level
2491:in general, terminal alkynes add to
7082:
2742:
367:with the general chemical formula
13:
5131:Azide-alkyne Huisgen cycloaddition
2502:
1948:azide alkyne Huisgen cycloaddition
1297:The addition of one equivalent of
563:Terminal alkynes have the formula
528:: they each have two unhybridized
276:
261:
234:
219:
138:
123:
14:
7121:
2893:Raphael, Ralph Alexander (1955).
2776:Nomenclature of Organic Chemistry
1962:, which allows the scrambling of
1037:Reactions, including applications
608:
583:itself, are mildly acidic, with p
7081:
7069:
7057:
7046:
7045:
3305:
2208:
1060:
995:
615:systematic chemical nomenclature
3213:
3188:
3153:
3118:
3089:
3027:
2999:
2936:
2911:
2886:
2509:Transition metal alkyne complex
1011:. Alkynes can be prepared from
2943:H. Lindlar; R. Dubuis (1973).
2918:Rosser & Williams (1977).
2859:
2830:
2767:
2711:
2678:
2653:
2641:
2521:Alkynes in nature and medicine
2417:
2411:
2262:
2154:
2093:converts alkynes to a pair of
2046:
2021:
1827:
1802:
1743:
1703:
1687:
1666:
1619:
1603:
1537:
1363:
1246:
1162:
1045:, alkynes participate in many
892:
285:
263:
243:
221:
147:
125:
1:
6410:Interface and colloid science
6164:Glossary of chemical formulae
5060:SeyferthâGilbert homologation
3073:10.1002/14356007.a01_097.pub3
2751:Organic Chemistry Demystified
2662:The CarbonâCarbon Triple Bond
2634:
2575:families). Some examples are
1025:SeyferthâGilbert homologation
544:Terminal and internal alkynes
468:, two depictions of propyne,
1890:Cycloadditions and oxidation
1456:
1049:. Such use was pioneered by
1007:, alkynes are prepared from
816:
685:Alkynes having four or more
388:also refers specifically to
7:
6687:Bioorganometallic chemistry
6174:List of inorganic compounds
5141:CadiotâChodkiewicz coupling
4772:
2617:
2344:CadiotâChodkiewicz coupling
2324:diamminesilver(I) hydroxide
1752:exists in equilibrium with
821:
669:Sometimes a number between
641:, the suffix often follows
10:
7126:
6613:Dynamic covalent chemistry
6584:Enantioselective synthesis
6564:Physical organic chemistry
6517:Organolanthanide chemistry
2959:, vol. 5, p. 880
2506:
1434:the substrate is a thiol.
18:
7041:
6944:
6705:
6621:
6542:
6492:
6368:
6311:
6202:Electroanalytical methods
6187:
6159:
6079:
6038:
5958:
5935:
5897:
5874:
5769:
5690:
5560:
5537:
5493:
5436:
5359:
5334:
5199:
5068:
5006:
4780:
4709:
4671:
4645:
4610:
4566:
4538:
4501:
4492:
4459:
4431:
4422:
4402:
4365:
4356:
4338:
4273:
4230:
4221:
4210:
4165:
4112:
4059:
4041:
4001:
3948:
3903:
3847:
3823:
3773:
3717:
3694:
3681:
3661:
3593:
3562:
3522:
3469:
3409:
3348:
3313:
2749:Bloch, Daniel R. (2012).
2650:. EncyclopĂŚdia Britannica
2567:and other members of the
1414:The addition of nonpolar
689:atoms can form different
579:. Terminal alkynes, like
6957:Nobel Prize in Chemistry
6873:Supramolecular chemistry
6512:Organometallic chemistry
3112:10.15227/orgsyn.054.0001
2983:10.1002/14356007.o06_o01
2880:10.15227/orgsyn.059.0010
2853:10.15227/orgsyn.030.0072
2814:10.1002/14356007.a04_455
2736:10.15227/orgsyn.030.0015
2660:Saul Patai, ed. (1978).
1894:Alkynes undergo diverse
518:molecular orbital theory
419:In acetylene, the HâCâĄC
347:containing at least one
19:Not to be confused with
6895:Combinatorial chemistry
6806:Food physical chemistry
6769:Environmental chemistry
6653:Bioorthogonal chemistry
6579:Retrosynthetic analysis
6400:Chemical thermodynamics
6383:Spectroelectrochemistry
6326:Computational chemistry
6090:chemical classification
3247:10.1073/pnas.89.10.4608
3199:. Amsterdam: Elsevier.
3067:. Weinheim: Wiley-VCH.
2977:. Weinheim: Wiley-VCH.
2808:. Weinheim: Wiley-VCH.
1316:and hydrogen halides.
657:" ending with "-yne").
6967:of element discoveries
6813:Agricultural chemistry
6801:Carbohydrate chemistry
6692:Bioinorganic chemistry
6557:Alkane stereochemistry
6502:Coordination chemistry
6331:Mathematical chemistry
6197:Instrumental chemistry
4633:1,3,5-Triheptylbenzene
3226:Proc Natl Acad Sci USA
3174:10.1002/anie.200502071
2495:compounds to give the
2474:
2432:
2287:
2191:
2091:potassium permanganate
2080:
1880:
1734:
1558:
1405:
1288:
1196:
1091:
1019:and from aldehydes or
971:can be generated from
934:
504:is very strong with a
495:
460:Illustrative alkynes:
329:
328:), the simplest alkyne
324:A 3D model of ethyne (
306:
168:
72:
6962:Timeline of chemistry
6859:Post-mortem chemistry
6844:Clandestine chemistry
6774:Atmospheric chemistry
6697:Biophysical chemistry
6529:Solid-state chemistry
6479:Equilibrium chemistry
6388:Photoelectrochemistry
6097:chemical nomenclature
5126:PausonâKhand reaction
4628:1,3,5-Triethylbenzene
3139:10.1055/s-2007-966002
2475:
2393:
2288:
2192:
2081:
1944:PausonâKhand reaction
1881:
1735:
1559:
1406:
1289:
1197:
1090:
1041:Featuring a reactive
935:
811:3,3-dimethyl-1-butyne
459:
415:Structure and bonding
323:
307:
169:
73:
6952:History of chemistry
6907:Chemical engineering
6682:Bioorganic chemistry
6432:Structural chemistry
6169:List of biomolecules
5136:Sonogashira coupling
5121:DielsâAlder reaction
5116:Alkyne trimerisation
5055:CoreyâFuchs reaction
4031:Isopropylcyclohexene
3613:Perhydrophenanthrene
3552:Isopropylcyclohexane
3195:Lam, Jørgen (1988).
3162:Angew. Chem. Int. Ed
2515:alkyne trimerization
2361:
2241:
2202:Sonogashira reaction
2116:
1973:
1928:alkyne trimerisation
1900:DielsâAlder reaction
1763:
1586:
1503:
1323:
1207:
1126:
1017:CoreyâFuchs reaction
845:
681:Structural isomerism
577:monosodium acetylide
399:, known formally as
184:
88:
34:
6975:The central science
6929:Ceramic engineering
6854:Forensic toxicology
6827:Chemistry education
6725:Radiation chemistry
6707:Interdisciplinarity
6660:Medicinal chemistry
6598:Fullerene chemistry
6474:Microwave chemistry
6343:Molecular mechanics
6338:Molecular modelling
5553:not C, H or O)
5041:Dehydrohalogenation
4727:Alicyclic compounds
4540:Tetramethylbenzenes
3238:1992PNAS...89.4608W
3021:10.1021/jo00011a058
2612:Bergman cyclization
2602:and the antifungal
2431:
2429:
2403:
2182:
2169:
2136:
2032:
1908:1,4-cyclohexadienes
1874:
1848:
1813:
1795:
1728:
1715:
1702:
1681:
1662:
1631:
1618:
1552:
1533:
1483:acetylene hydratase
1465:of acetylene gives
1399:
1378:
1362:
1282:
1261:
1245:
1161:
961:dehydrohalogenation
925:
891:
865:
647:inorganic compounds
522:valence bond theory
508:of 839 kJ/mol. The
443:(132 pm, for C
7018:Chemical substance
6880:Chemical synthesis
6849:Forensic chemistry
6730:Actinide chemistry
6672:Clinical chemistry
6353:Molecular geometry
6348:Molecular dynamics
6303:Elemental analysis
6256:Separation process
5995:Hypervalent iodine
5151:Favorskii reaction
5111:Thiol-yne reaction
4684:Cyclopropenylidene
4021:Methylcyclopentene
4011:Methylcyclopropene
3542:Methylcyclopentane
3532:Methylcyclopropane
2722:-Butylacetylene".
2695:10.1002/0470084960
2527:Ferdinand Bohlmann
2485:Favorskii reaction
2470:
2409:
2340:coupling reactions
2283:
2187:
2170:
2157:
2124:
2076:
2051:
1876:
1862:
1836:
1832:
1783:
1730:
1716:
1690:
1685:
1669:
1650:
1606:
1601:
1554:
1540:
1521:
1463:hydration reaction
1432:thiol-yne reaction
1430:or ketone. In the
1401:
1387:
1366:
1350:
1284:
1270:
1249:
1233:
1192:
1149:
1092:
947:of hydrocarbons.
930:
913:
879:
878:
853:
807:3-methyl-1-pentyne
803:4-methyl-2-pentyne
799:4-methyl-1-pentyne
691:structural isomers
643:IUPAC nomenclature
628:In chemistry, the
534:sp hybrid orbitals
496:
405:IUPAC nomenclature
330:
302:
283:
275:
273:
241:
233:
231:
164:
145:
137:
135:
68:
7097:
7096:
7033:Quantum mechanics
6998:Chemical compound
6981:Chemical reaction
6919:Materials science
6837:General chemistry
6832:Amateur chemistry
6760:Photogeochemistry
6745:Stellar chemistry
6715:Nuclear chemistry
6636:Molecular biology
6603:Polymer chemistry
6574:Organic synthesis
6569:Organic reactions
6534:Ceramic chemistry
6524:Cluster chemistry
6454:Chemical kinetics
6442:Molecular physics
6321:Quantum chemistry
6234:Mass spectrometry
6118:
6117:
6056:Sulfenyl chloride
6034:
6033:
5533:
5532:
5352:(only C, H and O)
5193:Functional groups
5159:
5158:
5101:Hydrohalogenation
4740:
4739:
4705:
4704:
4641:
4640:
4618:Hexamethylbenzene
4606:
4605:
4488:
4487:
4433:Trimethylbenzenes
4418:
4417:
4334:
4333:
4206:
4205:
4193:Cyclododecatriene
4188:Cyclooctatetraene
4026:Methylcyclohexene
4016:Methylcyclobutene
4003:Alkylcycloalkenes
3944:
3943:
3819:
3818:
3677:
3676:
3547:Methylcyclohexane
3537:Methylcyclobutane
3524:Alkylcycloalkanes
3465:
3464:
3099:Organic Syntheses
3041:Organic Syntheses
2957:Collected Volumes
2950:Organic Syntheses
2868:Organic Syntheses
2840:Organic Syntheses
2760:978-0-07-176797-2
2724:Organic Syntheses
2468:
2436:
2416:
2408:
2401:
2391:
2371:
2352:Eglinton coupling
2281:
2275:
2267:
2261:
2255:
2247:
2185:
2173:
2160:
2153:
2145:
2139:
2127:
2070:
2061:
2053:
2010:
2001:
1994:
1987:
1979:
1960:alkyne metathesis
1865:
1856:
1839:
1834:
1786:
1777:
1769:
1719:
1693:
1684:
1672:
1665:
1653:
1642:
1634:
1609:
1600:
1592:
1543:
1536:
1524:
1517:
1509:
1447:hydrogen chloride
1439:mercuric chloride
1390:
1382:
1369:
1353:
1338:
1329:
1273:
1265:
1252:
1236:
1229:
1222:
1213:
1190:
1183:
1174:
1169:
1152:
1141:
1132:
1047:organic reactions
981:styrene dibromide
928:
916:
905:
897:
882:
877:
856:
832:partial oxidation
771:3-methyl-1-butyne
639:organic chemistry
550:diphenylacetylene
365:homologous series
361:functional groups
334:organic chemistry
300:
290:
289:
281:
274:
271:
260:
257:
248:
247:
239:
232:
229:
218:
215:
206:
198:
190:
162:
152:
151:
143:
136:
133:
122:
119:
110:
102:
94:
66:
56:
48:
40:
7117:
7085:
7084:
7073:
7061:
7060:
7049:
7048:
6993:Chemical element
6648:Chemical biology
6507:Magnetochemistry
6484:Mechanochemistry
6437:Chemical physics
6378:Electrochemistry
6283:Characterization
6145:
6138:
6131:
6122:
6121:
6085:
5990:Trifluoromethoxy
5558:
5557:
5554:
5357:
5356:
5353:
5206:
5186:
5179:
5172:
5163:
5162:
4986:
4969:
4940:
4923:
4889:
4860:
4831:
4814:
4797:
4767:
4760:
4753:
4744:
4743:
4697:-Propenylbenzene
4499:
4498:
4429:
4428:
4363:
4362:
4354:
4353:
4228:
4227:
4219:
4218:
3904:Branched alkynes
3845:
3844:
3774:Branched alkenes
3715:
3714:
3692:
3691:
3595:Polycycloalkanes
3580:(bicycloheptane)
3574:(bicyclopentane)
3410:Branched alkanes
3346:
3345:
3322:
3321:
3300:
3293:
3286:
3277:
3276:
3270:
3269:
3259:
3249:
3217:
3211:
3210:
3192:
3186:
3185:
3168:(7): 1034â1057.
3157:
3151:
3150:
3133:(8): 1121â1150.
3122:
3116:
3114:
3093:
3087:
3086:
3057:
3051:
3049:
3031:
3025:
3024:
3003:
2997:
2996:
2968:
2962:
2960:
2953:
2940:
2934:
2933:
2915:
2909:
2908:
2890:
2884:
2883:
2863:
2857:
2855:
2834:
2828:
2827:
2799:
2790:
2789:
2771:
2765:
2764:
2746:
2740:
2739:
2715:
2709:
2708:
2682:
2676:
2675:
2657:
2651:
2645:
2479:
2477:
2476:
2471:
2469:
2466:
2465:
2459:
2453:
2447:
2441:
2434:
2433:
2430:
2428:
2425:
2420:
2414:
2406:
2402:
2399:
2389:
2388:
2382:
2376:
2369:
2342:, including the
2337:
2321:
2317:
2292:
2290:
2289:
2284:
2282:
2279:
2273:
2272:
2265:
2259:
2253:
2252:
2245:
2212:
2196:
2194:
2193:
2188:
2186:
2183:
2181:
2178:
2171:
2168:
2165:
2158:
2151:
2150:
2143:
2137:
2135:
2132:
2125:
2095:carboxylic acids
2085:
2083:
2082:
2077:
2075:
2074:
2068:
2066:
2059:
2054:
2052:
2050:
2049:
2042:
2034:
2033:
2031:
2024:
2016:
2014:
2008:
2006:
1999:
1998:
1992:
1985:
1984:
1977:
1956:enyne metathesis
1885:
1883:
1882:
1877:
1875:
1873:
1870:
1863:
1861:
1854:
1853:
1847:
1844:
1837:
1835:
1833:
1831:
1830:
1823:
1815:
1814:
1812:
1805:
1797:
1794:
1791:
1784:
1782:
1775:
1774:
1767:
1739:
1737:
1736:
1731:
1729:
1727:
1724:
1717:
1714:
1711:
1706:
1701:
1698:
1691:
1682:
1680:
1677:
1670:
1663:
1661:
1658:
1651:
1640:
1639:
1632:
1630:
1627:
1622:
1617:
1614:
1607:
1598:
1597:
1590:
1577:
1563:
1561:
1560:
1555:
1553:
1551:
1548:
1541:
1534:
1532:
1529:
1522:
1515:
1514:
1507:
1445:, acetylene and
1421:
1417:
1410:
1408:
1407:
1402:
1400:
1398:
1395:
1388:
1386:
1380:
1377:
1374:
1367:
1361:
1358:
1351:
1342:
1336:
1334:
1327:
1303:
1293:
1291:
1290:
1285:
1283:
1281:
1278:
1271:
1269:
1263:
1260:
1257:
1250:
1244:
1241:
1234:
1227:
1226:
1220:
1218:
1211:
1201:
1199:
1198:
1193:
1191:
1188:
1187:
1181:
1179:
1172:
1170:
1167:
1165:
1160:
1157:
1150:
1145:
1139:
1137:
1130:
1105:Lindlar catalyst
1075:
1043:functional group
999:
945:thermal cracking
939:
937:
936:
931:
929:
926:
924:
921:
914:
903:
902:
895:
890:
887:
880:
870:
864:
861:
854:
784:
760:
740:
723:
706:
571:. An example is
570:
493:
398:
383:
311:
309:
308:
303:
301:
298:
297:
291:
288:
282:
279:
272:
269:
266:
258:
256:
254:
249:
246:
240:
237:
230:
227:
224:
216:
214:
212:
207:
204:
203:
196:
195:
188:
173:
171:
170:
165:
163:
160:
159:
153:
150:
144:
141:
134:
131:
128:
120:
118:
116:
111:
108:
107:
100:
99:
92:
77:
75:
74:
69:
67:
64:
63:
57:
54:
53:
46:
45:
38:
7125:
7124:
7120:
7119:
7118:
7116:
7115:
7114:
7100:
7099:
7098:
7093:
7037:
6940:
6934:Polymer science
6890:Click chemistry
6885:Green chemistry
6779:Ocean chemistry
6755:Biogeochemistry
6701:
6617:
6589:Total synthesis
6552:Stereochemistry
6538:
6488:
6405:Surface science
6395:Thermochemistry
6364:
6307:
6278:Crystallography
6183:
6155:
6149:
6119:
6114:
6083:
6075:
6030:
5985:Trichloromethyl
5980:Trifluoromethyl
5954:
5931:
5893:
5870:
5765:
5734:Phosphine oxide
5686:
5552:
5550:
5549:
5547:
5545:
5543:
5541:
5539:
5529:
5489:
5432:
5351:
5350:
5345:
5340:
5330:
5204:
5203:
5195:
5190:
5160:
5155:
5146:Glaser coupling
5064:
5019:Dehydrogenation
5002:
4985:
4981:
4977:
4968:
4964:
4960:
4939:
4935:
4931:
4922:
4918:
4914:
4888:
4884:
4880:
4859:
4855:
4851:
4830:
4826:
4822:
4813:
4809:
4805:
4796:
4792:
4788:
4776:
4771:
4741:
4736:
4732:Petroleum jelly
4701:
4689:Phenylacetylene
4667:
4637:
4602:
4598:Isobutylbenzene
4562:
4534:
4484:
4455:
4414:
4398:
4352:
4330:
4269:
4213:
4202:
4161:
4108:
4055:
4037:
3997:
3940:
3899:
3841:
3833:
3827:
3815:
3769:
3711:
3704:
3698:
3687:
3685:
3673:
3657:
3589:
3586:(bicyclodecane)
3558:
3518:
3461:
3427:3-Methylpentane
3405:
3342:
3334:
3328:
3317:
3315:
3309:
3304:
3274:
3273:
3232:(10): 4608â12.
3218:
3214:
3207:
3193:
3189:
3158:
3154:
3123:
3119:
3094:
3090:
3083:
3058:
3054:
3032:
3028:
3004:
3000:
2993:
2969:
2965:
2955:
2941:
2937:
2930:
2916:
2912:
2891:
2887:
2864:
2860:
2835:
2831:
2824:
2800:
2793:
2786:
2772:
2768:
2761:
2747:
2743:
2716:
2712:
2705:
2683:
2679:
2672:
2658:
2654:
2646:
2642:
2637:
2620:
2523:
2511:
2505:
2503:Metal complexes
2461:
2455:
2449:
2443:
2437:
2426:
2421:
2410:
2405:
2398:
2392:
2384:
2378:
2372:
2364:
2362:
2359:
2358:
2348:Glaser coupling
2335:
2331:
2327:
2319:
2315:
2301:
2268:
2248:
2244:
2242:
2239:
2238:
2224:
2179:
2174:
2166:
2161:
2146:
2133:
2128:
2119:
2117:
2114:
2113:
2103:
2067:
2062:
2045:
2038:
2037:
2035:
2027:
2020:
2018:
2017:
2015:
2007:
2002:
1991:
1980:
1976:
1974:
1971:
1970:
1940:carbon monoxide
1898:reactions. The
1892:
1871:
1866:
1857:
1849:
1845:
1840:
1826:
1819:
1818:
1816:
1808:
1801:
1799:
1798:
1796:
1792:
1787:
1778:
1770:
1766:
1764:
1761:
1760:
1746:
1725:
1720:
1712:
1707:
1699:
1694:
1686:
1678:
1673:
1659:
1654:
1635:
1628:
1623:
1615:
1610:
1602:
1593:
1589:
1587:
1584:
1583:
1576:
1572:
1568:
1549:
1544:
1530:
1525:
1510:
1506:
1504:
1501:
1500:
1490:phenylacetylene
1459:
1419:
1415:
1396:
1391:
1379:
1375:
1370:
1359:
1354:
1335:
1330:
1326:
1324:
1321:
1320:
1310:
1302:
1298:
1279:
1274:
1262:
1258:
1253:
1242:
1237:
1219:
1214:
1210:
1208:
1205:
1204:
1180:
1175:
1171:
1166:
1158:
1153:
1138:
1133:
1129:
1127:
1124:
1123:
1109:phenylacetylene
1074:
1070:
1063:
1039:
969:phenylacetylene
953:
922:
917:
898:
888:
883:
862:
857:
848:
846:
843:
842:
824:
819:
783:
779:
775:
759:
755:
751:
739:
735:
731:
722:
718:
714:
705:
701:
697:
683:
611:
596:
589:
573:methylacetylene
568:
564:
546:
489:
450:
446:
438:
434:
417:
397:
393:
389:
382:
374:
368:
355:. The simplest
318:
317:
293:
292:
284:
278:
268:
262:
255:
250:
242:
236:
226:
220:
213:
208:
199:
191:
187:
185:
182:
181:
179:
155:
154:
146:
140:
130:
124:
117:
112:
103:
95:
91:
89:
86:
85:
83:
59:
58:
49:
41:
37:
35:
32:
31:
28:
17:
12:
11:
5:
7123:
7113:
7112:
7095:
7094:
7092:
7091:
7079:
7067:
7055:
7042:
7039:
7038:
7036:
7035:
7030:
7025:
7020:
7015:
7010:
7005:
7000:
6995:
6990:
6989:
6988:
6978:
6971:
6970:
6969:
6959:
6954:
6948:
6946:
6942:
6941:
6939:
6938:
6937:
6936:
6931:
6926:
6916:
6915:
6914:
6904:
6903:
6902:
6897:
6892:
6887:
6877:
6876:
6875:
6864:
6863:
6862:
6861:
6856:
6846:
6841:
6840:
6839:
6834:
6823:
6822:
6821:
6820:
6818:Soil chemistry
6810:
6809:
6808:
6803:
6796:Food chemistry
6793:
6791:Carbochemistry
6788:
6786:Clay chemistry
6783:
6782:
6781:
6776:
6765:
6764:
6763:
6762:
6757:
6747:
6741:Astrochemistry
6737:Cosmochemistry
6734:
6733:
6732:
6727:
6722:
6720:Radiochemistry
6711:
6709:
6703:
6702:
6700:
6699:
6694:
6689:
6684:
6679:
6677:Neurochemistry
6674:
6669:
6668:
6667:
6657:
6656:
6655:
6645:
6644:
6643:
6638:
6627:
6625:
6619:
6618:
6616:
6615:
6610:
6608:Petrochemistry
6605:
6600:
6595:
6586:
6581:
6576:
6571:
6566:
6561:
6560:
6559:
6548:
6546:
6540:
6539:
6537:
6536:
6531:
6526:
6521:
6520:
6519:
6509:
6504:
6498:
6496:
6490:
6489:
6487:
6486:
6481:
6476:
6471:
6469:Spin chemistry
6466:
6464:Photochemistry
6461:
6456:
6451:
6449:Femtochemistry
6446:
6445:
6444:
6434:
6429:
6424:
6419:
6418:
6417:
6407:
6402:
6397:
6392:
6391:
6390:
6385:
6374:
6372:
6366:
6365:
6363:
6362:
6361:
6360:
6350:
6345:
6340:
6335:
6334:
6333:
6323:
6317:
6315:
6309:
6308:
6306:
6305:
6300:
6295:
6290:
6285:
6280:
6275:
6274:
6273:
6268:
6261:Chromatography
6258:
6253:
6252:
6251:
6246:
6241:
6231:
6230:
6229:
6224:
6219:
6214:
6204:
6199:
6193:
6191:
6185:
6184:
6182:
6181:
6179:Periodic table
6176:
6171:
6166:
6160:
6157:
6156:
6148:
6147:
6140:
6133:
6125:
6116:
6115:
6113:
6112:
6111:
6110:
6105:
6093:
6086:
6080:
6077:
6076:
6074:
6073:
6071:Sulfinylamines
6068:
6063:
6058:
6053:
6051:Phosphoramides
6048:
6046:Isothiocyanate
6042:
6040:
6036:
6035:
6032:
6031:
6029:
6028:
6023:
6022:
6021:
6011:
6010:
6009:
5999:
5998:
5997:
5992:
5987:
5982:
5977:
5966:
5964:
5956:
5955:
5953:
5952:
5947:
5941:
5939:
5933:
5932:
5930:
5929:
5924:
5922:Selenenic acid
5919:
5917:Seleninic acid
5914:
5912:Selenonic acid
5909:
5903:
5901:
5895:
5894:
5892:
5891:
5886:
5880:
5878:
5872:
5871:
5869:
5868:
5863:
5858:
5853:
5848:
5843:
5838:
5833:
5828:
5823:
5818:
5813:
5808:
5803:
5798:
5793:
5792:
5791:
5781:
5775:
5773:
5767:
5766:
5764:
5763:
5758:
5753:
5748:
5747:
5746:
5736:
5731:
5726:
5721:
5720:
5719:
5709:
5708:
5707:
5705:Phosphodiester
5696:
5694:
5688:
5687:
5685:
5684:
5679:
5674:
5669:
5664:
5659:
5654:
5649:
5644:
5639:
5634:
5629:
5624:
5619:
5614:
5609:
5604:
5599:
5594:
5589:
5584:
5583:
5582:
5577:
5566:
5564:
5555:
5551:(one element,
5535:
5534:
5531:
5530:
5528:
5527:
5526:
5525:
5515:
5514:
5513:
5508:
5497:
5495:
5491:
5490:
5488:
5487:
5482:
5477:
5476:
5475:
5465:
5464:
5463:
5458:
5453:
5442:
5440:
5434:
5433:
5431:
5430:
5428:Methylenedioxy
5425:
5420:
5419:
5418:
5413:
5403:
5402:
5401:
5396:
5386:
5385:
5384:
5374:
5369:
5363:
5361:
5354:
5332:
5331:
5329:
5328:
5323:
5318:
5317:
5316:
5311:
5301:
5300:
5299:
5294:
5289:
5284:
5279:
5274:
5264:
5263:
5262:
5257:
5247:
5246:
5245:
5240:
5235:
5230:
5225:
5220:
5209:
5207:
5205:(only C and H)
5197:
5196:
5189:
5188:
5181:
5174:
5166:
5157:
5156:
5154:
5153:
5148:
5143:
5138:
5133:
5128:
5123:
5118:
5113:
5108:
5103:
5098:
5093:
5088:
5083:
5078:
5072:
5070:
5066:
5065:
5063:
5062:
5057:
5052:
5047:
5038:
5029:
5016:
5010:
5008:
5004:
5003:
5001:
5000:
4999:
4998:
4993:
4983:
4979:
4971:
4966:
4962:
4954:
4953:
4952:
4947:
4937:
4933:
4925:
4920:
4916:
4908:
4907:
4906:
4901:
4896:
4886:
4882:
4874:
4873:
4872:
4867:
4857:
4853:
4845:
4844:
4843:
4838:
4828:
4824:
4816:
4811:
4807:
4799:
4794:
4790:
4781:
4778:
4777:
4770:
4769:
4762:
4755:
4747:
4738:
4737:
4735:
4734:
4729:
4724:
4719:
4713:
4711:
4707:
4706:
4703:
4702:
4700:
4699:
4691:
4686:
4681:
4675:
4673:
4669:
4668:
4666:
4665:
4663:4-Vinyltoluene
4660:
4658:Divinylbenzene
4655:
4649:
4647:
4643:
4642:
4639:
4638:
4636:
4635:
4630:
4625:
4623:2-Phenylhexane
4620:
4614:
4612:
4608:
4607:
4604:
4603:
4601:
4600:
4595:
4587:
4579:
4570:
4568:
4564:
4563:
4561:
4560:
4555:
4550:
4544:
4542:
4536:
4535:
4533:
4532:
4524:
4516:
4507:
4505:
4496:
4490:
4489:
4486:
4485:
4483:
4482:
4480:4-Ethyltoluene
4477:
4475:-Propylbenzene
4469:
4463:
4461:
4457:
4456:
4454:
4453:
4448:
4443:
4437:
4435:
4426:
4420:
4419:
4416:
4415:
4413:
4412:
4406:
4404:
4400:
4399:
4397:
4396:
4388:
4380:
4371:
4369:
4360:
4351:
4350:
4344:
4342:
4336:
4335:
4332:
4331:
4329:
4328:
4323:
4318:
4313:
4308:
4303:
4298:
4293:
4288:
4283:
4277:
4275:
4271:
4270:
4268:
4267:
4262:
4257:
4252:
4247:
4242:
4236:
4234:
4225:
4216:
4208:
4207:
4204:
4203:
4201:
4200:
4195:
4190:
4185:
4180:
4175:
4169:
4167:
4163:
4162:
4160:
4159:
4154:
4149:
4144:
4139:
4134:
4129:
4124:
4118:
4116:
4110:
4109:
4107:
4106:
4101:
4096:
4091:
4086:
4081:
4076:
4071:
4065:
4063:
4057:
4056:
4054:
4053:
4047:
4045:
4043:Bicycloalkenes
4039:
4038:
4036:
4035:
4033:
4028:
4023:
4018:
4013:
4007:
4005:
3999:
3998:
3996:
3995:
3990:
3985:
3980:
3975:
3970:
3965:
3960:
3954:
3952:
3946:
3945:
3942:
3941:
3939:
3938:
3933:
3928:
3923:
3918:
3913:
3907:
3905:
3901:
3900:
3898:
3897:
3892:
3887:
3882:
3877:
3872:
3867:
3862:
3857:
3851:
3849:
3848:Linear alkynes
3842:
3835:
3829:
3821:
3820:
3817:
3816:
3814:
3813:
3808:
3803:
3798:
3793:
3788:
3783:
3777:
3775:
3771:
3770:
3768:
3767:
3762:
3757:
3752:
3747:
3742:
3737:
3732:
3727:
3721:
3719:
3718:Linear alkenes
3712:
3706:
3700:
3689:
3679:
3678:
3675:
3674:
3672:
3671:
3665:
3663:
3659:
3658:
3656:
3655:
3650:
3645:
3640:
3635:
3630:
3625:
3620:
3615:
3610:
3605:
3599:
3597:
3591:
3590:
3588:
3587:
3581:
3575:
3568:
3566:
3564:Bicycloalkanes
3560:
3559:
3557:
3556:
3554:
3549:
3544:
3539:
3534:
3528:
3526:
3520:
3519:
3517:
3516:
3511:
3506:
3501:
3496:
3491:
3486:
3481:
3475:
3473:
3467:
3466:
3463:
3462:
3460:
3459:
3454:
3449:
3444:
3439:
3434:
3429:
3424:
3419:
3413:
3411:
3407:
3406:
3404:
3403:
3398:
3393:
3388:
3383:
3378:
3373:
3368:
3363:
3358:
3352:
3350:
3349:Linear alkanes
3343:
3336:
3330:
3319:
3311:
3310:
3303:
3302:
3295:
3288:
3280:
3272:
3271:
3212:
3205:
3187:
3152:
3117:
3088:
3082:978-3527306732
3081:
3052:
3026:
2998:
2992:978-3527306732
2991:
2963:
2935:
2928:
2910:
2885:
2858:
2829:
2823:978-3527306732
2822:
2791:
2784:
2766:
2759:
2741:
2710:
2703:
2689:. p. 24.
2677:
2670:
2652:
2639:
2638:
2636:
2633:
2632:
2631:
2626:
2619:
2616:
2522:
2519:
2507:Main article:
2504:
2501:
2481:
2480:
2464:
2458:
2452:
2446:
2440:
2424:
2419:
2413:
2396:
2387:
2381:
2375:
2367:
2354:shown below:
2333:
2329:
2299:
2294:
2293:
2278:
2271:
2264:
2258:
2251:
2222:
2214:
2213:
2198:
2197:
2177:
2164:
2156:
2149:
2142:
2131:
2122:
2102:
2099:
2087:
2086:
2073:
2065:
2057:
2048:
2041:
2030:
2023:
2013:
2005:
1997:
1990:
1983:
1966:(RC) centers:
1920:carbon dioxide
1891:
1888:
1887:
1886:
1869:
1860:
1852:
1843:
1829:
1822:
1811:
1804:
1790:
1781:
1773:
1745:
1742:
1741:
1740:
1723:
1710:
1705:
1697:
1689:
1676:
1668:
1657:
1648:
1645:
1638:
1626:
1621:
1613:
1605:
1596:
1574:
1570:
1565:
1564:
1547:
1539:
1528:
1520:
1513:
1479:Wacker process
1458:
1455:
1451:vinyl chloride
1449:react to give
1412:
1411:
1394:
1385:
1373:
1365:
1357:
1348:
1345:
1341:
1333:
1309:
1306:
1300:
1295:
1294:
1277:
1268:
1256:
1248:
1240:
1232:
1225:
1217:
1202:
1186:
1178:
1164:
1156:
1148:
1144:
1136:
1072:
1062:
1059:
1038:
1035:
1009:vinyl bromides
1001:
1000:
952:
949:
941:
940:
920:
911:
908:
901:
894:
886:
876:
873:
868:
860:
851:
823:
820:
818:
815:
814:
813:
781:
777:
773:
757:
753:
749:
737:
733:
729:
720:
716:
712:
703:
699:
682:
679:
610:
609:Naming alkynes
607:
594:
587:
566:
545:
542:
498:
497:
448:
444:
436:
432:
416:
413:
395:
391:
376:
370:
313:
296:
287:
265:
253:
245:
223:
211:
202:
194:
175:
158:
149:
127:
115:
106:
98:
79:
62:
52:
44:
29:
15:
9:
6:
4:
3:
2:
7122:
7111:
7108:
7107:
7105:
7090:
7089:
7080:
7078:
7077:
7072:
7068:
7066:
7065:
7056:
7054:
7053:
7044:
7043:
7040:
7034:
7031:
7029:
7026:
7024:
7023:Chemical bond
7021:
7019:
7016:
7014:
7011:
7009:
7006:
7004:
7001:
6999:
6996:
6994:
6991:
6987:
6984:
6983:
6982:
6979:
6976:
6972:
6968:
6965:
6964:
6963:
6960:
6958:
6955:
6953:
6950:
6949:
6947:
6943:
6935:
6932:
6930:
6927:
6925:
6922:
6921:
6920:
6917:
6913:
6912:Stoichiometry
6910:
6909:
6908:
6905:
6901:
6898:
6896:
6893:
6891:
6888:
6886:
6883:
6882:
6881:
6878:
6874:
6871:
6870:
6869:
6868:Nanochemistry
6866:
6865:
6860:
6857:
6855:
6852:
6851:
6850:
6847:
6845:
6842:
6838:
6835:
6833:
6830:
6829:
6828:
6825:
6824:
6819:
6816:
6815:
6814:
6811:
6807:
6804:
6802:
6799:
6798:
6797:
6794:
6792:
6789:
6787:
6784:
6780:
6777:
6775:
6772:
6771:
6770:
6767:
6766:
6761:
6758:
6756:
6753:
6752:
6751:
6748:
6746:
6742:
6738:
6735:
6731:
6728:
6726:
6723:
6721:
6718:
6717:
6716:
6713:
6712:
6710:
6708:
6704:
6698:
6695:
6693:
6690:
6688:
6685:
6683:
6680:
6678:
6675:
6673:
6670:
6666:
6663:
6662:
6661:
6658:
6654:
6651:
6650:
6649:
6646:
6642:
6639:
6637:
6634:
6633:
6632:
6629:
6628:
6626:
6624:
6620:
6614:
6611:
6609:
6606:
6604:
6601:
6599:
6596:
6594:
6593:Semisynthesis
6590:
6587:
6585:
6582:
6580:
6577:
6575:
6572:
6570:
6567:
6565:
6562:
6558:
6555:
6554:
6553:
6550:
6549:
6547:
6545:
6541:
6535:
6532:
6530:
6527:
6525:
6522:
6518:
6515:
6514:
6513:
6510:
6508:
6505:
6503:
6500:
6499:
6497:
6495:
6491:
6485:
6482:
6480:
6477:
6475:
6472:
6470:
6467:
6465:
6462:
6460:
6457:
6455:
6452:
6450:
6447:
6443:
6440:
6439:
6438:
6435:
6433:
6430:
6428:
6427:Sonochemistry
6425:
6423:
6422:Cryochemistry
6420:
6416:
6415:Micromeritics
6413:
6412:
6411:
6408:
6406:
6403:
6401:
6398:
6396:
6393:
6389:
6386:
6384:
6381:
6380:
6379:
6376:
6375:
6373:
6371:
6367:
6359:
6356:
6355:
6354:
6351:
6349:
6346:
6344:
6341:
6339:
6336:
6332:
6329:
6328:
6327:
6324:
6322:
6319:
6318:
6316:
6314:
6310:
6304:
6301:
6299:
6296:
6294:
6293:Wet chemistry
6291:
6289:
6286:
6284:
6281:
6279:
6276:
6272:
6269:
6267:
6264:
6263:
6262:
6259:
6257:
6254:
6250:
6247:
6245:
6242:
6240:
6237:
6236:
6235:
6232:
6228:
6225:
6223:
6220:
6218:
6215:
6213:
6210:
6209:
6208:
6205:
6203:
6200:
6198:
6195:
6194:
6192:
6190:
6186:
6180:
6177:
6175:
6172:
6170:
6167:
6165:
6162:
6161:
6158:
6154:
6146:
6141:
6139:
6134:
6132:
6127:
6126:
6123:
6109:
6106:
6104:
6101:
6100:
6099:
6098:
6094:
6092:
6091:
6087:
6082:
6081:
6078:
6072:
6069:
6067:
6064:
6062:
6059:
6057:
6054:
6052:
6049:
6047:
6044:
6043:
6041:
6037:
6027:
6024:
6020:
6017:
6016:
6015:
6012:
6008:
6005:
6004:
6003:
6000:
5996:
5993:
5991:
5988:
5986:
5983:
5981:
5978:
5976:
5973:
5972:
5971:
5968:
5967:
5965:
5963:
5962:
5957:
5951:
5950:Telluroketone
5948:
5946:
5943:
5942:
5940:
5938:
5934:
5928:
5925:
5923:
5920:
5918:
5915:
5913:
5910:
5908:
5905:
5904:
5902:
5900:
5896:
5890:
5887:
5885:
5882:
5881:
5879:
5877:
5873:
5867:
5864:
5862:
5859:
5857:
5854:
5852:
5849:
5847:
5844:
5842:
5839:
5837:
5836:Sulfonic acid
5834:
5832:
5829:
5827:
5826:Sulfinic acid
5824:
5822:
5821:Thiosulfonate
5819:
5817:
5814:
5812:
5811:Thiosulfinate
5809:
5807:
5806:Sulfenic acid
5804:
5802:
5799:
5797:
5794:
5790:
5787:
5786:
5785:
5782:
5780:
5777:
5776:
5774:
5772:
5768:
5762:
5761:Phosphaallene
5759:
5757:
5756:Phosphaalkyne
5754:
5752:
5751:Phosphaalkene
5749:
5745:
5742:
5741:
5740:
5737:
5735:
5732:
5730:
5727:
5725:
5722:
5718:
5715:
5714:
5713:
5710:
5706:
5703:
5702:
5701:
5698:
5697:
5695:
5693:
5689:
5683:
5680:
5678:
5675:
5673:
5670:
5668:
5665:
5663:
5660:
5658:
5655:
5653:
5650:
5648:
5645:
5643:
5640:
5638:
5635:
5633:
5630:
5628:
5625:
5623:
5620:
5618:
5615:
5613:
5610:
5608:
5605:
5603:
5600:
5598:
5595:
5593:
5590:
5588:
5585:
5581:
5578:
5576:
5573:
5572:
5571:
5568:
5567:
5565:
5563:
5559:
5556:
5536:
5524:
5521:
5520:
5519:
5516:
5512:
5509:
5507:
5504:
5503:
5502:
5499:
5498:
5496:
5492:
5486:
5483:
5481:
5478:
5474:
5471:
5470:
5469:
5466:
5462:
5459:
5457:
5454:
5452:
5449:
5448:
5447:
5444:
5443:
5441:
5439:
5435:
5429:
5426:
5424:
5423:Ethylenedioxy
5421:
5417:
5414:
5412:
5409:
5408:
5407:
5404:
5400:
5397:
5395:
5392:
5391:
5390:
5387:
5383:
5380:
5379:
5378:
5375:
5373:
5370:
5368:
5365:
5364:
5362:
5358:
5355:
5349:
5343:
5338:
5333:
5327:
5324:
5322:
5319:
5315:
5312:
5310:
5307:
5306:
5305:
5302:
5298:
5295:
5293:
5290:
5288:
5285:
5283:
5280:
5278:
5275:
5273:
5270:
5269:
5268:
5265:
5261:
5258:
5256:
5253:
5252:
5251:
5248:
5244:
5241:
5239:
5236:
5234:
5231:
5229:
5226:
5224:
5221:
5219:
5216:
5215:
5214:
5211:
5210:
5208:
5202:
5198:
5194:
5187:
5182:
5180:
5175:
5173:
5168:
5167:
5164:
5152:
5149:
5147:
5144:
5142:
5139:
5137:
5134:
5132:
5129:
5127:
5124:
5122:
5119:
5117:
5114:
5112:
5109:
5107:
5104:
5102:
5099:
5097:
5096:Hydroboration
5094:
5092:
5089:
5087:
5084:
5082:
5081:Hydrogenation
5079:
5077:
5076:Deprotonation
5074:
5073:
5071:
5067:
5061:
5058:
5056:
5053:
5051:
5048:
5046:
5042:
5039:
5037:
5036:alkynyl anion
5033:
5030:
5028:
5024:
5020:
5017:
5015:
5012:
5011:
5009:
5005:
4997:
4994:
4992:
4989:
4988:
4975:
4972:
4958:
4955:
4951:
4948:
4946:
4943:
4942:
4929:
4926:
4912:
4909:
4905:
4902:
4900:
4897:
4895:
4892:
4891:
4878:
4875:
4871:
4868:
4866:
4863:
4862:
4849:
4846:
4842:
4839:
4837:
4834:
4833:
4820:
4817:
4803:
4800:
4786:
4783:
4782:
4779:
4775:
4768:
4763:
4761:
4756:
4754:
4749:
4748:
4745:
4733:
4730:
4728:
4725:
4723:
4720:
4718:
4715:
4714:
4712:
4708:
4698:
4696:
4692:
4690:
4687:
4685:
4682:
4680:
4677:
4676:
4674:
4670:
4664:
4661:
4659:
4656:
4654:
4651:
4650:
4648:
4646:Vinylbenzenes
4644:
4634:
4631:
4629:
4626:
4624:
4621:
4619:
4616:
4615:
4613:
4609:
4599:
4596:
4594:
4593:-Butylbenzene
4592:
4588:
4586:
4585:-Butylbenzene
4584:
4580:
4578:
4577:-Butylbenzene
4576:
4572:
4571:
4569:
4565:
4559:
4556:
4554:
4551:
4549:
4546:
4545:
4543:
4541:
4537:
4531:
4529:
4525:
4523:
4521:
4517:
4515:
4513:
4509:
4508:
4506:
4504:
4500:
4497:
4495:
4491:
4481:
4478:
4476:
4474:
4470:
4468:
4465:
4464:
4462:
4458:
4452:
4449:
4447:
4444:
4442:
4439:
4438:
4436:
4434:
4430:
4427:
4425:
4421:
4411:
4408:
4407:
4405:
4401:
4395:
4393:
4389:
4387:
4385:
4381:
4379:
4377:
4373:
4372:
4370:
4368:
4364:
4361:
4359:
4355:
4349:
4346:
4345:
4343:
4341:
4340:Alkylbenzenes
4337:
4327:
4324:
4322:
4319:
4317:
4314:
4312:
4309:
4307:
4304:
4302:
4299:
4297:
4294:
4292:
4289:
4287:
4284:
4282:
4279:
4278:
4276:
4272:
4266:
4263:
4261:
4258:
4256:
4253:
4251:
4248:
4246:
4243:
4241:
4238:
4237:
4235:
4233:
4229:
4226:
4224:
4220:
4217:
4215:
4209:
4199:
4196:
4194:
4191:
4189:
4186:
4184:
4181:
4179:
4176:
4174:
4171:
4170:
4168:
4164:
4158:
4155:
4153:
4150:
4148:
4145:
4143:
4140:
4138:
4135:
4133:
4130:
4128:
4125:
4123:
4120:
4119:
4117:
4115:
4111:
4105:
4102:
4100:
4097:
4095:
4092:
4090:
4087:
4085:
4082:
4080:
4077:
4075:
4072:
4070:
4067:
4066:
4064:
4062:
4058:
4052:
4049:
4048:
4046:
4044:
4040:
4034:
4032:
4029:
4027:
4024:
4022:
4019:
4017:
4014:
4012:
4009:
4008:
4006:
4004:
4000:
3994:
3991:
3989:
3986:
3984:
3981:
3979:
3976:
3974:
3971:
3969:
3966:
3964:
3961:
3959:
3956:
3955:
3953:
3951:
3947:
3937:
3934:
3932:
3929:
3927:
3924:
3922:
3919:
3917:
3914:
3912:
3909:
3908:
3906:
3902:
3896:
3893:
3891:
3888:
3886:
3883:
3881:
3878:
3876:
3873:
3871:
3868:
3866:
3863:
3861:
3858:
3856:
3853:
3852:
3850:
3846:
3843:
3839:
3832:
3826:
3822:
3812:
3809:
3807:
3804:
3802:
3799:
3797:
3794:
3792:
3789:
3787:
3784:
3782:
3779:
3778:
3776:
3772:
3766:
3763:
3761:
3758:
3756:
3753:
3751:
3748:
3746:
3743:
3741:
3738:
3736:
3733:
3731:
3728:
3726:
3723:
3722:
3720:
3716:
3713:
3710:
3703:
3697:
3693:
3690:
3684:
3680:
3670:
3667:
3666:
3664:
3660:
3654:
3651:
3649:
3646:
3644:
3641:
3639:
3636:
3634:
3633:Dodecahedrane
3631:
3629:
3626:
3624:
3621:
3619:
3616:
3614:
3611:
3609:
3606:
3604:
3601:
3600:
3598:
3596:
3592:
3585:
3582:
3579:
3576:
3573:
3570:
3569:
3567:
3565:
3561:
3555:
3553:
3550:
3548:
3545:
3543:
3540:
3538:
3535:
3533:
3530:
3529:
3527:
3525:
3521:
3515:
3512:
3510:
3507:
3505:
3502:
3500:
3497:
3495:
3492:
3490:
3487:
3485:
3482:
3480:
3477:
3476:
3474:
3472:
3468:
3458:
3455:
3453:
3450:
3448:
3445:
3443:
3440:
3438:
3435:
3433:
3430:
3428:
3425:
3423:
3420:
3418:
3415:
3414:
3412:
3408:
3402:
3399:
3397:
3394:
3392:
3389:
3387:
3384:
3382:
3379:
3377:
3374:
3372:
3369:
3367:
3364:
3362:
3359:
3357:
3354:
3353:
3351:
3347:
3344:
3340:
3333:
3327:
3323:
3320:
3312:
3308:
3301:
3296:
3294:
3289:
3287:
3282:
3281:
3278:
3267:
3263:
3258:
3253:
3248:
3243:
3239:
3235:
3231:
3227:
3223:
3216:
3208:
3206:0-444-87115-2
3202:
3198:
3191:
3183:
3179:
3175:
3171:
3167:
3163:
3156:
3148:
3144:
3140:
3136:
3132:
3128:
3121:
3113:
3109:
3105:
3101:
3100:
3092:
3084:
3078:
3074:
3070:
3066:
3065:
3056:
3047:
3043:
3042:
3037:
3030:
3022:
3018:
3014:
3011:
3010:
3009:J. Org. Chem.
3002:
2994:
2988:
2984:
2980:
2976:
2975:
2967:
2958:
2952:
2951:
2946:
2939:
2931:
2925:
2921:
2914:
2906:
2902:
2898:
2897:
2889:
2881:
2877:
2873:
2869:
2862:
2854:
2850:
2846:
2842:
2841:
2833:
2825:
2819:
2815:
2811:
2807:
2806:
2798:
2796:
2787:
2785:0-408-70144-7
2781:
2777:
2770:
2762:
2756:
2752:
2745:
2737:
2733:
2729:
2725:
2721:
2714:
2706:
2704:9780470084960
2700:
2696:
2692:
2688:
2681:
2673:
2671:9780470771563
2667:
2663:
2656:
2649:
2644:
2640:
2630:
2627:
2625:
2622:
2621:
2615:
2613:
2609:
2608:calicheamicin
2605:
2601:
2597:
2592:
2590:
2586:
2582:
2581:oenanthotoxin
2578:
2574:
2570:
2566:
2565:
2560:
2559:
2554:
2553:
2552:Chrysanthemum
2548:
2547:
2542:
2538:
2534:
2533:
2528:
2525:According to
2518:
2516:
2510:
2500:
2498:
2497:hydroxyalkyne
2494:
2490:
2489:alkynylations
2486:
2462:
2456:
2450:
2444:
2438:
2422:
2394:
2385:
2379:
2373:
2365:
2357:
2356:
2355:
2353:
2349:
2345:
2341:
2325:
2312:
2310:
2306:
2302:
2276:
2269:
2256:
2249:
2237:
2236:
2235:
2233:
2229:
2225:
2221:
2211:
2207:
2206:
2205:
2203:
2175:
2162:
2147:
2140:
2129:
2120:
2112:
2111:
2110:
2108:
2098:
2096:
2092:
2071:
2063:
2055:
2039:
2028:
2011:
2003:
1995:
1988:
1981:
1969:
1968:
1967:
1965:
1961:
1957:
1953:
1949:
1945:
1941:
1937:
1933:
1929:
1925:
1921:
1917:
1913:
1909:
1905:
1901:
1897:
1896:cycloaddition
1867:
1858:
1850:
1841:
1820:
1809:
1788:
1779:
1771:
1759:
1758:
1757:
1755:
1751:
1721:
1708:
1695:
1674:
1655:
1646:
1643:
1636:
1624:
1611:
1594:
1582:
1581:
1580:
1578:
1545:
1526:
1518:
1511:
1499:
1498:
1497:
1495:
1491:
1488:Hydration of
1486:
1484:
1480:
1476:
1472:
1471:vinyl alcohol
1468:
1464:
1454:
1452:
1448:
1444:
1440:
1435:
1433:
1429:
1425:
1424:hydroboration
1418:bonds across
1392:
1383:
1371:
1355:
1346:
1343:
1339:
1331:
1319:
1318:
1317:
1315:
1305:
1275:
1266:
1254:
1238:
1230:
1223:
1215:
1203:
1184:
1176:
1154:
1146:
1142:
1134:
1122:
1121:
1120:
1118:
1115:. Similarly,
1114:
1110:
1106:
1102:
1098:
1089:
1085:
1083:
1079:
1078:hydrogenation
1068:
1061:Hydrogenation
1058:
1056:
1052:
1051:Ralph Raphael
1048:
1044:
1034:
1032:
1031:Vinyl halides
1028:
1026:
1022:
1018:
1014:
1010:
1006:
998:
994:
993:
992:
990:
986:
982:
978:
974:
970:
966:
962:
958:
957:dihaloalkanes
948:
946:
918:
909:
906:
899:
884:
874:
871:
866:
858:
849:
841:
840:
839:
837:
833:
829:
812:
808:
804:
800:
796:
792:
788:
785:: 7 isomers:
774:
772:
768:
764:
761:: 3 isomers:
750:
748:
744:
741:: 2 isomers:
730:
727:
713:
710:
696:
695:
694:
692:
688:
678:
676:
672:
667:
664:
660:
656:
652:
648:
644:
640:
636:
635:
631:
626:
624:
620:
616:
606:
604:
600:
593:
586:
582:
578:
574:
561:
559:
555:
551:
541:
539:
535:
531:
527:
526:sp hybridized
523:
519:
515:
511:
507:
506:bond strength
503:
492:
487:
483:
479:
475:
471:
467:
464:, acetylene,
463:
458:
454:
453:
452:
442:
430:
426:
422:
412:
410:
406:
402:
387:
380:
373:
366:
362:
358:
354:
350:
346:
343:
339:
335:
327:
322:
316:
312:
294:
251:
209:
200:
192:
178:
174:
156:
113:
104:
96:
82:
78:
60:
50:
42:
26:
22:
7086:
7074:
7062:
7050:
6900:Biosynthesis
6750:Geochemistry
6665:Pharmacology
6641:Cell biology
6631:Biochemistry
6459:Spectroscopy
6358:VSEPR theory
6207:Spectroscopy
6151:Branches of
6095:
6088:
6002:Vinyl halide
5959:
5889:Borinic acid
5884:Boronic acid
5861:Thioxanthate
5320:
5201:Hydrocarbons
5106:Alkynylation
5086:Halogenation
5045:dihaloalkane
5007:Preparations
4773:
4694:
4590:
4582:
4574:
4527:
4519:
4511:
4472:
4446:Pseudocumene
4410:Ethylbenzene
4391:
4383:
4375:
4306:Phenanthrene
4214:hydrocarbons
4089:Cycloheptyne
4079:Cyclopentyne
4069:Cyclopropyne
4061:Cycloalkynes
3978:Cycloheptene
3968:Cyclopentene
3958:Cyclopropene
3950:Cycloalkenes
3837:
3830:
3824:
3708:
3701:
3688:hydrocarbons
3669:Spiroalkanes
3499:Cycloheptane
3489:Cyclopentane
3479:Cyclopropane
3471:Cycloalkanes
3338:
3331:
3318:hydrocarbons
3307:Hydrocarbons
3229:
3225:
3215:
3196:
3190:
3165:
3161:
3155:
3130:
3126:
3120:
3103:
3097:
3091:
3062:
3055:
3045:
3039:
3029:
3015:(11): 3729.
3012:
3007:
3001:
2972:
2966:
2956:
2948:
2938:
2919:
2913:
2895:
2888:
2871:
2867:
2861:
2844:
2838:
2832:
2803:
2775:
2769:
2750:
2744:
2727:
2723:
2719:
2713:
2686:
2680:
2661:
2655:
2643:
2596:noretynodrel
2593:
2562:
2556:
2550:
2546:Ichthyothere
2544:
2541:tariric acid
2530:
2524:
2512:
2482:
2313:
2295:
2219:
2215:
2199:
2104:
2088:
1922:to give the
1893:
1747:
1566:
1494:acetophenone
1487:
1475:tautomerizes
1467:acetaldehyde
1460:
1436:
1413:
1311:
1296:
1117:halogenation
1093:
1064:
1040:
1029:
1002:
985:sodium amide
954:
942:
825:
684:
668:
651:unsaturation
632:
627:
612:
591:
584:
562:
547:
499:
490:
485:
481:
473:
472:, 1-butyne,
469:
465:
461:
418:
385:
378:
371:
337:
331:
180:
84:
30:
7088:WikiProject
6313:Theoretical
6298:Calorimetry
6066:Thiocyanate
6061:Sulfonamide
6026:Perchlorate
6014:Acyl halide
5975:Fluoroethyl
5856:Thionoester
5744:Phosphonium
5729:Phosphinate
5724:Phosphonous
5712:Phosphonate
5411:Hydroperoxy
5233:Cyclopropyl
4494:C4-Benzenes
4451:Hemellitene
4424:C3-Benzenes
4358:C2-Benzenes
4321:Corannulene
4240:Naphthalene
4104:Cyclodecyne
4099:Cyclononyne
4094:Cyclooctyne
4084:Cyclohexyne
4074:Cyclobutyne
3993:Cyclodecene
3988:Cyclononene
3983:Cyclooctene
3973:Cyclohexene
3963:Cyclobutene
3683:Unsaturated
3514:Cyclodecane
3509:Cyclononane
3504:Cyclooctane
3494:Cyclohexane
3484:Cyclobutane
2629:cycloalkyne
2604:Terbinafine
2589:nematocides
2296:where MX =
1918:eliminates
1912:dienophiles
1744:Tautomerism
1067:unsaturated
1065:Being more
977:bromination
965:halogenated
836:natural gas
645:. However,
623:triple bond
502:triple bond
421:bond angles
409:hydrophobic
353:triple bond
345:hydrocarbon
342:unsaturated
6924:Metallurgy
6623:Biological
6189:Analytical
5970:Haloalkane
5841:Thioketone
5796:Persulfide
5692:Phosphorus
5657:Isocyanate
5647:Isonitrile
5548:or oxygen
5546:hydrogen,
5542:not being
5523:Orthoester
5416:Dioxiranes
5394:Enol ether
5282:1-Propenyl
5032:Alkylation
4553:Prehnitene
4441:Mesitylene
4296:Circulenes
4245:Anthracene
4173:Alkatriene
4142:Heptadiene
4132:Pentadiene
4122:Propadiene
4051:Norbornene
3921:Isoheptyne
3911:Isopentyne
3796:Isoheptene
3786:Isopentene
3608:Diamondoid
3603:Adamantane
3578:Norbornane
3442:Isoheptane
3432:Neopentane
3422:Isopentane
2929:0003277402
2635:References
2585:falcarinol
2569:Asteraceae
2350:, and the
2107:butynediol
1754:propadiene
1168: cis-
1015:using the
959:by double
649:featuring
603:acetylides
599:carbanions
538:sigma bond
530:p orbitals
510:sigma bond
429:picometers
6986:Catalysis
6494:Inorganic
6288:Titration
6153:chemistry
6103:inorganic
5937:Tellurium
5851:Thioester
5816:Sulfoxide
5801:Disulfide
5789:Sulfonium
5739:Phosphine
5717:Phosphite
5700:Phosphate
5632:Carbamate
5607:Hydrazone
5540:element,
5538:Only one
5511:Anhydride
5250:Methylene
5091:Hydration
5069:Reactions
4722:Annulynes
4717:Annulenes
4558:Isodurene
4291:Helicenes
4265:Heptacene
4255:Pentacene
4250:Tetracene
4178:Alkadiyne
4157:Decadiene
4152:Nonadiene
4147:Octadiene
4137:Hexadiene
4127:Butadiene
3936:Isodecyne
3931:Isononyne
3926:Isooctyne
3916:Isohexyne
3811:Isodecene
3806:Isononene
3801:Isooctene
3791:Isohexene
3781:Isobutene
3686:aliphatic
3643:Churchane
3638:Basketane
3457:Isodecane
3452:Isononane
3447:Isooctane
3437:Isohexane
3417:Isobutane
3316:aliphatic
3314:Saturated
3127:Synthesis
2600:Efavirenz
2577:cicutoxin
2532:Artemisia
2463:−
2457:≡
2451:−
2445:≡
2439:−
2386:−
2380:≡
2374:−
2270:≡
2263:⟶
2250:≡
2230:(35) and
2155:⟶
2148:≡
2064:≡
2047:⇀
2040:−
2029:−
2022:↽
2004:≡
1982:≡
1952:triazoles
1902:with 1,3-
1828:⇀
1821:−
1810:−
1803:↽
1780:−
1772:≡
1667:⟶
1637:≡
1595:≡
1538:⟶
1512:≡
1457:Hydration
1364:⟶
1332:≡
1247:⟶
1163:⟶
1135:≡
1097:palladium
1055:synthesis
1013:aldehydes
900:≡
893:⟶
828:acrylates
817:Synthesis
767:2-pentyne
763:1-pentyne
709:acetylene
675:acetylene
581:acetylene
558:2-pentyne
386:acetylene
326:acetylene
295:−
252:−
210:−
201:≡
193:−
157:−
114:−
105:≡
97:−
81:Acetylene
61:−
51:≡
43:−
7104:Category
7052:Category
7008:Molecule
6945:See also
6370:Physical
6084:See also
6019:Chloride
5945:Tellurol
5899:Selenium
5866:Xanthate
5580:Ammonium
5562:Nitrogen
5544:carbon,
5501:Carboxyl
5468:Aldehyde
5456:Acryloyl
5438:carbonyl
5342:hydrogen
5297:Cumulene
5014:Cracking
4326:Kekulene
4311:Chrysene
4301:Butalene
4286:Fluorene
4260:Hexacene
4212:Aromatic
4183:Cumulene
3653:Twistane
3648:Pagodane
3628:Prismane
3182:16447152
3147:95666091
2618:See also
2573:Apiaceae
2564:Oenanthe
2537:Polyynes
2493:carbonyl
2400:pyridine
2395:→
2072:′
2012:′
1996:′
1950:to give
1932:aromatic
1930:to give
1924:aromatic
1916:2-pyrone
1473:, which
1443:catalyst
1428:aldehyde
1384:′
1340:′
1314:halogens
1267:′
1224:′
1185:′
1143:′
1003:Via the
822:Cracking
795:3-hexyne
791:2-hexyne
787:1-hexyne
747:2-butyne
743:1-butyne
659:"-diyne"
554:3-hexyne
532:and two
478:2-butyne
351:âcarbon
315:1-Butyne
7110:Alkynes
7064:Commons
7028:Alchemy
6544:Organic
6108:organic
5907:Selenol
5831:Sulfone
5784:Sulfide
5682:NONOate
5677:Nitroso
5667:Nitrite
5662:Nitrate
5652:Cyanate
5642:Nitrile
5627:Amidine
5622:Imidate
5592:Nitrene
5587:Hydrazo
5575:Enamine
5506:Acetoxy
5494:carboxy
5461:Benzoyl
5399:Epoxide
5382:Methoxy
5372:Alcohol
5326:Carbene
5260:Methine
4911:Heptyne
4848:Pentyne
4802:Propyne
4774:Alkynes
4679:Benzene
4653:Styrene
4530:-Cymene
4522:-Cymene
4514:-Cymene
4503:Cymenes
4394:-Xylene
4386:-Xylene
4378:-Xylene
4367:Xylenes
4348:Toluene
4281:Azulene
3880:Heptyne
3870:Pentyne
3860:Propyne
3825:Alkynes
3750:Heptene
3740:Pentene
3730:Propene
3696:Alkenes
3618:Sterane
3584:Decalin
3572:Housane
3386:Heptane
3376:Pentane
3366:Propane
3356:Methane
3326:Alkanes
3266:1584797
3234:Bibcode
2905:3134811
2487:and in
2483:In the
2232:ethanol
2228:ammonia
2200:In the
1964:carbyne
1942:in the
1750:Propyne
1113:styrene
1023:by the
1021:ketones
989:ammonia
973:styrene
726:propyne
671:hyphens
514:pi bond
441:alkenes
425:Benzyne
363:form a
357:acyclic
177:Propyne
7076:Portal
6222:UV-Vis
6007:Iodide
5927:Selone
5771:Sulfur
5480:Ketone
5473:Ketene
5451:Acetyl
5406:Peroxy
5377:Alkoxy
5367:Acetal
5348:oxygen
5337:carbon
5321:Alkyne
5314:Benzyl
5309:Phenyl
5292:Allene
5287:Crotyl
5267:Alkene
5255:Bridge
5243:Pentyl
5228:Propyl
5218:Methyl
5027:alkene
5023:alkane
4974:Decyne
4957:Nonyne
4928:Octyne
4877:Hexyne
4819:Butyne
4785:Ethyne
4548:Durene
4467:Cumene
4316:Pyrene
4232:Acenes
4114:Dienes
3895:Decyne
3890:Nonyne
3885:Octyne
3875:Hexyne
3865:Butyne
3855:Ethyne
3765:Decene
3760:Nonene
3755:Octene
3745:Hexene
3735:Butene
3725:Ethene
3623:Cubane
3401:Decane
3396:Nonane
3391:Octane
3381:Hexane
3371:Butane
3361:Ethane
3264:
3254:
3203:
3180:
3145:
3079:
2989:
2926:
2903:
2874:: 10.
2847:: 72.
2820:
2782:
2757:
2730:: 15.
2701:
2668:
2648:Alkyne
2583:, and
2558:Cicuta
2234:(16):
1936:alkene
1906:gives
1904:dienes
1573:P)AuCH
1542:PhCOCH
1492:gives
1101:silver
1082:alkene
769:, and
745:, and
687:carbon
663:locant
630:suffix
619:octyne
431:(for C
403:using
401:ethyne
349:carbon
340:is an
338:alkyne
25:alkene
21:alkane
6249:MALDI
6217:Raman
6039:Other
5876:Boron
5846:Thial
5779:Thiol
5672:Nitro
5637:Imide
5617:Amide
5602:Oxime
5597:Imine
5570:Amine
5518:Ester
5485:Ynone
5389:Ether
5360:R-O-R
5335:Only
5277:Allyl
5272:Vinyl
5238:Butyl
5223:Ethyl
5213:Alkyl
4710:Other
4695:trans
4672:Other
4611:Other
4567:Other
4460:Other
4403:Other
4274:Other
4198:Enyne
4166:Other
3662:Other
3257:49132
3143:S2CID
3106:: 1.
2328:Ag(NH
2307:, or
1441:as a
983:with
336:, an
7003:Atom
6271:HPLC
5961:Halo
5446:Acyl
5346:and
5304:Aryl
4591:tert
4223:PAHs
3262:PMID
3201:ISBN
3178:PMID
3131:2007
3077:ISBN
3048:: 55
2987:ISBN
2924:ISBN
2901:OCLC
2818:ISBN
2780:ISBN
2755:ISBN
2699:ISBN
2666:ISBN
2624:-yne
2571:and
2318:and
2309:RMgX
2305:LiBu
2298:NaNH
2172:CCCH
2159:HOCH
2109::
1958:and
1938:and
1718:COCH
1461:The
1368:RCBr
1027:.
728:only
711:only
655:-ane
634:-yne
552:and
500:The
491:blue
7013:Ion
6244:ICP
6227:NMR
5612:Azo
5043:of
5034:of
5021:of
4583:sec
3840:â 2
3341:+ 2
3252:PMC
3242:doi
3170:doi
3135:doi
3108:doi
3069:doi
3017:doi
2979:doi
2876:doi
2849:doi
2810:doi
2732:doi
2691:doi
2415:OAc
1569:(Ph
1508:PhC
1420:CâĄC
1416:EâH
1251:RCH
1212:RCH
1173:RCH
1111:to
987:in
975:by
834:of
613:In
332:In
23:or
7106::
6743:/
6739:/
6591:/
6266:GC
6239:EI
6212:IR
5344:,
5339:,
5025:,
4987:)
4984:18
4980:10
4967:16
4941:)
4938:14
4921:12
4890:)
4887:10
4861:)
4832:)
3260:.
3250:.
3240:.
3230:89
3228:.
3224:.
3176:.
3166:45
3164:.
3141:.
3129:.
3104:54
3102:.
3075:.
3046:83
3044:.
3038:.
3013:56
2985:.
2961:..
2954:;
2947:.
2872:59
2870:.
2845:30
2843:.
2816:.
2794:^
2728:30
2726:.
2697:.
2579:,
2561:,
2555:,
2549:,
2499:.
2407:Cu
2346:,
2336:OH
2320:Cu
2316:Ag
2311:.
2303:,
2280:HX
2274:CM
2266:RC
2260:MX
2254:CH
2246:RC
2184:OH
2152:CH
2144:HC
2126:CH
2097:.
2069:CR
2060:RC
2009:CR
1986:CR
1978:RC
1864:CH
1838:CH
1785:CH
1768:HC
1756::
1692:CH
1683:CO
1671:CH
1641:CH
1608:CH
1591:HC
1516:CH
1496::
1485:.
1389:Br
1381:CR
1352:Br
1337:CR
1328:RC
1264:CR
1221:CR
1182:CR
1140:CR
1131:RC
1057:.
991::
904:CH
896:HC
855:CH
838::
809:,
805:,
801:,
797:,
793:,
789:,
782:10
765:,
724::
707::
605:.
565:RC
560:.
480:,
476:,
411:.
381:â2
6977:"
6973:"
6144:e
6137:t
6130:v
5185:e
5178:t
5171:v
4996:5
4991:1
4982:H
4978:C
4976:(
4970:)
4965:H
4963:9
4961:C
4959:(
4950:4
4945:2
4936:H
4934:8
4932:C
4930:(
4924:)
4919:H
4917:7
4915:C
4913:(
4904:3
4899:2
4894:1
4885:H
4883:6
4881:C
4879:(
4870:2
4865:1
4858:8
4856:H
4854:5
4852:C
4850:(
4841:2
4836:1
4829:6
4827:H
4825:4
4823:C
4821:(
4815:)
4812:4
4810:H
4808:3
4806:C
4804:(
4798:)
4795:2
4793:H
4791:2
4789:C
4787:(
4766:e
4759:t
4752:v
4575:n
4528:p
4520:m
4512:o
4473:n
4392:p
4384:m
4376:o
3838:n
3836:2
3834:H
3831:n
3828:C
3709:n
3707:2
3705:H
3702:n
3699:C
3339:n
3337:2
3335:H
3332:n
3329:C
3299:e
3292:t
3285:v
3268:.
3244::
3236::
3209:.
3184:.
3172::
3149:.
3137::
3115:.
3110::
3085:.
3071::
3050:.
3023:.
3019::
2995:.
2981::
2932:.
2907:.
2882:.
2878::
2856:.
2851::
2826:.
2812::
2788:.
2763:.
2738:.
2734::
2720:n
2707:.
2693::
2674:.
2467:R
2435:R
2423:2
2418:)
2412:(
2390:H
2370:R
2366:2
2334:2
2332:)
2330:3
2326:(
2300:2
2277:+
2257:+
2223:a
2220:K
2218:p
2176:2
2163:2
2141:+
2138:O
2130:2
2121:2
2056:2
2000:C
1993:R
1989:+
1868:2
1859:=
1855:C
1851:=
1842:2
1789:3
1776:C
1722:3
1709:5
1704:)
1696:2
1688:(
1675:3
1664:O
1656:2
1652:H
1647:2
1644:+
1633:C
1625:5
1620:)
1612:2
1604:(
1599:C
1575:3
1571:3
1546:3
1535:O
1527:2
1523:H
1519:+
1393:2
1372:2
1356:2
1347:2
1344:+
1301:2
1299:H
1276:2
1272:H
1255:2
1239:2
1235:H
1231:+
1228:H
1216:=
1189:H
1177:=
1155:2
1151:H
1147:+
1099:/
1073:2
1071:H
927:O
919:2
915:H
910:3
907:+
885:2
881:O
875:2
872:3
867:+
859:4
850:2
780:H
778:6
776:C
758:8
756:H
754:5
752:C
738:6
736:H
734:4
732:C
721:4
719:H
717:3
715:C
704:2
702:H
700:2
698:C
595:a
592:K
588:a
585:K
569:H
567:2
494:.
486:f
482:e
474:d
470:c
466:b
462:a
449:4
447:H
445:2
437:2
435:H
433:2
396:2
394:H
392:2
390:C
379:n
377:2
375:H
372:n
369:C
299:H
286:|
280:H
270:H
264:|
259:C
244:|
238:H
228:H
222:|
217:C
205:C
197:C
189:H
161:H
148:|
142:H
132:H
126:|
121:C
109:C
101:C
93:H
65:H
55:C
47:C
39:H
27:.
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