2221:
468:
1008:
7058:
7082:
332:
7094:
7070:
321:
1099:
551:. 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.
194:
183:
676:
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.
1211:
1105:
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
636:. 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.
2489:
628:, 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
316:{\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}}}
2095:
1749:
1420:
3208:
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)
1303:
3071:
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".
949:
2813:
Gräfje, Heinz; KĂśrnig, Wolfgang; Weitz, Hans-Martin; ReiĂ, Wolfgang; Steffan, Guido; Diehl, Herbert; Bosche, Horst; Schneider, Kurt; Kieczka, Heinz (2000). "Butanediols, Butenediol, and
Butynediol".
2206:
664:
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 "
98:
1895:
2302:
1573:
704:
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.
2528:. Terminal alkynes, including acetylene itself, react with water to give aldehydes. The transformation typically requires metal catalysts to give this anti-Markovnikov addition result.
2550:, 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
87:
2621:, 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
5060:
2116:
Terminal alkynes are readily converted to many derivatives, e.g. by coupling reactions and condensations. Via the condensation with formaldehyde and acetylene is produced
1015:
608:
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
3074:
2984:
2815:
6153:
6254:
6259:
5194:
1080:
than alkenes, alkynes characteristically undergo reactions that show that they are "doubly unsaturated". Alkynes are capable of adding two equivalents of
2546:
species in 1826. In the nearly two centuries that have followed, well over a thousand naturally occurring acetylenes have been discovered and reported.
6113:
2371:
6237:
6118:
415:
6281:
3308:
2769:
2349:) reacts with terminal alkynes signaled by formation of a white precipitate of the silver acetylide. This reactivity is the basis of alkyne
1087:, whereas an alkene adds only one equivalent. Depending on catalysts and conditions, alkynes add one or two equivalents of hydrogen. Partial
6232:
1136:
6293:
2554:
contain an alkyne group. Diynes and triynes, species with the linkage RCâĄCâCâĄCRⲠand RCâĄCâCâĄCâCâĄCRⲠrespectively, occur in certain plants (
1596:
6146:
1077:
661:
352:
5141:
3091:
3001:
2832:
1958:
5070:
3017:
Fukuda, Y.; Utimoto, K. (1991). "Effective transformation of unactivated alkynes into ketones or acetals with a gold(III) catalyst".
2617:. Molecules called ene-diynes feature a ring containing an alkene ("ene") between two alkyne groups ("diyne"). These compounds, e.g.
1035:
684:
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 "
4775:
3215:
2794:
2713:
2680:
2220:
632:, 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
1434:
5151:
2354:
178:{\displaystyle {\ce {H-C#C}}{-}{\ce {\overset {\displaystyle {H} \atop |}{\underset {| \atop \displaystyle {H}}{C}}}}{\ce {-H}}}
7098:
5187:
4233:
2877:
A. Le Coq and A. Gorgues (1979). "Alkyness via Phase
Transfer-Catalyzed Dehydrohalogenatiion: Propiolaldehyde Diethyl Acetal".
2519:
855:
1983:
6977:
6139:
2938:
2126:
1333:
6420:
6174:
6017:
1217:
2524:
Alkynes form complexes with transition metals. Such complexes occur also in metal catalyzed reactions of alkynes such as
1773:
837:
Commercially, the dominant alkyne is acetylene itself, which is used as a fuel and a precursor to other compounds, e.g.,
2251:
1578:
1513:
6697:
6184:
527:
contributes 268 kJ/mol. and the second pi bond 202 kJ/mol. Bonding is usually discussed in the context of
6623:
6594:
6574:
6527:
5590:
5180:
3301:
2228:
5136:
1954:
1485:
6212:
5131:
5065:
1910:
1027:
6967:
6883:
6522:
5627:
3136:
Hintermann, Lukas; Labonne, AurĂŠlie (2007). "Catalytic
Hydration of Alkynes and Its Application in Synthesis".
528:
2982:
Dreher, Eberhard-Ludwig; Torkelson, Theodore R.; Beutel, Klaus K. (2011). "Chlorethanes and
Chloroethylenes".
672:
is used when there are two triple bonds, and so on. The position of unsaturation is indicated by a numerical
6905:
6816:
6779:
6663:
6589:
6410:
6393:
6336:
6100:
3693:
2905:
44:
821:
6823:
6811:
6702:
6567:
6341:
6207:
6000:
4643:
4041:
3623:
3562:
3457:
2101:
1488:
to form the aldehyde. This reaction was once a major industrial process but it has been displaced by the
6972:
6869:
6854:
6784:
6707:
6539:
6489:
6398:
6323:
6222:
6107:
5995:
4768:
4704:
4638:
4031:
3294:
817:
813:
809:
653:
625:
544:
434:
are 180°. By virtue of this bond angle, alkynes are rod-like. Correspondingly, cyclic alkynes are rare.
7074:
4026:
3547:
1921:. This general reaction has been extensively developed. Electrophilic alkynes are especially effective
991:
781:
4013:
3534:
6962:
6917:
6692:
6512:
6442:
6199:
6179:
6076:
5521:
5146:
5126:
5024:
4222:
4021:
3605:
3244:
2525:
2212:
1938:
587:
559:
Internal alkynes feature carbon substituents on each acetylenic carbon. Symmetrical examples include
1464:. While this method has been abandoned in the West, it remains the main production method in China.
6985:
6939:
6864:
6837:
6735:
6717:
6670:
6608:
6504:
6484:
6353:
6348:
6249:
5382:
5051:
4550:
4053:
3574:
2622:
2540:, the first naturally occurring acetylenic compound, dehydromatricaria ester, was isolated from an
1918:
1493:
971:
532:
531:, which recognizes the triple bond as arising from overlap of s and p orbitals. In the language of
367:
7081:
4099:
7062:
7028:
6890:
6859:
6740:
6682:
6380:
6363:
6358:
6313:
6276:
6266:
6227:
5161:
5121:
5101:
4737:
4694:
4114:
4109:
4094:
3679:
3552:
3542:
3153:
2537:
2495:
1473:
1442:
657:
4183:
4152:
3931:
3921:
3806:
3171:
Annabelle L. K. Shi Shun; Rik R. Tykwinski (2006). "Synthesis of
Naturally Occurring Polyynes".
4188:
4167:
4162:
3946:
3941:
3936:
3926:
3821:
3816:
3811:
3801:
3467:
7043:
7008:
6991:
6929:
6847:
6842:
6770:
6755:
6725:
6646:
6613:
6584:
6579:
6554:
6544:
6464:
6452:
6331:
6244:
6066:
6036:
5794:
5416:
5111:
4628:
4600:
4443:
4203:
4198:
4036:
3557:
3272:
3211:
3188:
3109:
3087:
3051:
2997:
2960:
2934:
2911:
2850:
2828:
2790:
2765:
2709:
2676:
2542:
2362:
2350:
1970:
1457:
1449:
1065:
842:
801:
701:
649:
560:
467:
375:
344:
7120:
7086:
7003:
6658:
6517:
6494:
6447:
6388:
5771:
5265:
5203:
4761:
4592:
3262:
3252:
3180:
3145:
3118:
3079:
3027:
2989:
2886:
2859:
2820:
2742:
2701:
2574:
2319:
1966:
1115:
1057:
1053:
955:
371:
2609:. A carbonâcarbon triple bond is also present in marketed drugs such as the antiretroviral
688:". The final "-e" disappears if it is followed by another suffix that starts with a vowel.
6944:
6900:
6895:
6789:
6765:
6599:
6562:
6415:
6405:
6288:
5990:
5749:
5744:
5727:
5710:
5511:
5260:
5156:
5029:
4742:
4699:
4608:
4482:
3447:
3437:
2658:
2358:
2334:
2105:
1950:
1500:
1119:
979:
583:
2100:
Oxidative cleavage of alkynes proceeds via cycloaddition to metal oxides. Most famously,
1118:
is widely recommended to avoid formation of the alkane, for example in the conversion of
3248:
6828:
6806:
6801:
6796:
6751:
6747:
6730:
6687:
6618:
6479:
6474:
6459:
6271:
6189:
6061:
6056:
5932:
5927:
5922:
5715:
5682:
5466:
5448:
5438:
4673:
4668:
4633:
4584:
4490:
3462:
3452:
2315:
2117:
1930:
1489:
1461:
2227:
This reactivity exploits the fact that terminal alkynes are weak acids, whose typical
1007:
7114:
7033:
6922:
6878:
6603:
6437:
6432:
6425:
6303:
6081:
6029:
5960:
5846:
5836:
5831:
5821:
5816:
5766:
5761:
5677:
5672:
5662:
5516:
5471:
5433:
5421:
5392:
5270:
5106:
5091:
4350:
4157:
4147:
3643:
3267:
3232:
3019:
2625:, generating highly reactive radical intermediates that attack DNA within the tumor.
2618:
2591:
2562:
2507:
1906:
1481:
1088:
1061:
1019:
536:
516:
3157:
1937:
compound. Other specialized cycloadditions include multicomponent reactions such as
1064:, who in 1955 wrote the first book describing their versatility as intermediates in
601:
values of around 25. They are far more acidic than alkenes and alkanes, which have p
6910:
6760:
6675:
6651:
6641:
6633:
6534:
6469:
6368:
6217:
6012:
5899:
5894:
5871:
5622:
5461:
5387:
5324:
5319:
5297:
5253:
5238:
5228:
5116:
5096:
5055:
4456:
4420:
4316:
4089:
4079:
3988:
3978:
3968:
3509:
3499:
3489:
2606:
2556:
2551:
2499:
2308:
1504:
1477:
1127:
1041:
995:
967:
3083:
974:. The reaction provides a means to generate alkynes from alkenes, which are first
6308:
6071:
6024:
5985:
5866:
5754:
5739:
5734:
5722:
5287:
5282:
5248:
5243:
5233:
5211:
4504:
4461:
4434:
4368:
4331:
4250:
4104:
4084:
4071:
4003:
3998:
3993:
3983:
3973:
3960:
3791:
3524:
3519:
3514:
3504:
3494:
3481:
3317:
3046:
2955:
2639:
2614:
1965:. Cycloaddition processes involving alkynes are often catalyzed by metals, e.g.
987:
975:
846:
633:
512:
419:
363:
355:
17:
331:
6934:
5980:
5971:
5851:
5806:
5702:
5667:
5657:
5597:
5533:
5456:
5404:
5042:
4563:
4451:
4255:
4142:
4132:
4061:
3796:
3618:
3613:
3588:
3442:
3432:
2602:. 1-Phenylhepta-1,3,5-triyne is illustrative of a naturally occurring triyne.
2599:
2595:
2579:
2484:{\displaystyle {\ce {2R-\!{\equiv }\!-H->R-\!{\equiv }\!-\!{\equiv }\!-R}}}
1922:
1764:
586:(propyne using IUPAC nomenclature). They are often prepared by alkylation of
548:
520:
431:
3122:
2993:
2890:
2863:
2824:
2746:
6996:
6298:
6163:
5947:
5861:
5826:
5811:
5799:
5642:
5617:
5426:
5086:
5046:
4880:
4875:
4795:
4568:
4306:
4275:
4265:
4260:
4137:
3865:
3653:
3648:
3427:
3257:
2610:
2587:
1107:
777:
773:
719:
685:
613:
609:
591:
568:
540:
439:
336:
91:
3192:
3184:
3045:
Mizushima, E.; Cui, D.-M.; Nath, D. C. D.; Hayashi, T.; Tanaka, M. (2005).
2915:
1448:
Addition of hydrogen halides has long been of interest. In the presence of
3276:
3149:
7018:
5955:
5909:
5876:
5572:
5478:
5352:
5307:
5292:
5006:
5001:
4960:
4955:
4914:
4909:
4904:
4851:
4846:
4732:
4727:
4537:
4529:
4521:
4401:
4393:
4385:
4336:
4321:
4311:
4301:
4296:
4270:
4193:
3905:
3885:
3735:
3663:
3658:
3638:
2583:
2503:
1962:
1942:
1934:
1926:
1453:
1438:
1023:
838:
805:
797:
757:
753:
564:
488:
325:
6131:
3031:
2698:
March's
Advanced Organic Chemistry: Reactions, Mechanisms, and Structure
7038:
5917:
5841:
5692:
5687:
5652:
5637:
5632:
5602:
5585:
5409:
5336:
5302:
4921:
4858:
4812:
4689:
4663:
4513:
4358:
4291:
3890:
3880:
3870:
3760:
3750:
3740:
3628:
3594:
3582:
3396:
3386:
3376:
3366:
2705:
2547:
2242:
2238:
1974:
1760:
1324:
1206:{\displaystyle {\ce {RC#CR' + H2 ->}}{\text{ cis-}}{\ce {RCH=CR'H}}}
1123:
999:
983:
736:
669:
524:
435:
187:
1097:
6005:
5937:
5781:
5490:
5483:
5377:
5358:
5347:
5277:
5037:
5033:
4984:
4967:
4938:
4887:
4829:
4558:
4477:
4377:
4326:
3900:
3895:
3875:
3775:
3770:
3765:
3755:
3745:
3706:
3633:
3411:
3406:
3401:
3391:
3381:
3371:
3336:
2568:
2408:
1946:
1111:
1092:
1031:
697:
681:
673:
629:
451:
411:
359:
35:
31:
5172:
3231:
S. Walker; R. Landovitz; W.D. Ding; G.A. Ellestad; D. Kahne (1992).
2848:
Kenneth N. Campbell, Barbara K. Campbell (1950). "Phenylacetylene".
2415:
1744:{\displaystyle {\ce {HC#C(CH2)5C#CH + 2H2O -> CH3CO(CH2)5COCH3}}}
1437:
of alkynes gives vinylic boranes which oxidize to the corresponding
1323:
Alkynes characteristically are capable of adding two equivalents of
2605:
Alkynes occur in some pharmaceuticals, including the contraceptive
1098:
395:. Alkynes are traditionally known as acetylenes, although the name
5886:
5856:
5789:
5647:
5612:
5607:
5580:
5528:
5495:
5399:
5223:
4242:
4208:
4124:
1914:
640:
466:
330:
2785:
The
Commission on the Nomenclature of Organic Chemistry (1971) .
1091:, stopping after the addition of only one equivalent to give the
7013:
5314:
3233:"Cleavage behavior of calicheamicin gamma 1 and calicheamicin T"
2634:
665:
644:
6135:
5176:
4757:
3290:
3286:
7023:
1130:
of alkynes gives the alkene dihalides or alkyl tetrahalides:
841:. Hundreds of millions of kilograms are produced annually by
1925:. The "cycloadduct" derived from the addition of alkynes to
2215:, terminal alkynes are coupled with aryl or vinyl halides:
1433:
is general for silanes, boranes, and related hydrides. The
1095:, is usually more desirable since alkanes are less useful:
4753:
2325:
The reactions of alkynes with certain metal cations, e.g.
944:{\displaystyle {\ce {2 CH4 + 3/2 O2 -> HC#CH + 3 H2O}}}
612:
generated by deprotonation of terminal alkynes are called
547:. Overlap of an sp orbital from each atom forms one spâsp
499:, the strained cycloheptyne. Triple bonds are highlighted
495:, the naturally occurring 1-phenylhepta-1,3,5-triyne, and
3047:"Au(I)-Catalyzed hydratation of alkynes: 2,8-nonanedione"
2438:
2191:
2178:
2145:
2090:{\displaystyle {\ce {RC#CR + R'C#CR' <=> 2RC#CR'}}}
1883:
1857:
1804:
1737:
1724:
1711:
1690:
1671:
1640:
1627:
1590:
catalyzes hydration of 1,8-nonadiyne to 2,8-nonanedione:
1561:
1542:
1408:
1387:
1371:
1291:
1270:
1254:
1170:
934:
900:
874:
2956:"Palladium catalyst for partial reduction of acetylenes"
2201:{\displaystyle {\ce {2CH2O + HC#CH -> HOCH2CCCH2OH}}}
1415:{\displaystyle {\ce {RC#CR' + 2 Br2 -> RCBr2CR'Br2}}}
954:
Propyne, also industrially useful, is also prepared by
2047:
1828:
880:
2374:
2254:
2129:
1986:
1957:. Non-carbon reagents also undergo cyclization, e.g.
1776:
1599:
1516:
1492:. This reaction occurs in nature, the catalyst being
1336:
1298:{\displaystyle {\ce {RCH=CR'H + H2 -> RCH2CR'H2}}}
1220:
1139:
858:
288:
278:
246:
236:
197:
150:
140:
101:
47:
27:
Hydrocarbon compound containing one or more CâĄC bonds
1890:{\displaystyle {\ce {HC#C-CH3 <=> CH2=C=CH2}}}
648:
is used to denote the presence of a triple bond. In
6955:
6716:
6632:
6553:
6503:
6379:
6322:
6198:
6049:
5969:
5946:
5908:
5885:
5780:
5701:
5571:
5548:
5504:
5447:
5370:
5345:
5210:
5079:
5017:
4720:
4682:
4656:
4621:
4577:
4549:
4512:
4503:
4470:
4442:
4433:
4413:
4376:
4367:
4349:
4284:
4241:
4232:
4221:
4176:
4123:
4070:
4052:
4012:
3959:
3914:
3858:
3834:
3784:
3728:
3705:
3692:
3672:
3604:
3573:
3533:
3480:
3420:
3359:
3335:
3324:
2297:{\displaystyle {\ce {RC#CH + MX -> RC#CM + HX}}}
2483:
2296:
2200:
2089:
1889:
1743:
1568:{\displaystyle {\ce {PhC#CH + H2O -> PhCOCH3}}}
1567:
1414:
1297:
1205:
943:
315:
177:
81:
3107:K. StĂśckel and F. Sondheimer (1974). "Annulene".
2471:
2465:
2459:
2453:
2394:
2388:
2055:
2054:
2037:
2036:
1836:
1835:
1818:
1817:
438:cannot be isolated. The CâĄC bond distance of 118
418:. Like other hydrocarbons, alkynes are generally
2910:. London: Butterworths Scientific Publications.
2598:. These compounds are highly bioactive, e.g. as
1945:compounds and the -cycloaddition of an alkyne,
370:alkynes with only one triple bond and no other
3075:Ullmann's Encyclopedia of Industrial Chemistry
2985:Ullmann's Encyclopedia of Industrial Chemistry
2816:Ullmann's Encyclopedia of Industrial Chemistry
6147:
5188:
4769:
3302:
1759:Terminal alkyl alkynes exhibit tautomerism.
8:
2237:values around 25 place them between that of
567:. They may also be asymmetrical, such as in
462:) or the CâC bond in alkanes (153 pm).
450:) is much shorter than the C=C distance in
6154:
6140:
6132:
5568:
5367:
5195:
5181:
5173:
4776:
4762:
4754:
4509:
4439:
4373:
4364:
4238:
4229:
3855:
3725:
3702:
3356:
3332:
3309:
3295:
3287:
2333:also gives acetylides. Thus, few drops of
990:followed by treatment of the resulting of
978:and then dehydrohalogenated. For example,
5061:FritschâButtenbergâWiechell rearrangement
3266:
3256:
2907:Acetylenic compounds in organic synthesis
2808:
2806:
2764:(2nd ed.). McGraw-Hill. p. 57.
2472:
2466:
2460:
2454:
2448:
2437:
2432:
2421:
2416:
2409:
2403:
2395:
2389:
2383:
2379:
2375:
2373:
2279:
2259:
2255:
2253:
2190:
2185:
2177:
2172:
2157:
2144:
2139:
2134:
2130:
2128:
2073:
2069:
2056:
2049:
2048:
2046:
2038:
2031:
2029:
2028:
2026:
2013:
1991:
1987:
1985:
1882:
1877:
1868:
1860:
1856:
1851:
1837:
1830:
1829:
1827:
1819:
1812:
1810:
1809:
1807:
1803:
1798:
1789:
1781:
1777:
1775:
1736:
1731:
1723:
1718:
1710:
1705:
1697:
1689:
1684:
1670:
1665:
1660:
1646:
1639:
1634:
1626:
1621:
1613:
1604:
1600:
1598:
1560:
1555:
1541:
1536:
1521:
1517:
1515:
1480:. The reaction proceeds by formation of
1407:
1402:
1386:
1381:
1370:
1365:
1360:
1341:
1337:
1335:
1319:Addition of halogens and related reagents
1290:
1285:
1269:
1264:
1253:
1248:
1225:
1221:
1219:
1186:
1182:
1177:
1169:
1164:
1144:
1140:
1138:
1114:catalyst). For more complex alkynes, the
1016:FritschâButtenbergâWiechell rearrangement
962:Dehydrohalogenation and related reactions
933:
928:
923:
909:
899:
894:
873:
868:
863:
859:
857:
535:, the carbon atoms in an alkyne bond are
304:
303:
295:
289:
279:
273:
266:
261:
253:
247:
237:
231:
224:
219:
210:
202:
198:
196:
166:
165:
157:
151:
141:
135:
128:
123:
114:
106:
102:
100:
70:
69:
60:
52:
48:
46:
4994:
4990:
4977:
4973:
4948:
4944:
4931:
4927:
4897:
4893:
4868:
4864:
4839:
4835:
4822:
4818:
4805:
4801:
2729:K. N. Campbell, B. K. Campbell (1950). "
2696:Smith, Michael B.; March, Jerry (2006).
2344:
2340:
1585:
1581:
1311:
1083:
1044:are susceptible to dehydrohalogenation.
792:
788:
768:
764:
748:
744:
731:
727:
714:
710:
577:
406:
402:
387:
381:
2651:
2112:Reactions specific for terminal alkynes
2030:
1811:
1315:to internal alkynes gives cis-alkenes.
966:Alkynes are prepared from 1,1- and 1,2-
523:contributes 369 kJ/mol, the first
82:{\displaystyle {\ce {H-C#C}}{\ce {-H}}}
2933:. Great Britain: Collins. p. 82.
2789:(3rd ed.). London: Butterworths.
2675:. Vol. 1. John Wiley & Sons.
7:
7069:
2931:Modern Organic Chemistry for A-level
2502:in general, terminal alkynes add to
7093:
378:with the general chemical formula
5142:Azide-alkyne Huisgen cycloaddition
1959:azide alkyne Huisgen cycloaddition
1308:The addition of one equivalent of
574:Terminal alkynes have the formula
539:: they each have two unhybridized
287:
272:
245:
230:
149:
134:
25:
2904:Raphael, Ralph Alexander (1955).
2787:Nomenclature of Organic Chemistry
1973:, which allows the scrambling of
1048:Reactions, including applications
594:itself, are mildly acidic, with p
7092:
7080:
7068:
7057:
7056:
2219:
1006:
626:systematic chemical nomenclature
2520:Transition metal alkyne complex
1022:. Alkynes can be prepared from
2954:H. Lindlar; R. Dubuis (1973).
2929:Rosser & Williams (1977).
2532:Alkynes in nature and medicine
2428:
2422:
2273:
2165:
2104:converts alkynes to a pair of
2057:
2032:
1838:
1813:
1714:
1698:
1677:
1630:
1614:
1548:
1374:
1257:
1173:
1056:, alkynes participate in many
903:
296:
274:
254:
232:
158:
136:
1:
6421:Interface and colloid science
6175:Glossary of chemical formulae
5071:SeyferthâGilbert homologation
3084:10.1002/14356007.a01_097.pub3
2762:Organic Chemistry Demystified
2673:The CarbonâCarbon Triple Bond
2586:families). Some examples are
1036:SeyferthâGilbert homologation
555:Terminal and internal alkynes
479:, two depictions of propyne,
1901:Cycloadditions and oxidation
1060:. Such use was pioneered by
1018:, alkynes are prepared from
696:Alkynes having four or more
399:also refers specifically to
6698:Bioorganometallic chemistry
6185:List of inorganic compounds
5152:CadiotâChodkiewicz coupling
2355:CadiotâChodkiewicz coupling
2335:diamminesilver(I) hydroxide
1763:exists in equilibrium with
680:Sometimes a number between
652:, the suffix often follows
7137:
6624:Dynamic covalent chemistry
6595:Enantioselective synthesis
6575:Physical organic chemistry
6528:Organolanthanide chemistry
2970:, vol. 5, p. 880
2517:
1445:the substrate is a thiol.
29:
7052:
6213:Electroanalytical methods
6170:
6090:
4791:
2760:Bloch, Daniel R. (2012).
2661:. EncyclopĂŚdia Britannica
2578:and other members of the
1425:The addition of nonpolar
700:atoms can form different
590:. Terminal alkynes, like
6968:Nobel Prize in Chemistry
6884:Supramolecular chemistry
6523:Organometallic chemistry
3123:10.15227/orgsyn.054.0001
2994:10.1002/14356007.o06_o01
2891:10.15227/orgsyn.059.0010
2864:10.15227/orgsyn.030.0072
2825:10.1002/14356007.a04_455
2747:10.15227/orgsyn.030.0015
2671:Saul Patai, ed. (1978).
1905:Alkynes undergo diverse
529:molecular orbital theory
430:In acetylene, the HâCâĄC
358:containing at least one
30:Not to be confused with
6906:Combinatorial chemistry
6817:Food physical chemistry
6780:Environmental chemistry
6664:Bioorthogonal chemistry
6590:Retrosynthetic analysis
6411:Chemical thermodynamics
6394:Spectroelectrochemistry
6337:Computational chemistry
6101:chemical classification
3258:10.1073/pnas.89.10.4608
3210:. Amsterdam: Elsevier.
3078:. Weinheim: Wiley-VCH.
2988:. Weinheim: Wiley-VCH.
2819:. Weinheim: Wiley-VCH.
1327:and hydrogen halides.
668:" ending with "-yne").
6978:of element discoveries
6824:Agricultural chemistry
6812:Carbohydrate chemistry
6703:Bioinorganic chemistry
6568:Alkane stereochemistry
6513:Coordination chemistry
6342:Mathematical chemistry
6208:Instrumental chemistry
4644:1,3,5-Triheptylbenzene
3237:Proc Natl Acad Sci USA
3185:10.1002/anie.200502071
2506:compounds to give the
2485:
2443:
2298:
2202:
2102:potassium permanganate
2091:
1891:
1745:
1569:
1416:
1299:
1207:
1102:
1030:and from aldehydes or
982:can be generated from
945:
515:is very strong with a
506:
471:Illustrative alkynes:
340:
339:), the simplest alkyne
335:A 3D model of ethyne (
317:
179:
83:
6973:Timeline of chemistry
6870:Post-mortem chemistry
6855:Clandestine chemistry
6785:Atmospheric chemistry
6708:Biophysical chemistry
6540:Solid-state chemistry
6490:Equilibrium chemistry
6399:Photoelectrochemistry
6108:chemical nomenclature
5137:PausonâKhand reaction
4639:1,3,5-Triethylbenzene
3150:10.1055/s-2007-966002
2486:
2404:
2299:
2203:
2092:
1955:PausonâKhand reaction
1892:
1746:
1570:
1417:
1300:
1208:
1101:
1052:Featuring a reactive
946:
822:3,3-dimethyl-1-butyne
470:
426:Structure and bonding
334:
318:
180:
84:
6963:History of chemistry
6918:Chemical engineering
6693:Bioorganic chemistry
6443:Structural chemistry
6180:List of biomolecules
5147:Sonogashira coupling
5132:DielsâAlder reaction
5127:Alkyne trimerisation
5066:CoreyâFuchs reaction
4042:Isopropylcyclohexene
3624:Perhydrophenanthrene
3563:Isopropylcyclohexane
3206:Lam, Jørgen (1988).
3173:Angew. Chem. Int. Ed
2526:alkyne trimerization
2372:
2252:
2213:Sonogashira reaction
2127:
1984:
1939:alkyne trimerisation
1911:DielsâAlder reaction
1774:
1597:
1514:
1334:
1218:
1137:
1028:CoreyâFuchs reaction
856:
692:Structural isomerism
588:monosodium acetylide
410:, known formally as
195:
99:
45:
6986:The central science
6940:Ceramic engineering
6865:Forensic toxicology
6838:Chemistry education
6736:Radiation chemistry
6718:Interdisciplinarity
6671:Medicinal chemistry
6609:Fullerene chemistry
6485:Microwave chemistry
6354:Molecular mechanics
6349:Molecular modelling
5564:not C, H or O)
5052:Dehydrohalogenation
4738:Alicyclic compounds
4551:Tetramethylbenzenes
3249:1992PNAS...89.4608W
3032:10.1021/jo00011a058
2623:Bergman cyclization
2613:and the antifungal
2442:
2440:
2414:
2193:
2180:
2147:
2043:
1919:1,4-cyclohexadienes
1885:
1859:
1824:
1806:
1739:
1726:
1713:
1692:
1673:
1642:
1629:
1563:
1544:
1494:acetylene hydratase
1476:of acetylene gives
1410:
1389:
1373:
1293:
1272:
1256:
1172:
972:dehydrohalogenation
936:
902:
876:
658:inorganic compounds
533:valence bond theory
519:of 839 kJ/mol. The
454:(132 pm, for C
7029:Chemical substance
6891:Chemical synthesis
6860:Forensic chemistry
6741:Actinide chemistry
6683:Clinical chemistry
6364:Molecular geometry
6359:Molecular dynamics
6314:Elemental analysis
6267:Separation process
6006:Hypervalent iodine
5162:Favorskii reaction
5122:Thiol-yne reaction
4695:Cyclopropenylidene
4032:Methylcyclopentene
4022:Methylcyclopropene
3553:Methylcyclopentane
3543:Methylcyclopropane
2733:-Butylacetylene".
2706:10.1002/0470084960
2538:Ferdinand Bohlmann
2496:Favorskii reaction
2481:
2420:
2351:coupling reactions
2294:
2198:
2181:
2168:
2135:
2087:
2062:
1887:
1873:
1847:
1843:
1794:
1741:
1727:
1701:
1696:
1680:
1661:
1617:
1612:
1565:
1551:
1532:
1474:hydration reaction
1443:thiol-yne reaction
1441:or ketone. In the
1412:
1398:
1377:
1361:
1295:
1281:
1260:
1244:
1203:
1160:
1103:
958:of hydrocarbons.
941:
924:
890:
889:
864:
818:3-methyl-1-pentyne
814:4-methyl-2-pentyne
810:4-methyl-1-pentyne
702:structural isomers
654:IUPAC nomenclature
639:In chemistry, the
545:sp hybrid orbitals
507:
416:IUPAC nomenclature
341:
313:
294:
286:
284:
252:
244:
242:
175:
156:
148:
146:
79:
7108:
7107:
7044:Quantum mechanics
7009:Chemical compound
6992:Chemical reaction
6930:Materials science
6848:General chemistry
6843:Amateur chemistry
6771:Photogeochemistry
6756:Stellar chemistry
6726:Nuclear chemistry
6647:Molecular biology
6614:Polymer chemistry
6585:Organic synthesis
6580:Organic reactions
6545:Ceramic chemistry
6535:Cluster chemistry
6465:Chemical kinetics
6453:Molecular physics
6332:Quantum chemistry
6245:Mass spectrometry
6129:
6128:
6067:Sulfenyl chloride
6045:
6044:
5544:
5543:
5363:(only C, H and O)
5204:Functional groups
5170:
5169:
5112:Hydrohalogenation
4751:
4750:
4716:
4715:
4652:
4651:
4629:Hexamethylbenzene
4617:
4616:
4499:
4498:
4444:Trimethylbenzenes
4429:
4428:
4345:
4344:
4217:
4216:
4204:Cyclododecatriene
4199:Cyclooctatetraene
4037:Methylcyclohexene
4027:Methylcyclobutene
4014:Alkylcycloalkenes
3955:
3954:
3830:
3829:
3688:
3687:
3558:Methylcyclohexane
3548:Methylcyclobutane
3535:Alkylcycloalkanes
3476:
3475:
3110:Organic Syntheses
3052:Organic Syntheses
2968:Collected Volumes
2961:Organic Syntheses
2879:Organic Syntheses
2851:Organic Syntheses
2771:978-0-07-176797-2
2735:Organic Syntheses
2479:
2447:
2427:
2419:
2412:
2402:
2382:
2363:Eglinton coupling
2292:
2286:
2278:
2272:
2266:
2258:
2196:
2184:
2171:
2164:
2156:
2150:
2138:
2081:
2072:
2064:
2021:
2012:
2005:
1998:
1990:
1971:alkyne metathesis
1876:
1867:
1850:
1845:
1797:
1788:
1780:
1730:
1704:
1695:
1683:
1676:
1664:
1653:
1645:
1620:
1611:
1603:
1554:
1547:
1535:
1528:
1520:
1458:hydrogen chloride
1450:mercuric chloride
1401:
1393:
1380:
1364:
1349:
1340:
1284:
1276:
1263:
1247:
1240:
1233:
1224:
1201:
1194:
1185:
1180:
1163:
1152:
1143:
1058:organic reactions
992:styrene dibromide
939:
927:
916:
908:
893:
888:
867:
843:partial oxidation
782:3-methyl-1-butyne
650:organic chemistry
561:diphenylacetylene
376:homologous series
372:functional groups
345:organic chemistry
311:
301:
300:
292:
285:
282:
271:
268:
259:
258:
250:
243:
240:
229:
226:
217:
209:
201:
173:
163:
162:
154:
147:
144:
133:
130:
121:
113:
105:
77:
67:
59:
51:
16:(Redirected from
7128:
7096:
7095:
7084:
7072:
7071:
7060:
7059:
7004:Chemical element
6659:Chemical biology
6518:Magnetochemistry
6495:Mechanochemistry
6448:Chemical physics
6389:Electrochemistry
6294:Characterization
6156:
6149:
6142:
6133:
6096:
6001:Trifluoromethoxy
5569:
5565:
5368:
5364:
5217:
5197:
5190:
5183:
5174:
4997:
4980:
4951:
4934:
4900:
4871:
4842:
4825:
4808:
4778:
4771:
4764:
4755:
4708:-Propenylbenzene
4510:
4440:
4374:
4365:
4239:
4230:
3915:Branched alkynes
3856:
3785:Branched alkenes
3726:
3703:
3606:Polycycloalkanes
3591:(bicycloheptane)
3585:(bicyclopentane)
3421:Branched alkanes
3357:
3333:
3311:
3304:
3297:
3288:
3281:
3280:
3270:
3260:
3228:
3222:
3221:
3203:
3197:
3196:
3179:(7): 1034â1057.
3168:
3162:
3161:
3144:(8): 1121â1150.
3133:
3127:
3125:
3104:
3098:
3097:
3068:
3062:
3060:
3042:
3036:
3035:
3014:
3008:
3007:
2979:
2973:
2971:
2964:
2951:
2945:
2944:
2926:
2920:
2919:
2901:
2895:
2894:
2874:
2868:
2866:
2845:
2839:
2838:
2810:
2801:
2800:
2782:
2776:
2775:
2757:
2751:
2750:
2726:
2720:
2719:
2693:
2687:
2686:
2668:
2662:
2656:
2490:
2488:
2487:
2482:
2480:
2477:
2476:
2470:
2464:
2458:
2452:
2445:
2444:
2441:
2439:
2436:
2431:
2425:
2417:
2413:
2410:
2400:
2399:
2393:
2387:
2380:
2353:, including the
2348:
2332:
2328:
2303:
2301:
2300:
2295:
2293:
2290:
2284:
2283:
2276:
2270:
2264:
2263:
2256:
2223:
2207:
2205:
2204:
2199:
2197:
2194:
2192:
2189:
2182:
2179:
2176:
2169:
2162:
2161:
2154:
2148:
2146:
2143:
2136:
2106:carboxylic acids
2096:
2094:
2093:
2088:
2086:
2085:
2079:
2077:
2070:
2065:
2063:
2061:
2060:
2053:
2045:
2044:
2042:
2035:
2027:
2025:
2019:
2017:
2010:
2009:
2003:
1996:
1995:
1988:
1967:enyne metathesis
1896:
1894:
1893:
1888:
1886:
1884:
1881:
1874:
1872:
1865:
1864:
1858:
1855:
1848:
1846:
1844:
1842:
1841:
1834:
1826:
1825:
1823:
1816:
1808:
1805:
1802:
1795:
1793:
1786:
1785:
1778:
1750:
1748:
1747:
1742:
1740:
1738:
1735:
1728:
1725:
1722:
1717:
1712:
1709:
1702:
1693:
1691:
1688:
1681:
1674:
1672:
1669:
1662:
1651:
1650:
1643:
1641:
1638:
1633:
1628:
1625:
1618:
1609:
1608:
1601:
1588:
1574:
1572:
1571:
1566:
1564:
1562:
1559:
1552:
1545:
1543:
1540:
1533:
1526:
1525:
1518:
1456:, acetylene and
1432:
1428:
1421:
1419:
1418:
1413:
1411:
1409:
1406:
1399:
1397:
1391:
1388:
1385:
1378:
1372:
1369:
1362:
1353:
1347:
1345:
1338:
1314:
1304:
1302:
1301:
1296:
1294:
1292:
1289:
1282:
1280:
1274:
1271:
1268:
1261:
1255:
1252:
1245:
1238:
1237:
1231:
1229:
1222:
1212:
1210:
1209:
1204:
1202:
1199:
1198:
1192:
1190:
1183:
1181:
1178:
1176:
1171:
1168:
1161:
1156:
1150:
1148:
1141:
1116:Lindlar catalyst
1086:
1054:functional group
1010:
956:thermal cracking
950:
948:
947:
942:
940:
937:
935:
932:
925:
914:
913:
906:
901:
898:
891:
881:
875:
872:
865:
795:
771:
751:
734:
717:
582:. An example is
581:
504:
409:
394:
322:
320:
319:
314:
312:
309:
308:
302:
299:
293:
290:
283:
280:
277:
269:
267:
265:
260:
257:
251:
248:
241:
238:
235:
227:
225:
223:
218:
215:
214:
207:
206:
199:
184:
182:
181:
176:
174:
171:
170:
164:
161:
155:
152:
145:
142:
139:
131:
129:
127:
122:
119:
118:
111:
110:
103:
88:
86:
85:
80:
78:
75:
74:
68:
65:
64:
57:
56:
49:
21:
18:Alkyne hydration
7136:
7135:
7131:
7130:
7129:
7127:
7126:
7125:
7111:
7110:
7109:
7104:
7048:
6951:
6945:Polymer science
6901:Click chemistry
6896:Green chemistry
6790:Ocean chemistry
6766:Biogeochemistry
6712:
6628:
6600:Total synthesis
6563:Stereochemistry
6549:
6499:
6416:Surface science
6406:Thermochemistry
6375:
6318:
6289:Crystallography
6194:
6166:
6160:
6130:
6125:
6094:
6086:
6041:
5996:Trichloromethyl
5991:Trifluoromethyl
5965:
5942:
5904:
5881:
5776:
5745:Phosphine oxide
5697:
5563:
5561:
5560:
5558:
5556:
5554:
5552:
5550:
5540:
5500:
5443:
5362:
5361:
5356:
5351:
5341:
5215:
5214:
5206:
5201:
5171:
5166:
5157:Glaser coupling
5075:
5030:Dehydrogenation
5013:
4996:
4992:
4988:
4979:
4975:
4971:
4950:
4946:
4942:
4933:
4929:
4925:
4899:
4895:
4891:
4870:
4866:
4862:
4841:
4837:
4833:
4824:
4820:
4816:
4807:
4803:
4799:
4787:
4782:
4752:
4747:
4743:Petroleum jelly
4712:
4700:Phenylacetylene
4678:
4648:
4613:
4609:Isobutylbenzene
4573:
4545:
4495:
4466:
4425:
4409:
4363:
4341:
4280:
4224:
4213:
4172:
4119:
4066:
4048:
4008:
3951:
3910:
3852:
3844:
3838:
3826:
3780:
3722:
3715:
3709:
3698:
3696:
3684:
3668:
3600:
3597:(bicyclodecane)
3569:
3529:
3472:
3438:3-Methylpentane
3416:
3353:
3345:
3339:
3328:
3326:
3320:
3315:
3285:
3284:
3243:(10): 4608â12.
3230:
3229:
3225:
3218:
3205:
3204:
3200:
3170:
3169:
3165:
3135:
3134:
3130:
3106:
3105:
3101:
3094:
3070:
3069:
3065:
3044:
3043:
3039:
3016:
3015:
3011:
3004:
2981:
2980:
2976:
2966:
2953:
2952:
2948:
2941:
2928:
2927:
2923:
2903:
2902:
2898:
2876:
2875:
2871:
2847:
2846:
2842:
2835:
2812:
2811:
2804:
2797:
2784:
2783:
2779:
2772:
2759:
2758:
2754:
2728:
2727:
2723:
2716:
2695:
2694:
2690:
2683:
2670:
2669:
2665:
2657:
2653:
2648:
2631:
2534:
2522:
2516:
2514:Metal complexes
2370:
2369:
2359:Glaser coupling
2346:
2342:
2338:
2330:
2326:
2312:
2250:
2249:
2235:
2125:
2124:
2114:
2078:
2018:
2002:
1982:
1981:
1951:carbon monoxide
1909:reactions. The
1903:
1772:
1771:
1757:
1595:
1594:
1587:
1583:
1579:
1512:
1511:
1501:phenylacetylene
1470:
1430:
1426:
1390:
1346:
1332:
1331:
1321:
1313:
1309:
1273:
1230:
1216:
1215:
1191:
1149:
1135:
1134:
1120:phenylacetylene
1085:
1081:
1074:
1050:
980:phenylacetylene
964:
854:
853:
835:
830:
794:
790:
786:
770:
766:
762:
750:
746:
742:
733:
729:
725:
716:
712:
708:
694:
622:
607:
600:
584:methylacetylene
579:
575:
557:
500:
461:
457:
449:
445:
428:
408:
404:
400:
393:
385:
379:
366:. The simplest
329:
328:
193:
192:
190:
97:
96:
94:
43:
42:
39:
28:
23:
22:
15:
12:
11:
5:
7134:
7132:
7124:
7123:
7113:
7112:
7106:
7105:
7103:
7102:
7090:
7078:
7066:
7053:
7050:
7049:
7047:
7046:
7041:
7036:
7031:
7026:
7021:
7016:
7011:
7006:
7001:
7000:
6999:
6989:
6982:
6981:
6980:
6970:
6965:
6959:
6957:
6953:
6952:
6950:
6949:
6948:
6947:
6942:
6937:
6927:
6926:
6925:
6915:
6914:
6913:
6908:
6903:
6898:
6888:
6887:
6886:
6875:
6874:
6873:
6872:
6867:
6857:
6852:
6851:
6850:
6845:
6834:
6833:
6832:
6831:
6829:Soil chemistry
6821:
6820:
6819:
6814:
6807:Food chemistry
6804:
6802:Carbochemistry
6799:
6797:Clay chemistry
6794:
6793:
6792:
6787:
6776:
6775:
6774:
6773:
6768:
6758:
6752:Astrochemistry
6748:Cosmochemistry
6745:
6744:
6743:
6738:
6733:
6731:Radiochemistry
6722:
6720:
6714:
6713:
6711:
6710:
6705:
6700:
6695:
6690:
6688:Neurochemistry
6685:
6680:
6679:
6678:
6668:
6667:
6666:
6656:
6655:
6654:
6649:
6638:
6636:
6630:
6629:
6627:
6626:
6621:
6619:Petrochemistry
6616:
6611:
6606:
6597:
6592:
6587:
6582:
6577:
6572:
6571:
6570:
6559:
6557:
6551:
6550:
6548:
6547:
6542:
6537:
6532:
6531:
6530:
6520:
6515:
6509:
6507:
6501:
6500:
6498:
6497:
6492:
6487:
6482:
6480:Spin chemistry
6477:
6475:Photochemistry
6472:
6467:
6462:
6460:Femtochemistry
6457:
6456:
6455:
6445:
6440:
6435:
6430:
6429:
6428:
6418:
6413:
6408:
6403:
6402:
6401:
6396:
6385:
6383:
6377:
6376:
6374:
6373:
6372:
6371:
6361:
6356:
6351:
6346:
6345:
6344:
6334:
6328:
6326:
6320:
6319:
6317:
6316:
6311:
6306:
6301:
6296:
6291:
6286:
6285:
6284:
6279:
6272:Chromatography
6269:
6264:
6263:
6262:
6257:
6252:
6242:
6241:
6240:
6235:
6230:
6225:
6215:
6210:
6204:
6202:
6196:
6195:
6193:
6192:
6190:Periodic table
6187:
6182:
6177:
6171:
6168:
6167:
6161:
6159:
6158:
6151:
6144:
6136:
6127:
6126:
6124:
6123:
6122:
6121:
6116:
6104:
6097:
6091:
6088:
6087:
6085:
6084:
6082:Sulfinylamines
6079:
6074:
6069:
6064:
6062:Phosphoramides
6059:
6057:Isothiocyanate
6053:
6051:
6047:
6046:
6043:
6042:
6040:
6039:
6034:
6033:
6032:
6022:
6021:
6020:
6010:
6009:
6008:
6003:
5998:
5993:
5988:
5977:
5975:
5967:
5966:
5964:
5963:
5958:
5952:
5950:
5944:
5943:
5941:
5940:
5935:
5933:Selenenic acid
5930:
5928:Seleninic acid
5925:
5923:Selenonic acid
5920:
5914:
5912:
5906:
5905:
5903:
5902:
5897:
5891:
5889:
5883:
5882:
5880:
5879:
5874:
5869:
5864:
5859:
5854:
5849:
5844:
5839:
5834:
5829:
5824:
5819:
5814:
5809:
5804:
5803:
5802:
5792:
5786:
5784:
5778:
5777:
5775:
5774:
5769:
5764:
5759:
5758:
5757:
5747:
5742:
5737:
5732:
5731:
5730:
5720:
5719:
5718:
5716:Phosphodiester
5707:
5705:
5699:
5698:
5696:
5695:
5690:
5685:
5680:
5675:
5670:
5665:
5660:
5655:
5650:
5645:
5640:
5635:
5630:
5625:
5620:
5615:
5610:
5605:
5600:
5595:
5594:
5593:
5588:
5577:
5575:
5566:
5562:(one element,
5546:
5545:
5542:
5541:
5539:
5538:
5537:
5536:
5526:
5525:
5524:
5519:
5508:
5506:
5502:
5501:
5499:
5498:
5493:
5488:
5487:
5486:
5476:
5475:
5474:
5469:
5464:
5453:
5451:
5445:
5444:
5442:
5441:
5439:Methylenedioxy
5436:
5431:
5430:
5429:
5424:
5414:
5413:
5412:
5407:
5397:
5396:
5395:
5385:
5380:
5374:
5372:
5365:
5343:
5342:
5340:
5339:
5334:
5329:
5328:
5327:
5322:
5312:
5311:
5310:
5305:
5300:
5295:
5290:
5285:
5275:
5274:
5273:
5268:
5258:
5257:
5256:
5251:
5246:
5241:
5236:
5231:
5220:
5218:
5216:(only C and H)
5208:
5207:
5202:
5200:
5199:
5192:
5185:
5177:
5168:
5167:
5165:
5164:
5159:
5154:
5149:
5144:
5139:
5134:
5129:
5124:
5119:
5114:
5109:
5104:
5099:
5094:
5089:
5083:
5081:
5077:
5076:
5074:
5073:
5068:
5063:
5058:
5049:
5040:
5027:
5021:
5019:
5015:
5014:
5012:
5011:
5010:
5009:
5004:
4982:
4965:
4964:
4963:
4958:
4936:
4919:
4918:
4917:
4912:
4907:
4885:
4884:
4883:
4878:
4856:
4855:
4854:
4849:
4827:
4810:
4792:
4789:
4788:
4783:
4781:
4780:
4773:
4766:
4758:
4749:
4748:
4746:
4745:
4740:
4735:
4730:
4724:
4722:
4718:
4717:
4714:
4713:
4711:
4710:
4702:
4697:
4692:
4686:
4684:
4680:
4679:
4677:
4676:
4674:4-Vinyltoluene
4671:
4669:Divinylbenzene
4666:
4660:
4658:
4654:
4653:
4650:
4649:
4647:
4646:
4641:
4636:
4634:2-Phenylhexane
4631:
4625:
4623:
4619:
4618:
4615:
4614:
4612:
4611:
4606:
4598:
4590:
4581:
4579:
4575:
4574:
4572:
4571:
4566:
4561:
4555:
4553:
4547:
4546:
4544:
4543:
4535:
4527:
4518:
4516:
4507:
4501:
4500:
4497:
4496:
4494:
4493:
4491:4-Ethyltoluene
4488:
4486:-Propylbenzene
4480:
4474:
4472:
4468:
4467:
4465:
4464:
4459:
4454:
4448:
4446:
4437:
4431:
4430:
4427:
4426:
4424:
4423:
4417:
4415:
4411:
4410:
4408:
4407:
4399:
4391:
4382:
4380:
4371:
4362:
4361:
4355:
4353:
4347:
4346:
4343:
4342:
4340:
4339:
4334:
4329:
4324:
4319:
4314:
4309:
4304:
4299:
4294:
4288:
4286:
4282:
4281:
4279:
4278:
4273:
4268:
4263:
4258:
4253:
4247:
4245:
4236:
4227:
4219:
4218:
4215:
4214:
4212:
4211:
4206:
4201:
4196:
4191:
4186:
4180:
4178:
4174:
4173:
4171:
4170:
4165:
4160:
4155:
4150:
4145:
4140:
4135:
4129:
4127:
4121:
4120:
4118:
4117:
4112:
4107:
4102:
4097:
4092:
4087:
4082:
4076:
4074:
4068:
4067:
4065:
4064:
4058:
4056:
4054:Bicycloalkenes
4050:
4049:
4047:
4046:
4044:
4039:
4034:
4029:
4024:
4018:
4016:
4010:
4009:
4007:
4006:
4001:
3996:
3991:
3986:
3981:
3976:
3971:
3965:
3963:
3957:
3956:
3953:
3952:
3950:
3949:
3944:
3939:
3934:
3929:
3924:
3918:
3916:
3912:
3911:
3909:
3908:
3903:
3898:
3893:
3888:
3883:
3878:
3873:
3868:
3862:
3860:
3859:Linear alkynes
3853:
3846:
3840:
3832:
3831:
3828:
3827:
3825:
3824:
3819:
3814:
3809:
3804:
3799:
3794:
3788:
3786:
3782:
3781:
3779:
3778:
3773:
3768:
3763:
3758:
3753:
3748:
3743:
3738:
3732:
3730:
3729:Linear alkenes
3723:
3717:
3711:
3700:
3690:
3689:
3686:
3685:
3683:
3682:
3676:
3674:
3670:
3669:
3667:
3666:
3661:
3656:
3651:
3646:
3641:
3636:
3631:
3626:
3621:
3616:
3610:
3608:
3602:
3601:
3599:
3598:
3592:
3586:
3579:
3577:
3575:Bicycloalkanes
3571:
3570:
3568:
3567:
3565:
3560:
3555:
3550:
3545:
3539:
3537:
3531:
3530:
3528:
3527:
3522:
3517:
3512:
3507:
3502:
3497:
3492:
3486:
3484:
3478:
3477:
3474:
3473:
3471:
3470:
3465:
3460:
3455:
3450:
3445:
3440:
3435:
3430:
3424:
3422:
3418:
3417:
3415:
3414:
3409:
3404:
3399:
3394:
3389:
3384:
3379:
3374:
3369:
3363:
3361:
3360:Linear alkanes
3354:
3347:
3341:
3330:
3322:
3321:
3316:
3314:
3313:
3306:
3299:
3291:
3283:
3282:
3223:
3216:
3198:
3163:
3128:
3099:
3093:978-3527306732
3092:
3063:
3037:
3009:
3003:978-3527306732
3002:
2974:
2946:
2939:
2921:
2896:
2869:
2840:
2834:978-3527306732
2833:
2802:
2795:
2777:
2770:
2752:
2721:
2714:
2700:. p. 24.
2688:
2681:
2663:
2650:
2649:
2647:
2644:
2643:
2642:
2637:
2630:
2627:
2533:
2530:
2518:Main article:
2515:
2512:
2492:
2491:
2475:
2469:
2463:
2457:
2451:
2435:
2430:
2424:
2407:
2398:
2392:
2386:
2378:
2365:shown below:
2310:
2305:
2304:
2289:
2282:
2275:
2269:
2262:
2233:
2225:
2224:
2209:
2208:
2188:
2175:
2167:
2160:
2153:
2142:
2133:
2113:
2110:
2098:
2097:
2084:
2076:
2068:
2059:
2052:
2041:
2034:
2024:
2016:
2008:
2001:
1994:
1977:(RC) centers:
1931:carbon dioxide
1902:
1899:
1898:
1897:
1880:
1871:
1863:
1854:
1840:
1833:
1822:
1815:
1801:
1792:
1784:
1756:
1753:
1752:
1751:
1734:
1721:
1716:
1708:
1700:
1687:
1679:
1668:
1659:
1656:
1649:
1637:
1632:
1624:
1616:
1607:
1576:
1575:
1558:
1550:
1539:
1531:
1524:
1490:Wacker process
1469:
1466:
1462:vinyl chloride
1460:react to give
1423:
1422:
1405:
1396:
1384:
1376:
1368:
1359:
1356:
1352:
1344:
1320:
1317:
1306:
1305:
1288:
1279:
1267:
1259:
1251:
1243:
1236:
1228:
1213:
1197:
1189:
1175:
1167:
1159:
1155:
1147:
1073:
1070:
1049:
1046:
1020:vinyl bromides
1012:
1011:
963:
960:
952:
951:
931:
922:
919:
912:
905:
897:
887:
884:
879:
871:
862:
834:
831:
829:
826:
825:
824:
784:
760:
740:
723:
693:
690:
621:
620:Naming alkynes
618:
605:
598:
556:
553:
509:
508:
459:
455:
447:
443:
427:
424:
324:
307:
298:
276:
264:
256:
234:
222:
213:
205:
186:
169:
160:
138:
126:
117:
109:
90:
73:
63:
55:
40:
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
7133:
7122:
7119:
7118:
7116:
7101:
7100:
7091:
7089:
7088:
7083:
7079:
7077:
7076:
7067:
7065:
7064:
7055:
7054:
7051:
7045:
7042:
7040:
7037:
7035:
7034:Chemical bond
7032:
7030:
7027:
7025:
7022:
7020:
7017:
7015:
7012:
7010:
7007:
7005:
7002:
6998:
6995:
6994:
6993:
6990:
6987:
6983:
6979:
6976:
6975:
6974:
6971:
6969:
6966:
6964:
6961:
6960:
6958:
6954:
6946:
6943:
6941:
6938:
6936:
6933:
6932:
6931:
6928:
6924:
6923:Stoichiometry
6921:
6920:
6919:
6916:
6912:
6909:
6907:
6904:
6902:
6899:
6897:
6894:
6893:
6892:
6889:
6885:
6882:
6881:
6880:
6879:Nanochemistry
6877:
6876:
6871:
6868:
6866:
6863:
6862:
6861:
6858:
6856:
6853:
6849:
6846:
6844:
6841:
6840:
6839:
6836:
6835:
6830:
6827:
6826:
6825:
6822:
6818:
6815:
6813:
6810:
6809:
6808:
6805:
6803:
6800:
6798:
6795:
6791:
6788:
6786:
6783:
6782:
6781:
6778:
6777:
6772:
6769:
6767:
6764:
6763:
6762:
6759:
6757:
6753:
6749:
6746:
6742:
6739:
6737:
6734:
6732:
6729:
6728:
6727:
6724:
6723:
6721:
6719:
6715:
6709:
6706:
6704:
6701:
6699:
6696:
6694:
6691:
6689:
6686:
6684:
6681:
6677:
6674:
6673:
6672:
6669:
6665:
6662:
6661:
6660:
6657:
6653:
6650:
6648:
6645:
6644:
6643:
6640:
6639:
6637:
6635:
6631:
6625:
6622:
6620:
6617:
6615:
6612:
6610:
6607:
6605:
6604:Semisynthesis
6601:
6598:
6596:
6593:
6591:
6588:
6586:
6583:
6581:
6578:
6576:
6573:
6569:
6566:
6565:
6564:
6561:
6560:
6558:
6556:
6552:
6546:
6543:
6541:
6538:
6536:
6533:
6529:
6526:
6525:
6524:
6521:
6519:
6516:
6514:
6511:
6510:
6508:
6506:
6502:
6496:
6493:
6491:
6488:
6486:
6483:
6481:
6478:
6476:
6473:
6471:
6468:
6466:
6463:
6461:
6458:
6454:
6451:
6450:
6449:
6446:
6444:
6441:
6439:
6438:Sonochemistry
6436:
6434:
6433:Cryochemistry
6431:
6427:
6426:Micromeritics
6424:
6423:
6422:
6419:
6417:
6414:
6412:
6409:
6407:
6404:
6400:
6397:
6395:
6392:
6391:
6390:
6387:
6386:
6384:
6382:
6378:
6370:
6367:
6366:
6365:
6362:
6360:
6357:
6355:
6352:
6350:
6347:
6343:
6340:
6339:
6338:
6335:
6333:
6330:
6329:
6327:
6325:
6321:
6315:
6312:
6310:
6307:
6305:
6304:Wet chemistry
6302:
6300:
6297:
6295:
6292:
6290:
6287:
6283:
6280:
6278:
6275:
6274:
6273:
6270:
6268:
6265:
6261:
6258:
6256:
6253:
6251:
6248:
6247:
6246:
6243:
6239:
6236:
6234:
6231:
6229:
6226:
6224:
6221:
6220:
6219:
6216:
6214:
6211:
6209:
6206:
6205:
6203:
6201:
6197:
6191:
6188:
6186:
6183:
6181:
6178:
6176:
6173:
6172:
6169:
6165:
6157:
6152:
6150:
6145:
6143:
6138:
6137:
6134:
6120:
6117:
6115:
6112:
6111:
6110:
6109:
6105:
6103:
6102:
6098:
6093:
6092:
6089:
6083:
6080:
6078:
6075:
6073:
6070:
6068:
6065:
6063:
6060:
6058:
6055:
6054:
6052:
6048:
6038:
6035:
6031:
6028:
6027:
6026:
6023:
6019:
6016:
6015:
6014:
6011:
6007:
6004:
6002:
5999:
5997:
5994:
5992:
5989:
5987:
5984:
5983:
5982:
5979:
5978:
5976:
5974:
5973:
5968:
5962:
5961:Telluroketone
5959:
5957:
5954:
5953:
5951:
5949:
5945:
5939:
5936:
5934:
5931:
5929:
5926:
5924:
5921:
5919:
5916:
5915:
5913:
5911:
5907:
5901:
5898:
5896:
5893:
5892:
5890:
5888:
5884:
5878:
5875:
5873:
5870:
5868:
5865:
5863:
5860:
5858:
5855:
5853:
5850:
5848:
5847:Sulfonic acid
5845:
5843:
5840:
5838:
5837:Sulfinic acid
5835:
5833:
5832:Thiosulfonate
5830:
5828:
5825:
5823:
5822:Thiosulfinate
5820:
5818:
5817:Sulfenic acid
5815:
5813:
5810:
5808:
5805:
5801:
5798:
5797:
5796:
5793:
5791:
5788:
5787:
5785:
5783:
5779:
5773:
5772:Phosphaallene
5770:
5768:
5767:Phosphaalkyne
5765:
5763:
5762:Phosphaalkene
5760:
5756:
5753:
5752:
5751:
5748:
5746:
5743:
5741:
5738:
5736:
5733:
5729:
5726:
5725:
5724:
5721:
5717:
5714:
5713:
5712:
5709:
5708:
5706:
5704:
5700:
5694:
5691:
5689:
5686:
5684:
5681:
5679:
5676:
5674:
5671:
5669:
5666:
5664:
5661:
5659:
5656:
5654:
5651:
5649:
5646:
5644:
5641:
5639:
5636:
5634:
5631:
5629:
5626:
5624:
5621:
5619:
5616:
5614:
5611:
5609:
5606:
5604:
5601:
5599:
5596:
5592:
5589:
5587:
5584:
5583:
5582:
5579:
5578:
5576:
5574:
5570:
5567:
5547:
5535:
5532:
5531:
5530:
5527:
5523:
5520:
5518:
5515:
5514:
5513:
5510:
5509:
5507:
5503:
5497:
5494:
5492:
5489:
5485:
5482:
5481:
5480:
5477:
5473:
5470:
5468:
5465:
5463:
5460:
5459:
5458:
5455:
5454:
5452:
5450:
5446:
5440:
5437:
5435:
5434:Ethylenedioxy
5432:
5428:
5425:
5423:
5420:
5419:
5418:
5415:
5411:
5408:
5406:
5403:
5402:
5401:
5398:
5394:
5391:
5390:
5389:
5386:
5384:
5381:
5379:
5376:
5375:
5373:
5369:
5366:
5360:
5354:
5349:
5344:
5338:
5335:
5333:
5330:
5326:
5323:
5321:
5318:
5317:
5316:
5313:
5309:
5306:
5304:
5301:
5299:
5296:
5294:
5291:
5289:
5286:
5284:
5281:
5280:
5279:
5276:
5272:
5269:
5267:
5264:
5263:
5262:
5259:
5255:
5252:
5250:
5247:
5245:
5242:
5240:
5237:
5235:
5232:
5230:
5227:
5226:
5225:
5222:
5221:
5219:
5213:
5209:
5205:
5198:
5193:
5191:
5186:
5184:
5179:
5178:
5175:
5163:
5160:
5158:
5155:
5153:
5150:
5148:
5145:
5143:
5140:
5138:
5135:
5133:
5130:
5128:
5125:
5123:
5120:
5118:
5115:
5113:
5110:
5108:
5107:Hydroboration
5105:
5103:
5100:
5098:
5095:
5093:
5092:Hydrogenation
5090:
5088:
5087:Deprotonation
5085:
5084:
5082:
5078:
5072:
5069:
5067:
5064:
5062:
5059:
5057:
5053:
5050:
5048:
5047:alkynyl anion
5044:
5041:
5039:
5035:
5031:
5028:
5026:
5023:
5022:
5020:
5016:
5008:
5005:
5003:
5000:
4999:
4986:
4983:
4969:
4966:
4962:
4959:
4957:
4954:
4953:
4940:
4937:
4923:
4920:
4916:
4913:
4911:
4908:
4906:
4903:
4902:
4889:
4886:
4882:
4879:
4877:
4874:
4873:
4860:
4857:
4853:
4850:
4848:
4845:
4844:
4831:
4828:
4814:
4811:
4797:
4794:
4793:
4790:
4786:
4779:
4774:
4772:
4767:
4765:
4760:
4759:
4756:
4744:
4741:
4739:
4736:
4734:
4731:
4729:
4726:
4725:
4723:
4719:
4709:
4707:
4703:
4701:
4698:
4696:
4693:
4691:
4688:
4687:
4685:
4681:
4675:
4672:
4670:
4667:
4665:
4662:
4661:
4659:
4657:Vinylbenzenes
4655:
4645:
4642:
4640:
4637:
4635:
4632:
4630:
4627:
4626:
4624:
4620:
4610:
4607:
4605:
4604:-Butylbenzene
4603:
4599:
4597:
4596:-Butylbenzene
4595:
4591:
4589:
4588:-Butylbenzene
4587:
4583:
4582:
4580:
4576:
4570:
4567:
4565:
4562:
4560:
4557:
4556:
4554:
4552:
4548:
4542:
4540:
4536:
4534:
4532:
4528:
4526:
4524:
4520:
4519:
4517:
4515:
4511:
4508:
4506:
4502:
4492:
4489:
4487:
4485:
4481:
4479:
4476:
4475:
4473:
4469:
4463:
4460:
4458:
4455:
4453:
4450:
4449:
4447:
4445:
4441:
4438:
4436:
4432:
4422:
4419:
4418:
4416:
4412:
4406:
4404:
4400:
4398:
4396:
4392:
4390:
4388:
4384:
4383:
4381:
4379:
4375:
4372:
4370:
4366:
4360:
4357:
4356:
4354:
4352:
4351:Alkylbenzenes
4348:
4338:
4335:
4333:
4330:
4328:
4325:
4323:
4320:
4318:
4315:
4313:
4310:
4308:
4305:
4303:
4300:
4298:
4295:
4293:
4290:
4289:
4287:
4283:
4277:
4274:
4272:
4269:
4267:
4264:
4262:
4259:
4257:
4254:
4252:
4249:
4248:
4246:
4244:
4240:
4237:
4235:
4231:
4228:
4226:
4220:
4210:
4207:
4205:
4202:
4200:
4197:
4195:
4192:
4190:
4187:
4185:
4182:
4181:
4179:
4175:
4169:
4166:
4164:
4161:
4159:
4156:
4154:
4151:
4149:
4146:
4144:
4141:
4139:
4136:
4134:
4131:
4130:
4128:
4126:
4122:
4116:
4113:
4111:
4108:
4106:
4103:
4101:
4098:
4096:
4093:
4091:
4088:
4086:
4083:
4081:
4078:
4077:
4075:
4073:
4069:
4063:
4060:
4059:
4057:
4055:
4051:
4045:
4043:
4040:
4038:
4035:
4033:
4030:
4028:
4025:
4023:
4020:
4019:
4017:
4015:
4011:
4005:
4002:
4000:
3997:
3995:
3992:
3990:
3987:
3985:
3982:
3980:
3977:
3975:
3972:
3970:
3967:
3966:
3964:
3962:
3958:
3948:
3945:
3943:
3940:
3938:
3935:
3933:
3930:
3928:
3925:
3923:
3920:
3919:
3917:
3913:
3907:
3904:
3902:
3899:
3897:
3894:
3892:
3889:
3887:
3884:
3882:
3879:
3877:
3874:
3872:
3869:
3867:
3864:
3863:
3861:
3857:
3854:
3850:
3843:
3837:
3833:
3823:
3820:
3818:
3815:
3813:
3810:
3808:
3805:
3803:
3800:
3798:
3795:
3793:
3790:
3789:
3787:
3783:
3777:
3774:
3772:
3769:
3767:
3764:
3762:
3759:
3757:
3754:
3752:
3749:
3747:
3744:
3742:
3739:
3737:
3734:
3733:
3731:
3727:
3724:
3721:
3714:
3708:
3704:
3701:
3695:
3691:
3681:
3678:
3677:
3675:
3671:
3665:
3662:
3660:
3657:
3655:
3652:
3650:
3647:
3645:
3644:Dodecahedrane
3642:
3640:
3637:
3635:
3632:
3630:
3627:
3625:
3622:
3620:
3617:
3615:
3612:
3611:
3609:
3607:
3603:
3596:
3593:
3590:
3587:
3584:
3581:
3580:
3578:
3576:
3572:
3566:
3564:
3561:
3559:
3556:
3554:
3551:
3549:
3546:
3544:
3541:
3540:
3538:
3536:
3532:
3526:
3523:
3521:
3518:
3516:
3513:
3511:
3508:
3506:
3503:
3501:
3498:
3496:
3493:
3491:
3488:
3487:
3485:
3483:
3479:
3469:
3466:
3464:
3461:
3459:
3456:
3454:
3451:
3449:
3446:
3444:
3441:
3439:
3436:
3434:
3431:
3429:
3426:
3425:
3423:
3419:
3413:
3410:
3408:
3405:
3403:
3400:
3398:
3395:
3393:
3390:
3388:
3385:
3383:
3380:
3378:
3375:
3373:
3370:
3368:
3365:
3364:
3362:
3358:
3355:
3351:
3344:
3338:
3334:
3331:
3323:
3319:
3312:
3307:
3305:
3300:
3298:
3293:
3292:
3289:
3278:
3274:
3269:
3264:
3259:
3254:
3250:
3246:
3242:
3238:
3234:
3227:
3224:
3219:
3217:0-444-87115-2
3213:
3209:
3202:
3199:
3194:
3190:
3186:
3182:
3178:
3174:
3167:
3164:
3159:
3155:
3151:
3147:
3143:
3139:
3132:
3129:
3124:
3120:
3116:
3112:
3111:
3103:
3100:
3095:
3089:
3085:
3081:
3077:
3076:
3067:
3064:
3058:
3054:
3053:
3048:
3041:
3038:
3033:
3029:
3025:
3022:
3021:
3020:J. Org. Chem.
3013:
3010:
3005:
2999:
2995:
2991:
2987:
2986:
2978:
2975:
2969:
2963:
2962:
2957:
2950:
2947:
2942:
2936:
2932:
2925:
2922:
2917:
2913:
2909:
2908:
2900:
2897:
2892:
2888:
2884:
2880:
2873:
2870:
2865:
2861:
2857:
2853:
2852:
2844:
2841:
2836:
2830:
2826:
2822:
2818:
2817:
2809:
2807:
2803:
2798:
2796:0-408-70144-7
2792:
2788:
2781:
2778:
2773:
2767:
2763:
2756:
2753:
2748:
2744:
2740:
2736:
2732:
2725:
2722:
2717:
2715:9780470084960
2711:
2707:
2703:
2699:
2692:
2689:
2684:
2682:9780470771563
2678:
2674:
2667:
2664:
2660:
2655:
2652:
2645:
2641:
2638:
2636:
2633:
2632:
2628:
2626:
2624:
2620:
2619:calicheamicin
2616:
2612:
2608:
2603:
2601:
2597:
2593:
2592:oenanthotoxin
2589:
2585:
2581:
2577:
2576:
2571:
2570:
2565:
2564:
2563:Chrysanthemum
2559:
2558:
2553:
2549:
2545:
2544:
2539:
2536:According to
2531:
2529:
2527:
2521:
2513:
2511:
2509:
2508:hydroxyalkyne
2505:
2501:
2500:alkynylations
2497:
2473:
2467:
2461:
2455:
2449:
2433:
2405:
2396:
2390:
2384:
2376:
2368:
2367:
2366:
2364:
2360:
2356:
2352:
2336:
2323:
2321:
2317:
2313:
2287:
2280:
2267:
2260:
2248:
2247:
2246:
2244:
2240:
2236:
2232:
2222:
2218:
2217:
2216:
2214:
2186:
2173:
2158:
2151:
2140:
2131:
2123:
2122:
2121:
2119:
2111:
2109:
2107:
2103:
2082:
2074:
2066:
2050:
2039:
2022:
2014:
2006:
1999:
1992:
1980:
1979:
1978:
1976:
1972:
1968:
1964:
1960:
1956:
1952:
1948:
1944:
1940:
1936:
1932:
1928:
1924:
1920:
1916:
1912:
1908:
1907:cycloaddition
1900:
1878:
1869:
1861:
1852:
1831:
1820:
1799:
1790:
1782:
1770:
1769:
1768:
1766:
1762:
1754:
1732:
1719:
1706:
1685:
1666:
1657:
1654:
1647:
1635:
1622:
1605:
1593:
1592:
1591:
1589:
1556:
1537:
1529:
1522:
1510:
1509:
1508:
1506:
1502:
1499:Hydration of
1497:
1495:
1491:
1487:
1483:
1482:vinyl alcohol
1479:
1475:
1467:
1465:
1463:
1459:
1455:
1451:
1446:
1444:
1440:
1436:
1435:hydroboration
1429:bonds across
1403:
1394:
1382:
1366:
1357:
1354:
1350:
1342:
1330:
1329:
1328:
1326:
1318:
1316:
1286:
1277:
1265:
1249:
1241:
1234:
1226:
1214:
1195:
1187:
1165:
1157:
1153:
1145:
1133:
1132:
1131:
1129:
1126:. Similarly,
1125:
1121:
1117:
1113:
1109:
1100:
1096:
1094:
1090:
1089:hydrogenation
1079:
1072:Hydrogenation
1071:
1069:
1067:
1063:
1062:Ralph Raphael
1059:
1055:
1047:
1045:
1043:
1042:Vinyl halides
1039:
1037:
1033:
1029:
1025:
1021:
1017:
1009:
1005:
1004:
1003:
1001:
997:
993:
989:
985:
981:
977:
973:
969:
968:dihaloalkanes
961:
959:
957:
929:
920:
917:
910:
895:
885:
882:
877:
869:
860:
852:
851:
850:
848:
844:
840:
832:
827:
823:
819:
815:
811:
807:
803:
799:
796:: 7 isomers:
785:
783:
779:
775:
772:: 3 isomers:
761:
759:
755:
752:: 2 isomers:
741:
738:
724:
721:
707:
706:
705:
703:
699:
691:
689:
687:
683:
678:
675:
671:
667:
663:
659:
655:
651:
647:
646:
642:
637:
635:
631:
627:
619:
617:
615:
611:
604:
597:
593:
589:
585:
572:
570:
566:
562:
554:
552:
550:
546:
542:
538:
537:sp hybridized
534:
530:
526:
522:
518:
517:bond strength
514:
503:
498:
494:
490:
486:
482:
478:
475:, acetylene,
474:
469:
465:
464:
463:
453:
441:
437:
433:
425:
423:
421:
417:
413:
398:
391:
384:
377:
373:
369:
365:
361:
357:
354:
350:
346:
338:
333:
327:
323:
305:
262:
220:
211:
203:
189:
185:
167:
124:
115:
107:
93:
89:
71:
61:
53:
37:
33:
19:
7097:
7085:
7073:
7061:
6911:Biosynthesis
6761:Geochemistry
6676:Pharmacology
6652:Cell biology
6642:Biochemistry
6470:Spectroscopy
6369:VSEPR theory
6218:Spectroscopy
6162:Branches of
6106:
6099:
6013:Vinyl halide
5970:
5900:Borinic acid
5895:Boronic acid
5872:Thioxanthate
5331:
5212:Hydrocarbons
5117:Alkynylation
5097:Halogenation
5056:dihaloalkane
5018:Preparations
4784:
4705:
4601:
4593:
4585:
4538:
4530:
4522:
4483:
4457:Pseudocumene
4421:Ethylbenzene
4402:
4394:
4386:
4317:Phenanthrene
4225:hydrocarbons
4100:Cycloheptyne
4090:Cyclopentyne
4080:Cyclopropyne
4072:Cycloalkynes
3989:Cycloheptene
3979:Cyclopentene
3969:Cyclopropene
3961:Cycloalkenes
3848:
3841:
3835:
3719:
3712:
3699:hydrocarbons
3680:Spiroalkanes
3510:Cycloheptane
3500:Cyclopentane
3490:Cyclopropane
3482:Cycloalkanes
3349:
3342:
3329:hydrocarbons
3318:Hydrocarbons
3240:
3236:
3226:
3207:
3201:
3176:
3172:
3166:
3141:
3137:
3131:
3114:
3108:
3102:
3073:
3066:
3056:
3050:
3040:
3026:(11): 3729.
3023:
3018:
3012:
2983:
2977:
2967:
2959:
2949:
2930:
2924:
2906:
2899:
2882:
2878:
2872:
2855:
2849:
2843:
2814:
2786:
2780:
2761:
2755:
2738:
2734:
2730:
2724:
2697:
2691:
2672:
2666:
2654:
2607:noretynodrel
2604:
2573:
2567:
2561:
2557:Ichthyothere
2555:
2552:tariric acid
2541:
2535:
2523:
2493:
2324:
2306:
2230:
2226:
2210:
2115:
2099:
1933:to give the
1904:
1758:
1577:
1505:acetophenone
1498:
1486:tautomerizes
1478:acetaldehyde
1471:
1447:
1424:
1322:
1307:
1128:halogenation
1104:
1075:
1051:
1040:
1013:
996:sodium amide
965:
953:
836:
695:
679:
662:unsaturation
643:
638:
623:
602:
595:
573:
558:
510:
501:
496:
492:
484:
483:, 1-butyne,
480:
476:
472:
429:
396:
389:
382:
348:
342:
191:
95:
41:
7099:WikiProject
6324:Theoretical
6309:Calorimetry
6077:Thiocyanate
6072:Sulfonamide
6037:Perchlorate
6025:Acyl halide
5986:Fluoroethyl
5867:Thionoester
5755:Phosphonium
5740:Phosphinate
5735:Phosphonous
5723:Phosphonate
5422:Hydroperoxy
5244:Cyclopropyl
4505:C4-Benzenes
4462:Hemellitene
4435:C3-Benzenes
4369:C2-Benzenes
4332:Corannulene
4251:Naphthalene
4115:Cyclodecyne
4110:Cyclononyne
4105:Cyclooctyne
4095:Cyclohexyne
4085:Cyclobutyne
4004:Cyclodecene
3999:Cyclononene
3994:Cyclooctene
3984:Cyclohexene
3974:Cyclobutene
3694:Unsaturated
3525:Cyclodecane
3520:Cyclononane
3515:Cyclooctane
3505:Cyclohexane
3495:Cyclobutane
2640:cycloalkyne
2615:Terbinafine
2600:nematocides
2307:where MX =
1929:eliminates
1923:dienophiles
1755:Tautomerism
1078:unsaturated
1076:Being more
988:bromination
976:halogenated
847:natural gas
656:. However,
634:triple bond
513:triple bond
432:bond angles
420:hydrophobic
364:triple bond
356:hydrocarbon
353:unsaturated
6935:Metallurgy
6634:Biological
6200:Analytical
5981:Haloalkane
5852:Thioketone
5807:Persulfide
5703:Phosphorus
5668:Isocyanate
5658:Isonitrile
5559:or oxygen
5557:hydrogen,
5553:not being
5534:Orthoester
5427:Dioxiranes
5405:Enol ether
5293:1-Propenyl
5043:Alkylation
4564:Prehnitene
4452:Mesitylene
4307:Circulenes
4256:Anthracene
4184:Alkatriene
4153:Heptadiene
4143:Pentadiene
4133:Propadiene
4062:Norbornene
3932:Isoheptyne
3922:Isopentyne
3807:Isoheptene
3797:Isopentene
3619:Diamondoid
3614:Adamantane
3589:Norbornane
3453:Isoheptane
3443:Neopentane
3433:Isopentane
2940:0003277402
2646:References
2596:falcarinol
2580:Asteraceae
2361:, and the
2118:butynediol
1765:propadiene
1179: cis-
1026:using the
970:by double
660:featuring
614:acetylides
610:carbanions
549:sigma bond
541:p orbitals
521:sigma bond
440:picometers
6997:Catalysis
6505:Inorganic
6299:Titration
6164:chemistry
6114:inorganic
5948:Tellurium
5862:Thioester
5827:Sulfoxide
5812:Disulfide
5800:Sulfonium
5750:Phosphine
5728:Phosphite
5711:Phosphate
5643:Carbamate
5618:Hydrazone
5551:element,
5549:Only one
5522:Anhydride
5261:Methylene
5102:Hydration
5080:Reactions
4733:Annulynes
4728:Annulenes
4569:Isodurene
4302:Helicenes
4276:Heptacene
4266:Pentacene
4261:Tetracene
4189:Alkadiyne
4168:Decadiene
4163:Nonadiene
4158:Octadiene
4148:Hexadiene
4138:Butadiene
3947:Isodecyne
3942:Isononyne
3937:Isooctyne
3927:Isohexyne
3822:Isodecene
3817:Isononene
3812:Isooctene
3802:Isohexene
3792:Isobutene
3697:aliphatic
3654:Churchane
3649:Basketane
3468:Isodecane
3463:Isononane
3458:Isooctane
3448:Isohexane
3428:Isobutane
3327:aliphatic
3325:Saturated
3138:Synthesis
2611:Efavirenz
2588:cicutoxin
2543:Artemisia
2474:−
2468:≡
2462:−
2456:≡
2450:−
2397:−
2391:≡
2385:−
2281:≡
2274:⟶
2261:≡
2241:(35) and
2166:⟶
2159:≡
2075:≡
2058:⇀
2051:−
2040:−
2033:↽
2015:≡
1993:≡
1963:triazoles
1913:with 1,3-
1839:⇀
1832:−
1821:−
1814:↽
1791:−
1783:≡
1678:⟶
1648:≡
1606:≡
1549:⟶
1523:≡
1468:Hydration
1375:⟶
1343:≡
1258:⟶
1174:⟶
1146:≡
1108:palladium
1066:synthesis
1024:aldehydes
911:≡
904:⟶
839:acrylates
828:Synthesis
778:2-pentyne
774:1-pentyne
720:acetylene
686:acetylene
592:acetylene
569:2-pentyne
397:acetylene
337:acetylene
306:−
263:−
221:−
212:≡
204:−
168:−
125:−
116:≡
108:−
92:Acetylene
72:−
62:≡
54:−
7115:Category
7063:Category
7019:Molecule
6956:See also
6381:Physical
6095:See also
6030:Chloride
5956:Tellurol
5910:Selenium
5877:Xanthate
5591:Ammonium
5573:Nitrogen
5555:carbon,
5512:Carboxyl
5479:Aldehyde
5467:Acryloyl
5449:carbonyl
5353:hydrogen
5308:Cumulene
5025:Cracking
4337:Kekulene
4322:Chrysene
4312:Butalene
4297:Fluorene
4271:Hexacene
4223:Aromatic
4194:Cumulene
3664:Twistane
3659:Pagodane
3639:Prismane
3193:16447152
3158:95666091
2629:See also
2584:Apiaceae
2575:Oenanthe
2548:Polyynes
2504:carbonyl
2411:pyridine
2406:→
2083:′
2023:′
2007:′
1961:to give
1943:aromatic
1941:to give
1935:aromatic
1927:2-pyrone
1484:, which
1454:catalyst
1439:aldehyde
1395:′
1351:′
1325:halogens
1278:′
1235:′
1196:′
1154:′
1014:Via the
833:Cracking
806:3-hexyne
802:2-hexyne
798:1-hexyne
758:2-butyne
754:1-butyne
670:"-diyne"
565:3-hexyne
543:and two
489:2-butyne
362:âcarbon
326:1-Butyne
7121:Alkynes
7075:Commons
7039:Alchemy
6555:Organic
6119:organic
5918:Selenol
5842:Sulfone
5795:Sulfide
5693:NONOate
5688:Nitroso
5678:Nitrite
5673:Nitrate
5663:Cyanate
5653:Nitrile
5638:Amidine
5633:Imidate
5603:Nitrene
5598:Hydrazo
5586:Enamine
5517:Acetoxy
5505:carboxy
5472:Benzoyl
5410:Epoxide
5393:Methoxy
5383:Alcohol
5337:Carbene
5271:Methine
4922:Heptyne
4859:Pentyne
4813:Propyne
4785:Alkynes
4690:Benzene
4664:Styrene
4541:-Cymene
4533:-Cymene
4525:-Cymene
4514:Cymenes
4405:-Xylene
4397:-Xylene
4389:-Xylene
4378:Xylenes
4359:Toluene
4292:Azulene
3891:Heptyne
3881:Pentyne
3871:Propyne
3836:Alkynes
3761:Heptene
3751:Pentene
3741:Propene
3707:Alkenes
3629:Sterane
3595:Decalin
3583:Housane
3397:Heptane
3387:Pentane
3377:Propane
3367:Methane
3337:Alkanes
3277:1584797
3245:Bibcode
2916:3134811
2498:and in
2494:In the
2243:ethanol
2239:ammonia
2211:In the
1975:carbyne
1953:in the
1761:Propyne
1124:styrene
1034:by the
1032:ketones
1000:ammonia
984:styrene
737:propyne
682:hyphens
525:pi bond
452:alkenes
436:Benzyne
374:form a
368:acyclic
188:Propyne
7087:Portal
6233:UV-Vis
6018:Iodide
5938:Selone
5782:Sulfur
5491:Ketone
5484:Ketene
5462:Acetyl
5417:Peroxy
5388:Alkoxy
5378:Acetal
5359:oxygen
5348:carbon
5332:Alkyne
5325:Benzyl
5320:Phenyl
5303:Allene
5298:Crotyl
5278:Alkene
5266:Bridge
5254:Pentyl
5239:Propyl
5229:Methyl
5038:alkene
5034:alkane
4985:Decyne
4968:Nonyne
4939:Octyne
4888:Hexyne
4830:Butyne
4796:Ethyne
4559:Durene
4478:Cumene
4327:Pyrene
4243:Acenes
4125:Dienes
3906:Decyne
3901:Nonyne
3896:Octyne
3886:Hexyne
3876:Butyne
3866:Ethyne
3776:Decene
3771:Nonene
3766:Octene
3756:Hexene
3746:Butene
3736:Ethene
3634:Cubane
3412:Decane
3407:Nonane
3402:Octane
3392:Hexane
3382:Butane
3372:Ethane
3275:
3265:
3214:
3191:
3156:
3090:
3000:
2937:
2914:
2885:: 10.
2858:: 72.
2831:
2793:
2768:
2741:: 15.
2712:
2679:
2659:Alkyne
2594:, and
2569:Cicuta
2245:(16):
1947:alkene
1917:gives
1915:dienes
1584:P)AuCH
1553:PhCOCH
1503:gives
1112:silver
1093:alkene
780:, and
756:, and
698:carbon
674:locant
641:suffix
630:octyne
442:(for C
414:using
412:ethyne
360:carbon
351:is an
349:alkyne
36:alkene
32:alkane
6260:MALDI
6228:Raman
6050:Other
5887:Boron
5857:Thial
5790:Thiol
5683:Nitro
5648:Imide
5628:Amide
5613:Oxime
5608:Imine
5581:Amine
5529:Ester
5496:Ynone
5400:Ether
5371:R-O-R
5346:Only
5288:Allyl
5283:Vinyl
5249:Butyl
5234:Ethyl
5224:Alkyl
4721:Other
4706:trans
4683:Other
4622:Other
4578:Other
4471:Other
4414:Other
4285:Other
4209:Enyne
4177:Other
3673:Other
3268:49132
3154:S2CID
3117:: 1.
2339:Ag(NH
2318:, or
1452:as a
994:with
347:, an
7014:Atom
6282:HPLC
5972:Halo
5457:Acyl
5357:and
5315:Aryl
4602:tert
4234:PAHs
3273:PMID
3212:ISBN
3189:PMID
3142:2007
3088:ISBN
3059:: 55
2998:ISBN
2935:ISBN
2912:OCLC
2829:ISBN
2791:ISBN
2766:ISBN
2710:ISBN
2677:ISBN
2635:-yne
2582:and
2329:and
2320:RMgX
2316:LiBu
2309:NaNH
2183:CCCH
2170:HOCH
2120::
1969:and
1949:and
1729:COCH
1472:The
1379:RCBr
1038:.
739:only
722:only
666:-ane
645:-yne
563:and
511:The
502:blue
7024:Ion
6255:ICP
6238:NMR
5623:Azo
5054:of
5045:of
5032:of
4594:sec
3851:â 2
3352:+ 2
3263:PMC
3253:doi
3181:doi
3146:doi
3119:doi
3080:doi
3028:doi
2990:doi
2887:doi
2860:doi
2821:doi
2743:doi
2702:doi
2426:OAc
1580:(Ph
1519:PhC
1431:CâĄC
1427:EâH
1262:RCH
1223:RCH
1184:RCH
1122:to
998:in
986:by
845:of
624:In
343:In
34:or
7117::
6754:/
6750:/
6602:/
6277:GC
6250:EI
6223:IR
5355:,
5350:,
5036:,
4998:)
4995:18
4991:10
4978:16
4952:)
4949:14
4932:12
4901:)
4898:10
4872:)
4843:)
3271:.
3261:.
3251:.
3241:89
3239:.
3235:.
3187:.
3177:45
3175:.
3152:.
3140:.
3115:54
3113:.
3086:.
3057:83
3055:.
3049:.
3024:56
2996:.
2972:..
2965:;
2958:.
2883:59
2881:.
2856:30
2854:.
2827:.
2805:^
2739:30
2737:.
2708:.
2590:,
2572:,
2566:,
2560:,
2510:.
2418:Cu
2357:,
2347:OH
2331:Cu
2327:Ag
2322:.
2314:,
2291:HX
2285:CM
2277:RC
2271:MX
2265:CH
2257:RC
2195:OH
2163:CH
2155:HC
2137:CH
2108:.
2080:CR
2071:RC
2020:CR
1997:CR
1989:RC
1875:CH
1849:CH
1796:CH
1779:HC
1767::
1703:CH
1694:CO
1682:CH
1652:CH
1619:CH
1602:HC
1527:CH
1507::
1496:.
1400:Br
1392:CR
1363:Br
1348:CR
1339:RC
1275:CR
1232:CR
1193:CR
1151:CR
1142:RC
1068:.
1002::
915:CH
907:HC
866:CH
849::
820:,
816:,
812:,
808:,
804:,
800:,
793:10
776:,
735::
718::
616:.
576:RC
571:.
491:,
487:,
422:.
392:â2
6988:"
6984:"
6155:e
6148:t
6141:v
5196:e
5189:t
5182:v
5007:5
5002:1
4993:H
4989:C
4987:(
4981:)
4976:H
4974:9
4972:C
4970:(
4961:4
4956:2
4947:H
4945:8
4943:C
4941:(
4935:)
4930:H
4928:7
4926:C
4924:(
4915:3
4910:2
4905:1
4896:H
4894:6
4892:C
4890:(
4881:2
4876:1
4869:8
4867:H
4865:5
4863:C
4861:(
4852:2
4847:1
4840:6
4838:H
4836:4
4834:C
4832:(
4826:)
4823:4
4821:H
4819:3
4817:C
4815:(
4809:)
4806:2
4804:H
4802:2
4800:C
4798:(
4777:e
4770:t
4763:v
4586:n
4539:p
4531:m
4523:o
4484:n
4403:p
4395:m
4387:o
3849:n
3847:2
3845:H
3842:n
3839:C
3720:n
3718:2
3716:H
3713:n
3710:C
3350:n
3348:2
3346:H
3343:n
3340:C
3310:e
3303:t
3296:v
3279:.
3255::
3247::
3220:.
3195:.
3183::
3160:.
3148::
3126:.
3121::
3096:.
3082::
3061:.
3034:.
3030::
3006:.
2992::
2943:.
2918:.
2893:.
2889::
2867:.
2862::
2837:.
2823::
2799:.
2774:.
2749:.
2745::
2731:n
2718:.
2704::
2685:.
2478:R
2446:R
2434:2
2429:)
2423:(
2401:H
2381:R
2377:2
2345:2
2343:)
2341:3
2337:(
2311:2
2288:+
2268:+
2234:a
2231:K
2229:p
2187:2
2174:2
2152:+
2149:O
2141:2
2132:2
2067:2
2011:C
2004:R
2000:+
1879:2
1870:=
1866:C
1862:=
1853:2
1800:3
1787:C
1733:3
1720:5
1715:)
1707:2
1699:(
1686:3
1675:O
1667:2
1663:H
1658:2
1655:+
1644:C
1636:5
1631:)
1623:2
1615:(
1610:C
1586:3
1582:3
1557:3
1546:O
1538:2
1534:H
1530:+
1404:2
1383:2
1367:2
1358:2
1355:+
1312:2
1310:H
1287:2
1283:H
1266:2
1250:2
1246:H
1242:+
1239:H
1227:=
1200:H
1188:=
1166:2
1162:H
1158:+
1110:/
1084:2
1082:H
938:O
930:2
926:H
921:3
918:+
896:2
892:O
886:2
883:3
878:+
870:4
861:2
791:H
789:6
787:C
769:8
767:H
765:5
763:C
749:6
747:H
745:4
743:C
732:4
730:H
728:3
726:C
715:2
713:H
711:2
709:C
606:a
603:K
599:a
596:K
580:H
578:2
505:.
497:f
493:e
485:d
481:c
477:b
473:a
460:4
458:H
456:2
448:2
446:H
444:2
407:2
405:H
403:2
401:C
390:n
388:2
386:H
383:n
380:C
310:H
297:|
291:H
281:H
275:|
270:C
255:|
249:H
239:H
233:|
228:C
216:C
208:C
200:H
172:H
159:|
153:H
143:H
137:|
132:C
120:C
112:C
104:H
76:H
66:C
58:C
50:H
38:.
20:)
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