300:
to the seven carbons, and "-ane", indicating single bonding between carbons. Next, the numerical prefix is added in front of the base name, representing the number of carbons in each ring (excluding the shared carbons) and the number of carbons present in the bridge between the rings. In this example, there are two rings with two carbons each and a single bridge with one carbon, excluding the carbons shared by both the rings. The prefix consists of three numbers that are arranged in descending order, separated by dots: . Before the numerical prefix is another prefix indicating the number of rings (e.g., "bicyclo+"). Thus, the name is bicycloheptane.
839:
276:-"), and a numeric prefix before that indicating the number of carbons in each part of each ring, exclusive of junctions. For instance, a bicyclooctane that consists of a six-membered ring and a four-membered ring, which share two adjacent carbon atoms that form a shared edge, is -bicyclooctane. That part of the six-membered ring, exclusive of the shared edge has 4 carbons. That part of the four-membered ring, exclusive of the shared edge, has 2 carbons. The edge itself, exclusive of the two vertices that define it, has 0 carbons.
648:. At these ring sizes, one or more of these sources of strain must be present, resulting in an increase in strain energy, which peaks at 9 carbons (around 50 kJ mol). After that, strain energy slowly decreases until 12 carbon atoms, where it drops significantly; at 14, another significant drop occurs and the strain is on a level comparable with 10 kJ mol. At larger ring sizes there is little or no strain since there are many accessible conformations corresponding to a diamond lattice.
823:
31:
797:
203:
683:
284:, because this system is constantly being revised. In the above example -bicyclooctane would be written bicyclooctane to fit the conventions for IUPAC naming. It then has room for an additional numerical prefix if there is the need to include details of other attachments to the molecule such as chlorine or a methyl group. Another convention for the naming of compounds is the
597:
of 109° 28′ whenever possible. Owing to evident geometrical reasons, rings with 3, 4, and (to a small extent) also 5 atoms can only afford narrower angles; the consequent deviation from the ideal tetrahedral bond angles causes an increase in potential energy and an overall destabilizing effect.
299:
The IUPAC naming system for organic compounds can be demonstrated using the example provided in the adjacent image. The base name of the compound, indicating the total number of carbons in both rings (including the shared edge), is listed first. For instance, "heptane" denotes "hepta-", which refers
627:
the C–C–C bond angles would be 108°, very close to the measure of the tetrahedral angle. Actual cyclopentane molecules are puckered, but this changes only the bond angles slightly so that angle strain is relatively small. The eclipsing interactions are also reduced, leaving a ring strain of about
279:
There is more than one convention (method or nomenclature) for the naming of compounds, which can be confusing for those who are just learning, and inconvenient for those who are well-rehearsed in the older ways. For beginners, it is best to learn IUPAC nomenclature from
639:
of cyclohexane, axial hydrogens on adjacent carbon atoms are pointed in opposite directions, virtually eliminating eclipsing strain. In medium-sized rings (7 to 13 carbon atoms) conformations in which the angle strain is minimised create
619:
has the carbon atoms in a puckered square with approximately 90° bond angles; "puckering" reduces the eclipsing interactions between hydrogen atoms. Its ring strain is therefore slightly less, at around 110 kJ mol.
613:, in which the carbon atoms form a triangle and therefore have 60 °C–C–C bond angles. There are also three pairs of eclipsed hydrogens. The ring strain is calculated to be around 120 kJ mol.
675:
Cycloalkanes, referred to as naphthenes, are a major substrate for the catalytic reforming process. In the presence of a catalyst and at temperatures of about 495 to 525 °C, naphthenes undergo
606:
of the cycloalkane with the value calculated using average bond energies. Molecular mechanics calculations are well suited to identify the many conformations occurring particularly in medium rings.
217:
Unsubstituted cycloalkanes that contain a single ring in their molecular structure are typically named by adding the prefix "cyclo" to the name of the corresponding linear
1186:
884:
635:
the ring strain and eclipsing interactions are negligible because the puckering of the ring allows ideal tetrahedral bond angles to be achieved. In the most stable
667:, is noted for being one of the most strained compounds that is isolatable on a large scale; its strain energy is estimated at 267 kJ mol.
787:
Numerous methods exist for preparing cycloalkanes by ring-closing reactions of difunctional precursors. For example, diesters are cyclized in the
838:
2738:
1271:
603:
568:
because the ring shape allows for a larger area of contact. Containing only C–C and C–H bonds, unreactivity of cycloalkanes with little or no
984:
268:
alkanes is more complex, with the base name indicating the number of carbons in the ring system, a prefix indicating the number of rings ( "
765:
61:
1178:
Michael Tuttle Musser "Cyclohexanol and
Cyclohexanone" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005.
1163:
1098:
2196:
292:, the name of which can tell us only that it is an alcohol (because the suffix "-ol" is in the name) and it should then have a
602:
of a cycloalkane is the increase in energy caused by the compound's geometry, and is calculated by comparing the experimental
1054:
594:
796:
846:
The corresponding cycloaddition reactions, which usually require photochemical activation, result in cyclobutanes.
2731:
1264:
1244:
817:) more elaborate methods are required since intramolecular ring closure competes with intermolecular reactions.
860:
1656:
1240:
1209:
Organic
Chemistry IUPAC Nomenclature. Rule A-23. Hydrogenated Compounds from Fused Polycyclic Hydrocarbons
288:, which is a shorter name and it gives less information about the compound. An example of a common name is
2606:
2004:
1586:
1525:
1420:
788:
761:
2834:
2724:
2667:
2601:
1994:
1257:
1119:
590:
1989:
1510:
1976:
1497:
1004:
917:
2185:
1984:
1568:
832:
807:
749:
139:
includes also those saturated hydrocarbons that are polycyclic. In any case, the general form of the
1117:; Lampman, G. M.; Ciula, R. P.; Connor, D. S.; Schertler, P.; Lavanish, J. (1965). "Bicyclobutane".
2513:
2016:
1537:
641:
2062:
966:
2700:
2657:
2077:
2072:
2057:
1642:
1515:
1505:
1027:
737:, and this mixture ("KA oil" for ketone-alcohol oil) is the main feedstock for the production of
581:
191:
2146:
2115:
1894:
1884:
1769:
2151:
2130:
2125:
1909:
1904:
1899:
1889:
1784:
1779:
1774:
1764:
1430:
552:
Cycloalkanes are similar to alkanes in their general physical properties, but they have higher
30:
2591:
2563:
2406:
2166:
2161:
1999:
1520:
1227:
Organic
Chemistry IUPAC Nomenclature.Rules A-51, A-52, A-53, A-54:Hydrocarbon Ring Assemblies
1159:
1114:
1094:
1074:
1070:
1050:
980:
769:
652:
261:
42:
2813:
2555:
1200:
1151:
1128:
1019:
972:
898:
814:
140:
58:
1228:
1222:
1216:
2705:
2662:
2571:
2445:
1410:
1400:
1210:
676:
281:
682:
1215:
Organic
Chemistry IUPAC Nomenclature.Rule A-31. Bridged Hydrocarbons: Bicyclic Systems.
822:
2808:
2636:
2631:
2596:
2547:
2453:
1425:
1415:
1090:
293:
265:
202:
125:
1132:
2828:
2803:
2798:
2313:
2120:
2110:
1606:
855:
781:
748:
The small cycloalkanes – in particular, cyclopropane – have a lower stability due to
734:
656:
645:
565:
557:
553:
1196:
1031:
894:
2778:
2768:
2758:
2419:
2383:
2279:
2052:
2042:
1951:
1941:
1931:
1472:
1462:
1452:
624:
610:
447:
395:
344:
226:
117:
109:
101:
64:
169:
is the number of rings. The simpler form for cycloalkanes with only one ring is C
83:. The larger cycloalkanes, with more than 20 carbon atoms are typically called
2793:
2788:
2783:
2773:
2763:
2467:
2424:
2397:
2331:
2294:
2213:
2067:
2047:
2034:
1966:
1961:
1956:
1946:
1936:
1923:
1754:
1487:
1482:
1477:
1467:
1457:
1280:
1191:
889:
865:
753:
738:
698:
632:
616:
599:
569:
525:
499:
473:
421:
369:
225:
atoms in its chain as the cycloalkane has in its ring. For example, the name of
121:
113:
105:
80:
76:
54:
35:
780:
Many simple cycloalkanes are obtained from petroleum. They can be produced by
598:
Eclipsing of hydrogen atoms is an important destabilizing effect, as well. The
2526:
2414:
2218:
2105:
2095:
2024:
1759:
1581:
1576:
1551:
1405:
1395:
1023:
206:
1155:
2531:
2269:
2238:
2228:
2223:
2100:
1828:
1616:
1611:
1390:
1204:
976:
902:
694:
308:
289:
768:. These reactions are ring-opening reactions or ring-cleavage reactions of
1221:
Organic
Chemistry IUPAC Nomenclature.Rules A-41, A-42: Spiro Hydrocarbons
2695:
2690:
2500:
2492:
2484:
2364:
2356:
2348:
2299:
2284:
2274:
2264:
2259:
2233:
2156:
1868:
1848:
1698:
1626:
1621:
1601:
941:
702:
68:
17:
2652:
2626:
2476:
2321:
2254:
1853:
1843:
1833:
1723:
1713:
1703:
1591:
1557:
1545:
1359:
1349:
1339:
1329:
757:
561:
238:
197:
90:
1195:, 2nd ed. (the "Gold Book") (1997). Online corrected version: (1995) "
893:, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2014) "
75:
atoms arranged in a structure containing a single ring (possibly with
2521:
2440:
2340:
2289:
1863:
1858:
1838:
1798:
1738:
1733:
1728:
1718:
1708:
1669:
1596:
1374:
1369:
1364:
1354:
1344:
1334:
1299:
693:
In another major industrial process, cyclohexanol is produced by the
254:
250:
222:
218:
72:
2205:
2171:
2087:
742:
201:
132:
29:
2720:
2716:
1253:
1249:
1146:
Irion, Walther W.; Neuwirth, Otto S. (2000). "Oil
Refining".
1049:(5th ed.). Pacific Grove, CA: Brooks/Cole. p. 126.
837:
821:
795:
690:
The process provides a way to produce high octane gasoline.
681:
1229:
http://www.acdlabs.com/iupac/nomenclature/79/r79_158.htm
1223:
http://www.acdlabs.com/iupac/nomenclature/79/r79_196.htm
1217:
http://www.acdlabs.com/iupac/nomenclature/79/r79_163.htm
1211:
http://www.acdlabs.com/iupac/nomenclature/79/r79_73.htm
835:, a cycloaddition, provides a route to cyclohexenes:
133:
96:
The cycloalkanes without side chains (also known as
2683:
2645:
2619:
2584:
2540:
2512:
2475:
2466:
2433:
2405:
2396:
2376:
2339:
2330:
2312:
2247:
2204:
2195:
2184:
2139:
2086:
2033:
2015:
1975:
1922:
1877:
1821:
1797:
1747:
1691:
1668:
1655:
1635:
1567:
1536:
1496:
1443:
1383:
1322:
1298:
1287:
237:) containing a three-membered ring is derived from
572:(see below) are comparable to non-cyclic alkanes.
67:. In other words, a cycloalkane consists only of
1148:Ullmann's Encyclopedia of Industrial Chemistry
2732:
1265:
998:
996:
8:
784:of unsaturated, even aromatic precursors.
2739:
2725:
2717:
2472:
2402:
2336:
2327:
2201:
2192:
1818:
1688:
1665:
1319:
1295:
1272:
1258:
1250:
651:Ring strain can be considerably higher in
303:Cycloalkanes as a group are also known as
79:), and all of the carbon-carbon bonds are
1085:. In Hart, H.; Karabatsos, G. J. (eds.).
1005:"Conformational analysis of cycloalkanes"
260:The naming of polycyclic alkanes such as
135:(IUPAC), in some authors' usage the term
323:
877:
604:standard enthalpy change of combustion
586:In cycloalkanes, the carbon atoms are
564:than alkanes. This is due to stronger
912:
910:
7:
131:Besides this standard definition by
766:nucleophilic aliphatic substitution
1192:Compendium of Chemical Terminology
968:Fundamentals of Petroleum Refining
890:Compendium of Chemical Terminology
165:is the number of carbon atoms and
89:. All cycloalkanes are isomers of
25:
339:Liquid density (at 20 °C)
1087:Advances in Alicyclic Chemistry
965:Fahim, MA, et al. (2010).
701:in air, typically using cobalt
27:Saturated alicyclic hydrocarbon
760:, though they do not react in
679:to give aromatic derivatives:
128:), and large (all the rest).
1:
1133:10.1016/S0040-4020(01)98361-9
593:, which would imply an ideal
576:Conformations and ring strain
1003:Dragojlovic, Veljko (2015).
918:"Alkanes & Cycloalkanes"
810:can be deployed similarly.
307:, a term mainly used in the
609:Ring strain is highest for
282:a source that is up to date
100:) are classified as small (
2851:
842:The Dieckmann condensation
800:The Dieckmann condensation
756:. They react similarly to
579:
257:atoms in the main chain.
195:
189:
2754:
1024:10.1007/s40828-015-0014-0
623:For a theoretical planar
1156:10.1002/14356007.a18_051
1075:"Small Ring Bicyclo[
861:Conformational isomerism
221:with the same number of
34:Ball-and-stick model of
1245:Encyclopædia Britannica
1205:10.1351/goldbook.C01497
977:10.1016/C2009-0-16348-1
903:10.1351/goldbook.C01497
2607:1,3,5-Triheptylbenzene
1045:McMurry, John (2000).
922:www2.chemistry.msu.edu
843:
826:
801:
789:Dieckmann condensation
762:electrophilic addition
687:
595:tetrahedral bond angle
296:(–OH) attached to it.
214:
38:
2602:1,3,5-Triethylbenzene
841:
825:
799:
733:This process coforms
685:
628:25 kJ mol.
320:Table of cycloalkanes
205:
143:for cycloalkanes is C
33:
2005:Isopropylcyclohexene
1587:Perhydrophenanthrene
1526:Isopropylcyclohexane
1093:. pp. 185–254.
833:Diels-Alder reaction
808:acyloin condensation
53:, but distinct from
2701:Alicyclic compounds
2514:Tetramethylbenzenes
642:transannular strain
2658:Cyclopropenylidene
1995:Methylcyclopentene
1985:Methylcyclopropene
1516:Methylcyclopentane
1506:Methylcyclopropane
844:
827:
813:For larger rings (
802:
770:alkyl cycloalkanes
688:
582:Strain (chemistry)
215:
192:IUPAC nomenclature
39:
2822:
2821:
2714:
2713:
2679:
2678:
2615:
2614:
2592:Hexamethylbenzene
2580:
2579:
2462:
2461:
2407:Trimethylbenzenes
2392:
2391:
2308:
2307:
2180:
2179:
2167:Cyclododecatriene
2162:Cyclooctatetraene
2000:Methylcyclohexene
1990:Methylcyclobutene
1977:Alkylcycloalkenes
1918:
1917:
1793:
1792:
1651:
1650:
1521:Methylcyclohexane
1511:Methylcyclobutane
1498:Alkylcycloalkanes
1439:
1438:
1127:(10): 2749–2769.
1047:Organic chemistry
986:978-0-444-52785-1
815:macrocyclizations
550:
549:
43:organic chemistry
16:(Redirected from
2842:
2814:Cyclotetradecane
2741:
2734:
2727:
2718:
2671:-Propenylbenzene
2473:
2403:
2337:
2328:
2202:
2193:
1878:Branched alkynes
1819:
1748:Branched alkenes
1689:
1666:
1569:Polycycloalkanes
1554:(bicycloheptane)
1548:(bicyclopentane)
1384:Branched alkanes
1320:
1296:
1274:
1267:
1260:
1251:
1179:
1176:
1170:
1169:
1143:
1137:
1136:
1111:
1105:
1104:
1067:
1061:
1060:
1042:
1036:
1035:
1009:
1000:
991:
990:
962:
956:
955:
953:
952:
946:iupac.qmul.ac.uk
938:
932:
931:
929:
928:
914:
905:
882:
655:. For example,
653:bicyclic systems
324:
141:chemical formula
98:monocycloalkanes
21:
2850:
2849:
2845:
2844:
2843:
2841:
2840:
2839:
2825:
2824:
2823:
2818:
2750:
2745:
2715:
2710:
2706:Petroleum jelly
2675:
2663:Phenylacetylene
2641:
2611:
2576:
2572:Isobutylbenzene
2536:
2508:
2458:
2429:
2388:
2372:
2326:
2304:
2243:
2187:
2176:
2135:
2082:
2029:
2011:
1971:
1914:
1873:
1815:
1807:
1801:
1789:
1743:
1685:
1678:
1672:
1661:
1659:
1647:
1631:
1563:
1560:(bicyclodecane)
1532:
1492:
1435:
1401:3-Methylpentane
1379:
1316:
1308:
1302:
1291:
1289:
1283:
1278:
1237:
1183:
1182:
1177:
1173:
1166:
1145:
1144:
1140:
1113:
1112:
1108:
1101:
1089:. Vol. 2.
1083:.0]alkanes"
1069:
1068:
1064:
1057:
1044:
1043:
1039:
1007:
1002:
1001:
994:
987:
964:
963:
959:
950:
948:
940:
939:
935:
926:
924:
916:
915:
908:
883:
879:
874:
852:
778:
741:, used to make
728:
724:
720:
716:
712:
677:dehydrogenation
673:
666:
662:
584:
578:
537:
533:
511:
507:
485:
481:
459:
455:
433:
429:
407:
403:
381:
377:
356:
352:
336:Melting point
333:Boiling point
322:
317:
248:
244:
236:
232:
200:
194:
188:
181:
174:
160:
148:
28:
23:
22:
15:
12:
11:
5:
2848:
2846:
2838:
2837:
2827:
2826:
2820:
2819:
2817:
2816:
2811:
2809:Cyclotridecane
2806:
2801:
2796:
2791:
2786:
2781:
2776:
2771:
2766:
2761:
2755:
2752:
2751:
2746:
2744:
2743:
2736:
2729:
2721:
2712:
2711:
2709:
2708:
2703:
2698:
2693:
2687:
2685:
2681:
2680:
2677:
2676:
2674:
2673:
2665:
2660:
2655:
2649:
2647:
2643:
2642:
2640:
2639:
2637:4-Vinyltoluene
2634:
2632:Divinylbenzene
2629:
2623:
2621:
2617:
2616:
2613:
2612:
2610:
2609:
2604:
2599:
2597:2-Phenylhexane
2594:
2588:
2586:
2582:
2581:
2578:
2577:
2575:
2574:
2569:
2561:
2553:
2544:
2542:
2538:
2537:
2535:
2534:
2529:
2524:
2518:
2516:
2510:
2509:
2507:
2506:
2498:
2490:
2481:
2479:
2470:
2464:
2463:
2460:
2459:
2457:
2456:
2454:4-Ethyltoluene
2451:
2449:-Propylbenzene
2443:
2437:
2435:
2431:
2430:
2428:
2427:
2422:
2417:
2411:
2409:
2400:
2394:
2393:
2390:
2389:
2387:
2386:
2380:
2378:
2374:
2373:
2371:
2370:
2362:
2354:
2345:
2343:
2334:
2325:
2324:
2318:
2316:
2310:
2309:
2306:
2305:
2303:
2302:
2297:
2292:
2287:
2282:
2277:
2272:
2267:
2262:
2257:
2251:
2249:
2245:
2244:
2242:
2241:
2236:
2231:
2226:
2221:
2216:
2210:
2208:
2199:
2190:
2182:
2181:
2178:
2177:
2175:
2174:
2169:
2164:
2159:
2154:
2149:
2143:
2141:
2137:
2136:
2134:
2133:
2128:
2123:
2118:
2113:
2108:
2103:
2098:
2092:
2090:
2084:
2083:
2081:
2080:
2075:
2070:
2065:
2060:
2055:
2050:
2045:
2039:
2037:
2031:
2030:
2028:
2027:
2021:
2019:
2017:Bicycloalkenes
2013:
2012:
2010:
2009:
2007:
2002:
1997:
1992:
1987:
1981:
1979:
1973:
1972:
1970:
1969:
1964:
1959:
1954:
1949:
1944:
1939:
1934:
1928:
1926:
1920:
1919:
1916:
1915:
1913:
1912:
1907:
1902:
1897:
1892:
1887:
1881:
1879:
1875:
1874:
1872:
1871:
1866:
1861:
1856:
1851:
1846:
1841:
1836:
1831:
1825:
1823:
1822:Linear alkynes
1816:
1809:
1803:
1795:
1794:
1791:
1790:
1788:
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1777:
1772:
1767:
1762:
1757:
1751:
1749:
1745:
1744:
1742:
1741:
1736:
1731:
1726:
1721:
1716:
1711:
1706:
1701:
1695:
1693:
1692:Linear alkenes
1686:
1680:
1674:
1663:
1653:
1652:
1649:
1648:
1646:
1645:
1639:
1637:
1633:
1632:
1630:
1629:
1624:
1619:
1614:
1609:
1604:
1599:
1594:
1589:
1584:
1579:
1573:
1571:
1565:
1564:
1562:
1561:
1555:
1549:
1542:
1540:
1538:Bicycloalkanes
1534:
1533:
1531:
1530:
1528:
1523:
1518:
1513:
1508:
1502:
1500:
1494:
1493:
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1485:
1480:
1475:
1470:
1465:
1460:
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1428:
1423:
1418:
1413:
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1398:
1393:
1387:
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1380:
1378:
1377:
1372:
1367:
1362:
1357:
1352:
1347:
1342:
1337:
1332:
1326:
1324:
1323:Linear alkanes
1317:
1310:
1304:
1293:
1285:
1284:
1279:
1277:
1276:
1269:
1262:
1254:
1248:
1247:
1243:at the online
1241:"Cycloalkanes"
1236:
1235:External links
1233:
1232:
1231:
1225:
1219:
1213:
1207:
1181:
1180:
1171:
1164:
1138:
1106:
1099:
1091:Academic Press
1062:
1055:
1037:
992:
985:
971:. p. 14.
957:
933:
906:
876:
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873:
870:
869:
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848:
829:
828:
804:
803:
777:
774:
731:
730:
726:
722:
718:
714:
710:
672:
669:
664:
660:
580:Main article:
577:
574:
558:melting points
554:boiling points
548:
547:
544:
541:
538:
535:
531:
528:
522:
521:
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340:
337:
334:
331:
328:
321:
318:
316:
313:
294:hydroxyl group
246:
242:
234:
230:
211:bicycloheptane
187:
184:
176:
170:
150:
144:
126:cyclotridecane
86:cycloparaffins
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
2847:
2836:
2833:
2832:
2830:
2815:
2812:
2810:
2807:
2805:
2804:Cyclododecane
2802:
2800:
2799:Cycloundecane
2797:
2795:
2792:
2790:
2787:
2785:
2782:
2780:
2777:
2775:
2772:
2770:
2767:
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2648:
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2628:
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2620:Vinylbenzenes
2618:
2608:
2605:
2603:
2600:
2598:
2595:
2593:
2590:
2589:
2587:
2583:
2573:
2570:
2568:
2567:-Butylbenzene
2566:
2562:
2560:
2559:-Butylbenzene
2558:
2554:
2552:
2551:-Butylbenzene
2550:
2546:
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2314:Alkylbenzenes
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1607:Dodecahedrane
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1165:3-527-30673-0
1161:
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1130:
1126:
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1121:
1116:
1115:Wiberg, K. B.
1110:
1107:
1102:
1100:9781483224213
1096:
1092:
1088:
1084:
1082:
1078:
1072:
1071:Wiberg, K. B.
1066:
1063:
1058:
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1038:
1033:
1029:
1025:
1021:
1017:
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856:Prelog strain
854:
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824:
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819:
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792:
790:
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782:hydrogenation
775:
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771:
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763:
759:
755:
751:
750:Baeyer strain
746:
744:
740:
736:
735:cyclohexanone
708:
707:
706:
704:
700:
696:
691:
684:
680:
678:
670:
668:
658:
657:bicyclobutane
654:
649:
647:
646:Pitzer strain
643:
638:
634:
629:
626:
621:
618:
614:
612:
607:
605:
601:
600:strain energy
596:
592:
589:
583:
575:
573:
571:
567:
566:London forces
563:
559:
555:
545:
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348:
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314:
312:
310:
306:
301:
297:
295:
291:
287:
283:
277:
275:
271:
267:
263:
258:
256:
253:having three
252:
240:
228:
224:
220:
212:
209:(also called
208:
204:
199:
193:
185:
183:
180:
173:
168:
164:
158:
154:
147:
142:
138:
134:
129:
127:
123:
119:
115:
111:
107:
103:
99:
94:
92:
88:
87:
82:
78:
74:
70:
66:
63:
60:
56:
52:
49:(also called
48:
44:
37:
32:
19:
2835:Cycloalkanes
2779:Cycloheptane
2769:Cyclopentane
2759:Cyclopropane
2748:Cycloalkanes
2747:
2668:
2564:
2556:
2548:
2501:
2493:
2485:
2446:
2420:Pseudocumene
2384:Ethylbenzene
2365:
2357:
2349:
2280:Phenanthrene
2188:hydrocarbons
2063:Cycloheptyne
2053:Cyclopentyne
2043:Cyclopropyne
2035:Cycloalkynes
1952:Cycloheptene
1942:Cyclopentene
1932:Cyclopropene
1924:Cycloalkenes
1811:
1804:
1682:
1675:
1662:hydrocarbons
1643:Spiroalkanes
1473:Cycloheptane
1463:Cyclopentane
1453:Cyclopropane
1445:Cycloalkanes
1444:
1312:
1305:
1292:hydrocarbons
1281:Hydrocarbons
1197:Cycloalkanes
1190:
1174:
1147:
1141:
1124:
1118:
1109:
1086:
1080:
1076:
1065:
1046:
1040:
1015:
1011:
967:
960:
949:. Retrieved
945:
936:
925:. Retrieved
921:
888:
880:
845:
830:
812:
805:
786:
779:
747:
732:
692:
689:
674:
650:
636:
630:
625:cyclopentane
622:
615:
611:cyclopropane
608:
587:
585:
551:
448:Cycloheptane
396:Cyclopentane
345:Cyclopropane
304:
302:
298:
285:
278:
273:
269:
264:alkanes and
259:
227:cyclopropane
216:
210:
186:Nomenclature
178:
171:
166:
162:
156:
152:
145:
136:
130:
118:cycloheptane
110:cyclopentane
102:cyclopropane
97:
95:
85:
84:
65:hydrocarbons
50:
47:cycloalkanes
46:
40:
2794:Cyclodecane
2789:Cyclononane
2784:Cyclooctane
2774:Cyclohexane
2764:Cyclobutane
2468:C4-Benzenes
2425:Hemellitene
2398:C3-Benzenes
2332:C2-Benzenes
2295:Corannulene
2214:Naphthalene
2078:Cyclodecyne
2073:Cyclononyne
2068:Cyclooctyne
2058:Cyclohexyne
2048:Cyclobutyne
1967:Cyclodecene
1962:Cyclononene
1957:Cyclooctene
1947:Cyclohexene
1937:Cyclobutene
1657:Unsaturated
1488:Cyclodecane
1483:Cyclononane
1478:Cyclooctane
1468:Cyclohexane
1458:Cyclobutane
1120:Tetrahedron
942:"Blue Book"
895:Cycloalkane
866:Cycloalkene
776:Preparation
754:ring strain
739:adipic acid
699:cyclohexane
633:cyclohexane
617:Cyclobutane
570:ring strain
526:Cyclodecane
500:Cyclononane
474:Cyclooctane
422:Cyclohexane
370:Cyclobutane
286:common name
137:cycloalkane
122:cyclooctane
120:), medium (
114:cyclohexane
108:), common (
106:cyclobutane
77:side chains
55:naphthalene
36:cyclobutane
2527:Prehnitene
2415:Mesitylene
2270:Circulenes
2219:Anthracene
2147:Alkatriene
2116:Heptadiene
2106:Pentadiene
2096:Propadiene
2025:Norbornene
1895:Isoheptyne
1885:Isopentyne
1770:Isoheptene
1760:Isopentene
1582:Diamondoid
1577:Adamantane
1552:Norbornane
1416:Isoheptane
1406:Neopentane
1396:Isopentane
1056:0534373674
951:2023-04-01
927:2022-02-20
872:References
637:chair form
591:hybridized
315:Properties
311:industry.
305:naphthenes
207:Norbornane
196:See also:
190:See also:
59:monocyclic
57:) are the
51:naphthenes
2696:Annulynes
2691:Annulenes
2532:Isodurene
2265:Helicenes
2239:Heptacene
2229:Pentacene
2224:Tetracene
2152:Alkadiyne
2131:Decadiene
2126:Nonadiene
2121:Octadiene
2111:Hexadiene
2101:Butadiene
1910:Isodecyne
1905:Isononyne
1900:Isooctyne
1890:Isohexyne
1785:Isodecene
1780:Isononene
1775:Isooctene
1765:Isohexene
1755:Isobutene
1660:aliphatic
1617:Churchane
1612:Basketane
1431:Isodecane
1426:Isononane
1421:Isooctane
1411:Isohexane
1391:Isobutane
1290:aliphatic
1288:Saturated
1012:Chemtexts
764:, but in
703:catalysts
695:oxidation
671:Reactions
562:densities
309:petroleum
290:terpineol
62:saturated
18:Naphthene
2829:Category
2300:Kekulene
2285:Chrysene
2275:Butalene
2260:Fluorene
2234:Hexacene
2186:Aromatic
2157:Cumulene
1627:Twistane
1622:Pagodane
1602:Prismane
1073:(1968).
1032:94348487
850:See also
330:Formula
262:bicyclic
161:, where
124:through
69:hydrogen
2653:Benzene
2627:Styrene
2504:-Cymene
2496:-Cymene
2488:-Cymene
2477:Cymenes
2368:-Xylene
2360:-Xylene
2352:-Xylene
2341:Xylenes
2322:Toluene
2255:Azulene
1854:Heptyne
1844:Pentyne
1834:Propyne
1799:Alkynes
1724:Heptene
1714:Pentene
1704:Propene
1670:Alkenes
1592:Sterane
1558:Decalin
1546:Housane
1360:Heptane
1350:Pentane
1340:Propane
1330:Methane
1300:Alkanes
758:alkenes
520:0.8534
327:Alkane
272:-" or "
270:bicyclo
249:) - an
239:propane
198:Alkanes
91:alkenes
2522:Durene
2441:Cumene
2290:Pyrene
2206:Acenes
2088:Dienes
1869:Decyne
1864:Nonyne
1859:Octyne
1849:Hexyne
1839:Butyne
1829:Ethyne
1739:Decene
1734:Nonene
1729:Octene
1719:Hexene
1709:Butene
1699:Ethene
1597:Cubane
1375:Decane
1370:Nonane
1365:Octane
1355:Hexane
1345:Butane
1335:Ethane
1162:
1097:
1053:
1030:
983:
560:, and
546:0.871
517:10-11
494:0.834
468:0.811
462:118.4
442:0.778
416:0.751
413:−93.9
390:0.720
255:carbon
251:alkane
223:carbon
219:alkane
116:, and
81:single
73:carbon
45:, the
2684:Other
2669:trans
2646:Other
2585:Other
2541:Other
2434:Other
2377:Other
2248:Other
2172:Enyne
2140:Other
1636:Other
1187:IUPAC
1028:S2CID
1018:(3).
1008:(PDF)
885:IUPAC
743:nylon
721:→ 2 C
686:noice
543:9-10
491:14.6
436:80.7
410:49.2
384:12.5
362:−128
274:spiro
266:spiro
2565:tert
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