564:
634:
146:
509:
463:
821:
524:
2 mechanism has just one step. The attack of the reagent and the expulsion of the leaving group happen simultaneously. This mechanism always results in inversion of configuration. If the substrate that is under nucleophilic attack is chiral, the reaction will therefore lead to an inversion of its
763:
While it is common to discuss substitution reactions in the context of organic chemistry, the reaction is generic and applies to a wide range of compounds. Ligands in coordination complexes are susceptible to substitution. Both associative and dissociative mechanisms have been observed.
622:
In this example, the benzene ring's electron resonance structure is attacked by an electrophile E. The resonating bond is broken and a carbocation resonating structure results. Finally a proton is kicked out and a new aromatic compound is formed.
1079:
277:
90:. Detailed understanding of a reaction type helps to predict the product outcome in a reaction. It also is helpful for optimizing a reaction with regard to variables such as temperature and choice of
861:
is characteristically positive for these reactions, which indicates that the disorder of the reacting system increases in the rate-determining step. Dissociative pathways are characterized by a
400:
1165:
2781:
179:
selectively bonds with or attacks the positive or partially positive charge on an atom or a group of atoms. As it does so, it replaces a weaker nucleophile, which then becomes a
587:
group. The nucleophile attacks the carbon causing the double bond to break into a single bond. The double can then reform, kicking off the leaving group in the process.
4996:
891:
1084:
Normally the rate determining step is the dissociation of L from the complex, and does not affect the rate of reaction, leading to the simple rate equation:
306:. In such reactions, the nucleophile is usually electrically neutral or negatively charged, whereas the substrate is typically neutral or positively charged.
579:. Acyl substitution occurs when a nucleophile attacks a carbon that is doubly bonded to one oxygen and singly bonded to another oxygen (can be N or S or a
405:
Nucleophilic substitution reactions are commonplace in organic chemistry, and they can be broadly categorized as taking place at a carbon of a saturated
4112:
4057:
200:
4825:
4167:
4317:
2951:
501:
1 reactions usually occurring on atoms with at least two carbons bonded to them. A more detailed explanation of this can be found in the main
5046:
1384:
482:(C). In the second step, the nucleophilic reagent (Nuc:) attaches to the carbocation and forms a covalent sigma bond. If the substrate has a
865:
that involves release of a ligand from the coordination sphere of the metal undergoing substitution. The concentration of the substituting
4820:
2646:
3922:
1843:
302:. The prior state of charge is restored when the leaving group (LG) departs with an electron pair. The principal product in this case is
4492:
3692:
2436:
869:
has no influence on this rate, and an intermediate of reduced coordination number can be detected. The reaction can be described with k
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and grabs the hydrogen atom to form the electrically neutral HCl. The other radical reforms a covalent bond with the CH
712:
compound RM and an organic halide RâČX that together react to form a compound of the type R-RâČ with formation of a new
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1810:
1805:
854:
497:
The stability of a carbocation (C) depends on how many other carbon atoms are bonded to it. This results in S
5041:
4602:
4047:
431:
Nucleophilic substitutions can proceed by two different mechanisms, unimolecular nucleophilic substitution (
187:. The whole molecular entity of which the electrophile and the leaving group are part is usually called the
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4941:
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4850:
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1997:
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1502:
1402:
850:
827:
787:
725:
172:
166:
1992:
1320:
Basolo, F.; Pearson, R. G. "Mechanisms of
Inorganic Reactions." John Wiley and Son: New York: 1967.
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2017:
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771:
767:
118:
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2536:
2521:
2431:
2421:
2082:
2007:
1962:
1780:
1581:
1176:
Imyanitov, Naum S. (1993). "Is This
Reaction a Substitution, Oxidation-Reduction, or Transfer?".
1074:{\displaystyle {\ce {L_{\mathit {n}}M-L<=>L_{\mathit {n}}M-\Box ->L_{\mathit {n}}M-L'}}}
739:
are compounds where one or more hydrogen atoms have been replaced with something else such as an
2297:
1261:(6th ed.). 1900 E. Lake Ave., Glenview, IL 60025: Pearson Education Inc. pp. 332â365.
4775:
4497:
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3006:
2806:
2531:
2451:
2137:
2112:
1889:
1884:
1535:
713:
674:
590:
Aromatic substitution occurs on compounds with systems of double bonds connected in rings. See
1219:
5111:
4697:
4652:
4367:
4337:
4307:
4242:
4222:
4137:
4132:
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1947:
1765:
1697:
1555:
1545:
862:
858:
188:
79:
63:
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by substituents on the substrate. Therefore, this mechanism usually occurs at an unhindered
4880:
4830:
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4607:
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4297:
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2486:
2356:
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1869:
1760:
1488:
1185:
775:
752:
694:
686:
50:
is replaced by another functional group. Substitution reactions are of prime importance in
548:
center. If there is steric crowding on the substrate near the leaving group, such as at a
8:
5086:
5071:
4717:
4692:
4677:
4672:
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1977:
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1702:
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1630:
690:
541:
110:
75:
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2122:
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4007:
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3194:
3100:
2886:
2831:
2761:
2681:
2576:
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2411:
2336:
2182:
2047:
1982:
1967:
1795:
1565:
1394:
1339:
1276:
802:
406:
490:
or retention of configuration. Usually, both occur without preference. The result is
4572:
3892:
3777:
3742:
3707:
3652:
3607:
3522:
3502:
3452:
3447:
3417:
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1321:
1301:
1262:
1235:
1225:
783:
705:
591:
51:
47:
3567:
16:
Chemical reaction in which one functional group in a compound is replaced by another
5106:
4951:
4921:
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4790:
4722:
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4427:
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4077:
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2132:
2127:
2102:
2042:
1894:
1853:
1722:
1671:
1625:
1189:
721:
530:
478:
1 mechanism has two steps. In the first step, the leaving group departs, forming a
43:
2222:
5016:
4707:
4542:
4537:
3832:
3817:
3762:
3717:
3677:
3627:
3592:
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3412:
3332:
3160:
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3019:
2981:
2956:
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2926:
2861:
2736:
2686:
2676:
2656:
2616:
2426:
2416:
2401:
2197:
2117:
1987:
1957:
1942:
1937:
1800:
1712:
1661:
709:
549:
526:
487:
134:
272:{\displaystyle {\ce {Nuc{\mathbf {:}}- + R-LG -> R-Nuc{}+ LG{\mathbf {:}}-}}}
5021:
4931:
4870:
3962:
3872:
3842:
3617:
3472:
3209:
2986:
2856:
2671:
2641:
2341:
2237:
2012:
1874:
1507:
1496:
545:
1821:
797:
Examples of associative mechanisms are commonly found in the chemistry of 16e
5134:
5031:
4732:
4577:
4472:
4267:
3657:
3622:
3612:
3547:
3537:
3427:
3264:
3080:
2791:
2766:
2636:
2282:
2267:
2252:
2147:
2077:
2057:
1972:
1755:
1727:
1635:
1586:
1560:
1239:
1221:
Advanced
Organic Chemistry: Reactions, Mechanisms, and Structure, 3rd edition
882:
717:
448:
287:
180:
1362:
4072:
3432:
3184:
2961:
2561:
2361:
2212:
2207:
2072:
1927:
1707:
1513:
1420:
1410:
831:
791:
779:
608:
502:
491:
440:
432:
422:
418:
184:
114:
98:
55:
409:
carbon or (less often) at an aromatic or other unsaturated carbon center.
2571:
2217:
2187:
1952:
1666:
1601:
1215:
866:
508:
479:
462:
176:
67:
59:
4855:
4382:
3732:
839:
584:
54:. Substitution reactions in organic chemistry are classified either as
1717:
927:
849:
position. Complexes that undergo dissociative substitution are often
483:
83:
71:
1009:
953:
2262:
1932:
810:
744:
109:) is irradiated, some of the molecules are split into two chlorine
102:
87:
1922:
1341:
Kinetics and
Mechanism of Reactions of Transition Metal Complexes
838:
in organic chemistry. This pathway can be well described by the
748:
580:
91:
309:
An example of nucleophilic substitution is the hydrolysis of an
183:; the remaining positive or partially positive atom becomes an
1620:
740:
670:
486:
carbon, this mechanism can result in either inversion of the
310:
669:
Electrophilic reactions to other unsaturated compounds than
820:
540:
2 attack may occur if the backside route of attack is not
1440:
1137:
1118:
1051:
990:
908:
758:
194:
The most general form for the reaction may be given as
708:
are a class of metal-catalyzed reactions involving an
1093:
894:
338:
294:) from the nucleophile (Nuc:) attacks the substrate (
203:
4997:
ErlenmeyerâPlöchl azlactone and amino-acid synthesis
885:
of their corresponding intermediate reaction steps:
1295:
447:). The two reactions are named according tho their
395:{\displaystyle {\ce {R-Br + OH- -> R-OH + Br-}}}
1338:
1159:
1073:
571:Other types of nucleophilic substitution include,
394:
271:
4058:Divinylcyclopropane-cycloheptadiene rearrangement
5132:
1160:{\displaystyle {\ce {Rate={{\mathit {k}}_{1}}}}}
656:Resonance of benzene-electrophile intermediate;
470:1 reaction mechanism occurring through two steps
1851:
175:is a fundamental class of reactions in which a
62:depending upon the reagent involved, whether a
4318:Thermal rearrangement of aromatic hydrocarbons
2952:Thermal rearrangement of aromatic hydrocarbons
700:
5047:Lectka enantioselective beta-lactam synthesis
2307:
1837:
1392:
1378:
597:
439:) and bimolecular nucleophilic substitution (
97:A good example of a substitution reaction is
4826:Inverse electron-demand DielsâAlder reaction
2647:Heterogeneous metal catalyzed cross-coupling
1214:
814:
160:
19:"Aromatic substitution" redirects here. For
4168:Lobry de BruynâVan Ekenstein transformation
845:, or the labilization of CO ligands in the
1844:
1830:
1385:
1371:
552:center, the substitution will involve an S
4658:Petrenko-Kritschenko piperidone synthesis
4113:FritschâButtenbergâWiechell rearrangement
113:(Clâą), whose free electrons are strongly
4821:Intramolecular DielsâAlder cycloaddition
731:
567:Nucleophilic acyl substitution mechanism
562:
507:
461:
42:is a chemical reaction during which one
1336:
1298:Organometallics: A Concise Introduction
770:, for example, is typically applied to
680:
5133:
4841:Metal-centered cycloaddition reactions
4493:DebusâRadziszewski imidazole synthesis
2437:BodrouxâChichibabin aldehyde synthesis
1411:Unimolecular nucleophilic substitution
1296:Elschenbroich, C.; Salzer, A. (1992).
1256:
759:Inorganic and organometallic chemistry
455:1 having a first-order rate law, and S
171:In organic (and inorganic) chemistry,
4987:Diazoalkane 1,3-dipolar cycloaddition
4891:Vinylcyclopropane (5+2) cycloaddition
4796:Diazoalkane 1,3-dipolar cycloaddition
4568:HurdâMori 1,2,3-thiadiazole synthesis
4063:DowdâBeckwith ring-expansion reaction
3230:HurdâMori 1,2,3-thiadiazole synthesis
2306:
2143:LFER solvent coefficients (data page)
1825:
1421:Bimolecular nucleophilic substitution
1366:
1300:(2nd ed.). Weinheim: Wiley-VCH.
1252:
1250:
1248:
1131:
1107:
1045:
984:
902:
3798:Sharpless asymmetric dihydroxylation
3035:Methoxymethylenetriphenylphosphorane
1210:
1208:
1206:
627:Electrophilic aromatic substitution
617:electrophilic aromatic substitutions
317:, under basic conditions, where the
154:chlorination of methane by chlorine
3923:AllenâMillarâTrippett rearrangement
1474:Electrophilic aromatic substitution
13:
5062:Nitrone-olefin (3+2) cycloaddition
5057:Niementowski quinazoline synthesis
4846:Nitrone-olefin (3+2) cycloaddition
4771:Azide-alkyne Huisgen cycloaddition
4633:Niementowski quinazoline synthesis
4388:Azide-alkyne Huisgen cycloaddition
3693:MeerweinâPonndorfâVerley reduction
3245:LeimgruberâBatcho indole synthesis
1441:Nucleophilic internal substitution
1431:Nucleophilic aromatic substitution
1245:
1170:
1015:
958:
932:
819:
577:nucleophilic aromatic substitution
14:
5152:
4886:Trimethylenemethane cycloaddition
4588:JohnsonâCoreyâChaykovsky reaction
4453:CadoganâSundberg indole synthesis
4433:BohlmannâRahtz pyridine synthesis
4393:BaeyerâEmmerling indole synthesis
3200:CadoganâSundberg indole synthesis
2692:JohnsonâCoreyâChaykovsky reaction
1203:
4982:CookâHeilbron thiazole synthesis
4811:Hexadehydro DielsâAlder reaction
4638:Niementowski quinoline synthesis
4468:CookâHeilbron thiazole synthesis
4413:BischlerâMöhlau indole synthesis
4323:TiffeneauâDemjanov rearrangement
3953:BakerâVenkataraman rearrangement
3111:HornerâWadsworthâEmmons reaction
2782:Mizoroki-Heck vs. Reductive Heck
2667:HornerâWadsworthâEmmons reaction
2178:Neighbouring group participation
632:
258:
210:
144:
4518:Fiesselmann thiophene synthesis
4348:WestphalenâLettrĂ© rearrangement
4328:Vinylcyclopropane rearrangement
4158:KornblumâDeLaMare rearrangement
3803:Epoxidation of allylic alcohols
3713:Noyori asymmetric hydrogenation
3648:KornblumâDeLaMare rearrangement
3323:GallagherâHollander degradation
1597:LindemannâHinshelwood mechanism
1345:(2nd ed.). Weinheim: VCH.
1257:Bruice, Paula Yurkanis (2011).
298:), forming a new covalent bond
4977:Chichibabin pyridine synthesis
4463:Chichibabin pyridine synthesis
4423:BlumâIttah aziridine synthesis
4258:Ring expansion and contraction
2527:Cross dehydrogenative coupling
1646:Outer sphere electron transfer
1641:Inner sphere electron transfer
1451:Nucleophilic acyl substitution
1330:
1314:
1289:
1151:
1122:
573:nucleophilic acyl substitution
427:Nucleophilic acyl substitution
364:
234:
66:involved in the reaction is a
1:
4947:BischlerâNapieralski reaction
4905:Heterocycle forming reactions
4558:Hemetsberger indole synthesis
4418:BischlerâNapieralski reaction
4333:WagnerâMeerwein rearrangement
4303:SommeletâHauser rearrangement
4283:SeyferthâGilbert homologation
4148:IrelandâClaisen rearrangement
4143:HofmannâMartius rearrangement
3903:2,3-sigmatropic rearrangement
3518:CoreyâWinter olefin synthesis
3443:BartonâMcCombie deoxygenation
3086:CoreyâWinter olefin synthesis
3040:SeyferthâGilbert homologation
2907:SeyferthâGilbert homologation
1811:Diffusion-controlled reaction
1196:
855:octahedral molecular geometry
649:Benzene attacks electrophile;
645:Free benzene + electrophile;
412:
286:indicates the substrate. The
40:single substitution reaction)
5052:LehmstedtâTanasescu reaction
5012:GabrielâColman rearrangement
4967:Bucherer carbazole synthesis
4962:BorscheâDrechsel cyclization
4942:Bernthsen acridine synthesis
4927:Bamberger triazine synthesis
4912:AlgarâFlynnâOyamada reaction
4623:Nazarov cyclization reaction
4488:De Kimpe aziridine synthesis
4443:Bucherer carbazole synthesis
4438:BorscheâDrechsel cyclization
4208:Nazarov cyclization reaction
4188:MeyerâSchuster rearrangement
4118:GabrielâColman rearrangement
3868:WolffensteinâBöters reaction
3753:Reduction of nitro compounds
3603:Grundmann aldehyde synthesis
3408:AlgarâFlynnâOyamada reaction
2817:Olefin conversion technology
2812:NozakiâHiyamaâKishi reaction
2607:GabrielâColman rearrangement
2497:Claisen-Schmidt condensation
2442:Bouveault aldehyde synthesis
660:Substituted reaction product
639:
152:
141:
36:single displacement reaction
7:
5027:Hantzsch pyridine synthesis
4806:Enoneâalkene cycloadditions
4628:Nenitzescu indole synthesis
4548:Hantzsch pyridine synthesis
4513:FerrarioâAckermann reaction
4163:Kowalski ester homologation
4128:Halogen dance rearrangement
3973:Benzilic acid rearrangement
3398:Akabori amino-acid reaction
3358:Von Braun amide degradation
3303:BarbierâWieland degradation
3255:Nenitzescu indole synthesis
3235:KharaschâSosnovsky reaction
3126:JuliaâKocienski olefination
3030:Kowalski ester homologation
2727:Kowalski ester homologation
2702:JuliaâKocienski olefination
2457:CadiotâChodkiewicz coupling
2382:Aza-BaylisâHillman reaction
2327:Acetoacetic ester synthesis
2038:Dynamic binding (chemistry)
2028:Conrotatory and disrotatory
2003:Charge remote fragmentation
1466:Electrophilic substitutions
786:. The opposite pathway is
751:. More can be found on the
701:Organometallic substitution
615:reactions, particularly in
10:
5157:
5092:RobinsonâGabriel synthesis
5042:Kröhnke pyridine synthesis
4876:Retro-DielsâAlder reaction
4816:Imine DielsâAlder reaction
4603:Kröhnke pyridine synthesis
4218:NewmanâKwart rearrangement
4193:MislowâEvans rearrangement
4103:FischerâHepp rearrangement
4048:Di-Ï-methane rearrangement
3828:Stephen aldehyde synthesis
3563:EschweilerâClarke reaction
3280:Williamson ether synthesis
2597:FujiwaraâMoritani reaction
2502:Combes quinoline synthesis
2467:Carbonyl olefin metathesis
2168:More O'FerrallâJencks plot
2093:GrunwaldâWinstein equation
2063:Electron-withdrawing group
1998:Catalytic resonance theory
1776:Energy profile (chemistry)
1738:More O'FerrallâJencks plot
1403:Nucleophilic substitutions
677:rather than substitution.
613:electrophilic substitution
604:Electrophilic substitution
601:
598:Electrophilic substitution
416:
164:
25:Arene substitution pattern
18:
5102:Urech hydantoin synthesis
5082:PomeranzâFritsch reaction
5007:Fischer oxazole synthesis
4904:
4741:1,3-Dipolar cycloaddition
4731:
4713:Urech hydantoin synthesis
4683:Reissert indole synthesis
4668:PomeranzâFritsch reaction
4598:Knorr quinoline synthesis
4528:Fischer oxazole synthesis
4458:Camps quinoline synthesis
4378:1,3-Dipolar cycloaddition
4366:
4278:Semipinacol rearrangement
4253:RambergâBĂ€cklund reaction
4238:Piancatelli rearrangement
4178:McFadyenâStevens reaction
3933:Alpha-ketol rearrangement
3881:
3688:McFadyenâStevens reaction
3633:KilianiâFischer synthesis
3553:Elbs persulfate oxidation
3478:BouveaultâBlanc reduction
3438:BaeyerâVilliger oxidation
3376:
3293:
3270:SchottenâBaumann reaction
3173:
3146:RambergâBĂ€cklund reaction
3053:
3025:KilianiâFischer synthesis
3005:
2867:RambergâBĂ€cklund reaction
2852:Pinacol coupling reaction
2847:Piancatelli rearrangement
2742:LiebeskindâSrogl coupling
2592:FujimotoâBelleau reaction
2315:
2309:List of organic reactions
2173:Negative hyperconjugation
1918:
1860:
1806:MichaelisâMenten kinetics
1746:
1680:
1654:
1610:
1574:
1526:
1487:
1464:
1401:
828:Dissociative substitution
790:, being analogous to the
788:dissociative substitution
728:. Many variations exist.
459:2 having a second-order.
325:and the leaving group is
173:nucleophilic substitution
167:Nucleophilic substitution
161:Nucleophilic substitution
5077:PictetâSpengler reaction
4992:EinhornâBrunner reaction
4957:Boger pyridine synthesis
4851:Oxo-DielsâAlder reaction
4766:Aza-DielsâAlder reaction
4663:PictetâSpengler reaction
4563:HofmannâLöffler reaction
4553:Hegedus indole synthesis
4523:Fischer indole synthesis
4398:Bartoli indole synthesis
4353:Willgerodt rearrangement
4183:McLafferty rearrangement
4093:Ferrier carbocyclization
3908:2,3-Wittig rearrangement
3898:1,2-Wittig rearrangement
3738:ParikhâDoering oxidation
3728:Oxygen rebound mechanism
3393:AdkinsâPeterson reaction
3285:Yamaguchi esterification
3225:Hegedus indole synthesis
3190:Bartoli indole synthesis
3061:BamfordâStevens reaction
2977:Weinreb ketone synthesis
2937:Stork enamine alkylation
2712:Knoevenagel condensation
2582:Ferrier carbocyclization
2472:CastroâStephens coupling
2098:Hammett acidity function
2088:Free-energy relationship
2033:CurtinâHammett principle
2018:Conformational isomerism
1733:Potential energy surface
1612:Electron/Proton transfer
1497:Unimolecular elimination
1281:: CS1 maint: location (
851:coordinatively saturated
768:Associative substitution
716:. Examples include the
321:nucleophile is the base
5037:Knorr pyrrole synthesis
4972:BuchererâBergs reaction
4917:AllanâRobinson reaction
4896:Wagner-Jauregg reaction
4688:Ring-closing metathesis
4613:Larock indole synthesis
4593:Knorr pyrrole synthesis
4448:BuchererâBergs reaction
4313:Stieglitz rearrangement
4293:SkattebĂžl rearrangement
4263:Ring-closing metathesis
4123:Group transfer reaction
4088:Favorskii rearrangement
4028:Cornforth rearrangement
3958:Bamberger rearrangement
3863:WolffâKishner reduction
3683:MarkĂłâLam deoxygenation
3578:FlemingâTamao oxidation
3573:FischerâTropsch process
3260:Oxymercuration reaction
3240:Knorr pyrrole synthesis
3066:BartonâKellogg reaction
2972:Wagner-Jauregg reaction
2892:Ring-closing metathesis
2882:ReimerâTiemann reaction
2872:RauhutâCurrier reaction
2787:Nef isocyanide reaction
2747:Malonic ester synthesis
2717:Knorr pyrrole synthesis
2652:High dilution principle
2587:FriedelâCrafts reaction
2522:Cross-coupling reaction
2447:BuchererâBergs reaction
2432:Blanc chloromethylation
2422:Blaise ketone synthesis
2397:BaylisâHillman reaction
2392:BartonâKellogg reaction
2367:AllanâRobinson reaction
2273:WoodwardâHoffmann rules
2008:Charge-transfer complex
1781:Transition state theory
1582:Intramolecular reaction
1508:Bimolecular elimination
1337:Wilkins, R. G. (1991).
815:EigenâWilkins Mechanism
117:. One of them breaks a
5141:Substitution reactions
5002:FeistâBenary synthesis
4776:Bradsher cycloaddition
4746:4+4 Photocycloaddition
4703:SimmonsâSmith reaction
4648:PaternĂČâBĂŒchi reaction
4508:FeistâBenary synthesis
4498:Dieckmann condensation
4248:Pummerer rearrangement
4228:Oxy-Cope rearrangement
4203:Myers allene synthesis
4153:Jacobsen rearrangement
4068:Electrocyclic reaction
4043:Demjanov rearrangement
3998:Buchner ring expansion
3968:Beckmann rearrangement
3948:Aza-Cope rearrangement
3943:ArndtâEistert reaction
3918:Alkyne zipper reaction
3838:Transfer hydrogenation
3813:Sharpless oxyamination
3788:Selenoxide elimination
3673:Lombardo methylenation
3598:Griesbaum coozonolysis
3508:CoreyâItsuno reduction
3483:BoylandâSims oxidation
3423:AngeliâRimini reaction
3071:Boord olefin synthesis
3015:ArndtâEistert reaction
3007:Homologation reactions
2807:Nitro-Mannich reaction
2722:KolbeâSchmitt reaction
2532:Cross-coupling partner
2452:Buchner ring expansion
2372:ArndtâEistert reaction
2138:Kinetic isotope effect
1885:Rearrangement reaction
1575:Unimolecular reactions
1536:Electrophilic addition
1188::1993JChEd..70...14I.
1161:
1075:
976:
824:
801:metal complexes, e.g.
776:coordination complexes
675:electrophilic addition
568:
517:
471:
396:
273:
4861:PausonâKhand reaction
4698:Sharpless epoxidation
4653:Pechmann condensation
4533:FriedlÀnder synthesis
4483:DavisâBeirut reaction
4338:Wallach rearrangement
4308:Stevens rearrangement
4243:Pinacol rearrangement
4223:Overman rearrangement
4138:Hofmann rearrangement
4133:Hayashi rearrangement
4098:Ferrier rearrangement
4053:Dimroth rearrangement
4038:Curtius rearrangement
4033:Criegee rearrangement
4013:Claisen rearrangement
4003:Carroll rearrangement
3938:Amadori rearrangement
3928:Allylic rearrangement
3808:Sharpless epoxidation
3543:DessâMartin oxidation
3468:BohnâSchmidt reaction
3328:Hofmann rearrangement
3131:Kauffmann olefination
3054:Olefination reactions
2992:WurtzâFittig reaction
2827:PalladiumâNHC complex
2707:Kauffmann olefination
2662:Homologation reaction
2512:CoreyâHouse synthesis
2492:Claisen rearrangement
2288:YukawaâTsuno equation
2248:SwainâLupton equation
2228:Spherical aromaticity
2163:MöbiusâHĂŒckel concept
1948:Aromatic ring current
1910:Substitution reaction
1766:Rate-determining step
1698:Reactive intermediate
1556:Free-radical addition
1546:Nucleophilic addition
1489:Elimination reactions
1162:
1076:
923:
863:rate determining step
859:entropy of activation
823:
753:substituted compounds
737:Substituted compounds
732:Substituted compounds
726:WurtzâFittig reaction
566:
511:
465:
397:
274:
64:reactive intermediate
32:substitution reaction
5067:PaalâKnorr synthesis
4937:BartonâZard reaction
4881:Staudinger synthesis
4831:Ketene cycloaddition
4801:DielsâAlder reaction
4781:Cheletropic reaction
4761:Alkyne trimerisation
4643:PaalâKnorr synthesis
4608:Kulinkovich reaction
4583:Jacobsen epoxidation
4503:DielsâAlder reaction
4298:Smiles rearrangement
4288:Sigmatropic reaction
4173:Lossen rearrangement
4023:CoreyâFuchs reaction
3988:Boekelheide reaction
3983:Bergmann degradation
3913:Achmatowicz reaction
3698:Methionine sulfoxide
3498:Clemmensen reduction
3458:Bergmann degradation
3388:Acyloin condensation
3353:Strecker degradation
3308:Bergmann degradation
3275:Ullmann condensation
3141:Peterson olefination
3116:Hydrazone iodination
3096:Elimination reaction
2997:ZinckeâSuhl reaction
2917:Sonogashira coupling
2877:Reformatsky reaction
2837:Peterson olefination
2802:Nierenstein reaction
2732:Kulinkovich reaction
2547:DielsâAlder reaction
2507:CoreyâFuchs reaction
2487:Claisen condensation
2357:Alkyne trimerisation
2332:Acyloin condensation
2298:ÎŁ-bishomoaromaticity
2258:ThorpeâIngold effect
1870:Elimination reaction
1761:Equilibrium constant
1091:
892:
807:tetrachloroplatinate
778:, but resembles the
695:Hunsdiecker reaction
693:. An example is the
687:radical substitution
681:Radical substitution
516:2 reaction mechanism
336:
201:
5087:Prilezhaev reaction
5072:Pellizzari reaction
4751:(4+3) cycloaddition
4718:Van Leusen reaction
4693:Robinson annulation
4678:Pschorr cyclization
4673:Prilezhaev reaction
4403:Bergman cyclization
4358:Wolff rearrangement
4343:Weerman degradation
4233:Pericyclic reaction
4213:Neber rearrangement
4108:Fries rearrangement
3993:Brook rearrangement
3978:Bergman cyclization
3823:Staudinger reaction
3768:Rosenmund reduction
3758:Reductive amination
3723:Oppenauer oxidation
3513:CoreyâKim oxidation
3488:Cannizzaro reaction
3363:Weerman degradation
3338:Isosaccharinic acid
3250:Mukaiyama hydration
3106:Hofmann elimination
3091:Dehydrohalogenation
3076:Chugaev elimination
2897:Robinson annulation
2842:Pfitzinger reaction
2612:Gattermann reaction
2557:WulffâDötz reaction
2537:DakinâWest reaction
2462:Carbonyl allylation
2407:Bergman cyclization
2193:Kennedy J. P. Orton
2113:Hammond's postulate
2083:FlippinâLodge angle
2053:Electromeric effect
1978:Beta-silicon effect
1963:BakerâNathan effect
1771:Reaction coordinate
1703:Radical (chemistry)
1688:Elementary reaction
1631:Grotthuss mechanism
1395:reaction mechanisms
1224:, New York: Wiley,
1139:
1120:
1053:
1036:
992:
975:
952:
910:
813:is governed by the
628:
542:sterically hindered
4836:McCormack reaction
4786:Conia-ene reaction
4618:Madelung synthesis
4408:Biginelli reaction
4198:Mumm rearrangement
4083:Favorskii reaction
4018:Cope rearrangement
4008:Chan rearrangement
3773:Rubottom oxidation
3703:Miyaura borylation
3668:Lipid peroxidation
3663:Lindgren oxidation
3643:Kornblum oxidation
3638:Kolbe electrolysis
3583:Fukuyama reduction
3493:Carbonyl reduction
3343:Marker degradation
3205:Diazonium compound
3195:Boudouard reaction
3174:Carbon-heteroatom
3101:Grieco elimination
2887:Rieche formylation
2832:Passerini reaction
2762:Meerwein arylation
2682:Hydroxymethylation
2577:Favorskii reaction
2477:Chan rearrangement
2412:Biginelli reaction
2337:Aldol condensation
2183:2-Norbornyl cation
2158:Möbius aromaticity
2153:Markovnikov's rule
2048:Effective molarity
1993:BĂŒrgiâDunitz angle
1983:Bicycloaromaticity
1796:Arrhenius equation
1566:Oxidative addition
1528:Addition reactions
1192::10.1021/ed070p14.
1157:
1125:
1104:
1071:
1039:
978:
896:
825:
714:carbonâcarbon bond
706:Coupling reactions
689:reaction involves
673:generally lead to
626:
592:aromatic compounds
569:
556:1 rather than an S
518:
472:
407:aliphatic compound
392:
269:
78:, and whether the
5128:
5127:
5124:
5123:
5120:
5119:
5112:WohlâAue reaction
4756:6+4 Cycloaddition
4573:Iodolactonization
3893:1,2-rearrangement
3858:WohlâAue reaction
3778:Sabatier reaction
3743:Pinnick oxidation
3708:Mozingo reduction
3653:Leuckart reaction
3608:Haloform reaction
3523:Criegee oxidation
3503:Collins oxidation
3453:Benkeser reaction
3448:Bechamp reduction
3418:Andrussow process
3403:Alcohol oxidation
3313:Edman degradation
3220:Haloform reaction
3169:
3168:
3156:Takai olefination
3121:Julia olefination
2947:Takai olefination
2822:Olefin metathesis
2697:Julia olefination
2622:Grignard reaction
2602:Fukuyama coupling
2517:Coupling reaction
2482:ChanâLam coupling
2352:Alkyne metathesis
2347:Alkane metathesis
2203:Phosphaethynolate
2108:George S. Hammond
2068:Electronic effect
2023:Conjugated system
1905:Stereospecificity
1900:Stereoselectivity
1865:Addition reaction
1854:organic reactions
1819:
1818:
1791:Activated complex
1786:Activation energy
1748:Chemical kinetics
1693:Reaction dynamics
1592:Photodissociation
1268:978-0-321-66313-9
1259:Organic Chemistry
1150:
1142:
1133:
1128:
1109:
1097:
1065:
1056:
1047:
1042:
1037:
995:
986:
981:
921:
913:
904:
899:
784:organic chemistry
666:
665:
661:
650:
384:
377:
369:
357:
350:
342:
255:
247:
239:
233:
225:
207:
158:
157:
119:CâH covalent bond
52:organic chemistry
48:chemical compound
5148:
5107:Wenker synthesis
5097:Stollé synthesis
4952:Bobbitt reaction
4922:Auwers synthesis
4866:Povarov reaction
4791:Cyclopropanation
4729:
4728:
4723:Wenker synthesis
4478:Darzens reaction
4428:Bobbitt reaction
4273:Schmidt reaction
4078:Enyne metathesis
3853:Whiting reaction
3848:Wharton reaction
3793:Shapiro reaction
3783:Sarett oxidation
3748:Prévost reaction
3558:Emde degradation
3368:Wohl degradation
3348:Ruff degradation
3318:Emde degradation
3215:Grignard reagent
3151:Shapiro reaction
3136:McMurry reaction
3003:
3002:
2967:Ullmann reaction
2932:Stollé synthesis
2922:Stetter reaction
2912:Shapiro reaction
2902:Sakurai reaction
2797:Negishi coupling
2777:Minisci reaction
2772:Michael reaction
2757:McMurry reaction
2752:Mannich reaction
2632:Hammick reaction
2627:Grignard reagent
2567:Enyne metathesis
2552:Doebner reaction
2542:Darzens reaction
2387:Barbier reaction
2377:Auwers synthesis
2304:
2303:
2278:Woodward's rules
2243:Superaromaticity
2233:Spiroaromaticity
2133:Inductive effect
2128:Hyperconjugation
2103:Hammett equation
2043:Edwards equation
1895:Regioselectivity
1846:
1839:
1832:
1823:
1822:
1723:Collision theory
1672:Matrix isolation
1626:Harpoon reaction
1503:E1cB-elimination
1387:
1380:
1373:
1364:
1363:
1357:
1356:
1344:
1334:
1328:
1318:
1312:
1311:
1293:
1287:
1286:
1280:
1272:
1254:
1243:
1242:
1212:
1166:
1164:
1163:
1158:
1156:
1155:
1154:
1148:
1147:
1140:
1138:
1135:
1134:
1126:
1119:
1116:
1111:
1110:
1102:
1095:
1080:
1078:
1077:
1072:
1070:
1069:
1063:
1061:
1054:
1052:
1049:
1048:
1040:
1038:
1035:
1034:
1022:
1018:
1005:
1000:
993:
991:
988:
987:
979:
977:
974:
973:
961:
951:
950:
935:
919:
918:
911:
909:
906:
905:
897:
881:, which are the
722:Ullmann reaction
652:
641:
636:
629:
625:
611:are involved in
531:Walden inversion
401:
399:
398:
393:
391:
390:
389:
382:
375:
374:
367:
363:
362:
355:
348:
347:
340:
328:
324:
316:
305:
301:
297:
285:
278:
276:
275:
270:
268:
267:
262:
261:
253:
249:
245:
244:
237:
231:
230:
223:
219:
214:
213:
205:
148:
140:
139:
44:functional group
5156:
5155:
5151:
5150:
5149:
5147:
5146:
5145:
5131:
5130:
5129:
5116:
5017:Gewald reaction
4900:
4727:
4708:Skraup reaction
4543:Graham reaction
4538:Gewald reaction
4369:
4362:
3884:
3877:
3833:Swern oxidation
3818:Stahl oxidation
3763:Riley oxidation
3718:Omega oxidation
3678:Luche reduction
3628:Jones oxidation
3593:Glycol cleavage
3588:Ganem oxidation
3533:Davis oxidation
3528:Dakin oxidation
3463:Birch reduction
3413:Amide reduction
3379:
3372:
3333:Hooker reaction
3295:
3289:
3177:
3175:
3165:
3161:Wittig reaction
3049:
3045:Wittig reaction
3020:Hooker reaction
3001:
2982:Wittig reaction
2957:Thorpe reaction
2942:Suzuki reaction
2927:Stille reaction
2862:Quelet reaction
2737:Kumada coupling
2687:Ivanov reaction
2677:Hydrovinylation
2657:Hiyama coupling
2617:Glaser coupling
2427:Blaise reaction
2417:Bingel reaction
2402:Benary reaction
2319:
2317:
2311:
2302:
2198:Passive binding
2118:Homoaromaticity
1968:Baldwin's rules
1943:Antiaromaticity
1938:Anomeric effect
1914:
1856:
1850:
1820:
1815:
1801:Eyring equation
1742:
1713:Stereochemistry
1676:
1662:Solvent effects
1650:
1606:
1570:
1551:
1541:
1522:
1517:
1483:
1479:
1460:
1456:
1446:
1436:
1426:
1416:
1397:
1391:
1361:
1360:
1353:
1335:
1331:
1319:
1315:
1308:
1294:
1290:
1274:
1273:
1269:
1255:
1246:
1232:
1213:
1204:
1199:
1173:
1171:Further reading
1143:
1136:
1130:
1129:
1121:
1117:
1112:
1106:
1105:
1103:
1098:
1094:
1092:
1089:
1088:
1062:
1057:
1050:
1044:
1043:
1030:
1026:
1014:
1013:
1004:
996:
989:
983:
982:
969:
965:
957:
943:
939:
931:
922:
914:
907:
901:
900:
895:
893:
890:
889:
880:
876:
872:
853:and often have
835:
803:Vaska's complex
761:
734:
703:
683:
668:
606:
600:
559:
555:
550:tertiary carbon
539:
527:stereochemistry
523:
515:
500:
488:stereochemistry
477:
469:
458:
454:
444:
436:
429:
417:Main articles:
415:
385:
381:
370:
358:
354:
343:
339:
337:
334:
333:
326:
322:
314:
303:
299:
295:
283:
263:
257:
256:
248:
240:
226:
215:
209:
208:
204:
202:
199:
198:
169:
163:
135:methyl chloride
132:
128:
124:
108:
34:(also known as
28:
21:ortho/meta/para
17:
12:
11:
5:
5154:
5144:
5143:
5126:
5125:
5122:
5121:
5118:
5117:
5115:
5114:
5109:
5104:
5099:
5094:
5089:
5084:
5079:
5074:
5069:
5064:
5059:
5054:
5049:
5044:
5039:
5034:
5029:
5024:
5022:Hantzsch ester
5019:
5014:
5009:
5004:
4999:
4994:
4989:
4984:
4979:
4974:
4969:
4964:
4959:
4954:
4949:
4944:
4939:
4934:
4932:Banert cascade
4929:
4924:
4919:
4914:
4908:
4906:
4902:
4901:
4899:
4898:
4893:
4888:
4883:
4878:
4873:
4871:Prato reaction
4868:
4863:
4858:
4853:
4848:
4843:
4838:
4833:
4828:
4823:
4818:
4813:
4808:
4803:
4798:
4793:
4788:
4783:
4778:
4773:
4768:
4763:
4758:
4753:
4748:
4743:
4737:
4735:
4726:
4725:
4720:
4715:
4710:
4705:
4700:
4695:
4690:
4685:
4680:
4675:
4670:
4665:
4660:
4655:
4650:
4645:
4640:
4635:
4630:
4625:
4620:
4615:
4610:
4605:
4600:
4595:
4590:
4585:
4580:
4575:
4570:
4565:
4560:
4555:
4550:
4545:
4540:
4535:
4530:
4525:
4520:
4515:
4510:
4505:
4500:
4495:
4490:
4485:
4480:
4475:
4470:
4465:
4460:
4455:
4450:
4445:
4440:
4435:
4430:
4425:
4420:
4415:
4410:
4405:
4400:
4395:
4390:
4385:
4380:
4374:
4372:
4364:
4363:
4361:
4360:
4355:
4350:
4345:
4340:
4335:
4330:
4325:
4320:
4315:
4310:
4305:
4300:
4295:
4290:
4285:
4280:
4275:
4270:
4265:
4260:
4255:
4250:
4245:
4240:
4235:
4230:
4225:
4220:
4215:
4210:
4205:
4200:
4195:
4190:
4185:
4180:
4175:
4170:
4165:
4160:
4155:
4150:
4145:
4140:
4135:
4130:
4125:
4120:
4115:
4110:
4105:
4100:
4095:
4090:
4085:
4080:
4075:
4070:
4065:
4060:
4055:
4050:
4045:
4040:
4035:
4030:
4025:
4020:
4015:
4010:
4005:
4000:
3995:
3990:
3985:
3980:
3975:
3970:
3965:
3963:Banert cascade
3960:
3955:
3950:
3945:
3940:
3935:
3930:
3925:
3920:
3915:
3910:
3905:
3900:
3895:
3889:
3887:
3883:Rearrangement
3879:
3878:
3876:
3875:
3873:Zinin reaction
3870:
3865:
3860:
3855:
3850:
3845:
3843:Wacker process
3840:
3835:
3830:
3825:
3820:
3815:
3810:
3805:
3800:
3795:
3790:
3785:
3780:
3775:
3770:
3765:
3760:
3755:
3750:
3745:
3740:
3735:
3730:
3725:
3720:
3715:
3710:
3705:
3700:
3695:
3690:
3685:
3680:
3675:
3670:
3665:
3660:
3655:
3650:
3645:
3640:
3635:
3630:
3625:
3620:
3618:Hydrogenolysis
3615:
3610:
3605:
3600:
3595:
3590:
3585:
3580:
3575:
3570:
3568:Ătard reaction
3565:
3560:
3555:
3550:
3545:
3540:
3535:
3530:
3525:
3520:
3515:
3510:
3505:
3500:
3495:
3490:
3485:
3480:
3475:
3473:Bosch reaction
3470:
3465:
3460:
3455:
3450:
3445:
3440:
3435:
3430:
3425:
3420:
3415:
3410:
3405:
3400:
3395:
3390:
3384:
3382:
3378:Organic redox
3374:
3373:
3371:
3370:
3365:
3360:
3355:
3350:
3345:
3340:
3335:
3330:
3325:
3320:
3315:
3310:
3305:
3299:
3297:
3291:
3290:
3288:
3287:
3282:
3277:
3272:
3267:
3262:
3257:
3252:
3247:
3242:
3237:
3232:
3227:
3222:
3217:
3212:
3210:Esterification
3207:
3202:
3197:
3192:
3187:
3181:
3179:
3171:
3170:
3167:
3166:
3164:
3163:
3158:
3153:
3148:
3143:
3138:
3133:
3128:
3123:
3118:
3113:
3108:
3103:
3098:
3093:
3088:
3083:
3078:
3073:
3068:
3063:
3057:
3055:
3051:
3050:
3048:
3047:
3042:
3037:
3032:
3027:
3022:
3017:
3011:
3009:
3000:
2999:
2994:
2989:
2987:Wurtz reaction
2984:
2979:
2974:
2969:
2964:
2959:
2954:
2949:
2944:
2939:
2934:
2929:
2924:
2919:
2914:
2909:
2904:
2899:
2894:
2889:
2884:
2879:
2874:
2869:
2864:
2859:
2857:Prins reaction
2854:
2849:
2844:
2839:
2834:
2829:
2824:
2819:
2814:
2809:
2804:
2799:
2794:
2789:
2784:
2779:
2774:
2769:
2764:
2759:
2754:
2749:
2744:
2739:
2734:
2729:
2724:
2719:
2714:
2709:
2704:
2699:
2694:
2689:
2684:
2679:
2674:
2672:Hydrocyanation
2669:
2664:
2659:
2654:
2649:
2644:
2642:Henry reaction
2639:
2634:
2629:
2624:
2619:
2614:
2609:
2604:
2599:
2594:
2589:
2584:
2579:
2574:
2569:
2564:
2559:
2554:
2549:
2544:
2539:
2534:
2529:
2524:
2519:
2514:
2509:
2504:
2499:
2494:
2489:
2484:
2479:
2474:
2469:
2464:
2459:
2454:
2449:
2444:
2439:
2434:
2429:
2424:
2419:
2414:
2409:
2404:
2399:
2394:
2389:
2384:
2379:
2374:
2369:
2364:
2359:
2354:
2349:
2344:
2342:Aldol reaction
2339:
2334:
2329:
2323:
2321:
2316:Carbon-carbon
2313:
2312:
2301:
2300:
2295:
2293:Zaitsev's rule
2290:
2285:
2280:
2275:
2270:
2265:
2260:
2255:
2250:
2245:
2240:
2238:Steric effects
2235:
2230:
2225:
2220:
2215:
2210:
2205:
2200:
2195:
2190:
2185:
2180:
2175:
2170:
2165:
2160:
2155:
2150:
2145:
2140:
2135:
2130:
2125:
2120:
2115:
2110:
2105:
2100:
2095:
2090:
2085:
2080:
2075:
2070:
2065:
2060:
2055:
2050:
2045:
2040:
2035:
2030:
2025:
2020:
2015:
2010:
2005:
2000:
1995:
1990:
1985:
1980:
1975:
1970:
1965:
1960:
1955:
1950:
1945:
1940:
1935:
1930:
1925:
1919:
1916:
1915:
1913:
1912:
1907:
1902:
1897:
1892:
1890:Redox reaction
1887:
1882:
1877:
1875:Polymerization
1872:
1867:
1861:
1858:
1857:
1849:
1848:
1841:
1834:
1826:
1817:
1816:
1814:
1813:
1808:
1803:
1798:
1793:
1788:
1783:
1778:
1773:
1768:
1763:
1758:
1752:
1750:
1744:
1743:
1741:
1740:
1735:
1730:
1725:
1720:
1715:
1710:
1705:
1700:
1695:
1690:
1684:
1682:
1681:Related topics
1678:
1677:
1675:
1674:
1669:
1664:
1658:
1656:
1655:Medium effects
1652:
1651:
1649:
1648:
1643:
1638:
1633:
1628:
1623:
1617:
1615:
1608:
1607:
1605:
1604:
1599:
1594:
1589:
1584:
1578:
1576:
1572:
1571:
1569:
1568:
1563:
1558:
1553:
1549:
1543:
1539:
1532:
1530:
1524:
1523:
1521:
1520:
1515:
1511:
1505:
1500:
1493:
1491:
1485:
1484:
1482:
1481:
1477:
1470:
1468:
1462:
1461:
1459:
1458:
1454:
1448:
1444:
1438:
1434:
1428:
1424:
1418:
1414:
1407:
1405:
1399:
1398:
1390:
1389:
1382:
1375:
1367:
1359:
1358:
1351:
1329:
1313:
1306:
1288:
1267:
1244:
1230:
1201:
1200:
1198:
1195:
1194:
1193:
1172:
1169:
1168:
1167:
1153:
1146:
1124:
1115:
1101:
1082:
1081:
1068:
1060:
1033:
1029:
1025:
1021:
1017:
1012:
1008:
1003:
999:
972:
968:
964:
960:
956:
949:
946:
942:
938:
934:
930:
926:
917:
883:rate constants
878:
874:
870:
833:
830:resembles the
772:organometallic
760:
757:
733:
730:
710:organometallic
702:
699:
682:
679:
664:
663:
638:
637:
602:Main article:
599:
596:
557:
553:
546:primary carbon
537:
521:
513:
498:
475:
467:
456:
452:
442:
434:
414:
411:
403:
402:
388:
380:
373:
366:
361:
353:
346:
280:
279:
266:
260:
252:
243:
236:
229:
222:
218:
212:
165:Main article:
162:
159:
156:
155:
151:
150:
130:
126:
122:
106:
23:patterns, see
15:
9:
6:
4:
3:
2:
5153:
5142:
5139:
5138:
5136:
5113:
5110:
5108:
5105:
5103:
5100:
5098:
5095:
5093:
5090:
5088:
5085:
5083:
5080:
5078:
5075:
5073:
5070:
5068:
5065:
5063:
5060:
5058:
5055:
5053:
5050:
5048:
5045:
5043:
5040:
5038:
5035:
5033:
5032:Herz reaction
5030:
5028:
5025:
5023:
5020:
5018:
5015:
5013:
5010:
5008:
5005:
5003:
5000:
4998:
4995:
4993:
4990:
4988:
4985:
4983:
4980:
4978:
4975:
4973:
4970:
4968:
4965:
4963:
4960:
4958:
4955:
4953:
4950:
4948:
4945:
4943:
4940:
4938:
4935:
4933:
4930:
4928:
4925:
4923:
4920:
4918:
4915:
4913:
4910:
4909:
4907:
4903:
4897:
4894:
4892:
4889:
4887:
4884:
4882:
4879:
4877:
4874:
4872:
4869:
4867:
4864:
4862:
4859:
4857:
4854:
4852:
4849:
4847:
4844:
4842:
4839:
4837:
4834:
4832:
4829:
4827:
4824:
4822:
4819:
4817:
4814:
4812:
4809:
4807:
4804:
4802:
4799:
4797:
4794:
4792:
4789:
4787:
4784:
4782:
4779:
4777:
4774:
4772:
4769:
4767:
4764:
4762:
4759:
4757:
4754:
4752:
4749:
4747:
4744:
4742:
4739:
4738:
4736:
4734:
4733:Cycloaddition
4730:
4724:
4721:
4719:
4716:
4714:
4711:
4709:
4706:
4704:
4701:
4699:
4696:
4694:
4691:
4689:
4686:
4684:
4681:
4679:
4676:
4674:
4671:
4669:
4666:
4664:
4661:
4659:
4656:
4654:
4651:
4649:
4646:
4644:
4641:
4639:
4636:
4634:
4631:
4629:
4626:
4624:
4621:
4619:
4616:
4614:
4611:
4609:
4606:
4604:
4601:
4599:
4596:
4594:
4591:
4589:
4586:
4584:
4581:
4579:
4578:Isay reaction
4576:
4574:
4571:
4569:
4566:
4564:
4561:
4559:
4556:
4554:
4551:
4549:
4546:
4544:
4541:
4539:
4536:
4534:
4531:
4529:
4526:
4524:
4521:
4519:
4516:
4514:
4511:
4509:
4506:
4504:
4501:
4499:
4496:
4494:
4491:
4489:
4486:
4484:
4481:
4479:
4476:
4474:
4473:Cycloaddition
4471:
4469:
4466:
4464:
4461:
4459:
4456:
4454:
4451:
4449:
4446:
4444:
4441:
4439:
4436:
4434:
4431:
4429:
4426:
4424:
4421:
4419:
4416:
4414:
4411:
4409:
4406:
4404:
4401:
4399:
4396:
4394:
4391:
4389:
4386:
4384:
4381:
4379:
4376:
4375:
4373:
4371:
4368:Ring forming
4365:
4359:
4356:
4354:
4351:
4349:
4346:
4344:
4341:
4339:
4336:
4334:
4331:
4329:
4326:
4324:
4321:
4319:
4316:
4314:
4311:
4309:
4306:
4304:
4301:
4299:
4296:
4294:
4291:
4289:
4286:
4284:
4281:
4279:
4276:
4274:
4271:
4269:
4268:Rupe reaction
4266:
4264:
4261:
4259:
4256:
4254:
4251:
4249:
4246:
4244:
4241:
4239:
4236:
4234:
4231:
4229:
4226:
4224:
4221:
4219:
4216:
4214:
4211:
4209:
4206:
4204:
4201:
4199:
4196:
4194:
4191:
4189:
4186:
4184:
4181:
4179:
4176:
4174:
4171:
4169:
4166:
4164:
4161:
4159:
4156:
4154:
4151:
4149:
4146:
4144:
4141:
4139:
4136:
4134:
4131:
4129:
4126:
4124:
4121:
4119:
4116:
4114:
4111:
4109:
4106:
4104:
4101:
4099:
4096:
4094:
4091:
4089:
4086:
4084:
4081:
4079:
4076:
4074:
4071:
4069:
4066:
4064:
4061:
4059:
4056:
4054:
4051:
4049:
4046:
4044:
4041:
4039:
4036:
4034:
4031:
4029:
4026:
4024:
4021:
4019:
4016:
4014:
4011:
4009:
4006:
4004:
4001:
3999:
3996:
3994:
3991:
3989:
3986:
3984:
3981:
3979:
3976:
3974:
3971:
3969:
3966:
3964:
3961:
3959:
3956:
3954:
3951:
3949:
3946:
3944:
3941:
3939:
3936:
3934:
3931:
3929:
3926:
3924:
3921:
3919:
3916:
3914:
3911:
3909:
3906:
3904:
3901:
3899:
3896:
3894:
3891:
3890:
3888:
3886:
3880:
3874:
3871:
3869:
3866:
3864:
3861:
3859:
3856:
3854:
3851:
3849:
3846:
3844:
3841:
3839:
3836:
3834:
3831:
3829:
3826:
3824:
3821:
3819:
3816:
3814:
3811:
3809:
3806:
3804:
3801:
3799:
3796:
3794:
3791:
3789:
3786:
3784:
3781:
3779:
3776:
3774:
3771:
3769:
3766:
3764:
3761:
3759:
3756:
3754:
3751:
3749:
3746:
3744:
3741:
3739:
3736:
3734:
3731:
3729:
3726:
3724:
3721:
3719:
3716:
3714:
3711:
3709:
3706:
3704:
3701:
3699:
3696:
3694:
3691:
3689:
3686:
3684:
3681:
3679:
3676:
3674:
3671:
3669:
3666:
3664:
3661:
3659:
3658:Ley oxidation
3656:
3654:
3651:
3649:
3646:
3644:
3641:
3639:
3636:
3634:
3631:
3629:
3626:
3624:
3623:Hydroxylation
3621:
3619:
3616:
3614:
3613:Hydrogenation
3611:
3609:
3606:
3604:
3601:
3599:
3596:
3594:
3591:
3589:
3586:
3584:
3581:
3579:
3576:
3574:
3571:
3569:
3566:
3564:
3561:
3559:
3556:
3554:
3551:
3549:
3548:DNA oxidation
3546:
3544:
3541:
3539:
3538:Deoxygenation
3536:
3534:
3531:
3529:
3526:
3524:
3521:
3519:
3516:
3514:
3511:
3509:
3506:
3504:
3501:
3499:
3496:
3494:
3491:
3489:
3486:
3484:
3481:
3479:
3476:
3474:
3471:
3469:
3466:
3464:
3461:
3459:
3456:
3454:
3451:
3449:
3446:
3444:
3441:
3439:
3436:
3434:
3431:
3429:
3428:Aromatization
3426:
3424:
3421:
3419:
3416:
3414:
3411:
3409:
3406:
3404:
3401:
3399:
3396:
3394:
3391:
3389:
3386:
3385:
3383:
3381:
3375:
3369:
3366:
3364:
3361:
3359:
3356:
3354:
3351:
3349:
3346:
3344:
3341:
3339:
3336:
3334:
3331:
3329:
3326:
3324:
3321:
3319:
3316:
3314:
3311:
3309:
3306:
3304:
3301:
3300:
3298:
3292:
3286:
3283:
3281:
3278:
3276:
3273:
3271:
3268:
3266:
3265:Reed reaction
3263:
3261:
3258:
3256:
3253:
3251:
3248:
3246:
3243:
3241:
3238:
3236:
3233:
3231:
3228:
3226:
3223:
3221:
3218:
3216:
3213:
3211:
3208:
3206:
3203:
3201:
3198:
3196:
3193:
3191:
3188:
3186:
3183:
3182:
3180:
3176:bond forming
3172:
3162:
3159:
3157:
3154:
3152:
3149:
3147:
3144:
3142:
3139:
3137:
3134:
3132:
3129:
3127:
3124:
3122:
3119:
3117:
3114:
3112:
3109:
3107:
3104:
3102:
3099:
3097:
3094:
3092:
3089:
3087:
3084:
3082:
3081:Cope reaction
3079:
3077:
3074:
3072:
3069:
3067:
3064:
3062:
3059:
3058:
3056:
3052:
3046:
3043:
3041:
3038:
3036:
3033:
3031:
3028:
3026:
3023:
3021:
3018:
3016:
3013:
3012:
3010:
3008:
3004:
2998:
2995:
2993:
2990:
2988:
2985:
2983:
2980:
2978:
2975:
2973:
2970:
2968:
2965:
2963:
2960:
2958:
2955:
2953:
2950:
2948:
2945:
2943:
2940:
2938:
2935:
2933:
2930:
2928:
2925:
2923:
2920:
2918:
2915:
2913:
2910:
2908:
2905:
2903:
2900:
2898:
2895:
2893:
2890:
2888:
2885:
2883:
2880:
2878:
2875:
2873:
2870:
2868:
2865:
2863:
2860:
2858:
2855:
2853:
2850:
2848:
2845:
2843:
2840:
2838:
2835:
2833:
2830:
2828:
2825:
2823:
2820:
2818:
2815:
2813:
2810:
2808:
2805:
2803:
2800:
2798:
2795:
2793:
2792:Nef synthesis
2790:
2788:
2785:
2783:
2780:
2778:
2775:
2773:
2770:
2768:
2767:Methylenation
2765:
2763:
2760:
2758:
2755:
2753:
2750:
2748:
2745:
2743:
2740:
2738:
2735:
2733:
2730:
2728:
2725:
2723:
2720:
2718:
2715:
2713:
2710:
2708:
2705:
2703:
2700:
2698:
2695:
2693:
2690:
2688:
2685:
2683:
2680:
2678:
2675:
2673:
2670:
2668:
2665:
2663:
2660:
2658:
2655:
2653:
2650:
2648:
2645:
2643:
2640:
2638:
2637:Heck reaction
2635:
2633:
2630:
2628:
2625:
2623:
2620:
2618:
2615:
2613:
2610:
2608:
2605:
2603:
2600:
2598:
2595:
2593:
2590:
2588:
2585:
2583:
2580:
2578:
2575:
2573:
2570:
2568:
2565:
2563:
2560:
2558:
2555:
2553:
2550:
2548:
2545:
2543:
2540:
2538:
2535:
2533:
2530:
2528:
2525:
2523:
2520:
2518:
2515:
2513:
2510:
2508:
2505:
2503:
2500:
2498:
2495:
2493:
2490:
2488:
2485:
2483:
2480:
2478:
2475:
2473:
2470:
2468:
2465:
2463:
2460:
2458:
2455:
2453:
2450:
2448:
2445:
2443:
2440:
2438:
2435:
2433:
2430:
2428:
2425:
2423:
2420:
2418:
2415:
2413:
2410:
2408:
2405:
2403:
2400:
2398:
2395:
2393:
2390:
2388:
2385:
2383:
2380:
2378:
2375:
2373:
2370:
2368:
2365:
2363:
2360:
2358:
2355:
2353:
2350:
2348:
2345:
2343:
2340:
2338:
2335:
2333:
2330:
2328:
2325:
2324:
2322:
2318:bond forming
2314:
2310:
2305:
2299:
2296:
2294:
2291:
2289:
2286:
2284:
2283:Y-aromaticity
2281:
2279:
2276:
2274:
2271:
2269:
2268:Walsh diagram
2266:
2264:
2261:
2259:
2256:
2254:
2253:Taft equation
2251:
2249:
2246:
2244:
2241:
2239:
2236:
2234:
2231:
2229:
2226:
2224:
2223:ÎŁ-aromaticity
2221:
2219:
2216:
2214:
2211:
2209:
2206:
2204:
2201:
2199:
2196:
2194:
2191:
2189:
2186:
2184:
2181:
2179:
2176:
2174:
2171:
2169:
2166:
2164:
2161:
2159:
2156:
2154:
2151:
2149:
2148:Marcus theory
2146:
2144:
2141:
2139:
2136:
2134:
2131:
2129:
2126:
2124:
2123:HĂŒckel's rule
2121:
2119:
2116:
2114:
2111:
2109:
2106:
2104:
2101:
2099:
2096:
2094:
2091:
2089:
2086:
2084:
2081:
2079:
2078:Evelyn effect
2076:
2074:
2071:
2069:
2066:
2064:
2061:
2059:
2058:Electron-rich
2056:
2054:
2051:
2049:
2046:
2044:
2041:
2039:
2036:
2034:
2031:
2029:
2026:
2024:
2021:
2019:
2016:
2014:
2011:
2009:
2006:
2004:
2001:
1999:
1996:
1994:
1991:
1989:
1986:
1984:
1981:
1979:
1976:
1974:
1973:Bema Hapothle
1971:
1969:
1966:
1964:
1961:
1959:
1956:
1954:
1951:
1949:
1946:
1944:
1941:
1939:
1936:
1934:
1931:
1929:
1926:
1924:
1921:
1920:
1917:
1911:
1908:
1906:
1903:
1901:
1898:
1896:
1893:
1891:
1888:
1886:
1883:
1881:
1878:
1876:
1873:
1871:
1868:
1866:
1863:
1862:
1859:
1855:
1847:
1842:
1840:
1835:
1833:
1828:
1827:
1824:
1812:
1809:
1807:
1804:
1802:
1799:
1797:
1794:
1792:
1789:
1787:
1784:
1782:
1779:
1777:
1774:
1772:
1769:
1767:
1764:
1762:
1759:
1757:
1756:Rate equation
1754:
1753:
1751:
1749:
1745:
1739:
1736:
1734:
1731:
1729:
1728:Arrow pushing
1726:
1724:
1721:
1719:
1716:
1714:
1711:
1709:
1706:
1704:
1701:
1699:
1696:
1694:
1691:
1689:
1686:
1685:
1683:
1679:
1673:
1670:
1668:
1665:
1663:
1660:
1659:
1657:
1653:
1647:
1644:
1642:
1639:
1637:
1636:Marcus theory
1634:
1632:
1629:
1627:
1624:
1622:
1619:
1618:
1616:
1613:
1609:
1603:
1600:
1598:
1595:
1593:
1590:
1588:
1587:Isomerization
1585:
1583:
1580:
1579:
1577:
1573:
1567:
1564:
1562:
1561:Cycloaddition
1559:
1557:
1554:
1547:
1544:
1537:
1534:
1533:
1531:
1529:
1525:
1519:
1512:
1509:
1506:
1504:
1501:
1498:
1495:
1494:
1492:
1490:
1486:
1475:
1472:
1471:
1469:
1467:
1463:
1452:
1449:
1442:
1439:
1432:
1429:
1422:
1419:
1412:
1409:
1408:
1406:
1404:
1400:
1396:
1388:
1383:
1381:
1376:
1374:
1369:
1368:
1365:
1354:
1352:1-56081-125-0
1348:
1343:
1342:
1333:
1327:
1326:0-471-05545-X
1323:
1317:
1309:
1307:3-527-28165-7
1303:
1299:
1292:
1284:
1278:
1270:
1264:
1260:
1253:
1251:
1249:
1241:
1237:
1233:
1231:9780471854722
1227:
1223:
1222:
1217:
1211:
1209:
1207:
1202:
1191:
1187:
1183:
1179:
1178:J. Chem. Educ
1175:
1174:
1144:
1113:
1099:
1087:
1086:
1085:
1066:
1058:
1031:
1027:
1023:
1019:
1010:
1006:
1001:
997:
970:
966:
962:
954:
947:
944:
940:
936:
928:
924:
915:
888:
887:
886:
884:
868:
864:
860:
856:
852:
848:
844:
842:
837:
829:
822:
818:
816:
812:
808:
804:
800:
799:square planar
795:
793:
789:
785:
781:
780:Sn2 mechanism
777:
773:
769:
765:
756:
754:
750:
746:
742:
738:
729:
727:
723:
719:
718:Heck reaction
715:
711:
707:
698:
696:
692:
688:
678:
676:
672:
662:
659:
655:
648:
644:
640:
635:
631:
630:
624:
620:
618:
614:
610:
609:Electrophiles
605:
595:
593:
588:
586:
583:), called an
582:
578:
574:
565:
561:
551:
547:
543:
534:
532:
528:
510:
506:
504:
495:
493:
489:
485:
481:
464:
460:
450:
446:
438:
428:
424:
420:
410:
408:
386:
378:
371:
359:
351:
344:
332:
331:
330:
320:
312:
307:
293:
289:
288:electron pair
264:
250:
241:
227:
220:
216:
197:
196:
195:
192:
190:
186:
182:
181:leaving group
178:
174:
168:
153:
149:
147:
142:
138:
136:
120:
116:
112:
104:
100:
95:
93:
89:
85:
81:
77:
73:
69:
65:
61:
57:
56:electrophilic
53:
49:
45:
41:
37:
33:
26:
22:
4073:Ene reaction
3433:Autoxidation
3294:Degradation
3185:Azo coupling
2962:Ugi reaction
2562:Ene reaction
2362:Alkynylation
2213:Polyfluorene
2208:Polar effect
2073:Electrophile
1988:Bredt's rule
1958:Baird's rule
1928:Alpha effect
1909:
1708:Molecularity
1340:
1332:
1316:
1297:
1291:
1258:
1220:
1216:March, Jerry
1184:(1): 14â16.
1181:
1177:
1083:
846:
840:
826:
796:
766:
762:
736:
735:
704:
684:
667:
657:
653:
651:
646:
642:
621:
607:
589:
570:
535:
519:
503:SN1 reaction
496:
492:racemization
473:
430:
423:SN2 reaction
419:SN1 reaction
404:
318:
308:
291:
281:
193:
185:electrophile
170:
143:
129:âą to form CH
115:nucleophilic
99:halogenation
96:
76:free radical
60:nucleophilic
39:
35:
31:
29:
20:
2572:Ethenolysis
2218:Ring strain
2188:Nucleophile
2013:Clar's rule
1953:Aromaticity
1667:Cage effect
1602:RRKM theory
1518:elimination
867:nucleophile
836:1 mechanism
792:Sn1 pathway
529:, called a
480:carbocation
177:nucleophile
68:carbocation
4856:Ozonolysis
4383:Annulation
3733:Ozonolysis
1852:Topics in
1197:References
594:for more.
413:Mechanisms
4370:reactions
3885:reactions
3380:reactions
3296:reactions
3178:reactions
2320:reactions
1718:Catalysis
1614:reactions
1277:cite book
1240:642506595
1145:−
1059:−
1002:◻
998:−
955:−
945:−
916:−
387:−
372:−
365:⟶
360:−
345:−
319:attacking
313:bromide,
265:−
242:−
235:⟶
228:−
217:−
189:substrate
84:aliphatic
80:substrate
72:carbanion
5135:Category
2263:Vinylogy
1933:Annulene
1880:Reagents
1218:(1985),
1067:′
1020:′
1007:→
925:⇌
811:rate law
691:radicals
451:, with S
449:rate law
300:NucâRâLG
111:radicals
103:chlorine
88:aromatic
1923:A value
1186:Bibcode
749:halogen
745:hydroxy
581:halogen
105:gas (Cl
101:. When
92:solvent
1393:Basic
1349:
1324:
1304:
1265:
1238:
1228:
857:. The
843:effect
809:. The
755:page.
724:, and
671:arenes
575:, and
505:page.
484:chiral
425:, and
282:where
1621:Redox
1457:Acyl)
877:and k
747:, or
741:alkyl
520:The S
474:The S
311:alkyl
304:RâNuc
121:in CH
74:or a
46:in a
1510:(E2)
1499:(E1)
1347:ISBN
1322:ISBN
1302:ISBN
1283:link
1263:ISBN
1236:OCLC
1226:ISBN
1096:Rate
805:and
774:and
585:acyl
315:RâBr
296:RâLG
284:RâLG
133:Cl (
70:, a
1480:Ar)
1437:Ar)
1190:doi
873:, k
847:cis
841:cis
794:.
782:in
654:2b:
647:2a:
560:2.
246:Nuc
206:Nuc
137:).
86:or
82:is
58:or
38:or
5137::
1548:(A
1538:(A
1476:(S
1453:(S
1447:i)
1443:(S
1433:(S
1427:2)
1423:(S
1417:1)
1413:(S
1279:}}
1275:{{
1247:^
1234:,
1205:^
1182:70
1180:.
875:â1
817:.
743:,
720:,
697:.
685:A
658:3:
643:1:
619:.
533:.
494:.
421:,
383:Br
376:OH
356:OH
349:Br
329::
327:Br
323:OH
254:LG
232:LG
191:.
94:.
30:A
1845:e
1838:t
1831:v
1552:)
1550:N
1542:)
1540:E
1516:i
1514:E
1478:E
1455:N
1445:N
1435:N
1425:N
1415:N
1386:e
1379:t
1372:v
1355:.
1310:.
1285:)
1271:.
1152:]
1149:L
1141:M
1132:n
1127:L
1123:[
1114:1
1108:k
1100:=
1064:L
1055:M
1046:n
1041:L
1032:2
1028:k
1024:,
1016:L
1011:+
994:M
985:n
980:L
971:1
967:k
963:,
959:L
948:1
941:k
937:,
933:L
929:+
920:L
912:M
903:n
898:L
879:2
871:1
834:N
832:S
558:N
554:N
538:N
536:S
522:N
514:N
512:S
499:N
476:N
468:N
466:S
457:N
453:N
445:2
443:N
441:S
437:1
435:N
433:S
379:+
368:R
352:+
341:R
292::
290:(
259::
251:+
238:R
224:R
221:+
211::
131:3
127:3
123:4
107:2
27:.
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
