575:
645:
157:
520:
474:
832:
535:
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
774:
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.
633:
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.
1090:
288:
101:. 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
872:
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
411:
1176:
2792:
190:
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
598:
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.
5007:
902:
1095:
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:
317:. In such reactions, the nucleophile is usually electrically neutral or negatively charged, whereas the substrate is typically neutral or positively charged.
590:. 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
416:
Nucleophilic substitution reactions are commonplace in organic chemistry, and they can be broadly categorized as taking place at a carbon of a saturated
4123:
4068:
211:
4836:
4178:
4328:
2962:
512:
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
5057:
1395:
493:(C). In the second step, the nucleophilic reagent (Nuc:) attaches to the carbocation and forms a covalent sigma bond. If the substrate has a
876:
that involves release of a ligand from the coordination sphere of the metal undergoing substitution. The concentration of the substituting
4831:
2657:
3933:
1854:
313:. The prior state of charge is restored when the leaving group (LG) departs with an electron pair. The principal product in this case is
4503:
3703:
2447:
880:
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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2153:
1277:
4992:
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627:
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136:
and grabs the hydrogen atom to form the electrically neutral HCl. The other radical reforms a covalent bond with the CH
723:
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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508:
The stability of a carbocation (C) depends on how many other carbon atoms are bonded to it. This results in S
5052:
4613:
4058:
442:
Nucleophilic substitutions can proceed by two different mechanisms, unimolecular nucleophilic substitution (
198:. The whole molecular entity of which the electrophile and the leaving group are part is usually called the
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2003:
1331:
Basolo, F.; Pearson, R. G. "Mechanisms of
Inorganic Reactions." John Wiley and Son: New York: 1967.
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2442:
2432:
2093:
2018:
1973:
1791:
1592:
1187:
Imyanitov, Naum S. (1993). "Is This
Reaction a Substitution, Oxidation-Reduction, or Transfer?".
1085:{\displaystyle {\ce {L_{\mathit {n}}M-L<=>L_{\mathit {n}}M-\Box ->L_{\mathit {n}}M-L'}}}
750:
are compounds where one or more hydrogen atoms have been replaced with something else such as an
2308:
1272:(6th ed.). 1900 E. Lake Ave., Glenview, IL 60025: Pearson Education Inc. pp. 332â365.
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2148:
2123:
1900:
1895:
1546:
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685:
601:
Aromatic substitution occurs on compounds with systems of double bonds connected in rings. See
1230:
5122:
4708:
4663:
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4348:
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1958:
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1708:
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by substituents on the substrate. Therefore, this mechanism usually occurs at an unhindered
4891:
4841:
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1499:
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786:
763:
705:
697:
61:
is replaced by another functional group. Substitution reactions are of prime importance in
559:
center. If there is steric crowding on the substrate near the leaving group, such as at a
8:
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4728:
4703:
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2347:
2193:
2058:
1993:
1978:
1806:
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1405:
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813:
417:
501:
or retention of configuration. Usually, both occur without preference. The result is
4583:
3903:
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3753:
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3463:
3458:
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Chemical reaction in which one functional group in a compound is replaced by another
5117:
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2143:
2138:
2113:
2053:
1905:
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1682:
1636:
1200:
732:
541:
489:
1 mechanism has two steps. In the first step, the leaving group departs, forming a
54:
2233:
5027:
4718:
4553:
4548:
3843:
3828:
3773:
3728:
3688:
3638:
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2427:
2412:
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2128:
1998:
1968:
1953:
1948:
1811:
1723:
1672:
720:
560:
537:
498:
145:
283:{\displaystyle {\ce {Nuc{\mathbf {:}}- + R-LG -> R-Nuc{}+ LG{\mathbf {:}}-}}}
5032:
4942:
4881:
3973:
3883:
3853:
3628:
3483:
3220:
2997:
2867:
2682:
2652:
2352:
2248:
2023:
1885:
1518:
1507:
556:
1832:
808:
Examples of associative mechanisms are commonly found in the chemistry of 16e
5145:
5042:
4743:
4588:
4483:
4278:
3668:
3633:
3623:
3558:
3548:
3438:
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3091:
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2777:
2647:
2293:
2278:
2263:
2158:
2088:
2068:
1983:
1766:
1738:
1646:
1597:
1571:
1250:
1232:
Advanced
Organic Chemistry: Reactions, Mechanisms, and Structure, 3rd edition
893:
728:
459:
298:
191:
1373:
4083:
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2572:
2372:
2223:
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2083:
1938:
1718:
1524:
1431:
1421:
842:
802:
790:
619:
513:
502:
451:
443:
433:
429:
195:
125:
109:
66:
420:
carbon or (less often) at an aromatic or other unsaturated carbon center.
2582:
2228:
2198:
1963:
1677:
1612:
1226:
877:
519:
490:
473:
187:
78:
70:
4866:
4393:
3743:
850:
595:
65:. Substitution reactions in organic chemistry are classified either as
1728:
938:
860:
position. Complexes that undergo dissociative substitution are often
494:
94:
82:
1020:
964:
2273:
1943:
821:
755:
120:) is irradiated, some of the molecules are split into two chlorine
113:
98:
1933:
1352:
Kinetics and
Mechanism of Reactions of Transition Metal Complexes
849:
in organic chemistry. This pathway can be well described by the
759:
591:
102:
320:
An example of nucleophilic substitution is the hydrolysis of an
194:; the remaining positive or partially positive atom becomes an
1631:
751:
681:
497:
carbon, this mechanism can result in either inversion of the
321:
680:
Electrophilic reactions to other unsaturated compounds than
831:
551:
2 attack may occur if the backside route of attack is not
1451:
1148:
1129:
1062:
1001:
919:
769:
205:
The most general form for the reaction may be given as
719:
are a class of metal-catalyzed reactions involving an
1104:
905:
349:
305:) from the nucleophile (Nuc:) attacks the substrate (
214:
5008:
ErlenmeyerâPlöchl azlactone and amino-acid synthesis
896:
of their corresponding intermediate reaction steps:
1306:
458:). The two reactions are named according tho their
406:{\displaystyle {\ce {R-Br + OH- -> R-OH + Br-}}}
1349:
1170:
1084:
582:Other types of nucleophilic substitution include,
405:
282:
4069:Divinylcyclopropane-cycloheptadiene rearrangement
5143:
1171:{\displaystyle {\ce {Rate={{\mathit {k}}_{1}}}}}
667:Resonance of benzene-electrophile intermediate;
481:1 reaction mechanism occurring through two steps
1862:
186:is a fundamental class of reactions in which a
73:depending upon the reagent involved, whether a
4329:Thermal rearrangement of aromatic hydrocarbons
2963:Thermal rearrangement of aromatic hydrocarbons
711:
5058:Lectka enantioselective beta-lactam synthesis
2318:
1848:
1403:
1389:
608:
450:) and bimolecular nucleophilic substitution (
108:A good example of a substitution reaction is
4837:Inverse electron-demand DielsâAlder reaction
2658:Heterogeneous metal catalyzed cross-coupling
1225:
825:
171:
30:"Aromatic substitution" redirects here. For
4179:Lobry de BruynâVan Ekenstein transformation
856:, or the labilization of CO ligands in the
1855:
1841:
1396:
1382:
563:center, the substitution will involve an S
4669:Petrenko-Kritschenko piperidone synthesis
4124:FritschâButtenbergâWiechell rearrangement
124:(Clâą), whose free electrons are strongly
4832:Intramolecular DielsâAlder cycloaddition
742:
578:Nucleophilic acyl substitution mechanism
573:
518:
472:
53:is a chemical reaction during which one
1347:
1309:Organometallics: A Concise Introduction
781:, for example, is typically applied to
691:
14:
5144:
4852:Metal-centered cycloaddition reactions
4504:DebusâRadziszewski imidazole synthesis
2448:BodrouxâChichibabin aldehyde synthesis
1422:Unimolecular nucleophilic substitution
1307:Elschenbroich, C.; Salzer, A. (1992).
1267:
770:Inorganic and organometallic chemistry
466:1 having a first-order rate law, and S
182:In organic (and inorganic) chemistry,
4998:Diazoalkane 1,3-dipolar cycloaddition
4902:Vinylcyclopropane (5+2) cycloaddition
4807:Diazoalkane 1,3-dipolar cycloaddition
4579:HurdâMori 1,2,3-thiadiazole synthesis
4074:DowdâBeckwith ring-expansion reaction
3241:HurdâMori 1,2,3-thiadiazole synthesis
2317:
2154:LFER solvent coefficients (data page)
1836:
1432:Bimolecular nucleophilic substitution
1377:
1311:(2nd ed.). Weinheim: Wiley-VCH.
1263:
1261:
1259:
1142:
1118:
1056:
995:
913:
3809:Sharpless asymmetric dihydroxylation
3046:Methoxymethylenetriphenylphosphorane
1221:
1219:
1217:
638:Electrophilic aromatic substitution
628:electrophilic aromatic substitutions
328:, under basic conditions, where the
165:chlorination of methane by chlorine
3934:AllenâMillarâTrippett rearrangement
1485:Electrophilic aromatic substitution
24:
5073:Nitrone-olefin (3+2) cycloaddition
5068:Niementowski quinazoline synthesis
4857:Nitrone-olefin (3+2) cycloaddition
4782:Azide-alkyne Huisgen cycloaddition
4644:Niementowski quinazoline synthesis
4399:Azide-alkyne Huisgen cycloaddition
3704:MeerweinâPonndorfâVerley reduction
3256:LeimgruberâBatcho indole synthesis
1452:Nucleophilic internal substitution
1442:Nucleophilic aromatic substitution
1256:
1181:
1026:
969:
943:
830:
588:nucleophilic aromatic substitution
25:
5163:
4897:Trimethylenemethane cycloaddition
4599:JohnsonâCoreyâChaykovsky reaction
4464:CadoganâSundberg indole synthesis
4444:BohlmannâRahtz pyridine synthesis
4404:BaeyerâEmmerling indole synthesis
3211:CadoganâSundberg indole synthesis
2703:JohnsonâCoreyâChaykovsky reaction
1214:
4993:CookâHeilbron thiazole synthesis
4822:Hexadehydro DielsâAlder reaction
4649:Niementowski quinoline synthesis
4479:CookâHeilbron thiazole synthesis
4424:BischlerâMöhlau indole synthesis
4334:TiffeneauâDemjanov rearrangement
3964:BakerâVenkataraman rearrangement
3122:HornerâWadsworthâEmmons reaction
2793:Mizoroki-Heck vs. Reductive Heck
2678:HornerâWadsworthâEmmons reaction
2189:Neighbouring group participation
643:
269:
221:
155:
4529:Fiesselmann thiophene synthesis
4359:WestphalenâLettrĂ© rearrangement
4339:Vinylcyclopropane rearrangement
4169:KornblumâDeLaMare rearrangement
3814:Epoxidation of allylic alcohols
3724:Noyori asymmetric hydrogenation
3659:KornblumâDeLaMare rearrangement
3334:GallagherâHollander degradation
1608:LindemannâHinshelwood mechanism
1356:(2nd ed.). Weinheim: VCH.
1268:Bruice, Paula Yurkanis (2011).
309:), forming a new covalent bond
4988:Chichibabin pyridine synthesis
4474:Chichibabin pyridine synthesis
4434:BlumâIttah aziridine synthesis
4269:Ring expansion and contraction
2538:Cross dehydrogenative coupling
1657:Outer sphere electron transfer
1652:Inner sphere electron transfer
1462:Nucleophilic acyl substitution
1341:
1325:
1300:
1162:
1133:
584:nucleophilic acyl substitution
438:Nucleophilic acyl substitution
375:
245:
77:involved in the reaction is a
13:
1:
4958:BischlerâNapieralski reaction
4916:Heterocycle forming reactions
4569:Hemetsberger indole synthesis
4429:BischlerâNapieralski reaction
4344:WagnerâMeerwein rearrangement
4314:SommeletâHauser rearrangement
4294:SeyferthâGilbert homologation
4159:IrelandâClaisen rearrangement
4154:HofmannâMartius rearrangement
3914:2,3-sigmatropic rearrangement
3529:CoreyâWinter olefin synthesis
3454:BartonâMcCombie deoxygenation
3097:CoreyâWinter olefin synthesis
3051:SeyferthâGilbert homologation
2918:SeyferthâGilbert homologation
1822:Diffusion-controlled reaction
1207:
866:octahedral molecular geometry
660:Benzene attacks electrophile;
656:Free benzene + electrophile;
423:
297:indicates the substrate. The
51:single substitution reaction)
5063:LehmstedtâTanasescu reaction
5023:GabrielâColman rearrangement
4978:Bucherer carbazole synthesis
4973:BorscheâDrechsel cyclization
4953:Bernthsen acridine synthesis
4938:Bamberger triazine synthesis
4923:AlgarâFlynnâOyamada reaction
4634:Nazarov cyclization reaction
4499:De Kimpe aziridine synthesis
4454:Bucherer carbazole synthesis
4449:BorscheâDrechsel cyclization
4219:Nazarov cyclization reaction
4199:MeyerâSchuster rearrangement
4129:GabrielâColman rearrangement
3879:WolffensteinâBöters reaction
3764:Reduction of nitro compounds
3614:Grundmann aldehyde synthesis
3419:AlgarâFlynnâOyamada reaction
2828:Olefin conversion technology
2823:NozakiâHiyamaâKishi reaction
2618:GabrielâColman rearrangement
2508:Claisen-Schmidt condensation
2453:Bouveault aldehyde synthesis
671:Substituted reaction product
650:
163:
152:
47:single displacement reaction
7:
5038:Hantzsch pyridine synthesis
4817:Enoneâalkene cycloadditions
4639:Nenitzescu indole synthesis
4559:Hantzsch pyridine synthesis
4524:FerrarioâAckermann reaction
4174:Kowalski ester homologation
4139:Halogen dance rearrangement
3984:Benzilic acid rearrangement
3409:Akabori amino-acid reaction
3369:Von Braun amide degradation
3314:BarbierâWieland degradation
3266:Nenitzescu indole synthesis
3246:KharaschâSosnovsky reaction
3137:JuliaâKocienski olefination
3041:Kowalski ester homologation
2738:Kowalski ester homologation
2713:JuliaâKocienski olefination
2468:CadiotâChodkiewicz coupling
2393:Aza-BaylisâHillman reaction
2338:Acetoacetic ester synthesis
2049:Dynamic binding (chemistry)
2039:Conrotatory and disrotatory
2014:Charge remote fragmentation
1477:Electrophilic substitutions
797:. The opposite pathway is
762:. More can be found on the
712:Organometallic substitution
626:reactions, particularly in
10:
5168:
5103:RobinsonâGabriel synthesis
5053:Kröhnke pyridine synthesis
4887:Retro-DielsâAlder reaction
4827:Imine DielsâAlder reaction
4614:Kröhnke pyridine synthesis
4229:NewmanâKwart rearrangement
4204:MislowâEvans rearrangement
4114:FischerâHepp rearrangement
4059:Di-Ï-methane rearrangement
3839:Stephen aldehyde synthesis
3574:EschweilerâClarke reaction
3291:Williamson ether synthesis
2608:FujiwaraâMoritani reaction
2513:Combes quinoline synthesis
2478:Carbonyl olefin metathesis
2179:More O'FerrallâJencks plot
2104:GrunwaldâWinstein equation
2074:Electron-withdrawing group
2009:Catalytic resonance theory
1787:Energy profile (chemistry)
1749:More O'FerrallâJencks plot
1414:Nucleophilic substitutions
688:rather than substitution.
624:electrophilic substitution
615:Electrophilic substitution
612:
609:Electrophilic substitution
427:
175:
36:Arene substitution pattern
29:
5113:Urech hydantoin synthesis
5093:PomeranzâFritsch reaction
5018:Fischer oxazole synthesis
4915:
4752:1,3-Dipolar cycloaddition
4742:
4724:Urech hydantoin synthesis
4694:Reissert indole synthesis
4679:PomeranzâFritsch reaction
4609:Knorr quinoline synthesis
4539:Fischer oxazole synthesis
4469:Camps quinoline synthesis
4389:1,3-Dipolar cycloaddition
4377:
4289:Semipinacol rearrangement
4264:RambergâBĂ€cklund reaction
4249:Piancatelli rearrangement
4189:McFadyenâStevens reaction
3944:Alpha-ketol rearrangement
3892:
3699:McFadyenâStevens reaction
3644:KilianiâFischer synthesis
3564:Elbs persulfate oxidation
3489:BouveaultâBlanc reduction
3449:BaeyerâVilliger oxidation
3387:
3304:
3281:SchottenâBaumann reaction
3184:
3157:RambergâBĂ€cklund reaction
3064:
3036:KilianiâFischer synthesis
3016:
2878:RambergâBĂ€cklund reaction
2863:Pinacol coupling reaction
2858:Piancatelli rearrangement
2753:LiebeskindâSrogl coupling
2603:FujimotoâBelleau reaction
2326:
2320:List of organic reactions
2184:Negative hyperconjugation
1929:
1871:
1817:MichaelisâMenten kinetics
1757:
1691:
1665:
1621:
1585:
1537:
1498:
1475:
1412:
839:Dissociative substitution
801:, being analogous to the
799:dissociative substitution
739:. Many variations exist.
470:2 having a second-order.
336:and the leaving group is
184:nucleophilic substitution
178:Nucleophilic substitution
172:Nucleophilic substitution
5088:PictetâSpengler reaction
5003:EinhornâBrunner reaction
4968:Boger pyridine synthesis
4862:Oxo-DielsâAlder reaction
4777:Aza-DielsâAlder reaction
4674:PictetâSpengler reaction
4574:HofmannâLöffler reaction
4564:Hegedus indole synthesis
4534:Fischer indole synthesis
4409:Bartoli indole synthesis
4364:Willgerodt rearrangement
4194:McLafferty rearrangement
4104:Ferrier carbocyclization
3919:2,3-Wittig rearrangement
3909:1,2-Wittig rearrangement
3749:ParikhâDoering oxidation
3739:Oxygen rebound mechanism
3404:AdkinsâPeterson reaction
3296:Yamaguchi esterification
3236:Hegedus indole synthesis
3201:Bartoli indole synthesis
3072:BamfordâStevens reaction
2988:Weinreb ketone synthesis
2948:Stork enamine alkylation
2723:Knoevenagel condensation
2593:Ferrier carbocyclization
2483:CastroâStephens coupling
2109:Hammett acidity function
2099:Free-energy relationship
2044:CurtinâHammett principle
2029:Conformational isomerism
1744:Potential energy surface
1623:Electron/Proton transfer
1508:Unimolecular elimination
1292:: CS1 maint: location (
862:coordinatively saturated
779:Associative substitution
727:. Examples include the
332:nucleophile is the base
5048:Knorr pyrrole synthesis
4983:BuchererâBergs reaction
4928:AllanâRobinson reaction
4907:Wagner-Jauregg reaction
4699:Ring-closing metathesis
4624:Larock indole synthesis
4604:Knorr pyrrole synthesis
4459:BuchererâBergs reaction
4324:Stieglitz rearrangement
4304:SkattebĂžl rearrangement
4274:Ring-closing metathesis
4134:Group transfer reaction
4099:Favorskii rearrangement
4039:Cornforth rearrangement
3969:Bamberger rearrangement
3874:WolffâKishner reduction
3694:MarkĂłâLam deoxygenation
3589:FlemingâTamao oxidation
3584:FischerâTropsch process
3271:Oxymercuration reaction
3251:Knorr pyrrole synthesis
3077:BartonâKellogg reaction
2983:Wagner-Jauregg reaction
2903:Ring-closing metathesis
2893:ReimerâTiemann reaction
2883:RauhutâCurrier reaction
2798:Nef isocyanide reaction
2758:Malonic ester synthesis
2728:Knorr pyrrole synthesis
2663:High dilution principle
2598:FriedelâCrafts reaction
2533:Cross-coupling reaction
2458:BuchererâBergs reaction
2443:Blanc chloromethylation
2433:Blaise ketone synthesis
2408:BaylisâHillman reaction
2403:BartonâKellogg reaction
2378:AllanâRobinson reaction
2284:WoodwardâHoffmann rules
2019:Charge-transfer complex
1792:Transition state theory
1593:Intramolecular reaction
1519:Bimolecular elimination
1348:Wilkins, R. G. (1991).
826:EigenâWilkins Mechanism
128:. One of them breaks a
5152:Substitution reactions
5013:FeistâBenary synthesis
4787:Bradsher cycloaddition
4757:4+4 Photocycloaddition
4714:SimmonsâSmith reaction
4659:PaternĂČâBĂŒchi reaction
4519:FeistâBenary synthesis
4509:Dieckmann condensation
4259:Pummerer rearrangement
4239:Oxy-Cope rearrangement
4214:Myers allene synthesis
4164:Jacobsen rearrangement
4079:Electrocyclic reaction
4054:Demjanov rearrangement
4009:Buchner ring expansion
3979:Beckmann rearrangement
3959:Aza-Cope rearrangement
3954:ArndtâEistert reaction
3929:Alkyne zipper reaction
3849:Transfer hydrogenation
3824:Sharpless oxyamination
3799:Selenoxide elimination
3684:Lombardo methylenation
3609:Griesbaum coozonolysis
3519:CoreyâItsuno reduction
3494:BoylandâSims oxidation
3434:AngeliâRimini reaction
3082:Boord olefin synthesis
3026:ArndtâEistert reaction
3018:Homologation reactions
2818:Nitro-Mannich reaction
2733:KolbeâSchmitt reaction
2543:Cross-coupling partner
2463:Buchner ring expansion
2383:ArndtâEistert reaction
2149:Kinetic isotope effect
1896:Rearrangement reaction
1586:Unimolecular reactions
1547:Electrophilic addition
1199::1993JChEd..70...14I.
1172:
1086:
987:
835:
812:metal complexes, e.g.
787:coordination complexes
686:electrophilic addition
579:
528:
482:
407:
284:
4872:PausonâKhand reaction
4709:Sharpless epoxidation
4664:Pechmann condensation
4544:FriedlÀnder synthesis
4494:DavisâBeirut reaction
4349:Wallach rearrangement
4319:Stevens rearrangement
4254:Pinacol rearrangement
4234:Overman rearrangement
4149:Hofmann rearrangement
4144:Hayashi rearrangement
4109:Ferrier rearrangement
4064:Dimroth rearrangement
4049:Curtius rearrangement
4044:Criegee rearrangement
4024:Claisen rearrangement
4014:Carroll rearrangement
3949:Amadori rearrangement
3939:Allylic rearrangement
3819:Sharpless epoxidation
3554:DessâMartin oxidation
3479:BohnâSchmidt reaction
3339:Hofmann rearrangement
3142:Kauffmann olefination
3065:Olefination reactions
3003:WurtzâFittig reaction
2838:PalladiumâNHC complex
2718:Kauffmann olefination
2673:Homologation reaction
2523:CoreyâHouse synthesis
2503:Claisen rearrangement
2299:YukawaâTsuno equation
2259:SwainâLupton equation
2239:Spherical aromaticity
2174:MöbiusâHĂŒckel concept
1959:Aromatic ring current
1921:Substitution reaction
1777:Rate-determining step
1709:Reactive intermediate
1567:Free-radical addition
1557:Nucleophilic addition
1500:Elimination reactions
1173:
1087:
934:
874:rate determining step
870:entropy of activation
834:
764:substituted compounds
748:Substituted compounds
743:Substituted compounds
737:WurtzâFittig reaction
577:
522:
476:
408:
285:
75:reactive intermediate
43:substitution reaction
5078:PaalâKnorr synthesis
4948:BartonâZard reaction
4892:Staudinger synthesis
4842:Ketene cycloaddition
4812:DielsâAlder reaction
4792:Cheletropic reaction
4772:Alkyne trimerisation
4654:PaalâKnorr synthesis
4619:Kulinkovich reaction
4594:Jacobsen epoxidation
4514:DielsâAlder reaction
4309:Smiles rearrangement
4299:Sigmatropic reaction
4184:Lossen rearrangement
4034:CoreyâFuchs reaction
3999:Boekelheide reaction
3994:Bergmann degradation
3924:Achmatowicz reaction
3709:Methionine sulfoxide
3509:Clemmensen reduction
3469:Bergmann degradation
3399:Acyloin condensation
3364:Strecker degradation
3319:Bergmann degradation
3286:Ullmann condensation
3152:Peterson olefination
3127:Hydrazone iodination
3107:Elimination reaction
3008:ZinckeâSuhl reaction
2928:Sonogashira coupling
2888:Reformatsky reaction
2848:Peterson olefination
2813:Nierenstein reaction
2743:Kulinkovich reaction
2558:DielsâAlder reaction
2518:CoreyâFuchs reaction
2498:Claisen condensation
2368:Alkyne trimerisation
2343:Acyloin condensation
2309:ÎŁ-bishomoaromaticity
2269:ThorpeâIngold effect
1881:Elimination reaction
1772:Equilibrium constant
1102:
903:
818:tetrachloroplatinate
789:, but resembles the
706:Hunsdiecker reaction
704:. An example is the
698:radical substitution
692:Radical substitution
527:2 reaction mechanism
347:
212:
5098:Prilezhaev reaction
5083:Pellizzari reaction
4762:(4+3) cycloaddition
4729:Van Leusen reaction
4704:Robinson annulation
4689:Pschorr cyclization
4684:Prilezhaev reaction
4414:Bergman cyclization
4369:Wolff rearrangement
4354:Weerman degradation
4244:Pericyclic reaction
4224:Neber rearrangement
4119:Fries rearrangement
4004:Brook rearrangement
3989:Bergman cyclization
3834:Staudinger reaction
3779:Rosenmund reduction
3769:Reductive amination
3734:Oppenauer oxidation
3524:CoreyâKim oxidation
3499:Cannizzaro reaction
3374:Weerman degradation
3349:Isosaccharinic acid
3261:Mukaiyama hydration
3117:Hofmann elimination
3102:Dehydrohalogenation
3087:Chugaev elimination
2908:Robinson annulation
2853:Pfitzinger reaction
2623:Gattermann reaction
2568:WulffâDötz reaction
2548:DakinâWest reaction
2473:Carbonyl allylation
2418:Bergman cyclization
2204:Kennedy J. P. Orton
2124:Hammond's postulate
2094:FlippinâLodge angle
2064:Electromeric effect
1989:Beta-silicon effect
1974:BakerâNathan effect
1782:Reaction coordinate
1714:Radical (chemistry)
1699:Elementary reaction
1642:Grotthuss mechanism
1406:reaction mechanisms
1235:, New York: Wiley,
1150:
1131:
1064:
1047:
1003:
986:
963:
921:
824:is governed by the
639:
553:sterically hindered
4847:McCormack reaction
4797:Conia-ene reaction
4629:Madelung synthesis
4419:Biginelli reaction
4209:Mumm rearrangement
4094:Favorskii reaction
4029:Cope rearrangement
4019:Chan rearrangement
3784:Rubottom oxidation
3714:Miyaura borylation
3679:Lipid peroxidation
3674:Lindgren oxidation
3654:Kornblum oxidation
3649:Kolbe electrolysis
3594:Fukuyama reduction
3504:Carbonyl reduction
3354:Marker degradation
3216:Diazonium compound
3206:Boudouard reaction
3185:Carbon-heteroatom
3112:Grieco elimination
2898:Rieche formylation
2843:Passerini reaction
2773:Meerwein arylation
2693:Hydroxymethylation
2588:Favorskii reaction
2488:Chan rearrangement
2423:Biginelli reaction
2348:Aldol condensation
2194:2-Norbornyl cation
2169:Möbius aromaticity
2164:Markovnikov's rule
2059:Effective molarity
2004:BĂŒrgiâDunitz angle
1994:Bicycloaromaticity
1807:Arrhenius equation
1577:Oxidative addition
1539:Addition reactions
1203::10.1021/ed070p14.
1168:
1136:
1115:
1082:
1050:
989:
907:
836:
725:carbonâcarbon bond
717:Coupling reactions
700:reaction involves
684:generally lead to
637:
603:aromatic compounds
580:
567:1 rather than an S
529:
483:
418:aliphatic compound
403:
280:
89:, and whether the
5139:
5138:
5135:
5134:
5131:
5130:
5123:WohlâAue reaction
4767:6+4 Cycloaddition
4584:Iodolactonization
3904:1,2-rearrangement
3869:WohlâAue reaction
3789:Sabatier reaction
3754:Pinnick oxidation
3719:Mozingo reduction
3664:Leuckart reaction
3619:Haloform reaction
3534:Criegee oxidation
3514:Collins oxidation
3464:Benkeser reaction
3459:Bechamp reduction
3429:Andrussow process
3414:Alcohol oxidation
3324:Edman degradation
3231:Haloform reaction
3180:
3179:
3167:Takai olefination
3132:Julia olefination
2958:Takai olefination
2833:Olefin metathesis
2708:Julia olefination
2633:Grignard reaction
2613:Fukuyama coupling
2528:Coupling reaction
2493:ChanâLam coupling
2363:Alkyne metathesis
2358:Alkane metathesis
2214:Phosphaethynolate
2119:George S. Hammond
2079:Electronic effect
2034:Conjugated system
1916:Stereospecificity
1911:Stereoselectivity
1876:Addition reaction
1865:organic reactions
1830:
1829:
1802:Activated complex
1797:Activation energy
1759:Chemical kinetics
1704:Reaction dynamics
1603:Photodissociation
1279:978-0-321-66313-9
1270:Organic Chemistry
1161:
1153:
1144:
1139:
1120:
1108:
1076:
1067:
1058:
1053:
1048:
1006:
997:
992:
932:
924:
915:
910:
795:organic chemistry
677:
676:
672:
661:
395:
388:
380:
368:
361:
353:
266:
258:
250:
244:
236:
218:
169:
168:
130:CâH covalent bond
63:organic chemistry
59:chemical compound
16:(Redirected from
5159:
5118:Wenker synthesis
5108:Stollé synthesis
4963:Bobbitt reaction
4933:Auwers synthesis
4877:Povarov reaction
4802:Cyclopropanation
4740:
4739:
4734:Wenker synthesis
4489:Darzens reaction
4439:Bobbitt reaction
4284:Schmidt reaction
4089:Enyne metathesis
3864:Whiting reaction
3859:Wharton reaction
3804:Shapiro reaction
3794:Sarett oxidation
3759:Prévost reaction
3569:Emde degradation
3379:Wohl degradation
3359:Ruff degradation
3329:Emde degradation
3226:Grignard reagent
3162:Shapiro reaction
3147:McMurry reaction
3014:
3013:
2978:Ullmann reaction
2943:Stollé synthesis
2933:Stetter reaction
2923:Shapiro reaction
2913:Sakurai reaction
2808:Negishi coupling
2788:Minisci reaction
2783:Michael reaction
2768:McMurry reaction
2763:Mannich reaction
2643:Hammick reaction
2638:Grignard reagent
2578:Enyne metathesis
2563:Doebner reaction
2553:Darzens reaction
2398:Barbier reaction
2388:Auwers synthesis
2315:
2314:
2289:Woodward's rules
2254:Superaromaticity
2244:Spiroaromaticity
2144:Inductive effect
2139:Hyperconjugation
2114:Hammett equation
2054:Edwards equation
1906:Regioselectivity
1857:
1850:
1843:
1834:
1833:
1734:Collision theory
1683:Matrix isolation
1637:Harpoon reaction
1514:E1cB-elimination
1398:
1391:
1384:
1375:
1374:
1368:
1367:
1355:
1345:
1339:
1329:
1323:
1322:
1304:
1298:
1297:
1291:
1283:
1265:
1254:
1253:
1223:
1177:
1175:
1174:
1169:
1167:
1166:
1165:
1159:
1158:
1151:
1149:
1146:
1145:
1137:
1130:
1127:
1122:
1121:
1113:
1106:
1091:
1089:
1088:
1083:
1081:
1080:
1074:
1072:
1065:
1063:
1060:
1059:
1051:
1049:
1046:
1045:
1033:
1029:
1016:
1011:
1004:
1002:
999:
998:
990:
988:
985:
984:
972:
962:
961:
946:
930:
929:
922:
920:
917:
916:
908:
892:, which are the
733:Ullmann reaction
663:
652:
647:
640:
636:
622:are involved in
542:Walden inversion
412:
410:
409:
404:
402:
401:
400:
393:
386:
385:
378:
374:
373:
366:
359:
358:
351:
339:
335:
327:
316:
312:
308:
296:
289:
287:
286:
281:
279:
278:
273:
272:
264:
260:
256:
255:
248:
242:
241:
234:
230:
225:
224:
216:
159:
151:
150:
55:functional group
21:
5167:
5166:
5162:
5161:
5160:
5158:
5157:
5156:
5142:
5141:
5140:
5127:
5028:Gewald reaction
4911:
4738:
4719:Skraup reaction
4554:Graham reaction
4549:Gewald reaction
4380:
4373:
3895:
3888:
3844:Swern oxidation
3829:Stahl oxidation
3774:Riley oxidation
3729:Omega oxidation
3689:Luche reduction
3639:Jones oxidation
3604:Glycol cleavage
3599:Ganem oxidation
3544:Davis oxidation
3539:Dakin oxidation
3474:Birch reduction
3424:Amide reduction
3390:
3383:
3344:Hooker reaction
3306:
3300:
3188:
3186:
3176:
3172:Wittig reaction
3060:
3056:Wittig reaction
3031:Hooker reaction
3012:
2993:Wittig reaction
2968:Thorpe reaction
2953:Suzuki reaction
2938:Stille reaction
2873:Quelet reaction
2748:Kumada coupling
2698:Ivanov reaction
2688:Hydrovinylation
2668:Hiyama coupling
2628:Glaser coupling
2438:Blaise reaction
2428:Bingel reaction
2413:Benary reaction
2330:
2328:
2322:
2313:
2209:Passive binding
2129:Homoaromaticity
1979:Baldwin's rules
1954:Antiaromaticity
1949:Anomeric effect
1925:
1867:
1861:
1831:
1826:
1812:Eyring equation
1753:
1724:Stereochemistry
1687:
1673:Solvent effects
1661:
1617:
1581:
1562:
1552:
1533:
1528:
1494:
1490:
1471:
1467:
1457:
1447:
1437:
1427:
1408:
1402:
1372:
1371:
1364:
1346:
1342:
1330:
1326:
1319:
1305:
1301:
1285:
1284:
1280:
1266:
1257:
1243:
1224:
1215:
1210:
1184:
1182:Further reading
1154:
1147:
1141:
1140:
1132:
1128:
1123:
1117:
1116:
1114:
1109:
1105:
1103:
1100:
1099:
1073:
1068:
1061:
1055:
1054:
1041:
1037:
1025:
1024:
1015:
1007:
1000:
994:
993:
980:
976:
968:
954:
950:
942:
933:
925:
918:
912:
911:
906:
904:
901:
900:
891:
887:
883:
864:and often have
846:
814:Vaska's complex
772:
745:
714:
694:
679:
617:
611:
570:
566:
561:tertiary carbon
550:
538:stereochemistry
534:
526:
511:
499:stereochemistry
488:
480:
469:
465:
455:
447:
440:
428:Main articles:
426:
396:
392:
381:
369:
365:
354:
350:
348:
345:
344:
337:
333:
325:
314:
310:
306:
294:
274:
268:
267:
259:
251:
237:
226:
220:
219:
215:
213:
210:
209:
180:
174:
146:methyl chloride
143:
139:
135:
119:
45:(also known as
39:
32:ortho/meta/para
28:
23:
22:
15:
12:
11:
5:
5165:
5155:
5154:
5137:
5136:
5133:
5132:
5129:
5128:
5126:
5125:
5120:
5115:
5110:
5105:
5100:
5095:
5090:
5085:
5080:
5075:
5070:
5065:
5060:
5055:
5050:
5045:
5040:
5035:
5033:Hantzsch ester
5030:
5025:
5020:
5015:
5010:
5005:
5000:
4995:
4990:
4985:
4980:
4975:
4970:
4965:
4960:
4955:
4950:
4945:
4943:Banert cascade
4940:
4935:
4930:
4925:
4919:
4917:
4913:
4912:
4910:
4909:
4904:
4899:
4894:
4889:
4884:
4882:Prato reaction
4879:
4874:
4869:
4864:
4859:
4854:
4849:
4844:
4839:
4834:
4829:
4824:
4819:
4814:
4809:
4804:
4799:
4794:
4789:
4784:
4779:
4774:
4769:
4764:
4759:
4754:
4748:
4746:
4737:
4736:
4731:
4726:
4721:
4716:
4711:
4706:
4701:
4696:
4691:
4686:
4681:
4676:
4671:
4666:
4661:
4656:
4651:
4646:
4641:
4636:
4631:
4626:
4621:
4616:
4611:
4606:
4601:
4596:
4591:
4586:
4581:
4576:
4571:
4566:
4561:
4556:
4551:
4546:
4541:
4536:
4531:
4526:
4521:
4516:
4511:
4506:
4501:
4496:
4491:
4486:
4481:
4476:
4471:
4466:
4461:
4456:
4451:
4446:
4441:
4436:
4431:
4426:
4421:
4416:
4411:
4406:
4401:
4396:
4391:
4385:
4383:
4375:
4374:
4372:
4371:
4366:
4361:
4356:
4351:
4346:
4341:
4336:
4331:
4326:
4321:
4316:
4311:
4306:
4301:
4296:
4291:
4286:
4281:
4276:
4271:
4266:
4261:
4256:
4251:
4246:
4241:
4236:
4231:
4226:
4221:
4216:
4211:
4206:
4201:
4196:
4191:
4186:
4181:
4176:
4171:
4166:
4161:
4156:
4151:
4146:
4141:
4136:
4131:
4126:
4121:
4116:
4111:
4106:
4101:
4096:
4091:
4086:
4081:
4076:
4071:
4066:
4061:
4056:
4051:
4046:
4041:
4036:
4031:
4026:
4021:
4016:
4011:
4006:
4001:
3996:
3991:
3986:
3981:
3976:
3974:Banert cascade
3971:
3966:
3961:
3956:
3951:
3946:
3941:
3936:
3931:
3926:
3921:
3916:
3911:
3906:
3900:
3898:
3894:Rearrangement
3890:
3889:
3887:
3886:
3884:Zinin reaction
3881:
3876:
3871:
3866:
3861:
3856:
3854:Wacker process
3851:
3846:
3841:
3836:
3831:
3826:
3821:
3816:
3811:
3806:
3801:
3796:
3791:
3786:
3781:
3776:
3771:
3766:
3761:
3756:
3751:
3746:
3741:
3736:
3731:
3726:
3721:
3716:
3711:
3706:
3701:
3696:
3691:
3686:
3681:
3676:
3671:
3666:
3661:
3656:
3651:
3646:
3641:
3636:
3631:
3629:Hydrogenolysis
3626:
3621:
3616:
3611:
3606:
3601:
3596:
3591:
3586:
3581:
3579:Ătard reaction
3576:
3571:
3566:
3561:
3556:
3551:
3546:
3541:
3536:
3531:
3526:
3521:
3516:
3511:
3506:
3501:
3496:
3491:
3486:
3484:Bosch reaction
3481:
3476:
3471:
3466:
3461:
3456:
3451:
3446:
3441:
3436:
3431:
3426:
3421:
3416:
3411:
3406:
3401:
3395:
3393:
3389:Organic redox
3385:
3384:
3382:
3381:
3376:
3371:
3366:
3361:
3356:
3351:
3346:
3341:
3336:
3331:
3326:
3321:
3316:
3310:
3308:
3302:
3301:
3299:
3298:
3293:
3288:
3283:
3278:
3273:
3268:
3263:
3258:
3253:
3248:
3243:
3238:
3233:
3228:
3223:
3221:Esterification
3218:
3213:
3208:
3203:
3198:
3192:
3190:
3182:
3181:
3178:
3177:
3175:
3174:
3169:
3164:
3159:
3154:
3149:
3144:
3139:
3134:
3129:
3124:
3119:
3114:
3109:
3104:
3099:
3094:
3089:
3084:
3079:
3074:
3068:
3066:
3062:
3061:
3059:
3058:
3053:
3048:
3043:
3038:
3033:
3028:
3022:
3020:
3011:
3010:
3005:
3000:
2998:Wurtz reaction
2995:
2990:
2985:
2980:
2975:
2970:
2965:
2960:
2955:
2950:
2945:
2940:
2935:
2930:
2925:
2920:
2915:
2910:
2905:
2900:
2895:
2890:
2885:
2880:
2875:
2870:
2868:Prins reaction
2865:
2860:
2855:
2850:
2845:
2840:
2835:
2830:
2825:
2820:
2815:
2810:
2805:
2800:
2795:
2790:
2785:
2780:
2775:
2770:
2765:
2760:
2755:
2750:
2745:
2740:
2735:
2730:
2725:
2720:
2715:
2710:
2705:
2700:
2695:
2690:
2685:
2683:Hydrocyanation
2680:
2675:
2670:
2665:
2660:
2655:
2653:Henry reaction
2650:
2645:
2640:
2635:
2630:
2625:
2620:
2615:
2610:
2605:
2600:
2595:
2590:
2585:
2580:
2575:
2570:
2565:
2560:
2555:
2550:
2545:
2540:
2535:
2530:
2525:
2520:
2515:
2510:
2505:
2500:
2495:
2490:
2485:
2480:
2475:
2470:
2465:
2460:
2455:
2450:
2445:
2440:
2435:
2430:
2425:
2420:
2415:
2410:
2405:
2400:
2395:
2390:
2385:
2380:
2375:
2370:
2365:
2360:
2355:
2353:Aldol reaction
2350:
2345:
2340:
2334:
2332:
2327:Carbon-carbon
2324:
2323:
2312:
2311:
2306:
2304:Zaitsev's rule
2301:
2296:
2291:
2286:
2281:
2276:
2271:
2266:
2261:
2256:
2251:
2249:Steric effects
2246:
2241:
2236:
2231:
2226:
2221:
2216:
2211:
2206:
2201:
2196:
2191:
2186:
2181:
2176:
2171:
2166:
2161:
2156:
2151:
2146:
2141:
2136:
2131:
2126:
2121:
2116:
2111:
2106:
2101:
2096:
2091:
2086:
2081:
2076:
2071:
2066:
2061:
2056:
2051:
2046:
2041:
2036:
2031:
2026:
2021:
2016:
2011:
2006:
2001:
1996:
1991:
1986:
1981:
1976:
1971:
1966:
1961:
1956:
1951:
1946:
1941:
1936:
1930:
1927:
1926:
1924:
1923:
1918:
1913:
1908:
1903:
1901:Redox reaction
1898:
1893:
1888:
1886:Polymerization
1883:
1878:
1872:
1869:
1868:
1860:
1859:
1852:
1845:
1837:
1828:
1827:
1825:
1824:
1819:
1814:
1809:
1804:
1799:
1794:
1789:
1784:
1779:
1774:
1769:
1763:
1761:
1755:
1754:
1752:
1751:
1746:
1741:
1736:
1731:
1726:
1721:
1716:
1711:
1706:
1701:
1695:
1693:
1692:Related topics
1689:
1688:
1686:
1685:
1680:
1675:
1669:
1667:
1666:Medium effects
1663:
1662:
1660:
1659:
1654:
1649:
1644:
1639:
1634:
1628:
1626:
1619:
1618:
1616:
1615:
1610:
1605:
1600:
1595:
1589:
1587:
1583:
1582:
1580:
1579:
1574:
1569:
1564:
1560:
1554:
1550:
1543:
1541:
1535:
1534:
1532:
1531:
1526:
1522:
1516:
1511:
1504:
1502:
1496:
1495:
1493:
1492:
1488:
1481:
1479:
1473:
1472:
1470:
1469:
1465:
1459:
1455:
1449:
1445:
1439:
1435:
1429:
1425:
1418:
1416:
1410:
1409:
1401:
1400:
1393:
1386:
1378:
1370:
1369:
1362:
1340:
1324:
1317:
1299:
1278:
1255:
1241:
1212:
1211:
1209:
1206:
1205:
1204:
1183:
1180:
1179:
1178:
1164:
1157:
1135:
1126:
1112:
1093:
1092:
1079:
1071:
1044:
1040:
1036:
1032:
1028:
1023:
1019:
1014:
1010:
983:
979:
975:
971:
967:
960:
957:
953:
949:
945:
941:
937:
928:
894:rate constants
889:
885:
881:
844:
841:resembles the
783:organometallic
771:
768:
744:
741:
721:organometallic
713:
710:
693:
690:
675:
674:
649:
648:
613:Main article:
610:
607:
568:
564:
557:primary carbon
548:
532:
524:
509:
486:
478:
467:
463:
453:
445:
425:
422:
414:
413:
399:
391:
384:
377:
372:
364:
357:
291:
290:
277:
271:
263:
254:
247:
240:
233:
229:
223:
176:Main article:
173:
170:
167:
166:
162:
161:
141:
137:
133:
117:
34:patterns, see
26:
9:
6:
4:
3:
2:
5164:
5153:
5150:
5149:
5147:
5124:
5121:
5119:
5116:
5114:
5111:
5109:
5106:
5104:
5101:
5099:
5096:
5094:
5091:
5089:
5086:
5084:
5081:
5079:
5076:
5074:
5071:
5069:
5066:
5064:
5061:
5059:
5056:
5054:
5051:
5049:
5046:
5044:
5043:Herz reaction
5041:
5039:
5036:
5034:
5031:
5029:
5026:
5024:
5021:
5019:
5016:
5014:
5011:
5009:
5006:
5004:
5001:
4999:
4996:
4994:
4991:
4989:
4986:
4984:
4981:
4979:
4976:
4974:
4971:
4969:
4966:
4964:
4961:
4959:
4956:
4954:
4951:
4949:
4946:
4944:
4941:
4939:
4936:
4934:
4931:
4929:
4926:
4924:
4921:
4920:
4918:
4914:
4908:
4905:
4903:
4900:
4898:
4895:
4893:
4890:
4888:
4885:
4883:
4880:
4878:
4875:
4873:
4870:
4868:
4865:
4863:
4860:
4858:
4855:
4853:
4850:
4848:
4845:
4843:
4840:
4838:
4835:
4833:
4830:
4828:
4825:
4823:
4820:
4818:
4815:
4813:
4810:
4808:
4805:
4803:
4800:
4798:
4795:
4793:
4790:
4788:
4785:
4783:
4780:
4778:
4775:
4773:
4770:
4768:
4765:
4763:
4760:
4758:
4755:
4753:
4750:
4749:
4747:
4745:
4744:Cycloaddition
4741:
4735:
4732:
4730:
4727:
4725:
4722:
4720:
4717:
4715:
4712:
4710:
4707:
4705:
4702:
4700:
4697:
4695:
4692:
4690:
4687:
4685:
4682:
4680:
4677:
4675:
4672:
4670:
4667:
4665:
4662:
4660:
4657:
4655:
4652:
4650:
4647:
4645:
4642:
4640:
4637:
4635:
4632:
4630:
4627:
4625:
4622:
4620:
4617:
4615:
4612:
4610:
4607:
4605:
4602:
4600:
4597:
4595:
4592:
4590:
4589:Isay reaction
4587:
4585:
4582:
4580:
4577:
4575:
4572:
4570:
4567:
4565:
4562:
4560:
4557:
4555:
4552:
4550:
4547:
4545:
4542:
4540:
4537:
4535:
4532:
4530:
4527:
4525:
4522:
4520:
4517:
4515:
4512:
4510:
4507:
4505:
4502:
4500:
4497:
4495:
4492:
4490:
4487:
4485:
4484:Cycloaddition
4482:
4480:
4477:
4475:
4472:
4470:
4467:
4465:
4462:
4460:
4457:
4455:
4452:
4450:
4447:
4445:
4442:
4440:
4437:
4435:
4432:
4430:
4427:
4425:
4422:
4420:
4417:
4415:
4412:
4410:
4407:
4405:
4402:
4400:
4397:
4395:
4392:
4390:
4387:
4386:
4384:
4382:
4379:Ring forming
4376:
4370:
4367:
4365:
4362:
4360:
4357:
4355:
4352:
4350:
4347:
4345:
4342:
4340:
4337:
4335:
4332:
4330:
4327:
4325:
4322:
4320:
4317:
4315:
4312:
4310:
4307:
4305:
4302:
4300:
4297:
4295:
4292:
4290:
4287:
4285:
4282:
4280:
4279:Rupe reaction
4277:
4275:
4272:
4270:
4267:
4265:
4262:
4260:
4257:
4255:
4252:
4250:
4247:
4245:
4242:
4240:
4237:
4235:
4232:
4230:
4227:
4225:
4222:
4220:
4217:
4215:
4212:
4210:
4207:
4205:
4202:
4200:
4197:
4195:
4192:
4190:
4187:
4185:
4182:
4180:
4177:
4175:
4172:
4170:
4167:
4165:
4162:
4160:
4157:
4155:
4152:
4150:
4147:
4145:
4142:
4140:
4137:
4135:
4132:
4130:
4127:
4125:
4122:
4120:
4117:
4115:
4112:
4110:
4107:
4105:
4102:
4100:
4097:
4095:
4092:
4090:
4087:
4085:
4082:
4080:
4077:
4075:
4072:
4070:
4067:
4065:
4062:
4060:
4057:
4055:
4052:
4050:
4047:
4045:
4042:
4040:
4037:
4035:
4032:
4030:
4027:
4025:
4022:
4020:
4017:
4015:
4012:
4010:
4007:
4005:
4002:
4000:
3997:
3995:
3992:
3990:
3987:
3985:
3982:
3980:
3977:
3975:
3972:
3970:
3967:
3965:
3962:
3960:
3957:
3955:
3952:
3950:
3947:
3945:
3942:
3940:
3937:
3935:
3932:
3930:
3927:
3925:
3922:
3920:
3917:
3915:
3912:
3910:
3907:
3905:
3902:
3901:
3899:
3897:
3891:
3885:
3882:
3880:
3877:
3875:
3872:
3870:
3867:
3865:
3862:
3860:
3857:
3855:
3852:
3850:
3847:
3845:
3842:
3840:
3837:
3835:
3832:
3830:
3827:
3825:
3822:
3820:
3817:
3815:
3812:
3810:
3807:
3805:
3802:
3800:
3797:
3795:
3792:
3790:
3787:
3785:
3782:
3780:
3777:
3775:
3772:
3770:
3767:
3765:
3762:
3760:
3757:
3755:
3752:
3750:
3747:
3745:
3742:
3740:
3737:
3735:
3732:
3730:
3727:
3725:
3722:
3720:
3717:
3715:
3712:
3710:
3707:
3705:
3702:
3700:
3697:
3695:
3692:
3690:
3687:
3685:
3682:
3680:
3677:
3675:
3672:
3670:
3669:Ley oxidation
3667:
3665:
3662:
3660:
3657:
3655:
3652:
3650:
3647:
3645:
3642:
3640:
3637:
3635:
3634:Hydroxylation
3632:
3630:
3627:
3625:
3624:Hydrogenation
3622:
3620:
3617:
3615:
3612:
3610:
3607:
3605:
3602:
3600:
3597:
3595:
3592:
3590:
3587:
3585:
3582:
3580:
3577:
3575:
3572:
3570:
3567:
3565:
3562:
3560:
3559:DNA oxidation
3557:
3555:
3552:
3550:
3549:Deoxygenation
3547:
3545:
3542:
3540:
3537:
3535:
3532:
3530:
3527:
3525:
3522:
3520:
3517:
3515:
3512:
3510:
3507:
3505:
3502:
3500:
3497:
3495:
3492:
3490:
3487:
3485:
3482:
3480:
3477:
3475:
3472:
3470:
3467:
3465:
3462:
3460:
3457:
3455:
3452:
3450:
3447:
3445:
3442:
3440:
3439:Aromatization
3437:
3435:
3432:
3430:
3427:
3425:
3422:
3420:
3417:
3415:
3412:
3410:
3407:
3405:
3402:
3400:
3397:
3396:
3394:
3392:
3386:
3380:
3377:
3375:
3372:
3370:
3367:
3365:
3362:
3360:
3357:
3355:
3352:
3350:
3347:
3345:
3342:
3340:
3337:
3335:
3332:
3330:
3327:
3325:
3322:
3320:
3317:
3315:
3312:
3311:
3309:
3303:
3297:
3294:
3292:
3289:
3287:
3284:
3282:
3279:
3277:
3276:Reed reaction
3274:
3272:
3269:
3267:
3264:
3262:
3259:
3257:
3254:
3252:
3249:
3247:
3244:
3242:
3239:
3237:
3234:
3232:
3229:
3227:
3224:
3222:
3219:
3217:
3214:
3212:
3209:
3207:
3204:
3202:
3199:
3197:
3194:
3193:
3191:
3187:bond forming
3183:
3173:
3170:
3168:
3165:
3163:
3160:
3158:
3155:
3153:
3150:
3148:
3145:
3143:
3140:
3138:
3135:
3133:
3130:
3128:
3125:
3123:
3120:
3118:
3115:
3113:
3110:
3108:
3105:
3103:
3100:
3098:
3095:
3093:
3092:Cope reaction
3090:
3088:
3085:
3083:
3080:
3078:
3075:
3073:
3070:
3069:
3067:
3063:
3057:
3054:
3052:
3049:
3047:
3044:
3042:
3039:
3037:
3034:
3032:
3029:
3027:
3024:
3023:
3021:
3019:
3015:
3009:
3006:
3004:
3001:
2999:
2996:
2994:
2991:
2989:
2986:
2984:
2981:
2979:
2976:
2974:
2971:
2969:
2966:
2964:
2961:
2959:
2956:
2954:
2951:
2949:
2946:
2944:
2941:
2939:
2936:
2934:
2931:
2929:
2926:
2924:
2921:
2919:
2916:
2914:
2911:
2909:
2906:
2904:
2901:
2899:
2896:
2894:
2891:
2889:
2886:
2884:
2881:
2879:
2876:
2874:
2871:
2869:
2866:
2864:
2861:
2859:
2856:
2854:
2851:
2849:
2846:
2844:
2841:
2839:
2836:
2834:
2831:
2829:
2826:
2824:
2821:
2819:
2816:
2814:
2811:
2809:
2806:
2804:
2803:Nef synthesis
2801:
2799:
2796:
2794:
2791:
2789:
2786:
2784:
2781:
2779:
2778:Methylenation
2776:
2774:
2771:
2769:
2766:
2764:
2761:
2759:
2756:
2754:
2751:
2749:
2746:
2744:
2741:
2739:
2736:
2734:
2731:
2729:
2726:
2724:
2721:
2719:
2716:
2714:
2711:
2709:
2706:
2704:
2701:
2699:
2696:
2694:
2691:
2689:
2686:
2684:
2681:
2679:
2676:
2674:
2671:
2669:
2666:
2664:
2661:
2659:
2656:
2654:
2651:
2649:
2648:Heck reaction
2646:
2644:
2641:
2639:
2636:
2634:
2631:
2629:
2626:
2624:
2621:
2619:
2616:
2614:
2611:
2609:
2606:
2604:
2601:
2599:
2596:
2594:
2591:
2589:
2586:
2584:
2581:
2579:
2576:
2574:
2571:
2569:
2566:
2564:
2561:
2559:
2556:
2554:
2551:
2549:
2546:
2544:
2541:
2539:
2536:
2534:
2531:
2529:
2526:
2524:
2521:
2519:
2516:
2514:
2511:
2509:
2506:
2504:
2501:
2499:
2496:
2494:
2491:
2489:
2486:
2484:
2481:
2479:
2476:
2474:
2471:
2469:
2466:
2464:
2461:
2459:
2456:
2454:
2451:
2449:
2446:
2444:
2441:
2439:
2436:
2434:
2431:
2429:
2426:
2424:
2421:
2419:
2416:
2414:
2411:
2409:
2406:
2404:
2401:
2399:
2396:
2394:
2391:
2389:
2386:
2384:
2381:
2379:
2376:
2374:
2371:
2369:
2366:
2364:
2361:
2359:
2356:
2354:
2351:
2349:
2346:
2344:
2341:
2339:
2336:
2335:
2333:
2329:bond forming
2325:
2321:
2316:
2310:
2307:
2305:
2302:
2300:
2297:
2295:
2294:Y-aromaticity
2292:
2290:
2287:
2285:
2282:
2280:
2279:Walsh diagram
2277:
2275:
2272:
2270:
2267:
2265:
2264:Taft equation
2262:
2260:
2257:
2255:
2252:
2250:
2247:
2245:
2242:
2240:
2237:
2235:
2234:ÎŁ-aromaticity
2232:
2230:
2227:
2225:
2222:
2220:
2217:
2215:
2212:
2210:
2207:
2205:
2202:
2200:
2197:
2195:
2192:
2190:
2187:
2185:
2182:
2180:
2177:
2175:
2172:
2170:
2167:
2165:
2162:
2160:
2159:Marcus theory
2157:
2155:
2152:
2150:
2147:
2145:
2142:
2140:
2137:
2135:
2134:HĂŒckel's rule
2132:
2130:
2127:
2125:
2122:
2120:
2117:
2115:
2112:
2110:
2107:
2105:
2102:
2100:
2097:
2095:
2092:
2090:
2089:Evelyn effect
2087:
2085:
2082:
2080:
2077:
2075:
2072:
2070:
2069:Electron-rich
2067:
2065:
2062:
2060:
2057:
2055:
2052:
2050:
2047:
2045:
2042:
2040:
2037:
2035:
2032:
2030:
2027:
2025:
2022:
2020:
2017:
2015:
2012:
2010:
2007:
2005:
2002:
2000:
1997:
1995:
1992:
1990:
1987:
1985:
1984:Bema Hapothle
1982:
1980:
1977:
1975:
1972:
1970:
1967:
1965:
1962:
1960:
1957:
1955:
1952:
1950:
1947:
1945:
1942:
1940:
1937:
1935:
1932:
1931:
1928:
1922:
1919:
1917:
1914:
1912:
1909:
1907:
1904:
1902:
1899:
1897:
1894:
1892:
1889:
1887:
1884:
1882:
1879:
1877:
1874:
1873:
1870:
1866:
1858:
1853:
1851:
1846:
1844:
1839:
1838:
1835:
1823:
1820:
1818:
1815:
1813:
1810:
1808:
1805:
1803:
1800:
1798:
1795:
1793:
1790:
1788:
1785:
1783:
1780:
1778:
1775:
1773:
1770:
1768:
1767:Rate equation
1765:
1764:
1762:
1760:
1756:
1750:
1747:
1745:
1742:
1740:
1739:Arrow pushing
1737:
1735:
1732:
1730:
1727:
1725:
1722:
1720:
1717:
1715:
1712:
1710:
1707:
1705:
1702:
1700:
1697:
1696:
1694:
1690:
1684:
1681:
1679:
1676:
1674:
1671:
1670:
1668:
1664:
1658:
1655:
1653:
1650:
1648:
1647:Marcus theory
1645:
1643:
1640:
1638:
1635:
1633:
1630:
1629:
1627:
1624:
1620:
1614:
1611:
1609:
1606:
1604:
1601:
1599:
1598:Isomerization
1596:
1594:
1591:
1590:
1588:
1584:
1578:
1575:
1573:
1572:Cycloaddition
1570:
1568:
1565:
1558:
1555:
1548:
1545:
1544:
1542:
1540:
1536:
1530:
1523:
1520:
1517:
1515:
1512:
1509:
1506:
1505:
1503:
1501:
1497:
1486:
1483:
1482:
1480:
1478:
1474:
1463:
1460:
1453:
1450:
1443:
1440:
1433:
1430:
1423:
1420:
1419:
1417:
1415:
1411:
1407:
1399:
1394:
1392:
1387:
1385:
1380:
1379:
1376:
1365:
1363:1-56081-125-0
1359:
1354:
1353:
1344:
1338:
1337:0-471-05545-X
1334:
1328:
1320:
1318:3-527-28165-7
1314:
1310:
1303:
1295:
1289:
1281:
1275:
1271:
1264:
1262:
1260:
1252:
1248:
1244:
1242:9780471854722
1238:
1234:
1233:
1228:
1222:
1220:
1218:
1213:
1202:
1198:
1194:
1190:
1189:J. Chem. Educ
1186:
1185:
1155:
1124:
1110:
1098:
1097:
1096:
1077:
1069:
1042:
1038:
1034:
1030:
1021:
1017:
1012:
1008:
981:
977:
973:
965:
958:
955:
951:
947:
939:
935:
926:
899:
898:
897:
895:
879:
875:
871:
867:
863:
859:
855:
853:
848:
840:
833:
829:
827:
823:
819:
815:
811:
810:square planar
806:
804:
800:
796:
792:
791:Sn2 mechanism
788:
784:
780:
776:
767:
765:
761:
757:
753:
749:
740:
738:
734:
730:
729:Heck reaction
726:
722:
718:
709:
707:
703:
699:
689:
687:
683:
673:
670:
666:
659:
655:
651:
646:
642:
641:
635:
631:
629:
625:
621:
620:Electrophiles
616:
606:
604:
599:
597:
594:), called an
593:
589:
585:
576:
572:
562:
558:
554:
545:
543:
539:
521:
517:
515:
506:
504:
500:
496:
492:
475:
471:
461:
457:
449:
439:
435:
431:
421:
419:
397:
389:
382:
370:
362:
355:
343:
342:
341:
331:
323:
318:
304:
300:
299:electron pair
275:
261:
252:
238:
231:
227:
208:
207:
206:
203:
201:
197:
193:
192:leaving group
189:
185:
179:
164:
160:
158:
153:
149:
147:
131:
127:
123:
115:
111:
106:
104:
100:
96:
92:
88:
84:
80:
76:
72:
68:
67:electrophilic
64:
60:
56:
52:
48:
44:
37:
33:
19:
4084:Ene reaction
3444:Autoxidation
3305:Degradation
3196:Azo coupling
2973:Ugi reaction
2573:Ene reaction
2373:Alkynylation
2224:Polyfluorene
2219:Polar effect
2084:Electrophile
1999:Bredt's rule
1969:Baird's rule
1939:Alpha effect
1920:
1719:Molecularity
1351:
1343:
1327:
1308:
1302:
1269:
1231:
1227:March, Jerry
1195:(1): 14â16.
1192:
1188:
1094:
857:
851:
837:
807:
777:
773:
747:
746:
715:
695:
678:
668:
664:
662:
657:
653:
632:
618:
600:
581:
546:
530:
514:SN1 reaction
507:
503:racemization
484:
441:
434:SN2 reaction
430:SN1 reaction
415:
329:
319:
302:
292:
204:
196:electrophile
181:
154:
140:âą to form CH
126:nucleophilic
110:halogenation
107:
87:free radical
71:nucleophilic
50:
46:
42:
40:
31:
2583:Ethenolysis
2229:Ring strain
2199:Nucleophile
2024:Clar's rule
1964:Aromaticity
1678:Cage effect
1613:RRKM theory
1529:elimination
878:nucleophile
847:1 mechanism
803:Sn1 pathway
540:, called a
491:carbocation
188:nucleophile
79:carbocation
18:Substituted
4867:Ozonolysis
4394:Annulation
3744:Ozonolysis
1863:Topics in
1208:References
605:for more.
424:Mechanisms
4381:reactions
3896:reactions
3391:reactions
3307:reactions
3189:reactions
2331:reactions
1729:Catalysis
1625:reactions
1288:cite book
1251:642506595
1156:−
1070:−
1013:◻
1009:−
966:−
956:−
927:−
398:−
383:−
376:⟶
371:−
356:−
330:attacking
324:bromide,
276:−
253:−
246:⟶
239:−
228:−
200:substrate
95:aliphatic
91:substrate
83:carbanion
5146:Category
2274:Vinylogy
1944:Annulene
1891:Reagents
1229:(1985),
1078:′
1031:′
1018:→
936:⇌
822:rate law
702:radicals
462:, with S
460:rate law
311:NucâRâLG
122:radicals
114:chlorine
99:aromatic
1934:A value
1197:Bibcode
760:halogen
756:hydroxy
592:halogen
116:gas (Cl
112:. When
103:solvent
1404:Basic
1360:
1335:
1315:
1276:
1249:
1239:
868:. The
854:effect
820:. The
766:page.
735:, and
682:arenes
586:, and
516:page.
495:chiral
436:, and
293:where
1632:Redox
1468:Acyl)
888:and k
758:, or
752:alkyl
531:The S
485:The S
322:alkyl
315:RâNuc
132:in CH
85:or a
57:in a
1521:(E2)
1510:(E1)
1358:ISBN
1333:ISBN
1313:ISBN
1294:link
1274:ISBN
1247:OCLC
1237:ISBN
1107:Rate
816:and
785:and
596:acyl
326:RâBr
307:RâLG
295:RâLG
144:Cl (
81:, a
1491:Ar)
1448:Ar)
1201:doi
884:, k
858:cis
852:cis
805:.
793:in
665:2b:
658:2a:
571:2.
257:Nuc
217:Nuc
148:).
97:or
93:is
69:or
49:or
5148::
1559:(A
1549:(A
1487:(S
1464:(S
1458:i)
1454:(S
1444:(S
1438:2)
1434:(S
1428:1)
1424:(S
1290:}}
1286:{{
1258:^
1245:,
1216:^
1193:70
1191:.
886:â1
828:.
754:,
731:,
708:.
696:A
669:3:
654:1:
630:.
544:.
505:.
432:,
394:Br
387:OH
367:OH
360:Br
340::
338:Br
334:OH
265:LG
243:LG
202:.
105:.
41:A
1856:e
1849:t
1842:v
1563:)
1561:N
1553:)
1551:E
1527:i
1525:E
1489:E
1466:N
1456:N
1446:N
1436:N
1426:N
1397:e
1390:t
1383:v
1366:.
1321:.
1296:)
1282:.
1163:]
1160:L
1152:M
1143:n
1138:L
1134:[
1125:1
1119:k
1111:=
1075:L
1066:M
1057:n
1052:L
1043:2
1039:k
1035:,
1027:L
1022:+
1005:M
996:n
991:L
982:1
978:k
974:,
970:L
959:1
952:k
948:,
944:L
940:+
931:L
923:M
914:n
909:L
890:2
882:1
845:N
843:S
569:N
565:N
549:N
547:S
533:N
525:N
523:S
510:N
487:N
479:N
477:S
468:N
464:N
456:2
454:N
452:S
448:1
446:N
444:S
390:+
379:R
363:+
352:R
303::
301:(
270::
262:+
249:R
235:R
232:+
222::
142:3
138:3
134:4
118:2
38:.
20:)
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