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Dehydration reaction

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Alkenes can be made from alcohols by dehydration. This conversion, among others, is used in converting biomass to liquid fuels. The conversion of ethanol to
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J. Brent Friesen; Robert Schretzman (2011). "Dehydration of 2-Methyl-1-cyclohexanol: New Findings from a Popular Undergraduate Laboratory Experiment".
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This article is about chemical reactions resulting in the loss of water from a molecule. For the removal of water from solvents and reagents, see
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The reaction is induced by dehydrating reagents. For example, 2-methyl-cyclohexan-1-ol dehydrates to 1-methylcyclohexene in the presence of
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Franz Wirsching "Calcium Sulfate" in Ullmann's Encyclopedia of Industrial Chemistry, 2012 Wiley-VCH, Weinheim.
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Often such reactions require the presence of a dehydrating agent, i.e. a substance that reacts with water.
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The resulting dry powder is ready to be mixed with water to form a stiff but workable paste that hardens.
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Katryniok, Benjamin; Paul, Sébastien; Bellière-Baca, Virginie; Rey, Patrick; Dumeignil, Franck (2010).
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Roden, Brian A. (2001). "Diphenylbis(1,1,1,3,3,3-hexafluoro-2-phenyl-2-propoxy)sulfurane".
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Miller, Raimund; Abaecherli, Claudio; Said, Adel; Jackson, Barry (2001). "Ketenes".
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Some alcohols are prone to dehydration. 3-Hydroxylcarbonyls, called
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Besson, Michèle; Gallezot, Pierre; Pinel, Catherine (2014-02-12).
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Nitriles are often prepared by dehydration of primary amides.
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Various construction materials are produced by dehydration.
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bond is an important dehydration relevant to bioenergetics.
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Chemical reaction in which water is produced as a byproduct
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Double dehydration is illustrated by the conversion of
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G. H. Coleman, H. F. Johnstone (1925). "Cyclohexene".
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The classic example of a dehydration reaction is the
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Erlenmeyer–Plöchl azlactone and amino-acid synthesis
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Zimmermann, Heinz; Walz, Roland (2008). "Ethylene".
581: 259:, release water upon standing at room temperature: 494: 401: 377: 3148:Divinylcyclopropane-cycloheptadiene rearrangement 4222: 941: 668:Industrial & Engineering Chemistry Research 495:{\displaystyle {\ce {CaSO4.1/2H2O + 1 1/2H2O}}} 3408:Thermal rearrangement of aromatic hydrocarbons 2042:Thermal rearrangement of aromatic hydrocarbons 766:Encyclopedia of Reagents for Organic Synthesis 631:Ullmann's Encyclopedia of Industrial Chemistry 628: 550:Ullmann's Encyclopedia of Industrial Chemistry 232:intermediates as shown for the dehydration of 4137:Lectka enantioselective beta-lactam synthesis 1397: 927: 3916:Inverse electron-demand Diels–Alder reaction 1737:Heterogeneous metal catalyzed cross-coupling 303:Dehydration reactions in inorganic chemistry 3258:Lobry de Bruyn–Van Ekenstein transformation 934: 920: 58:Dehydration reactions in organic chemistry 3748:Petrenko-Kritschenko piperidone synthesis 3203:Fritsch–Buttenberg–Wiechell rearrangement 662:Zhang, Minhua; Yu, Yingzhe (2013-07-17). 464: 352: 3911:Intramolecular Diels–Alder cycloaddition 861: 279:, which reacts irreversibly with water. 877: 661: 4223: 3931:Metal-centered cycloaddition reactions 3583:Debus–Radziszewski imidazole synthesis 1527:Bodroux–Chichibabin aldehyde synthesis 378:{\displaystyle {\ce {CaSO4.2H2O +{}}}} 4077:Diazoalkane 1,3-dipolar cycloaddition 3981:Vinylcyclopropane (5+2) cycloaddition 3886:Diazoalkane 1,3-dipolar cycloaddition 3658:Hurd–Mori 1,2,3-thiadiazole synthesis 3153:Dowd–Beckwith ring-expansion reaction 2320:Hurd–Mori 1,2,3-thiadiazole synthesis 1396: 1233:LFER solvent coefficients (data page) 915: 763: 2888:Sharpless asymmetric dihydroxylation 2125:Methoxymethylenetriphenylphosphorane 800:; W. H. Hartung (1926). "Acrolein". 664:"Dehydration of Ethanol to Ethylene" 228:. These reactions often proceed via 122: 3013:Allen–Millar–Trippett rearrangement 179: 143: 13: 4152:Nitrone-olefin (3+2) cycloaddition 4147:Niementowski quinazoline synthesis 3936:Nitrone-olefin (3+2) cycloaddition 3861:Azide-alkyne Huisgen cycloaddition 3723:Niementowski quinazoline synthesis 3478:Azide-alkyne Huisgen cycloaddition 2783:Meerwein–Ponndorf–Verley reduction 2335:Leimgruber–Batcho indole synthesis 111:, can be joined together (to form 14: 4242: 3976:Trimethylenemethane cycloaddition 3678:Johnson–Corey–Chaykovsky reaction 3543:Cadogan–Sundberg indole synthesis 3523:Bohlmann–Rahtz pyridine synthesis 3483:Baeyer–Emmerling indole synthesis 2290:Cadogan–Sundberg indole synthesis 1782:Johnson–Corey–Chaykovsky reaction 883: 94: 62: 4072:Cook–Heilbron thiazole synthesis 3901:Hexadehydro Diels–Alder reaction 3728:Niementowski quinoline synthesis 3558:Cook–Heilbron thiazole synthesis 3503:Bischler–Möhlau indole synthesis 3413:Tiffeneau–Demjanov rearrangement 3043:Baker–Venkataraman rearrangement 2201:Horner–Wadsworth–Emmons reaction 1872:Mizoroki-Heck vs. Reductive Heck 1757:Horner–Wadsworth–Emmons reaction 1268:Neighbouring group participation 294: 247: 240: 3608:Fiesselmann thiophene synthesis 3438:Westphalen–LettrĂ© rearrangement 3418:Vinylcyclopropane rearrangement 3248:Kornblum–DeLaMare rearrangement 2893:Epoxidation of allylic alcohols 2803:Noyori asymmetric hydrogenation 2738:Kornblum–DeLaMare rearrangement 2413:Gallagher–Hollander degradation 267:CH(OH)R' → RC(O)CH=CHR' + H 216:The reaction is accelerated by 4067:Chichibabin pyridine synthesis 3553:Chichibabin pyridine synthesis 3513:Blum–Ittah aziridine synthesis 3348:Ring expansion and contraction 1617:Cross dehydrogenative coupling 822: 790: 757: 721: 694: 655: 622: 575: 540: 395: 318:is produced by dehydration of 1: 4037:Bischler–Napieralski reaction 3995:Heterocycle forming reactions 3648:Hemetsberger indole synthesis 3508:Bischler–Napieralski reaction 3423:Wagner–Meerwein rearrangement 3393:Sommelet–Hauser rearrangement 3373:Seyferth–Gilbert homologation 3238:Ireland–Claisen rearrangement 3233:Hofmann–Martius rearrangement 2993:2,3-sigmatropic rearrangement 2608:Corey–Winter olefin synthesis 2533:Barton–McCombie deoxygenation 2176:Corey–Winter olefin synthesis 2130:Seyferth–Gilbert homologation 1997:Seyferth–Gilbert homologation 639:10.1002/14356007.a10_045.pub3 533: 402:{\displaystyle {\ce {->}}} 4142:Lehmstedt–Tanasescu reaction 4102:Gabriel–Colman rearrangement 4057:Bucherer carbazole synthesis 4052:Borsche–Drechsel cyclization 4032:Bernthsen acridine synthesis 4017:Bamberger triazine synthesis 4002:Algar–Flynn–Oyamada reaction 3713:Nazarov cyclization reaction 3578:De Kimpe aziridine synthesis 3533:Bucherer carbazole synthesis 3528:Borsche–Drechsel cyclization 3298:Nazarov cyclization reaction 3278:Meyer–Schuster rearrangement 3208:Gabriel–Colman rearrangement 2958:Wolffenstein–Böters reaction 2843:Reduction of nitro compounds 2693:Grundmann aldehyde synthesis 2498:Algar–Flynn–Oyamada reaction 1907:Olefin conversion technology 1902:Nozaki–Hiyama–Kishi reaction 1697:Gabriel–Colman rearrangement 1587:Claisen-Schmidt condensation 1532:Bouveault aldehyde synthesis 7: 4117:Hantzsch pyridine synthesis 3896:Enone–alkene cycloadditions 3718:Nenitzescu indole synthesis 3638:Hantzsch pyridine synthesis 3603:Ferrario–Ackermann reaction 3253:Kowalski ester homologation 3218:Halogen dance rearrangement 3063:Benzilic acid rearrangement 2488:Akabori amino-acid reaction 2448:Von Braun amide degradation 2393:Barbier–Wieland degradation 2345:Nenitzescu indole synthesis 2325:Kharasch–Sosnovsky reaction 2216:Julia–Kocienski olefination 2120:Kowalski ester homologation 1817:Kowalski ester homologation 1792:Julia–Kocienski olefination 1547:Cadiot–Chodkiewicz coupling 1472:Aza-Baylis–Hillman reaction 1417:Acetoacetic ester synthesis 1128:Dynamic binding (chemistry) 1118:Conrotatory and disrotatory 1093:Charge remote fragmentation 511: 10: 4247: 4182:Robinson–Gabriel synthesis 4132:Kröhnke pyridine synthesis 3966:Retro-Diels–Alder reaction 3906:Imine Diels–Alder reaction 3693:Kröhnke pyridine synthesis 3308:Newman–Kwart rearrangement 3283:Mislow–Evans rearrangement 3193:Fischer–Hepp rearrangement 3138:Di-Ď€-methane rearrangement 2918:Stephen aldehyde synthesis 2653:Eschweiler–Clarke reaction 2370:Williamson ether synthesis 1687:Fujiwara–Moritani reaction 1592:Combes quinoline synthesis 1557:Carbonyl olefin metathesis 1258:More O'Ferrall–Jencks plot 1183:Grunwald–Winstein equation 1153:Electron-withdrawing group 1088:Catalytic resonance theory 188:is a fundamental example: 155:and trapping the product: 38:that involves the loss of 18: 4192:Urech hydantoin synthesis 4172:Pomeranz–Fritsch reaction 4097:Fischer oxazole synthesis 3994: 3831:1,3-Dipolar cycloaddition 3821: 3803:Urech hydantoin synthesis 3773:Reissert indole synthesis 3758:Pomeranz–Fritsch reaction 3688:Knorr quinoline synthesis 3618:Fischer oxazole synthesis 3548:Camps quinoline synthesis 3468:1,3-Dipolar cycloaddition 3456: 3368:Semipinacol rearrangement 3343:Ramberg–Bäcklund reaction 3328:Piancatelli rearrangement 3268:McFadyen–Stevens reaction 3023:Alpha-ketol rearrangement 2971: 2778:McFadyen–Stevens reaction 2723:Kiliani–Fischer synthesis 2643:Elbs persulfate oxidation 2568:Bouveault–Blanc reduction 2528:Baeyer–Villiger oxidation 2466: 2383: 2360:Schotten–Baumann reaction 2263: 2236:Ramberg–Bäcklund reaction 2143: 2115:Kiliani–Fischer synthesis 2095: 1957:Ramberg–Bäcklund reaction 1942:Pinacol coupling reaction 1937:Piancatelli rearrangement 1832:Liebeskind–Srogl coupling 1682:Fujimoto–Belleau reaction 1405: 1399:List of organic reactions 1263:Negative hyperconjugation 1008: 950: 4167:Pictet–Spengler reaction 4082:Einhorn–Brunner reaction 4047:Boger pyridine synthesis 3941:Oxo-Diels–Alder reaction 3856:Aza-Diels–Alder reaction 3753:Pictet–Spengler reaction 3653:Hofmann–Löffler reaction 3643:Hegedus indole synthesis 3613:Fischer indole synthesis 3488:Bartoli indole synthesis 3443:Willgerodt rearrangement 3273:McLafferty rearrangement 3183:Ferrier carbocyclization 2998:2,3-Wittig rearrangement 2988:1,2-Wittig rearrangement 2828:Parikh–Doering oxidation 2818:Oxygen rebound mechanism 2483:Adkins–Peterson reaction 2375:Yamaguchi esterification 2315:Hegedus indole synthesis 2280:Bartoli indole synthesis 2151:Bamford–Stevens reaction 2067:Weinreb ketone synthesis 2027:Stork enamine alkylation 1802:Knoevenagel condensation 1672:Ferrier carbocyclization 1562:Castro–Stephens coupling 1188:Hammett acidity function 1178:Free-energy relationship 1123:Curtin–Hammett principle 1108:Conformational isomerism 873:10.1002/14356007.a04_555 816:10.15227/orgsyn.006.0001 774:10.1002/047084289X.rd409 715:10.15227/orgsyn.005.0033 559:10.1002/14356007.a15_063 4127:Knorr pyrrole synthesis 4062:Bucherer–Bergs reaction 4007:Allan–Robinson reaction 3986:Wagner-Jauregg reaction 3778:Ring-closing metathesis 3703:Larock indole synthesis 3683:Knorr pyrrole synthesis 3538:Bucherer–Bergs reaction 3403:Stieglitz rearrangement 3383:Skattebøl rearrangement 3353:Ring-closing metathesis 3213:Group transfer reaction 3178:Favorskii rearrangement 3118:Cornforth rearrangement 3048:Bamberger rearrangement 2953:Wolff–Kishner reduction 2773:Markó–Lam deoxygenation 2668:Fleming–Tamao oxidation 2663:Fischer–Tropsch process 2350:Oxymercuration reaction 2330:Knorr pyrrole synthesis 2156:Barton–Kellogg reaction 2062:Wagner-Jauregg reaction 1982:Ring-closing metathesis 1972:Reimer–Tiemann reaction 1962:Rauhut–Currier reaction 1877:Nef isocyanide reaction 1837:Malonic ester synthesis 1807:Knorr pyrrole synthesis 1742:High dilution principle 1677:Friedel–Crafts reaction 1612:Cross-coupling reaction 1537:Bucherer–Bergs reaction 1522:Blanc chloromethylation 1512:Blaise ketone synthesis 1487:Baylis–Hillman reaction 1482:Barton–Kellogg reaction 1457:Allan–Robinson reaction 1363:Woodward–Hoffmann rules 1098:Charge-transfer complex 633:. Weinheim: Wiley-VCH. 553:. Weinheim: Wiley-VCH. 151:is produced by heating 4092:Feist–Benary synthesis 3866:Bradsher cycloaddition 3836:4+4 Photocycloaddition 3793:Simmons–Smith reaction 3738:Paternò–BĂĽchi reaction 3598:Feist–Benary synthesis 3588:Dieckmann condensation 3338:Pummerer rearrangement 3318:Oxy-Cope rearrangement 3293:Myers allene synthesis 3243:Jacobsen rearrangement 3158:Electrocyclic reaction 3133:Demjanov rearrangement 3088:Buchner ring expansion 3058:Beckmann rearrangement 3038:Aza-Cope rearrangement 3033:Arndt–Eistert reaction 3008:Alkyne zipper reaction 2928:Transfer hydrogenation 2903:Sharpless oxyamination 2878:Selenoxide elimination 2763:Lombardo methylenation 2688:Griesbaum coozonolysis 2598:Corey–Itsuno reduction 2573:Boyland–Sims oxidation 2513:Angeli–Rimini reaction 2161:Boord olefin synthesis 2105:Arndt–Eistert reaction 2097:Homologation reactions 1897:Nitro-Mannich reaction 1812:Kolbe–Schmitt reaction 1622:Cross-coupling partner 1542:Buchner ring expansion 1462:Arndt–Eistert reaction 1228:Kinetic isotope effect 975:Rearrangement reaction 496: 403: 379: 69:Fischer esterification 4231:Elimination reactions 3951:Pauson–Khand reaction 3788:Sharpless epoxidation 3743:Pechmann condensation 3623:Friedländer synthesis 3573:Davis–Beirut reaction 3428:Wallach rearrangement 3398:Stevens rearrangement 3333:Pinacol rearrangement 3313:Overman rearrangement 3228:Hofmann rearrangement 3223:Hayashi rearrangement 3188:Ferrier rearrangement 3143:Dimroth rearrangement 3128:Curtius rearrangement 3123:Criegee rearrangement 3103:Claisen rearrangement 3093:Carroll rearrangement 3028:Amadori rearrangement 3018:Allylic rearrangement 2898:Sharpless epoxidation 2633:Dess–Martin oxidation 2558:Bohn–Schmidt reaction 2418:Hofmann rearrangement 2221:Kauffmann olefination 2144:Olefination reactions 2082:Wurtz–Fittig reaction 1917:Palladium–NHC complex 1797:Kauffmann olefination 1752:Homologation reaction 1602:Corey–House synthesis 1582:Claisen rearrangement 1378:Yukawa–Tsuno equation 1338:Swain–Lupton equation 1318:Spherical aromaticity 1253:Möbius–HĂĽckel concept 1038:Aromatic ring current 1000:Substitution reaction 523:Condensation reaction 497: 404: 380: 307:The formation of the 4157:Paal–Knorr synthesis 4027:Barton–Zard reaction 3971:Staudinger synthesis 3921:Ketene cycloaddition 3891:Diels–Alder reaction 3871:Cheletropic reaction 3851:Alkyne trimerisation 3733:Paal–Knorr synthesis 3698:Kulinkovich reaction 3673:Jacobsen epoxidation 3593:Diels–Alder reaction 3388:Smiles rearrangement 3378:Sigmatropic reaction 3263:Lossen rearrangement 3113:Corey–Fuchs reaction 3078:Boekelheide reaction 3073:Bergmann degradation 3003:Achmatowicz reaction 2788:Methionine sulfoxide 2588:Clemmensen reduction 2548:Bergmann degradation 2478:Acyloin condensation 2443:Strecker degradation 2398:Bergmann degradation 2365:Ullmann condensation 2231:Peterson olefination 2206:Hydrazone iodination 2186:Elimination reaction 2087:Zincke–Suhl reaction 2007:Sonogashira coupling 1967:Reformatsky reaction 1927:Peterson olefination 1892:Nierenstein reaction 1822:Kulinkovich reaction 1637:Diels–Alder reaction 1597:Corey–Fuchs reaction 1577:Claisen condensation 1447:Alkyne trimerisation 1422:Acyloin condensation 1388:ÎŁ-bishomoaromaticity 1348:Thorpe–Ingold effect 960:Elimination reaction 896:on November 20, 2008 503:(released as steam). 412: 391: 329: 32:dehydration reaction 4177:Prilezhaev reaction 4162:Pellizzari reaction 3841:(4+3) cycloaddition 3808:Van Leusen reaction 3783:Robinson annulation 3768:Pschorr cyclization 3763:Prilezhaev reaction 3493:Bergman cyclization 3448:Wolff rearrangement 3433:Weerman degradation 3323:Pericyclic reaction 3303:Neber rearrangement 3198:Fries rearrangement 3083:Brook rearrangement 3068:Bergman cyclization 2913:Staudinger reaction 2858:Rosenmund reduction 2848:Reductive amination 2813:Oppenauer oxidation 2603:Corey–Kim oxidation 2578:Cannizzaro reaction 2453:Weerman degradation 2428:Isosaccharinic acid 2340:Mukaiyama hydration 2196:Hofmann elimination 2181:Dehydrohalogenation 2166:Chugaev elimination 1987:Robinson annulation 1932:Pfitzinger reaction 1702:Gattermann reaction 1647:Wulff–Dötz reaction 1627:Dakin–West reaction 1552:Carbonyl allylation 1497:Bergman cyclization 1283:Kennedy J. P. Orton 1203:Hammond's postulate 1173:Flippin–Lodge angle 1143:Electromeric effect 1068:Beta-silicon effect 1053:Baker–Nathan effect 743:2011JChEd..88.1141F 487: 454: 428: 365: 345: 3926:McCormack reaction 3876:Conia-ene reaction 3708:Madelung synthesis 3498:Biginelli reaction 3288:Mumm rearrangement 3173:Favorskii reaction 3108:Cope rearrangement 3098:Chan rearrangement 2863:Rubottom oxidation 2793:Miyaura borylation 2758:Lipid peroxidation 2753:Lindgren oxidation 2733:Kornblum oxidation 2728:Kolbe electrolysis 2673:Fukuyama reduction 2583:Carbonyl reduction 2433:Marker degradation 2295:Diazonium compound 2285:Boudouard reaction 2264:Carbon-heteroatom 2191:Grieco elimination 1977:Rieche formylation 1922:Passerini reaction 1852:Meerwein arylation 1772:Hydroxymethylation 1667:Favorskii reaction 1567:Chan rearrangement 1502:Biginelli reaction 1427:Aldol condensation 1273:2-Norbornyl cation 1248:Möbius aromaticity 1243:Markovnikov's rule 1138:Effective molarity 1083:BĂĽrgi–Dunitz angle 1073:Bicycloaromaticity 847:10.1039/c0gc00307g 518:Hydration reaction 492: 475: 474: 442: 441: 416: 399: 375: 353: 333: 277:Martin's sulfurane 52:hydration reaction 42:from the reacting 4218: 4217: 4214: 4213: 4210: 4209: 4202:Wohl–Aue reaction 3846:6+4 Cycloaddition 3663:Iodolactonization 2983:1,2-rearrangement 2948:Wohl–Aue reaction 2868:Sabatier reaction 2833:Pinnick oxidation 2798:Mozingo reduction 2743:Leuckart reaction 2698:Haloform reaction 2613:Criegee oxidation 2593:Collins oxidation 2543:Benkeser reaction 2538:Bechamp reduction 2508:Andrussow process 2493:Alcohol oxidation 2403:Edman degradation 2310:Haloform reaction 2259: 2258: 2246:Takai olefination 2211:Julia olefination 2037:Takai olefination 1912:Olefin metathesis 1787:Julia olefination 1712:Grignard reaction 1692:Fukuyama coupling 1607:Coupling reaction 1572:Chan–Lam coupling 1442:Alkyne metathesis 1437:Alkane metathesis 1293:Phosphaethynolate 1198:George S. Hammond 1158:Electronic effect 1113:Conjugated system 995:Stereospecificity 990:Stereoselectivity 955:Addition reaction 944:organic reactions 803:Organic Syntheses 751:10.1021/ed900049b 703:Organic Syntheses 680:10.1021/ie401157c 674:(28): 9505–9514. 600:10.1021/cr4002269 490: 478: 473: 457: 445: 440: 419: 368: 356: 336: 123:Nitrile formation 36:chemical reaction 4238: 4197:Wenker synthesis 4187:StollĂ© synthesis 4042:Bobbitt reaction 4012:Auwers synthesis 3956:Povarov reaction 3881:Cyclopropanation 3819: 3818: 3813:Wenker synthesis 3568:Darzens reaction 3518:Bobbitt reaction 3363:Schmidt reaction 3168:Enyne metathesis 2943:Whiting reaction 2938:Wharton reaction 2883:Shapiro reaction 2873:Sarett oxidation 2838:PrĂ©vost reaction 2648:Emde degradation 2458:Wohl degradation 2438:Ruff degradation 2408:Emde degradation 2305:Grignard reagent 2241:Shapiro reaction 2226:McMurry reaction 2093: 2092: 2057:Ullmann reaction 2022:StollĂ© synthesis 2012:Stetter reaction 2002:Shapiro reaction 1992:Sakurai reaction 1887:Negishi coupling 1867:Minisci reaction 1862:Michael reaction 1847:McMurry reaction 1842:Mannich reaction 1722:Hammick reaction 1717:Grignard reagent 1657:Enyne metathesis 1642:Doebner reaction 1632:Darzens reaction 1477:Barbier reaction 1467:Auwers synthesis 1394: 1393: 1368:Woodward's rules 1333:Superaromaticity 1323:Spiroaromaticity 1223:Inductive effect 1218:Hyperconjugation 1193:Hammett equation 1133:Edwards equation 985:Regioselectivity 936: 929: 922: 913: 912: 906: 905: 903: 901: 892:. Archived from 881: 875: 865: 859: 858: 826: 820: 818: 794: 788: 787: 761: 755: 754: 737:(8): 1141–1147. 725: 719: 718: 698: 692: 691: 659: 653: 652: 626: 620: 619: 594:(3): 1827–1870. 588:Chemical Reviews 579: 573: 572: 544: 501: 499: 498: 493: 491: 488: 486: 483: 476: 466: 455: 453: 450: 443: 433: 427: 424: 417: 408: 406: 405: 400: 398: 384: 382: 381: 376: 374: 373: 366: 364: 361: 354: 344: 341: 334: 316:Plaster of Paris 298: 251: 244: 180:Alkene formation 144:Ketene formation 4246: 4245: 4241: 4240: 4239: 4237: 4236: 4235: 4221: 4220: 4219: 4206: 4107:Gewald reaction 3990: 3817: 3798:Skraup reaction 3633:Graham reaction 3628:Gewald reaction 3459: 3452: 2974: 2967: 2923:Swern oxidation 2908:Stahl oxidation 2853:Riley oxidation 2808:Omega oxidation 2768:Luche reduction 2718:Jones oxidation 2683:Glycol cleavage 2678:Ganem oxidation 2623:Davis oxidation 2618:Dakin oxidation 2553:Birch reduction 2503:Amide reduction 2469: 2462: 2423:Hooker reaction 2385: 2379: 2267: 2265: 2255: 2251:Wittig reaction 2139: 2135:Wittig reaction 2110:Hooker reaction 2091: 2072:Wittig reaction 2047:Thorpe reaction 2032:Suzuki reaction 2017:Stille reaction 1952:Quelet reaction 1827:Kumada coupling 1777:Ivanov reaction 1767:Hydrovinylation 1747:Hiyama coupling 1707:Glaser coupling 1517:Blaise reaction 1507:Bingel reaction 1492:Benary reaction 1409: 1407: 1401: 1392: 1288:Passive binding 1208:Homoaromaticity 1058:Baldwin's rules 1033:Antiaromaticity 1028:Anomeric effect 1004: 946: 940: 910: 909: 899: 897: 882: 878: 866: 862: 835:Green Chemistry 827: 823: 795: 791: 784: 762: 758: 726: 722: 699: 695: 660: 656: 649: 627: 623: 580: 576: 569: 545: 541: 536: 514: 484: 479: 451: 446: 425: 420: 415: 413: 410: 409: 394: 392: 389: 388: 372: 362: 357: 342: 337: 332: 330: 327: 326: 305: 270: 266: 211: 207: 203: 199: 195: 192:   CH 182: 174: 170: 166: 162: 146: 138: 134: 125: 101:monosaccharides 97: 86: 82: 78: 65: 60: 24: 17: 12: 11: 5: 4244: 4234: 4233: 4216: 4215: 4212: 4211: 4208: 4207: 4205: 4204: 4199: 4194: 4189: 4184: 4179: 4174: 4169: 4164: 4159: 4154: 4149: 4144: 4139: 4134: 4129: 4124: 4119: 4114: 4112:Hantzsch ester 4109: 4104: 4099: 4094: 4089: 4084: 4079: 4074: 4069: 4064: 4059: 4054: 4049: 4044: 4039: 4034: 4029: 4024: 4022:Banert cascade 4019: 4014: 4009: 4004: 3998: 3996: 3992: 3991: 3989: 3988: 3983: 3978: 3973: 3968: 3963: 3961:Prato reaction 3958: 3953: 3948: 3943: 3938: 3933: 3928: 3923: 3918: 3913: 3908: 3903: 3898: 3893: 3888: 3883: 3878: 3873: 3868: 3863: 3858: 3853: 3848: 3843: 3838: 3833: 3827: 3825: 3816: 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: 3615: 3610: 3605: 3600: 3595: 3590: 3585: 3580: 3575: 3570: 3565: 3560: 3555: 3550: 3545: 3540: 3535: 3530: 3525: 3520: 3515: 3510: 3505: 3500: 3495: 3490: 3485: 3480: 3475: 3470: 3464: 3462: 3454: 3453: 3451: 3450: 3445: 3440: 3435: 3430: 3425: 3420: 3415: 3410: 3405: 3400: 3395: 3390: 3385: 3380: 3375: 3370: 3365: 3360: 3355: 3350: 3345: 3340: 3335: 3330: 3325: 3320: 3315: 3310: 3305: 3300: 3295: 3290: 3285: 3280: 3275: 3270: 3265: 3260: 3255: 3250: 3245: 3240: 3235: 3230: 3225: 3220: 3215: 3210: 3205: 3200: 3195: 3190: 3185: 3180: 3175: 3170: 3165: 3160: 3155: 3150: 3145: 3140: 3135: 3130: 3125: 3120: 3115: 3110: 3105: 3100: 3095: 3090: 3085: 3080: 3075: 3070: 3065: 3060: 3055: 3053:Banert cascade 3050: 3045: 3040: 3035: 3030: 3025: 3020: 3015: 3010: 3005: 3000: 2995: 2990: 2985: 2979: 2977: 2973:Rearrangement 2969: 2968: 2966: 2965: 2963:Zinin reaction 2960: 2955: 2950: 2945: 2940: 2935: 2933:Wacker process 2930: 2925: 2920: 2915: 2910: 2905: 2900: 2895: 2890: 2885: 2880: 2875: 2870: 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: 2708:Hydrogenolysis 2705: 2700: 2695: 2690: 2685: 2680: 2675: 2670: 2665: 2660: 2658:Étard reaction 2655: 2650: 2645: 2640: 2635: 2630: 2625: 2620: 2615: 2610: 2605: 2600: 2595: 2590: 2585: 2580: 2575: 2570: 2565: 2563:Bosch reaction 2560: 2555: 2550: 2545: 2540: 2535: 2530: 2525: 2520: 2515: 2510: 2505: 2500: 2495: 2490: 2485: 2480: 2474: 2472: 2468:Organic redox 2464: 2463: 2461: 2460: 2455: 2450: 2445: 2440: 2435: 2430: 2425: 2420: 2415: 2410: 2405: 2400: 2395: 2389: 2387: 2381: 2380: 2378: 2377: 2372: 2367: 2362: 2357: 2352: 2347: 2342: 2337: 2332: 2327: 2322: 2317: 2312: 2307: 2302: 2300:Esterification 2297: 2292: 2287: 2282: 2277: 2271: 2269: 2261: 2260: 2257: 2256: 2254: 2253: 2248: 2243: 2238: 2233: 2228: 2223: 2218: 2213: 2208: 2203: 2198: 2193: 2188: 2183: 2178: 2173: 2168: 2163: 2158: 2153: 2147: 2145: 2141: 2140: 2138: 2137: 2132: 2127: 2122: 2117: 2112: 2107: 2101: 2099: 2090: 2089: 2084: 2079: 2077:Wurtz reaction 2074: 2069: 2064: 2059: 2054: 2049: 2044: 2039: 2034: 2029: 2024: 2019: 2014: 2009: 2004: 1999: 1994: 1989: 1984: 1979: 1974: 1969: 1964: 1959: 1954: 1949: 1947:Prins reaction 1944: 1939: 1934: 1929: 1924: 1919: 1914: 1909: 1904: 1899: 1894: 1889: 1884: 1879: 1874: 1869: 1864: 1859: 1854: 1849: 1844: 1839: 1834: 1829: 1824: 1819: 1814: 1809: 1804: 1799: 1794: 1789: 1784: 1779: 1774: 1769: 1764: 1762:Hydrocyanation 1759: 1754: 1749: 1744: 1739: 1734: 1732:Henry reaction 1729: 1724: 1719: 1714: 1709: 1704: 1699: 1694: 1689: 1684: 1679: 1674: 1669: 1664: 1659: 1654: 1649: 1644: 1639: 1634: 1629: 1624: 1619: 1614: 1609: 1604: 1599: 1594: 1589: 1584: 1579: 1574: 1569: 1564: 1559: 1554: 1549: 1544: 1539: 1534: 1529: 1524: 1519: 1514: 1509: 1504: 1499: 1494: 1489: 1484: 1479: 1474: 1469: 1464: 1459: 1454: 1449: 1444: 1439: 1434: 1432:Aldol reaction 1429: 1424: 1419: 1413: 1411: 1406:Carbon-carbon 1403: 1402: 1391: 1390: 1385: 1383:Zaitsev's rule 1380: 1375: 1370: 1365: 1360: 1355: 1350: 1345: 1340: 1335: 1330: 1328:Steric effects 1325: 1320: 1315: 1310: 1305: 1300: 1295: 1290: 1285: 1280: 1275: 1270: 1265: 1260: 1255: 1250: 1245: 1240: 1235: 1230: 1225: 1220: 1215: 1210: 1205: 1200: 1195: 1190: 1185: 1180: 1175: 1170: 1165: 1160: 1155: 1150: 1145: 1140: 1135: 1130: 1125: 1120: 1115: 1110: 1105: 1100: 1095: 1090: 1085: 1080: 1075: 1070: 1065: 1060: 1055: 1050: 1045: 1040: 1035: 1030: 1025: 1020: 1015: 1009: 1006: 1005: 1003: 1002: 997: 992: 987: 982: 980:Redox reaction 977: 972: 967: 965:Polymerization 962: 957: 951: 948: 947: 939: 938: 931: 924: 916: 908: 907: 890:LaFargePrestia 886:"CaSO4, ½ H2O" 876: 860: 821: 789: 782: 756: 731:J. Chem. Educ. 720: 693: 654: 648:978-3527306732 647: 621: 574: 567: 538: 537: 535: 532: 531: 530: 525: 520: 513: 510: 506: 505: 482: 472: 469: 463: 460: 449: 439: 436: 431: 423: 397: 371: 360: 351: 348: 340: 304: 301: 300: 299: 273: 272: 268: 264: 253: 252: 245: 218:acid catalysts 214: 213: 209: 205: 201: 197: 193: 181: 178: 177: 176: 172: 168: 164: 160: 145: 142: 141: 140: 136: 132: 124: 121: 96: 95:Etherification 93: 89: 88: 84: 80: 79:H + R′OH ⇌ RCO 76: 64: 63:Esterification 61: 59: 56: 15: 9: 6: 4: 3: 2: 4243: 4232: 4229: 4228: 4226: 4203: 4200: 4198: 4195: 4193: 4190: 4188: 4185: 4183: 4180: 4178: 4175: 4173: 4170: 4168: 4165: 4163: 4160: 4158: 4155: 4153: 4150: 4148: 4145: 4143: 4140: 4138: 4135: 4133: 4130: 4128: 4125: 4123: 4122:Herz reaction 4120: 4118: 4115: 4113: 4110: 4108: 4105: 4103: 4100: 4098: 4095: 4093: 4090: 4088: 4085: 4083: 4080: 4078: 4075: 4073: 4070: 4068: 4065: 4063: 4060: 4058: 4055: 4053: 4050: 4048: 4045: 4043: 4040: 4038: 4035: 4033: 4030: 4028: 4025: 4023: 4020: 4018: 4015: 4013: 4010: 4008: 4005: 4003: 4000: 3999: 3997: 3993: 3987: 3984: 3982: 3979: 3977: 3974: 3972: 3969: 3967: 3964: 3962: 3959: 3957: 3954: 3952: 3949: 3947: 3944: 3942: 3939: 3937: 3934: 3932: 3929: 3927: 3924: 3922: 3919: 3917: 3914: 3912: 3909: 3907: 3904: 3902: 3899: 3897: 3894: 3892: 3889: 3887: 3884: 3882: 3879: 3877: 3874: 3872: 3869: 3867: 3864: 3862: 3859: 3857: 3854: 3852: 3849: 3847: 3844: 3842: 3839: 3837: 3834: 3832: 3829: 3828: 3826: 3824: 3823:Cycloaddition 3820: 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: 3668:Isay reaction 3666: 3664: 3661: 3659: 3656: 3654: 3651: 3649: 3646: 3644: 3641: 3639: 3636: 3634: 3631: 3629: 3626: 3624: 3621: 3619: 3616: 3614: 3611: 3609: 3606: 3604: 3601: 3599: 3596: 3594: 3591: 3589: 3586: 3584: 3581: 3579: 3576: 3574: 3571: 3569: 3566: 3564: 3563:Cycloaddition 3561: 3559: 3556: 3554: 3551: 3549: 3546: 3544: 3541: 3539: 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: 3465: 3463: 3461: 3458:Ring forming 3455: 3449: 3446: 3444: 3441: 3439: 3436: 3434: 3431: 3429: 3426: 3424: 3421: 3419: 3416: 3414: 3411: 3409: 3406: 3404: 3401: 3399: 3396: 3394: 3391: 3389: 3386: 3384: 3381: 3379: 3376: 3374: 3371: 3369: 3366: 3364: 3361: 3359: 3358:Rupe reaction 3356: 3354: 3351: 3349: 3346: 3344: 3341: 3339: 3336: 3334: 3331: 3329: 3326: 3324: 3321: 3319: 3316: 3314: 3311: 3309: 3306: 3304: 3301: 3299: 3296: 3294: 3291: 3289: 3286: 3284: 3281: 3279: 3276: 3274: 3271: 3269: 3266: 3264: 3261: 3259: 3256: 3254: 3251: 3249: 3246: 3244: 3241: 3239: 3236: 3234: 3231: 3229: 3226: 3224: 3221: 3219: 3216: 3214: 3211: 3209: 3206: 3204: 3201: 3199: 3196: 3194: 3191: 3189: 3186: 3184: 3181: 3179: 3176: 3174: 3171: 3169: 3166: 3164: 3161: 3159: 3156: 3154: 3151: 3149: 3146: 3144: 3141: 3139: 3136: 3134: 3131: 3129: 3126: 3124: 3121: 3119: 3116: 3114: 3111: 3109: 3106: 3104: 3101: 3099: 3096: 3094: 3091: 3089: 3086: 3084: 3081: 3079: 3076: 3074: 3071: 3069: 3066: 3064: 3061: 3059: 3056: 3054: 3051: 3049: 3046: 3044: 3041: 3039: 3036: 3034: 3031: 3029: 3026: 3024: 3021: 3019: 3016: 3014: 3011: 3009: 3006: 3004: 3001: 2999: 2996: 2994: 2991: 2989: 2986: 2984: 2981: 2980: 2978: 2976: 2970: 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: 2801: 2799: 2796: 2794: 2791: 2789: 2786: 2784: 2781: 2779: 2776: 2774: 2771: 2769: 2766: 2764: 2761: 2759: 2756: 2754: 2751: 2749: 2748:Ley oxidation 2746: 2744: 2741: 2739: 2736: 2734: 2731: 2729: 2726: 2724: 2721: 2719: 2716: 2714: 2713:Hydroxylation 2711: 2709: 2706: 2704: 2703:Hydrogenation 2701: 2699: 2696: 2694: 2691: 2689: 2686: 2684: 2681: 2679: 2676: 2674: 2671: 2669: 2666: 2664: 2661: 2659: 2656: 2654: 2651: 2649: 2646: 2644: 2641: 2639: 2638:DNA oxidation 2636: 2634: 2631: 2629: 2628:Deoxygenation 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: 2518:Aromatization 2516: 2514: 2511: 2509: 2506: 2504: 2501: 2499: 2496: 2494: 2491: 2489: 2486: 2484: 2481: 2479: 2476: 2475: 2473: 2471: 2465: 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: 2390: 2388: 2382: 2376: 2373: 2371: 2368: 2366: 2363: 2361: 2358: 2356: 2355:Reed reaction 2353: 2351: 2348: 2346: 2343: 2341: 2338: 2336: 2333: 2331: 2328: 2326: 2323: 2321: 2318: 2316: 2313: 2311: 2308: 2306: 2303: 2301: 2298: 2296: 2293: 2291: 2288: 2286: 2283: 2281: 2278: 2276: 2273: 2272: 2270: 2266:bond forming 2262: 2252: 2249: 2247: 2244: 2242: 2239: 2237: 2234: 2232: 2229: 2227: 2224: 2222: 2219: 2217: 2214: 2212: 2209: 2207: 2204: 2202: 2199: 2197: 2194: 2192: 2189: 2187: 2184: 2182: 2179: 2177: 2174: 2172: 2171:Cope reaction 2169: 2167: 2164: 2162: 2159: 2157: 2154: 2152: 2149: 2148: 2146: 2142: 2136: 2133: 2131: 2128: 2126: 2123: 2121: 2118: 2116: 2113: 2111: 2108: 2106: 2103: 2102: 2100: 2098: 2094: 2088: 2085: 2083: 2080: 2078: 2075: 2073: 2070: 2068: 2065: 2063: 2060: 2058: 2055: 2053: 2050: 2048: 2045: 2043: 2040: 2038: 2035: 2033: 2030: 2028: 2025: 2023: 2020: 2018: 2015: 2013: 2010: 2008: 2005: 2003: 2000: 1998: 1995: 1993: 1990: 1988: 1985: 1983: 1980: 1978: 1975: 1973: 1970: 1968: 1965: 1963: 1960: 1958: 1955: 1953: 1950: 1948: 1945: 1943: 1940: 1938: 1935: 1933: 1930: 1928: 1925: 1923: 1920: 1918: 1915: 1913: 1910: 1908: 1905: 1903: 1900: 1898: 1895: 1893: 1890: 1888: 1885: 1883: 1882:Nef synthesis 1880: 1878: 1875: 1873: 1870: 1868: 1865: 1863: 1860: 1858: 1857:Methylenation 1855: 1853: 1850: 1848: 1845: 1843: 1840: 1838: 1835: 1833: 1830: 1828: 1825: 1823: 1820: 1818: 1815: 1813: 1810: 1808: 1805: 1803: 1800: 1798: 1795: 1793: 1790: 1788: 1785: 1783: 1780: 1778: 1775: 1773: 1770: 1768: 1765: 1763: 1760: 1758: 1755: 1753: 1750: 1748: 1745: 1743: 1740: 1738: 1735: 1733: 1730: 1728: 1727:Heck reaction 1725: 1723: 1720: 1718: 1715: 1713: 1710: 1708: 1705: 1703: 1700: 1698: 1695: 1693: 1690: 1688: 1685: 1683: 1680: 1678: 1675: 1673: 1670: 1668: 1665: 1663: 1660: 1658: 1655: 1653: 1650: 1648: 1645: 1643: 1640: 1638: 1635: 1633: 1630: 1628: 1625: 1623: 1620: 1618: 1615: 1613: 1610: 1608: 1605: 1603: 1600: 1598: 1595: 1593: 1590: 1588: 1585: 1583: 1580: 1578: 1575: 1573: 1570: 1568: 1565: 1563: 1560: 1558: 1555: 1553: 1550: 1548: 1545: 1543: 1540: 1538: 1535: 1533: 1530: 1528: 1525: 1523: 1520: 1518: 1515: 1513: 1510: 1508: 1505: 1503: 1500: 1498: 1495: 1493: 1490: 1488: 1485: 1483: 1480: 1478: 1475: 1473: 1470: 1468: 1465: 1463: 1460: 1458: 1455: 1453: 1450: 1448: 1445: 1443: 1440: 1438: 1435: 1433: 1430: 1428: 1425: 1423: 1420: 1418: 1415: 1414: 1412: 1408:bond forming 1404: 1400: 1395: 1389: 1386: 1384: 1381: 1379: 1376: 1374: 1373:Y-aromaticity 1371: 1369: 1366: 1364: 1361: 1359: 1358:Walsh diagram 1356: 1354: 1351: 1349: 1346: 1344: 1343:Taft equation 1341: 1339: 1336: 1334: 1331: 1329: 1326: 1324: 1321: 1319: 1316: 1314: 1313:ÎŁ-aromaticity 1311: 1309: 1306: 1304: 1301: 1299: 1296: 1294: 1291: 1289: 1286: 1284: 1281: 1279: 1276: 1274: 1271: 1269: 1266: 1264: 1261: 1259: 1256: 1254: 1251: 1249: 1246: 1244: 1241: 1239: 1238:Marcus theory 1236: 1234: 1231: 1229: 1226: 1224: 1221: 1219: 1216: 1214: 1213:HĂĽckel's rule 1211: 1209: 1206: 1204: 1201: 1199: 1196: 1194: 1191: 1189: 1186: 1184: 1181: 1179: 1176: 1174: 1171: 1169: 1168:Evelyn effect 1166: 1164: 1161: 1159: 1156: 1154: 1151: 1149: 1148:Electron-rich 1146: 1144: 1141: 1139: 1136: 1134: 1131: 1129: 1126: 1124: 1121: 1119: 1116: 1114: 1111: 1109: 1106: 1104: 1101: 1099: 1096: 1094: 1091: 1089: 1086: 1084: 1081: 1079: 1076: 1074: 1071: 1069: 1066: 1064: 1063:Bema Hapothle 1061: 1059: 1056: 1054: 1051: 1049: 1046: 1044: 1041: 1039: 1036: 1034: 1031: 1029: 1026: 1024: 1021: 1019: 1016: 1014: 1011: 1010: 1007: 1001: 998: 996: 993: 991: 988: 986: 983: 981: 978: 976: 973: 971: 968: 966: 963: 961: 958: 956: 953: 952: 949: 945: 937: 932: 930: 925: 923: 918: 917: 914: 895: 891: 887: 880: 874: 870: 864: 856: 852: 848: 844: 840: 836: 832: 825: 817: 813: 809: 805: 804: 799: 793: 785: 779: 775: 771: 767: 760: 752: 748: 744: 740: 736: 733: 732: 724: 716: 712: 708: 704: 697: 689: 685: 681: 677: 673: 669: 665: 658: 650: 644: 640: 636: 632: 625: 617: 613: 609: 605: 601: 597: 593: 589: 585: 578: 570: 564: 560: 556: 552: 551: 543: 539: 529: 526: 524: 521: 519: 516: 515: 509: 504: 480: 470: 467: 461: 458: 447: 437: 434: 429: 421: 387: 369: 358: 349: 346: 338: 325: 324: 323: 321: 317: 312: 310: 309:pyrophosphate 297: 293: 292: 291: 289: 285: 280: 278: 262: 261: 260: 258: 250: 246: 243: 239: 238: 237: 235: 231: 227: 223: 222:sulfuric acid 219: 191: 190: 189: 187: 158: 157: 156: 154: 150: 130: 129: 128: 120: 118: 114: 110: 106: 102: 92: 74: 73: 72: 70: 55: 53: 49: 45: 41: 37: 33: 29: 22: 3163:Ene reaction 2523:Autoxidation 2384:Degradation 2275:Azo coupling 2052:Ugi reaction 1652:Ene reaction 1452:Alkynylation 1303:Polyfluorene 1298:Polar effect 1163:Electrophile 1078:Bredt's rule 1048:Baird's rule 1018:Alpha effect 898:. Retrieved 894:the original 879: 863: 841:(12): 2079. 838: 834: 824: 807: 801: 792: 765: 759: 734: 729: 723: 706: 702: 696: 671: 667: 657: 630: 624: 591: 587: 577: 548: 542: 507: 502: 385: 313: 306: 281: 274: 254: 234:cyclohexanol 224:and certain 215: 183: 147: 135:→ RCN + H 126: 117:disaccharide 98: 90: 66: 31: 25: 1662:Ethenolysis 1308:Ring strain 1278:Nucleophile 1103:Clar's rule 1043:Aromaticity 900:27 November 322:in a kiln: 230:carbocation 153:acetic acid 21:Desiccation 3946:Ozonolysis 3473:Annulation 2823:Ozonolysis 942:Topics in 783:0471936235 568:3527306730 534:References 528:Hydrolysis 113:saccharose 103:, such as 3460:reactions 2975:reactions 2470:reactions 2386:reactions 2268:reactions 1410:reactions 855:1463-9262 798:H. Adkins 688:0888-5885 608:0009-2665 430:⋅ 396:⟶ 347:⋅ 171:=C=O + H 167:H → CH 28:chemistry 4225:Category 1353:Vinylogy 1023:Annulene 970:Reagents 616:24083630 512:See also 288:acrolein 284:glycerol 226:zeolites 220:such as 186:ethylene 109:fructose 44:molecule 1013:A value 884:Staff. 739:Bibcode 263:RC(O)CH 131:RC(O)NH 105:glucose 853:  780:  709:: 33. 686:  645:  614:  606:  565:  320:gypsum 257:aldols 200:OH → H 149:Ketene 83:R′ + H 810:: 1. 40:water 34:is a 902:2008 851:ISSN 778:ISBN 684:ISSN 643:ISBN 612:PMID 604:ISSN 563:ISBN 418:CaSO 386:heat 335:CaSO 204:C=CH 107:and 99:Two 30:, a 869:doi 843:doi 812:doi 770:doi 747:doi 711:doi 676:doi 635:doi 596:doi 592:114 555:doi 286:to 208:+ H 75:RCO 54:. 48:ion 46:or 26:In 4227:: 888:. 849:. 839:12 837:. 833:. 806:. 776:. 768:. 745:. 735:88 705:. 682:. 672:52 670:. 666:. 641:. 610:. 602:. 590:. 586:. 561:. 290:: 236:. 196:CH 163:CO 159:CH 119:. 935:e 928:t 921:v 904:. 871:: 857:. 845:: 819:. 814:: 808:6 786:. 772:: 753:. 749:: 741:: 717:. 713:: 707:5 690:. 678:: 651:. 637:: 618:. 598:: 571:. 557:: 489:O 481:2 477:H 471:2 468:1 462:1 459:+ 456:O 448:2 444:H 438:2 435:1 422:4 370:+ 367:O 359:2 355:H 350:2 339:4 271:O 269:2 265:2 212:O 210:2 206:2 202:2 198:2 194:3 175:O 173:2 169:2 165:2 161:3 139:O 137:2 133:2 87:O 85:2 81:2 77:2 23:.

Index

Desiccation
chemistry
chemical reaction
water
molecule
ion
hydration reaction
Fischer esterification
monosaccharides
glucose
fructose
saccharose
disaccharide
Ketene
acetic acid
ethylene
acid catalysts
sulfuric acid
zeolites
carbocation
cyclohexanol


aldols
Martin's sulfurane
glycerol
acrolein
Elimination reaction of glycerol to acrolein
pyrophosphate
Plaster of Paris

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