93:
430:
69:
Nucleophilic addition reactions of nucleophiles with electrophilic double or triple bond (Ï bonds) create a new carbon center with two additional single, or Ï, bonds. Addition of a nucleophile to carbonâheteroatom double or triple bonds such as >C=O or -CâĄN show great variety. These types of bonds
78:
between the two atoms); consequently, their carbon atoms carries a partial positive charge. This makes the molecule an electrophile, and the carbon atom the electrophilic center; this atom is the primary target for the nucleophile. Chemists have developed a geometric system to describe the approach
61:
in that the former reactions involve the group to which atoms are added accepting electron pairs, whereas the latter reactions involve the group donating electron pairs.
119:. Addition reactions of this type are numerous. When the addition reaction is accompanied by an elimination the reaction is a type of substitution or an
107:
of this type of nucleophilic attack is not an issue, when both alkyl substituents are dissimilar and there are not any other controlling issues such as
376:
751:
436:
Unsubstituted and unstrained alkenes are typically insufficiently polar to admit nucleophilic addition, but a few exceptions are known.
525:
March Jerry; (1985). Advanced
Organic Chemistry reactions, mechanisms and structure (3rd ed.). New York: John Wiley & Sons, inc.
1198:
243:
92:
551:
687:
Weiberth, Franz J.; Hall, Stan S. (1986). "Tandem alkylation-reduction of nitriles. Synthesis of branched primary amines".
963:
840:
429:
397:
797:
1104:
744:
530:
633:
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H. B. BĂŒrgi; J. D. Dunitz; J. M. Lehn; G. Wipff (1974). "Stereochemistry of reaction paths at carbonyl centres".
1012:
1007:
817:
1177:
1172:
120:
1203:
737:
233:
471:
347:
276:
In many nucleophilic reactions, addition to the carbonyl group is very important. In some cases, the C=O
199:
1142:
832:
455:
288:
when the nucleophile bonds with carbon. For example, in the cyanohydrin reaction a cyanide ion forms a
628:
869:
769:
80:
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84:
902:
289:
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1127:
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270:
237:
571:; Lehn, J. M.; Wipff, G. (1974). "Stereochemistry of reaction paths at carbonyl centres".
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between X and one carbon atom, concomitant with the transfer of electron density from the
8:
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409:
212:
75:
39:
35:
20:
57:, such that the double or triple bond is broken. Nucleophilic additions differ from
1089:
1038:
992:
717:
696:
669:
609:
580:
479:
396:, the driving force is the transfer of negative charge from X to the electron-poor
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Chemical reaction involving the addition of a nucleophile to an electrophile
1074:
880:
787:
777:
487:
421:
259:
43:
716:
Herman Pines, Dieter
Wunderlich J. Am. Chem. Soc.; 1958; 80(22)6001â6004.
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112:
71:
714:
Sodium-catalyzed Side Chain
Aralkylation of Alkylbenzenes with Styrene
79:
of the nucleophile to the electrophilic center, using two angles, the
1084:
440:
417:
255:
131:
With a carbonyl compound as an electrophile, the nucleophile can be:
108:
467:
116:
495:
491:
463:
405:
393:
313:
305:
167:
143:
660:
Moffett, R. B.; Shriner, R. L. (1941). "Ï-Methoxyacetophenone".
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angles after scientists that first studied and described them.
987:
490:, can also sometimes stabilize negative charge; for example,
372:
357:
317:
225:
181:
135:
64:
146:
807:
470:) readily admit nucleophilic addition. In this process,
383:
400:-C=C- system. This occurs through the formation of a
566:
308:
electrophiles, nucleophilic addition take place by:
478:to the substituent, because then said substituent
544:Molecular orbitals and organic chemical reactions
292:by breaking the carbonyl's double bond to form a
184:with formaldehyde and a carbonyl compound in the
1190:
408:onto the other carbon atom (step 1). During a
659:
626:
126:
759:
745:
686:
541:
627:Moureu, Charles; Mignonac, Georges (1920).
482:stabilizes the product's negative charge.
416:(step 2), the resulting negatively charged
346:. The intramolecular version is called the
752:
738:
535:
65:Addition to carbonâheteroatom double bonds
521:
519:
517:
515:
299:
99:This type of reaction is also called a
1191:
778:Unimolecular nucleophilic substitution
384:Addition to carbonâcarbon double bonds
788:Bimolecular nucleophilic substitution
733:
512:
424:Y to form the second covalent bond.
841:Electrophilic aromatic substitution
560:
342:the (same) nitrile α-carbon in the
13:
808:Nucleophilic internal substitution
798:Nucleophilic aromatic substitution
14:
1215:
486:substituents, although typically
634:Annales de chimie et de physique
428:
244:HornerâWadsworthâEmmons reaction
91:
1199:Nucleophilic addition reactions
964:LindemannâHinshelwood mechanism
326:organozinc nucleophiles in the
242:a phosphonate carbanion in the
1013:Outer sphere electron transfer
1008:Inner sphere electron transfer
818:Nucleophilic acyl substitution
707:
680:
653:
620:
591:
1:
1178:Diffusion-controlled reaction
614:10.1016/S0040-4020(01)90678-7
585:10.1016/S0040-4020(01)90678-7
505:
502:to give 1,3-diphenylpropane:
248:a pyridine zwitterion in the
236:or α-silyl carbanions in the
121:addition-elimination reaction
689:Journal of Organic Chemistry
115:, the reaction product is a
74:(have a large difference in
7:
833:Electrophilic substitutions
127:Addition to carbonyl groups
10:
1220:
1143:Energy profile (chemistry)
1105:More O'FerrallâJencks plot
770:Nucleophilic substitutions
447:; addition thereto is the
410:telescoped second reaction
1173:MichaelisâMenten kinetics
1113:
1047:
1021:
977:
941:
893:
854:
831:
768:
474:, the nucleophile X adds
101:1,2-nucleophilic addition
1100:Potential energy surface
979:Electron/Proton transfer
864:Unimolecular elimination
674:10.15227/orgsyn.021.0079
234:CoreyâChaykovsky reagent
1148:Transition state theory
949:Intramolecular reaction
875:Bimolecular elimination
348:ThorpeâZiegler reaction
200:BaylisâHillman reaction
59:electrophilic additions
942:Unimolecular reactions
903:Electrophilic addition
1133:Rate-determining step
1065:Reactive intermediate
923:Free-radical addition
913:Nucleophilic addition
856:Elimination reactions
542:Fleming, Ian (2010).
454:Bonds adjacent to an
439:The strain energy in
271:cyanohydrin reactions
221:Reformatskii reaction
25:nucleophilic addition
1128:Equilibrium constant
458:substituent (e.g. a
456:electron-withdrawing
360:. The route affords
300:Addition to nitriles
238:Peterson olefination
1204:Reaction mechanisms
1138:Reaction coordinate
1070:Radical (chemistry)
1055:Elementary reaction
998:Grotthuss mechanism
762:reaction mechanisms
722:10.1021/ja01555a029
701:10.1021/jo00376a053
546:. New York: Wiley.
1163:Arrhenius equation
933:Oxidative addition
895:Addition reactions
472:conjugate addition
1186:
1185:
1158:Activated complex
1153:Activation energy
1115:Chemical kinetics
1060:Reaction dynamics
959:Photodissociation
695:(26): 5338â5341.
662:Organic Syntheses
608:(12): 1563â1572.
553:978-0-470-74658-5
420:combines with an
354:Grignard reagents
213:Grignard reaction
76:electronegativity
40:chemical compound
36:addition reaction
34:) reaction is an
21:organic chemistry
1211:
1090:Collision theory
1039:Matrix isolation
993:Harpoon reaction
870:E1cB-elimination
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312:hydrolysis of a
250:Hammick reaction
217:Barbier reaction
186:Mannich reaction
95:
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1168:Eyring equation
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1080:Stereochemistry
1043:
1029:Solvent effects
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629:"Les Cetimines"
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508:
449:Bingel reaction
386:
377:imine reduction
344:Thorpe reaction
337:Pinner reaction
328:Blaise reaction
322:carboxylic acid
302:
215:or the related
129:
105:stereochemistry
67:
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17:
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1048:Related topics
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1022:Medium effects
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590:
567:BĂŒrgi, H. B.;
559:
552:
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510:
509:
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460:carbonyl group
443:weakens their
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385:
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381:
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330:
324:
301:
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274:
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230:Wittig reagent
223:
206:organometallic
202:
196:aldol reaction
188:
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150:
128:
125:
97:
96:
66:
63:
53:reacts with a
30:
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9:
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3:
2:
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1123:Rate equation
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1120:
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1095:Arrow pushing
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1003:Marcus theory
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954:Isomerization
952:
950:
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928:Cycloaddition
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641:(13): 322â359
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582:
578:
574:
570:
569:Dunitz, J. D.
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555:
549:
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532:
531:0-471-85472-7
528:
522:
520:
518:
516:
511:
503:
501:
497:
493:
489:
488:electrophilic
485:
481:
477:
473:
469:
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461:
457:
452:
450:
446:
442:
437:
431:
427:
426:
425:
423:
422:electrophilic
419:
415:
411:
407:
403:
402:covalent bond
399:
395:
392:X adds to an
391:
378:
374:
371:
367:
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158:acetalisation
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89:
88:
86:
85:FlippinâLodge
82:
77:
73:
62:
60:
56:
52:
48:
45:
44:electrophilic
41:
37:
33:
26:
22:
1075:Molecularity
912:
713:
709:
692:
688:
682:
665:
661:
655:
643:. Retrieved
638:
632:
622:
605:
599:
593:
579:(12): 1563.
576:
572:
562:
543:
537:
453:
445:double-bonds
438:
435:
387:
303:
275:
260:alkynylation
130:
100:
98:
81:BĂŒrgiâDunitz
68:
28:
24:
18:
1034:Cage effect
969:RRKM theory
885:elimination
601:Tetrahedron
573:Tetrahedron
480:inductively
398:unsaturated
390:nucleophile
316:to form an
294:cyanohydrin
286:single bond
278:double bond
267:cyanide ion
209:nucleophile
192:enolate ion
55:nucleophile
51:triple bond
1193:Categories
506:References
494:reacts in
441:fullerenes
375:following
366:hydrolysis
364:following
262:reactions.
228:such as a
113:Lewis acid
1085:Catalysis
981:reactions
418:carbanion
284:to a C-O
256:acetylide
172:reduction
149:(hydrate)
140:hydration
109:chelation
484:Aromatic
468:fluoride
356:to form
333:alcohols
290:C-C bond
117:racemate
83:and the
42:with an
38:where a
645:18 June
496:toluene
492:styrene
464:nitrile
406:pi bond
388:When a
370:primary
362:ketones
335:in the
314:nitrile
306:nitrile
282:reduced
232:or the
211:in the
176:alcohol
168:hydride
154:alcohol
144:geminal
111:with a
760:Basic
668:: 79.
550:
529:
500:sodium
414:workup
394:alkene
373:amines
358:imines
226:ylides
194:in an
174:to an
162:acetal
160:to an
103:. The
47:double
988:Redox
824:Acyl)
498:with
466:, or
320:or a
318:amide
304:With
219:or a
182:amine
142:to a
136:water
72:polar
877:(E2)
866:(E1)
647:2014
548:ISBN
527:ISBN
147:diol
70:are
23:, a
847:Ar)
804:Ar)
718:doi
697:doi
670:doi
610:doi
581:doi
412:or
368:or
280:is
269:in
258:in
254:an
204:an
198:or
190:an
180:an
170:in
156:in
152:an
138:in
49:or
19:In
1195::
915:(A
905:(A
843:(S
820:(S
814:i)
810:(S
800:(S
794:2)
790:(S
784:1)
780:(S
693:51
691:.
666:21
664:.
637:.
631:.
606:30
604:.
577:30
575:.
514:^
462:,
451:.
296:.
265:a
166:a
123:.
919:)
917:N
909:)
907:E
883:i
881:E
845:E
822:N
812:N
802:N
792:N
782:N
753:e
746:t
739:v
720::
703:.
699::
676:.
672::
649:.
639:9
616:.
612::
587:.
583::
556:.
476:ÎČ
379:.
350:.
339:.
31:N
29:A
27:(
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
