488:
381:
384:
383:
388:
387:
382:
389:
386:
533:
385:
1092:
T. Mori; R. Rathore (1998). "X-Ray structure of bridged 2,2′-bi(adamant-2-ylidene) chloronium cation and comparison of its reactivity with a singly bonded chloroarenium cation".
76:. This kind of conversion is in fact so common that a comprehensive overview is challenging. This article mainly deals with halogenation using elemental halogens (
1059:
Aigueperse, Jean; Mollard, Paul; Devilliers, Didier; Chemla, Marius; Faron, Robert; Romano, René; Cuer, Jean Pierre (2000). "Fluorine
Compounds, Inorganic".
999:
1210:
312:) represents a special category with respect to halogenation. Most organic compounds, saturated or otherwise, burn upon contact with
1241:
1153:
1016:
688:
atom with respect to the carbon chain of the particular carboxylic acid. The carboxylic acid is first converted to its
1124:
1076:
982:
1262:
965:
Hudlicky, Milos; Hudlicky, Tomas (1983). "Formation of Carbon-Halogen Bonds". In S. Patai; Z. Rappoport (eds.).
1136:
Beck, Uwe; Löser, Eckhard (2011). "Chlorinated
Benzenes and Other Nucleus-Chlorinated Aromatic Hydrocarbons".
68:-containing compounds are pervasive, making this type of transformation important, e.g. in the production of
487:
1272:
353:
657:
17:
1267:
945:
596:
135:
106:). Halides are also commonly introduced using salts of the halides and halogen acids. Many specialized
935:
139:
127:
203:
532:
752:
357:
901:
869:
653:
571:
244:
1233:
1204:
499:
211:
187:
183:
143:
111:
1168:
Organic chemistry by
Jonathan Clayden, Nick Grieves, Stuart Warren, Oxford University Press
1032:
Gribble, Gordon W. (1999). "The diversity of naturally occurring organobromine compounds".
669:
509:
404:
346:
342:
320:
207:
326:
Highly specialised conditions and apparatus are required for fluorinations with elemental
8:
1177:
905:
897:
547:
to alkenes. The reaction, which conveniently proceeds with the discharge of the color of
323:. By contrast, the heavier halogens are far less reactive toward saturated hydrocarbons.
167:
131:
877:
450:
338:
38:
31:
368:. The method avoids the hazards of handling fluorine gas. Many commercially important
1277:
1237:
1184:
1149:
1120:
1072:
1012:
978:
893:
592:
559:
524:
438:
369:
365:
290:
170:
follows the reverse trend: iodine is most easily removed from organic compounds, and
61:
53:
1225:
1193:
1141:
1099:
1064:
1041:
1004:
970:
829:
816:
673:
146:
determines the pathway. The facility of halogenation is influenced by the halogen.
115:
30:"Fluorination" redirects here. For the addition of fluoride to drinking water, see
1008:
884:. The chlorination of metals is usually not very important industrially since the
645:
434:
255:
918:
876:
least of all. Of the many reactions possible, illustrative is the formation of
796:
769:
723:
716:
709:
677:
567:
195:
171:
974:
1256:
1197:
1145:
1094:
1068:
929:
563:
492:
294:
155:
126:
Several pathways exist for the halogenation of organic compounds, including
735:
681:
502:
394:
283:
191:
587:
217:
Free radical chlorination is used for the industrial production of some
37:
For the addition of chlorine, hypochlorite, etc. to drinking water, see
940:
923:
638:
517:
513:
27:
Chemical reaction which adds one or more halogen elements to a compound
162:
is a weaker halogenating agent than both fluorine and chlorine, while
1103:
1045:
885:
861:
845:
520:
279:
248:
45:
1178:
Edward R. Atkinson, Donald M. Murphy, and James E. Lufkin (1951). "
853:
849:
789:
649:
641:
630:
516:. Illustrative of the bromination of an alkene is the route to the
446:
327:
218:
151:
147:
85:
78:
69:
900:
is practiced on a relatively large scale is for the production of
1058:
865:
702:
693:
634:
544:
412:
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361:
275:
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199:
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107:
92:
57:
889:
873:
857:
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689:
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540:
442:
398:
271:
263:
252:
163:
99:
65:
969:. PATAI's Chemistry of Functional Groups. pp. 1021–1172.
539:
Iodination and bromination can be effected by the addition of
375:
833:
73:
881:
837:
505:. In special cases, such intermediates have been isolated.
330:. Commonly, fluorination reagents are employed instead of
575:
856:
is slightly more selective, but still reacts with most
660:, are used to prepare fluorinated aromatic compounds.
202:
is largely determined by the relative weakness of the
581:
360:. It generates small amounts of elemental fluorine
206:. This trend is reflected by the faster reaction at
166:is the least reactive of them all. The facility of
648:. Many detailed procedures are available. Because
1224:
1091:
967:Halides, Pseudo-Halides and Azides: Part 2 (1983)
498:The addition of halogens to alkenes proceeds via
1254:
964:
755:react with halogens to give the organic halide:
110:exist for and introducing halogens into diverse
1119:, Ruben Vardanyan, Victor Hruby; Elsevier 2005
629:This kind of reaction typically works well for
512:than chlorination because the reaction is less
1138:Ullmann's Encyclopedia of Industrial Chemistry
1061:Ullmann's Encyclopedia of Industrial Chemistry
1000:Ullmann's Encyclopedia of Industrial Chemistry
663:
305:Because of its extreme reactivity, fluorine (
247:are usually produced by free radical pathway
158:and are more aggressive halogenating agents.
1209:: CS1 maint: multiple names: authors list (
177:
376:Addition of halogens to alkenes and alkynes
356:is used commercially for the production of
297:, proceeds by the free radical iodination.
1135:
486:
379:
1031:
372:are fluorinated using this technology.
14:
1255:
1182:-4,4′,6,6′-Tetrachlorodiphenic Acid".
991:
823:
121:
1129:
24:
692:salt, which is then oxidized with
582:Halogenation of aromatic compounds
449:, as illustrated by this route to
190:. The reaction typically involves
25:
1289:
531:
293:, which involves degradation of
1218:
300:
1171:
1162:
1110:
1085:
1052:
1025:
958:
888:are more easily made from the
13:
1:
1009:10.1002/14356007.a06_233.pub2
952:
864:. Following the usual trend,
656:, other methods, such as the
578:and other organic compounds.
274:are estimated to release 1–2
174:compounds are highly stable.
56:which introduces one or more
1117:Synthesis of Essential Drugs
445:serves as the equivalent of
354:electrochemical fluorination
7:
911:
10:
1294:
946:Electrophilic substitution
664:Other halogenation methods
597:electrophilic halogenation
585:
136:electrophilic halogenation
36:
29:
1230:Chemistry of the Elements
1228:; Earnshaw, Alan (1997).
975:10.1002/9780470771723.ch3
936:Free radical halogenation
178:Free radical halogenation
140:halogen addition reaction
128:free radical halogenation
1198:10.15227/orgsyn.031.0096
1146:10.1002/14356007.o06_o03
1069:10.1002/14356007.a11_307
1034:Chemical Society Reviews
896:. Where chlorination of
848:by direct reaction with
753:organometallic compounds
358:perfluorinated compounds
337:. Such reagents include
258:. The reaction requires
1003:. Weinheim: Wiley-VCH.
880:by the chlorination of
658:Balz–Schiemann reaction
245:organobromine compounds
198:of the halogenation of
1263:Halogenation reactions
902:phosphorus trichloride
572:degree of unsaturation
558:, is the basis of the
495:
401:
319:, ultimately yielding
184:saturated hydrocarbons
1234:Butterworth-Heinemann
1226:Greenwood, Norman N.
490:
437:, the combination of
405:Unsaturated compounds
392:
188:substitution reaction
684:is shortened by one
670:Hunsdiecker reaction
570:are measures of the
508:Bromination is more
347:iodine pentafluoride
343:chlorine trifluoride
321:carbon tetrafluoride
262:in combination with
243:Naturally-occurring
142:. The nature of the
1273:Inorganic reactions
906:disulfur dichloride
898:inorganic compounds
824:Inorganic chemistry
393:Double-addition of
282:and 56,000 tons of
168:dehydrohalogenation
132:ketone halogenation
878:gold(III) chloride
593:Aromatic compounds
496:
451:1,2-dichloroethane
402:
339:cobalt trifluoride
39:Water chlorination
32:Water fluoridation
1268:Organic reactions
1243:978-0-08-037941-8
1185:Organic Syntheses
894:hydrogen chloride
676:are converted to
644:is used, such as
560:analytical method
525:trichloroethylene
439:hydrogen chloride
390:
370:organic compounds
366:hydrogen fluoride
291:iodoform reaction
122:Organic chemistry
62:chemical compound
54:chemical reaction
16:(Redirected from
1285:
1248:
1247:
1232:(2nd ed.).
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1083:
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1046:10.1039/a900201d
1029:
1023:
1022:
995:
989:
988:
962:
819:
765:
747:
719:
674:carboxylic acids
625:
557:
535:
483:
429:
391:
336:
318:
311:
239:
182:Halogenation of
116:thionyl chloride
105:
21:
1293:
1292:
1288:
1287:
1286:
1284:
1283:
1282:
1253:
1252:
1251:
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1057:
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996:
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985:
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914:
826:
812:
808:
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777:
773:
768:
763:
759:
745:
739:
733:
727:
722:
713:
706:
700:
666:
646:ferric chloride
623:
619:
615:
611:
607:
603:
595:are subject to
590:
584:
556:
552:
548:
491:Structure of a
481:
477:
473:
469:
465:
461:
457:
435:oxychlorination
427:
423:
380:
378:
335:
331:
317:
313:
310:
306:
303:
256:bromoperoxidase
237:
233:
229:
225:
180:
124:
103:
96:
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82:
77:
42:
35:
28:
23:
22:
15:
12:
11:
5:
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1155:978-3527306732
1154:
1128:
1109:
1098:(8): 927–928.
1084:
1077:
1051:
1040:(5): 335–346.
1024:
1018:978-3527306732
1017:
990:
983:
956:
954:
951:
949:
948:
943:
938:
933:
927:
926:(Alkyl halide)
921:
919:Dehalogenation
915:
913:
910:
825:
822:
821:
820:
810:
806:
802:
798:
791:
783:
779:
775:
771:
766:
761:
749:
748:
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737:
731:
725:
720:
711:
704:
678:organic halide
665:
662:
627:
626:
621:
617:
613:
609:
605:
586:Main article:
583:
580:
568:bromine number
554:
550:
537:
536:
485:
484:
479:
475:
471:
467:
463:
459:
431:
430:
428:→ R−CHX−CHX−R'
425:
424:R−CH=CH−R' + X
377:
374:
333:
315:
308:
302:
299:
295:methyl ketones
241:
240:
235:
231:
227:
196:regiochemistry
194:pathways. The
179:
176:
172:organofluorine
123:
120:
101:
94:
87:
80:
26:
9:
6:
4:
3:
2:
1290:
1279:
1276:
1274:
1271:
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1266:
1264:
1261:
1260:
1258:
1245:
1239:
1235:
1231:
1227:
1221:
1212:
1206:
1199:
1195:
1191:
1187:
1186:
1181:
1174:
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1157:
1151:
1147:
1143:
1139:
1132:
1126:
1125:0-444-52166-6
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1118:
1113:
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1101:
1097:
1096:
1095:Chem. Commun.
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1080:
1078:3-527-30673-0
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1002:
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994:
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984:9780470771723
980:
976:
972:
968:
961:
957:
947:
944:
942:
939:
937:
934:
932:(Aryl halide)
931:
930:Halogenoarene
928:
925:
922:
920:
917:
916:
909:
907:
903:
899:
895:
891:
887:
883:
879:
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871:
867:
863:
859:
855:
851:
847:
843:
839:
835:
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767:
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721:
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679:
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671:
661:
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643:
640:
636:
632:
602:
601:
600:
598:
594:
589:
579:
577:
573:
569:
565:
564:iodine number
561:
546:
542:
534:
530:
529:
528:
526:
522:
519:
515:
511:
506:
504:
503:halonium ions
501:
494:
493:bromonium ion
489:
456:
455:
454:
452:
448:
444:
440:
436:
422:
421:
420:
418:
414:
410:
407:, especially
406:
400:
396:
373:
371:
367:
363:
359:
355:
350:
348:
344:
340:
329:
324:
322:
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281:
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273:
269:
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261:
257:
254:
250:
246:
224:
223:
222:
220:
215:
213:
209:
205:
201:
197:
193:
189:
185:
175:
173:
169:
165:
161:
157:
156:electrophilic
153:
149:
145:
141:
137:
133:
129:
119:
117:
113:
109:
104:
97:
90:
83:
75:
71:
67:
63:
59:
55:
51:
47:
40:
33:
19:
1229:
1220:
1205:cite journal
1189:
1183:
1179:
1173:
1164:
1137:
1131:
1116:
1112:
1093:
1087:
1060:
1054:
1037:
1033:
1027:
998:
993:
966:
960:
860:and heavier
827:
750:
682:carbon chain
667:
639:Lewis acidic
628:
591:
538:
507:
500:intermediate
497:
458:4 HCl + 2 CH
432:
416:
403:
395:chlorine gas
351:
325:
304:
301:Fluorination
288:
284:bromomethane
242:
216:
214:positions.
192:free radical
181:
125:
50:halogenation
49:
43:
832:aside from
588:Aryl halide
352:The method
18:Chlorinated
1257:Categories
953:References
941:Haloketone
924:Haloalkane
701:R−COOAg +
637:. Often a
616:→ HX + R−C
518:anesthetic
514:exothermic
419:halogens:
286:annually.
112:substrates
886:chlorides
862:nonmetals
846:fluorides
764:→ RX + MX
708:→ R−Br +
521:halothane
510:selective
478:−Cl + 2 H
470:→ 2 Cl−CH
280:bromoform
249:catalyzed
212:secondary
204:C–H bonds
154:are more
144:substrate
46:chemistry
1278:Halogens
912:See also
870:reactive
868:is less
854:Chlorine
850:fluorine
830:elements
680:, whose
654:reactive
650:fluorine
642:catalyst
631:chlorine
447:chlorine
328:fluorine
278:tons of
238:Cl + HCl
219:solvents
208:tertiary
152:chlorine
148:Fluorine
108:reagents
70:polymers
58:halogens
866:bromine
694:halogen
668:In the
635:bromine
545:bromine
413:alkynes
409:alkenes
362:in situ
276:million
268:oxidant
260:bromide
251:by the
200:alkanes
160:Bromine
114:, e.g.
60:into a
1240:
1192:: 96.
1152:
1123:
1075:
1015:
981:
890:oxides
874:iodine
858:metals
842:helium
840:, and
760:RM + X
746:+ AgBr
728:−COOAg
690:silver
686:carbon
652:is so
562:. The
553:and Br
541:iodine
443:oxygen
399:ethyne
345:, and
272:oceans
270:. The
266:as an
264:oxygen
253:enzyme
164:iodine
138:, and
66:Halide
844:form
834:argon
751:Many
523:from
364:from
186:is a
74:drugs
52:is a
1238:ISBN
1211:link
1150:ISBN
1121:ISBN
1073:ISBN
1013:ISBN
979:ISBN
904:and
892:and
882:gold
872:and
838:neon
828:All
817:LiCl
742:+ CO
730:+ Br
717:AgBr
633:and
576:fats
574:for
566:and
543:and
441:and
411:and
289:The
234:→ CH
230:+ Cl
210:and
150:and
1194:doi
1142:doi
1100:doi
1065:doi
1042:doi
1005:doi
971:doi
740:−Br
612:+ X
604:R−C
474:−CH
466:+ O
462:=CH
433:In
417:add
397:to
44:In
1259::
1236:.
1207:}}
1203:{{
1190:31
1188:.
1180:dl
1148:.
1140:.
1071:.
1063:.
1038:28
1036:.
1011:.
977:.
908:.
852:.
836:,
815:+
813:Cl
809:CH
805:CH
801:CH
797:CH
795:→
790:Cl
788:+
786:Li
782:CH
778:CH
774:CH
770:CH
736:CH
734:→
724:CH
715:+
710:CO
703:Br
696::
672:,
624:−X
599::
527::
453::
415:,
349:.
341:,
226:CH
221::
134:,
130:,
118:.
98:,
93:Br
91:,
86:Cl
84:,
72:,
64:.
48:,
1246:.
1215:.
1213:)
1196::
1158:.
1144::
1106:.
1102::
1081:.
1067::
1048:.
1044::
1021:.
1007::
987:.
973::
811:2
807:2
803:2
799:3
792:2
784:2
780:2
776:2
772:3
762:2
744:2
738:3
732:2
726:3
712:2
705:2
622:4
620:H
618:6
614:2
610:5
608:H
606:6
555:2
551:2
549:I
482:O
480:2
476:2
472:2
468:2
464:2
460:2
426:2
334:2
332:F
316:2
314:F
309:2
307:F
236:3
232:2
228:4
102:2
100:I
95:2
88:2
81:2
79:F
41:.
34:.
20:)
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.