{"id":7708,"date":"2013-11-25T14:38:07","date_gmt":"2013-11-25T19:38:07","guid":{"rendered":"https:\/\/www.masterorganicchemistry.com\/?p=7708"},"modified":"2026-04-20T04:53:20","modified_gmt":"2026-04-20T09:53:20","slug":"allylic-bromination","status":"publish","type":"post","link":"https:\/\/www.masterorganicchemistry.com\/2013\/11\/25\/allylic-bromination\/","title":{"rendered":"Allylic Bromination"},"content":{"rendered":"<p><strong>Allylic Bromination and Benzylic Bromination: What Is It,\u00a0 And How Does It Work?<\/strong><\/p>\n<ul>\n<li>In previous articles on radicals, we&#8217;ve seen how bromine (Br<sub>2<\/sub>) can selectively react with tertiary C-H bonds (bond strength <strong>93<\/strong> kcal\/mol) over secondary (96 kcal\/mol) and primary (100 kcal\/mol) C\u2013H bonds <em>(<span style=\"color: #800080;\"><a style=\"color: #800080;\" href=\"https:\/\/www.masterorganicchemistry.com\/2013\/10\/31\/selectivity-in-free-radical-reactions-bromine-vs-chlorine\/\">See: Selectivity in Free Radical Reactions &#8211; Bromination vs. Chlorination<\/a><\/span>)<\/em><\/li>\n<li>If you recall that bond dissociation energies (BDE&#8217;s) are a good guide for predicting radical stability, then you won&#8217;t be surprised to learn that &#8220;<strong>benzylic<\/strong>&#8221; and &#8220;<strong>allyllic<\/strong>&#8221; C\u2013H bonds can also be brominated selectively. These C-H bonds are particularly weak because the free radical formed through the homolytic \u00a0breaking of the allylic C-H \u00a0is<strong> stabilized by resonance<\/strong>.<\/li>\n<\/ul>\n<p><img fetchpriority=\"high\" decoding=\"async\" class=\"alignnone wp-image-37397\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2024\/09\/0-summary-allylic-bromination-free-radical-mechanism-weak-C-H-bonds-use-NBS-for-low-quantities-of-Br2.gif\" alt=\"summary allylic bromination free radical mechanism weak C-H bonds use NBS for low quantities of Br2\" width=\"640\" height=\"688\" \/><\/a><\/p>\n<p><strong>Table of Contents<\/strong><\/p>\n<ol>\n<li><a href=\"#one\">Allylic and Benzylic Bromination: Examples<\/a><\/li>\n<li><a href=\"#two\">Free Radicals Are Stabilized By Resonance<\/a><\/li>\n<li><a href=\"#three\">The Mechanism of Benzylic Bromination With Br<sub>2<\/sub> and Light\/Heat<\/a><\/li>\n<li><a href=\"#four\">Br<sub>2<\/sub> Is Not An Appropriate Reagent For Allylic Bromination Since It Forms Vicinal Dibromides<\/a><\/li>\n<li><a href=\"#five\">Using N-Bromo Succinimide (NBS) Ensures A Low Concentration Of Br<sub>2\u00a0<\/sub><\/a><\/li>\n<li><a href=\"#notes\">Notes<\/a><\/li>\n<li><a href=\"#quizzes\">Quiz Yourself!<\/a><\/li>\n<li><a href=\"#furtherreading\">(Advanced) References and Further Reading<\/a><\/li>\n<\/ol>\n<hr \/>\n<h2><a id=\"one\"><\/a>1. Allylic and Benzylic Bromination: Examples<\/h2>\n<p>So what is allylic and benzylic halogenation, anyway?\u00a0 Here&#8217;s an example of each.<\/p>\n<p>Take toluene and treat with either Br<sub>2<\/sub> in the presence of light, <a href=\"http:\/\/www.orgsyn.org\/demo.aspx?prep=CV4P0984\">as per this procedure<\/a>, or N-Bromosuccinimide (NBS) in the presence of a radical initiator + heat (or\u00a0 light) and one of the <strong>benzylic<\/strong> C\u2013H bonds is replaced with C\u2013Br.<\/p>\n<p><span style=\"color: #993366;\"><em>(Note that the &#8220;benzylic&#8221; position is the carbon attached to the benzene ring; the C-H bonds of the\u00a0 benzene ring itself are the &#8220;phenyl&#8221; C-H bonds).\u00a0<\/em><\/span><\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-45741\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2026\/04\/1-example-of-benzylic-bromination-toluene.gif\" alt=\"example of benzylic bromination toluene\" width=\"640\" height=\"304\" \/><\/a><\/p>\n<p>Here&#8217;s an example of the <strong>allylic<\/strong> bromination of propene, this time using NBS and peroxides (or heat)<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-45745\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2026\/04\/2-example-of-allylic-bromination-of-propene-with-peroxides-and-nbs.gif\" alt=\"example of allylic bromination of propene with peroxides and nbs\" width=\"640\" height=\"330\" \/><\/a><\/p>\n<p>We&#8217;ve spent a considerable amount of time discussing the <a href=\"https:\/\/www.masterorganicchemistry.com\/2013\/08\/02\/3-factors-that-stabilize-free-radicals\/\">stability of free radicals<\/a>, particularly that primary radicals are particularly unstable.<\/p>\n<p>So what&#8217;s different in this case? And what&#8217;s this &#8220;NBS&#8221; stuff?<\/p>\n<h2><a id=\"two\"><\/a>2. Free Radicals Are Stabilized By Resonance<\/h2>\n<p>Recall that free radicals are stabilized by resonance, and bond dissociation energies (BDE&#8217;s) aka &#8220;bond strengths&#8221; measure homolytic bond cleavage.<\/p>\n<p>So the methyl\u00a0 groups (above) aren&#8217;t ordinary methyl groups &#8211; the resulting radicals are greatly stabilized by resonance!<\/p>\n<p>Therefore when we look at bond dissociation energies for benzylic and allylic C\u2013H bonds it should not be surprising to find that these bond strengths\u00a0 are quite weak\u00a0 (89-90 kcal\/mol for a primary allylic or benzylic radical) relative to tertiary C-H bonds (93 kcal\/mol).<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-45750\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2026\/04\/3-free-radicals-stabilized-by-resonance.gif\" alt=\"free radicals stabilized by resonance\" width=\"640\" height=\"529\" \/><\/a><\/p>\n<p>So how might allylic or benzylic bromination work?<\/p>\n<h2><a id=\"three\"><\/a>3. The Mechanism of Benzylic Bromination With Br<sub>2<\/sub> and Light\/Heat<\/h2>\n<p>For benzylic bromination, hopefully imagining the mechanism will be straightforward: after <strong>initiation<\/strong> (by heat or light), bromine radical then breaks the C-H bond (forming the benzylic radical) [<strong>propagation step #1<\/strong>] and the benzylic radical attacks Br<sub>2<\/sub> to re-generate bromine radical [<strong>propagation step #2<\/strong>]. These two steps repeat until the concentration of Br<sub>2<\/sub> runs low, whereupon radical chain<strong> termination<\/strong> will occur.<\/p>\n<p><em>[See <a href=\"https:\/\/www.masterorganicchemistry.com\/2013\/09\/06\/initiation-propagation-termination\/\">Initiation, Propagation, Termination<\/a>]<\/em><\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-45752\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2026\/04\/4-benzylic-bromination-full-mechanism.gif\" alt=\"benzylic bromination full mechanism\" width=\"640\" height=\"759\" \/><\/a><\/p>\n<h2><a id=\"four\"><\/a>4. Br<sub>2<\/sub> Is Not An Appropriate Reagent For Allylic Bromination Since It Forms Vicinal Dibromides<\/h2>\n<p>Let&#8217;s turn to allylic bromination. Do you see any reason why treating the molecule below with Br<sub>2<\/sub> might lead to problems?<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-45757\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2026\/04\/5-allylic-bromination-side-reaction-addition-of-br2-to-alkene-how-to-prevent.gif\" alt=\"allylic bromination side reaction addition of br2 to alkene how to prevent\" width=\"640\" height=\"273\" \/><\/a><\/p>\n<p>You might recall that <a href=\"https:\/\/www.masterorganicchemistry.com\/2013\/03\/15\/alkene-bromination-mechanism\/\">alkenes react with Br<sub>2<\/sub> to form vicinal dibromides<\/a>, and that is in fact exactly what would occur if we were to just dump in 1 equivalent of Br<sub>2<\/sub> with an alkene.<\/p>\n<p>At issue here is the fact that we have 1 equivalent of Br<sub>2<\/sub> swimming around, of which only a small proportion at any given time will exist as bromine radical [due to the initiation step].<\/p>\n<p>How might we solve this problem and favour the radical substitution over the dibromination?<\/p>\n<p>Imagine, if you will, we had a <i>very low<\/i> concentration of Br<sub>2<\/sub>. If the concentration of Br<sub>2<\/sub> is kept low, not only will the rate of dibromination be lower, the relative concentration of bromine radical relative to Br<sub>2<\/sub> will increase. Therefore, the rate of C-H abstraction relative to dibromination will increase, which will allow our allylic bromination product to be formed in a higher yield. [<a href=\"#noteone\">Note 1<\/a>]<\/p>\n<p>Of course, this creates a new question: how do we generate a low, constant concentration of Br<sub>2<\/sub>?<\/p>\n<h2><a id=\"five\"><\/a>5. Using N-Bromo Succinimide (NBS) Ensures A Low Concentration Of Br<sub>2\u00a0<\/sub><\/h2>\n<p>As it turns out, there&#8217;s a way. If the bromonium ion source <a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/06\/10\/reagent-friday-nbs-n-bromo-succinimide\/\">N-bromosuccinimide (NBS)<\/a> is present with a <i>trace <\/i>amount of acid (HBr), HBr will react with NBS to give succinimide and Br<sub>2<\/sub>.[<a href=\"#notetwo\">Note 2<\/a>]<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-45760\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2026\/04\/6-nbs-reaction-with-trace-acid-results-in-a-low-concentration-of-br2.gif\" alt=\"-nbs reaction with trace acid results in a low concentration of br2\" width=\"640\" height=\"487\" \/><\/a>Since one equivalent of HBr generates one equivalent of Br<sub>2<\/sub>, \u00a0Br<sub>2<\/sub> will be generated only after the completion of Propagation Step #1.[<a href=\"#notethree\">Note 3<\/a>].This keeps the concentration of Br<sub>2<\/sub> low and allows the free-radical reaction to out-compete the alkene addition reaction.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-45763\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2026\/04\/7-allylic-bromination-of-cyclopentene-with-nbs.gif\" alt=\"allylic bromination of cyclopentene with nbs\" width=\"640\" height=\"274\" \/><\/a><\/p>\n<p>In all other respects the allylic bromination reaction is identical to the benzylic bromination reaction mechanism shown above. However in *some* situations there is an extra twist of allylic rearrangement, which we will briefly discuss in the next post.<\/p>\n<p><strong>Next Post: <a href=\"https:\/\/www.masterorganicchemistry.com\/2013\/12\/02\/bonus-topic-allylic-rearrangements\/\">Allylic Rearrangement<\/a><\/strong><\/p>\n<hr \/>\n<h2><strong><a id=\"notes\"><\/a>Notes<\/strong><\/h2>\n<div class=\"related-articles\"><p><strong>Related Articles<\/strong><\/p><ul><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2013\/10\/31\/selectivity-in-free-radical-reactions-bromine-vs-chlorine\/\" class=\"\"><span>Selectivity in Free Radical Reactions: Bromination vs. Chlorination<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2013\/08\/30\/radical-initiation-why-is-light-or-heat-required\/\" class=\"\"><span>Free Radical Initiation: Why Is \u201cLight\u201d Or \u201cHeat\u201d Required?<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2013\/08\/02\/3-factors-that-stabilize-free-radicals\/\" class=\"\"><span>3 Factors That Stabilize Free Radicals<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2010\/06\/25\/bond-dissociation-energies-homolytic-cleavage\/\" class=\"\"><span>Bond Dissociation Energies = Homolytic Cleavage<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2013\/12\/09\/in-summary-free-radicals\/\" class=\"\"><span>In Summary: Free Radicals<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2013\/11\/25\/allylic-bromination\/\" class=\"\"><span>Allylic Bromination<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2012\/08\/31\/elimination-reactions-2-zaitsevs-rule\/\" class=\"\"><span>Elimination Reactions (2): The Zaitsev Rule<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2020\/04\/30\/alkene-stability\/\" class=\"\"><span>Alkene Stability<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/organic-chemistry-practice-problems\/radicals-practice-quizzes\/\" class=\"\"><span>Free Radicals Practice Quizzes (MOC Membership required)<\/span><\/a><\/li><\/ul><\/div>\n<p><a id=\"noteone\"><\/a><strong>Note 1.<\/strong>\u00a0If this explanation sounds somewhat unsatisfactory, you&#8217;re on to something. After all, doesn&#8217;t this decrease the concentration of Br\u2022 as well? One additional complication is that theoretical studies show strong evidence for a<a href=\"http:\/\/pubs.rsc.org\/en\/content\/articlelanding\/1939\/jr\/jr9390001509#!divAbstract\"> <i>ter<\/i>molecular<\/a> rate determining step in formation of the bromonium ion (that is, involvement by the alkene and <em>two<\/em> molecules of Br<sub>2<\/sub>). Decreasing the concentration of Br<sub>2<\/sub> would therefore vastly decrease the rate of bromonium ion formation (and thus dibromination) relative to free radical halogenation.<\/p>\n<p><strong><a id=\"notetwo\"><\/a>Note 2. <\/strong>As it happens, NBS which has been left out for awhile will usually be contaminated with trace HBr (as well as Br<sub>2<\/sub>, which gives it a yellow or orange colour). For this reason if doing a radical reaction with NBS it&#8217;s common to\u00a0<em>avoid<\/em> recrystallizing it before use, as it will remove the trace acid that jump starts the reaction in the first place.<\/p>\n<p><strong><a id=\"notethree\"><\/a>Note 3. <\/strong>As long as the initial concentration of HBr is low (i.e. it is used as a catalyst)<\/p>\n<hr \/>\n<h2><a id=\"quizzes\"><\/a>Quiz Yourself!<\/h2>\n\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/3152-Front-Image-Only.png\" alt=\"\" width=\"640\" height=\"616\" \/><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a\u00a0 MOC member<\/strong><\/a> to see the clickable quiz with answers on the back. <br \/>\n<\/p>\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/3153-Front-Image-Only.png\" alt=\"\" width=\"640\" height=\"616\" \/><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a\u00a0 MOC member<\/strong><\/a> to see the clickable quiz with answers on the back. <br \/>\n<\/p>\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/3154-Front-Image-Only.png\" alt=\"\" width=\"640\" height=\"616\" \/><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a\u00a0 MOC member<\/strong><\/a> to see the clickable quiz with answers on the back. <\/p>\n\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/1665-Front-Image-Only.png\" alt=\"\" width=\"640\" height=\"616\" \/><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a\u00a0 MOC member<\/strong><\/a> to see the clickable quiz with answers on the back. <br \/>\n<\/p>\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/1187-Front-Image-Only.png\" alt=\"\" width=\"640\" height=\"616\" \/><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a\u00a0 MOC member<\/strong><\/a> to see the clickable quiz with answers on the back. <br \/>\n<\/p>\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/1189-Front-Image-Only.png\" alt=\"\" width=\"640\" height=\"616\" \/><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a\u00a0 MOC member<\/strong><\/a> to see the clickable quiz with answers on the back. <br \/>\n<\/p>\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/1193-Front-Image-Only.png\" alt=\"\" width=\"640\" height=\"616\" \/><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a\u00a0 MOC member<\/strong><\/a> to see the clickable quiz with answers on the back. <\/p>\n<p>&nbsp;<\/p>\n<hr \/>\n<h2><a id=\"furtherreading\"><\/a>(Advanced) References and Further Reading<\/h2>\n<p>Allylic bromination with NBS is sometimes called the Wohl-Ziegler reaction.<\/p>\n<ol>\n<li><strong>Die Synthese des Cantharidins<\/strong>.<br \/>\nZiegler, K., Schenck, G., Krockow, E.W., Siebert, A., Wenz, A. and Weber, H. (1942),<br \/>\n<em>Justus Liebigs Ann. Chem<\/em>., 551: 1-79.<br \/>\n<strong>DOI<\/strong>:<a href=\"https:\/\/doi.org\/10.1002\/jlac.19425510102\">10.1002\/jlac.19425510102<\/a><br \/>\nZiegler&#8217;s report on using NBS for allylic bromination, from 1942.<\/li>\n<li><strong>Brominations with N-Bromosuccinimide and Related Compounds. The Wohl-Ziegler Reaction.<br \/>\n<\/strong>Carl. Djerassi<br \/>\n<cite>Chemical Reviews<\/cite>\u00a0<strong>1948<\/strong>\u00a0<em>43<\/em> (2), 271-317<br \/>\n<strong>DOI:<\/strong> <a href=\"https:\/\/pubs.acs.org\/doi\/10.1021\/cr60135a004\">10.1021\/cr60135a004<\/a><br \/>\nAn early but useful review of allylic bromination by Prof. Carl Djerassi (Stanford), who made many important contributions to steroid chemistry.<\/li>\n<li><strong>Laws of Addition and Substitution in Atomic Reactions of Halogens<\/strong><br \/>\nADAM, J., GOSSELAIN, P. &amp; GOLDFINGER, P. .<br \/>\n<i>Nature<\/i>\u00a0<b>171,\u00a0<\/b>704\u2013705 (1953).<br \/>\n<strong>DOI:<\/strong> <a href=\"https:\/\/doi.org\/10.1038\/171704b0\">10.1038\/171704b0<\/a><br \/>\nThe &#8220;Goldfinger Mechanism&#8221; for allylic bromination, which proposed that NBS serves to provide a low concentration of Br2. Earlier proposed mechanisms involved the succinimidyl radical as the chain carrier, which is incorrect. It should be noted that addition of Br\u2022 to alkenes *does* occur to some extent, but the reaction is reversible, and if Br2 and HBr concentrations are kept low, any addition product will revert to the starting alkene.<\/li>\n<li><strong>THE HIGH-TEMPERATURE CHLORINATION OF OLEFIN HYDROCARBONS<br \/>\n<\/strong>FREDERICK F. RUST and WILLIAM E. VAUGHAN<br \/>\n<cite>The Journal of Organic Chemistry<\/cite>\u00a0<strong>1940<\/strong>\u00a0<em>05<\/em> (5), 472-503<br \/>\n<strong>DOI<\/strong>: <a href=\"https:\/\/pubs.acs.org\/doi\/10.1021\/jo01211a002\">10.1021\/jo01211a002<\/a><br \/>\nAn early, key observation. Rust and Vaughn found that addition of Cl<sub>2<\/sub> to alkenes is favored at low temperatures, whereas at higher temperatures allylic substitution dominates.<\/li>\n<li><strong>The Ratio of Substitution to Addition in the Reaction of Chlorine with Olefins in Dilute Carbon Tetrachloride Solution<br \/>\n<\/strong>T. D. Stewart, Kenneth Dod, and George Stenmark<br \/>\n<cite>Journal of the American Chemical Society<\/cite>\u00a0<strong>1937<\/strong>\u00a0<em>59<\/em> (9), 1765-1766<br \/>\n<strong>DOI<\/strong>: <a href=\"https:\/\/pubs.acs.org\/doi\/10.1021\/ja01288a507\">10.1021\/ja01288a507<\/a><br \/>\nAn important piece of the puzzle to figuring out the mechanism for allylic halogenation, from 1937.\u00a0 Allylic substitution is favored over addition at lower concentrations of halogen (Cl2).<\/li>\n<li><strong>Mechanisms of Benzylic Bromination<br \/>\n<\/strong>Glen A. Russell, Charles. DeBoer, and Kathleen M. Desmond<strong><br \/>\n<\/strong><em>Journal of the American Chemical Society<\/em> <strong>1963<\/strong> <em>85<\/em> (3), 365-366<br \/>\n<strong>DOI: <\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/ja00886a040\">1021\/ja00886a040<\/a><br \/>\nBenzylic bromination follows the same mechanism as allylic bromination, as this paper explains.NBS (N-Bromosuccinimide) is a convenient reagent for free-radical bromination, and the following papers are mechanistic studies involving NBS:<\/li>\n<li><strong>The Mechanism of Benzylic Bromination with N-Bromosuccinimide<br \/>\n<\/strong> E. Pearson and J. C. Martin<strong><br \/>\n<\/strong><em>Journal of the American Chemical Society<\/em> <strong>1963<\/strong> <em>85<\/em> (3), 354-355<strong><br \/>\nDOI: <\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/ja00886a029\">10.1021\/ja00886a029<\/a><br \/>\nThese papers by Prof J. C. Martin (UIUC) were early in his career, before he did the work that he is most well-known for (studies on \u2018hypervalent\u2019 molecules, including the development of the \u2018Dess-Martin Periodinane\u2019).<\/li>\n<li><strong>The Identity of the Chain-Carrying Species in Brominations with N-Bromosuccinimide: Selectivity of Substituted N-Bromosuccinimides toward Substituted Toluenes<br \/>\n<\/strong> E. Pearson and J. C. Martin<br \/>\n<em>Journal of the American Chemical Society<\/em> <strong>1963<\/strong> <em>85<\/em> (20), 3142-3146<br \/>\n<strong>DOI:<\/strong> <a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/ja00903a021\">10.1021\/ja00903a021<\/a><\/li>\n<li><strong>N-bromosuccinimide. Mechanisms of allylic bromination and related reactions<br \/>\n<\/strong> H. Incremona and James Cullen Martin<br \/>\n<em>Journal of the American Chemical Society<\/em> <strong>1970<\/strong> <em>92<\/em> (3), 627-634<br \/>\n<strong>DOI:<\/strong> <a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/ja00706a034\">10.1021\/ja00706a034<\/a><\/li>\n<li><strong>Radical Bromination of Cyclohexene in CCl4 by Bromine: Addition versus Substitution<br \/>\n<\/strong> W. McMillen and John B. Grutzner<br \/>\n<em>The Journal of Organic Chemistry<\/em> <strong>1994<\/strong> <em>59<\/em> (16), 4516-4528<br \/>\n<strong>DOI:<\/strong> <a href=\"https:\/\/pubs.acs.org\/doi\/10.1021\/jo00095a029\">10.1021\/jo00095a029<\/a><br \/>\nThis paper describes careful kinetic studies that demonstrate that a low concentration of Br<sub>2<\/sub> (such as that provided by <em>impure<\/em> NBS) will favor radical substitution over a polar addition reaction.<\/li>\n<li><strong>4-BROMO-2-HEPTENE<br \/>\n<\/strong> L. Greenwood, M. D. Kellert, and J. Sedlak<br \/>\n<em>Org. Synth. Vol. 38, p.8 (1958).<br \/>\n<\/em><strong>DOI: <\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/10.1021\/jo00095a029\">10.115227\/orgsyn.038.0008<\/a><br \/>\nA reliable procedure for allylic bromination with NBS in <em>Organic Syntheses<\/em>.<\/li>\n<li><strong>o-XYLYLENE DIBROMIDE<br \/>\n<\/strong>Emily F. M. Stephenson<br \/>\n<em>Org. Synth.<\/em> Vol. 34, p.100 (1954)<strong><br \/>\nDOI: <\/strong><a href=\"http:\/\/www.orgsyn.org\/demo.aspx?prep=CV4P0984\">10.15227\/orgsyn.034.0100<\/a><br \/>\nA reliable procedure for benzylic bromination with Br<sub>2<\/sub> in <em>Organic Syntheses.<\/em><\/li>\n<li><strong>The evolution of free radical chemistry at Chicago<br \/>\n<\/strong>Frank R. Mayo<br \/>\n<em>Journal of Chemical Education<\/em> <strong>1986<\/strong> <em>63<\/em> (2), 97<br \/>\n<strong>DOI: <\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/ed063p97\">1021\/ed063p97<\/a><br \/>\nFor those interested in the history of science, this retrospective by Mayo tells the story of how he and Kharasch discovered the \u2018peroxide effect\u2019 and thereby a new area of organic chemistry.<\/li>\n<\/ol>\n","protected":false},"excerpt":{"rendered":"<p>Allylic Bromination and Benzylic Bromination: What Is It,\u00a0 And How Does It Work? In previous articles on radicals, we&#8217;ve seen how bromine (Br2) can selectively <\/p>\n","protected":false},"author":1,"featured_media":37397,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[1411],"tags":[170,463,241,933,261,934],"post_folder":[],"class_list":["post-7708","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-free-radical-reactions","tag-allylic-bromination","tag-initiation","tag-nbs","tag-propagation","tag-radicals","tag-termination"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.7 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>What is Allylic Bromination? &#8211; Master Organic Chemistry<\/title>\n<meta name=\"description\" content=\"What is allylic bromination and how does it work? 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