{"id":598,"date":"2018-11-29T22:29:43","date_gmt":"2018-11-29T22:29:43","guid":{"rendered":"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry2\/?post_type=chapter&#038;p=598"},"modified":"2020-06-11T05:08:36","modified_gmt":"2020-06-11T05:08:36","slug":"16-3-reactions-of-alkylbenzenes","status":"publish","type":"chapter","link":"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry2\/chapter\/16-3-reactions-of-alkylbenzenes\/","title":{"raw":"16.3. Reactions of alkylbenzenes","rendered":"16.3. Reactions of alkylbenzenes"},"content":{"raw":"<article id=\"elm-main-content\" class=\"elm-content-container\"><section class=\"mt-content-container\">\r\n<div>\r\n<div class=\"textbox key-takeaways\">\r\n<h3>key terms<\/h3>\r\nMake certain that you can define, and use in context, the key terms below.\r\n<ul>\r\n \t<li>benzylic oxidation<\/li>\r\n \t<li>benzylic position<\/li>\r\n \t<li>side-chain oxidation<\/li>\r\n<\/ul>\r\n<\/div>\r\n<\/div>\r\n<div id=\"note\">\r\n<div class=\"textbox shaded\">\r\n<div id=\"note\">\r\n<h3 class=\"boxtitle\">Study Notes<\/h3>\r\nAs you can see from the examples, no matter what the length of the alkyl group in the arene substrate, the product is always a one-carbon carboxyl group. Thus, the benzylic carbon atom has been oxidized and the term <em>benzylic oxidation<\/em> is appropriate. The term <em>side-chain oxidation<\/em> is also commonly used.\r\n\r\nIn alkylbenzenes, the carbon atom which is attached to the aromatic ring is particularly reactive. Reactions taking place at this carbon atom are said to occur at the <em>benzylic position<\/em>.\r\n\r\nBenzylic halides undergo the typical reactions of alkyl halides; thus, you can expect to see such compounds used frequently in multistep syntheses.\r\n\r\nNote that we have adopted the terminology given below.\r\n\r\nAny compound of the type\r\n\r\n<img class=\"aligncenter\" src=\"http:\/\/chem.libretexts.org\/@api\/deki\/files\/87356\/16-9a.png?origin=mt-web\" alt=\"organobenzene with halogen on first carbon external to the ring\" \/>\r\n\r\n(where X = halogen) will be referred to as a \u201cbenzylic halide.\u201d\r\n\r\nCompounds of the type\r\n\r\n<img class=\"aligncenter\" src=\"http:\/\/chem.libretexts.org\/@api\/deki\/files\/87357\/16-9b.png?origin=mt-web\" alt=\"methyl hydrogen of toluene replaced by a halogen atom\" \/>\r\n\r\n<\/div>\r\n<div id=\"note\">\r\n\r\nare actually called benzyl chloride, benzyl bromide, etc.\r\n\r\nThe compound\r\n\r\n<img class=\"aligncenter\" src=\"http:\/\/chem.libretexts.org\/@api\/deki\/files\/87358\/16-9c.png?origin=mt-web\" alt=\"methyl hydrogen of toluene replaced by a hydroxide group\" \/>\r\n\r\nis called benzyl alcohol.\r\n\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<div id=\"section_1\" class=\"mt-section\">\r\n<h3 class=\"editable\">Oxidation of Alkyl Side-Chains<\/h3>\r\nAs noted earlier in <a href=\"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry2\/chapter\/16-1-overview-of-alkylbenzene-chemistry\/\">section 16.1<\/a>, alkyl side chains are activated towards oxidation at the benzylic position, because free radicals are stabilized at that position through resonance (see <a href=\"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry2\/chapter\/benzylic-carbocation-chemistry-libretexts\/\">section 16.4.<\/a>).\u00a0 When heated with aqueous potassium permanganate (KMnO<sub>4<\/sub>) under acidic conditions, alkylbenzenes are oxidized to benzoic acids, as long as the alkyl group contains at least one hydrogen at the benzylic position.\u00a0 This means that tert-butylbenzene (shown below) does not react.\u00a0 Aryl methyl ketones (acetophenones), made by the Friedel-Crafts reaction, can also be oxidized to benzoic acids using hot aqueous permanganate.\r\n\r\n<img class=\"alignnone wp-image-3134\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/11043611\/SideChainOxidation.skc_.png\" alt=\"Hot KMnO4 oxidation of alkylbenzenes or acetophenones produces benzoic acids, unless the alkyl group doesn't contain a benzylic H (tert-butylbenzene doesn't react)\" width=\"628\" height=\"273\" \/>\r\n\r\n&nbsp;\r\n\r\n&nbsp;\r\n<div class=\"mt-page-section\">\r\n<div id=\"section_2\" class=\"mt-section\">\r\n<h3 class=\"editable\">Bromination of the benzylic Carbon<\/h3>\r\nThe benzylic C-H bonds weaker than most <em>sp<sup>3<\/sup><\/em> hybridized C-H.\u00a0 This is because the radical formed from homolysis is resonance stabilized, as discussed in <a href=\"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry2\/chapter\/benzylic-carbocation-chemistry-libretexts\/\">section 16.4<\/a>.\u00a0 We will study radicals in more detail in <a href=\"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry2\/chapter\/18-1-what-is-a-free-radical\/\">chapter 18<\/a>.\r\n\r\n<img class=\"alignnone wp-image-2774\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/07075134\/Benzylic-radical.png\" alt=\"\" width=\"284\" height=\"231\" \/>\r\n\r\nBecause of the weak C-H bonds, benzylic hydrogens can form benzylic halides under radical conditions.\r\n\r\n<img class=\"alignnone wp-image-3135\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/11044503\/NBSbrominationOfEthylbenzene.png\" alt=\"Ethylbenzene reacts when heated with NBS\/AIBN to give 1-phenyl-1-bromoethane\" width=\"307\" height=\"92\" \/>\r\n\r\n<\/div>\r\n<\/div>\r\n&nbsp;\r\n<div class=\"mt-page-section\">\r\n<div id=\"section_2\" class=\"mt-section\">\r\n<div id=\"section_3\" class=\"mt-section\">\r\n<h4 class=\"editable\">NBS as a Bromine Source<\/h4>\r\nNBS (N-bromosuccinimide) is the most commonly used reagent to produce low concentrations of bromine. When suspended in tetrachloride (CCl<sub>4<\/sub>), NBS reacts with trace amounts of HBr to produce a low enough concentration of bromine to facilitate the benzylic bromination reaction via a radical process.\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/26162533\/Slide1_1.jpg\" alt=\"Slide1 (1).jpg\" width=\"307px\" height=\"104px\" \/>\r\n\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<div id=\"section_5\" class=\"mt-section\">\r\n<h3 class=\"editable\">Exercises<\/h3>\r\n<div id=\"s61721\" class=\"mt-include\">\r\n<div id=\"section_34\" class=\"mt-section\">\r\n<h4 id=\"Questions-61721\">Questions<\/h4>\r\n<strong>Q16.9.1<\/strong>\r\n\r\n<span class=\"mt-font-Times New Roman,serif\"><span class=\"mt-font-size-12.0pt\">Predict the products.<\/span><\/span>\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/26162537\/16-9-1qu.png\" alt=\"\" width=\"311\" height=\"291\" \/>\r\n\r\n<strong>Q16.9.2<\/strong>\r\n\r\nConsider a benzyl radical. Would it be more stable than an alkyl radical? Explain.\r\n\r\n<\/div>\r\n<div id=\"section_35\" class=\"mt-section\">\r\n<h4 id=\"Solutions-61721\">Solutions<\/h4>\r\n<strong>S16.9.1<\/strong>\r\n\r\nThe second one leads to no reaction because it requires a hydrogen on the carbon next to the phenyl ring.\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/26162541\/16.9.png\" alt=\"\" width=\"503\" height=\"293\" \/>\r\n\r\n<strong>S16.9.2<\/strong>\r\n\r\n<span class=\"mt-font-Times New Roman,serif\"><span class=\"mt-font-size-12.0pt\">Yes it would be more stable than an alkyl radical, consider the pi system able to stabilize through resonance. <\/span><\/span>\r\n\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<div id=\"section_6\" class=\"mt-section\">\r\n<h3 class=\"editable\">Contributors<\/h3>\r\n<ul>\r\n \t<li><a class=\"external\" title=\"http:\/\/science.athabascau.ca\/staff-pages\/dietmark\" href=\"http:\/\/science.athabascau.ca\/staff-pages\/dietmark\" target=\"_blank\" rel=\"external nofollow noopener\">Dr. Dietmar Kennepohl<\/a> FCIC (Professor of Chemistry, <a class=\"external\" title=\"http:\/\/www.athabascau.ca\/\" href=\"http:\/\/www.athabascau.ca\/\" target=\"_blank\" rel=\"external nofollow noopener\">Athabasca University<\/a>)<\/li>\r\n \t<li>Prof. Steven Farmer (<a class=\"external\" title=\"http:\/\/www.sonoma.edu\" href=\"http:\/\/www.sonoma.edu\" target=\"_blank\" rel=\"external nofollow noopener\">Sonoma State University<\/a>)<\/li>\r\n<\/ul>\r\n<\/div>\r\n<\/div>\r\n<\/section><\/article>","rendered":"<article id=\"elm-main-content\" class=\"elm-content-container\">\n<section class=\"mt-content-container\">\n<div>\n<div class=\"textbox key-takeaways\">\n<h3>key terms<\/h3>\n<p>Make certain that you can define, and use in context, the key terms below.<\/p>\n<ul>\n<li>benzylic oxidation<\/li>\n<li>benzylic position<\/li>\n<li>side-chain oxidation<\/li>\n<\/ul>\n<\/div>\n<\/div>\n<div id=\"note\">\n<div class=\"textbox shaded\">\n<div id=\"note\">\n<h3 class=\"boxtitle\">Study Notes<\/h3>\n<p>As you can see from the examples, no matter what the length of the alkyl group in the arene substrate, the product is always a one-carbon carboxyl group. Thus, the benzylic carbon atom has been oxidized and the term <em>benzylic oxidation<\/em> is appropriate. The term <em>side-chain oxidation<\/em> is also commonly used.<\/p>\n<p>In alkylbenzenes, the carbon atom which is attached to the aromatic ring is particularly reactive. Reactions taking place at this carbon atom are said to occur at the <em>benzylic position<\/em>.<\/p>\n<p>Benzylic halides undergo the typical reactions of alkyl halides; thus, you can expect to see such compounds used frequently in multistep syntheses.<\/p>\n<p>Note that we have adopted the terminology given below.<\/p>\n<p>Any compound of the type<\/p>\n<p><img decoding=\"async\" class=\"aligncenter\" src=\"http:\/\/chem.libretexts.org\/@api\/deki\/files\/87356\/16-9a.png?origin=mt-web\" alt=\"organobenzene with halogen on first carbon external to the ring\" \/><\/p>\n<p>(where X = halogen) will be referred to as a \u201cbenzylic halide.\u201d<\/p>\n<p>Compounds of the type<\/p>\n<p><img decoding=\"async\" class=\"aligncenter\" src=\"http:\/\/chem.libretexts.org\/@api\/deki\/files\/87357\/16-9b.png?origin=mt-web\" alt=\"methyl hydrogen of toluene replaced by a halogen atom\" \/><\/p>\n<\/div>\n<div id=\"note\">\n<p>are actually called benzyl chloride, benzyl bromide, etc.<\/p>\n<p>The compound<\/p>\n<p><img decoding=\"async\" class=\"aligncenter\" src=\"http:\/\/chem.libretexts.org\/@api\/deki\/files\/87358\/16-9c.png?origin=mt-web\" alt=\"methyl hydrogen of toluene replaced by a hydroxide group\" \/><\/p>\n<p>is called benzyl alcohol.<\/p>\n<\/div>\n<\/div>\n<\/div>\n<div id=\"section_1\" class=\"mt-section\">\n<h3 class=\"editable\">Oxidation of Alkyl Side-Chains<\/h3>\n<p>As noted earlier in <a href=\"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry2\/chapter\/16-1-overview-of-alkylbenzene-chemistry\/\">section 16.1<\/a>, alkyl side chains are activated towards oxidation at the benzylic position, because free radicals are stabilized at that position through resonance (see <a href=\"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry2\/chapter\/benzylic-carbocation-chemistry-libretexts\/\">section 16.4.<\/a>).\u00a0 When heated with aqueous potassium permanganate (KMnO<sub>4<\/sub>) under acidic conditions, alkylbenzenes are oxidized to benzoic acids, as long as the alkyl group contains at least one hydrogen at the benzylic position.\u00a0 This means that tert-butylbenzene (shown below) does not react.\u00a0 Aryl methyl ketones (acetophenones), made by the Friedel-Crafts reaction, can also be oxidized to benzoic acids using hot aqueous permanganate.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-3134\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/11043611\/SideChainOxidation.skc_.png\" alt=\"Hot KMnO4 oxidation of alkylbenzenes or acetophenones produces benzoic acids, unless the alkyl group doesn't contain a benzylic H (tert-butylbenzene doesn't react)\" width=\"628\" height=\"273\" \/><\/p>\n<p>&nbsp;<\/p>\n<p>&nbsp;<\/p>\n<div class=\"mt-page-section\">\n<div id=\"section_2\" class=\"mt-section\">\n<h3 class=\"editable\">Bromination of the benzylic Carbon<\/h3>\n<p>The benzylic C-H bonds weaker than most <em>sp<sup>3<\/sup><\/em> hybridized C-H.\u00a0 This is because the radical formed from homolysis is resonance stabilized, as discussed in <a href=\"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry2\/chapter\/benzylic-carbocation-chemistry-libretexts\/\">section 16.4<\/a>.\u00a0 We will study radicals in more detail in <a href=\"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry2\/chapter\/18-1-what-is-a-free-radical\/\">chapter 18<\/a>.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-2774\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/07075134\/Benzylic-radical.png\" alt=\"\" width=\"284\" height=\"231\" \/><\/p>\n<p>Because of the weak C-H bonds, benzylic hydrogens can form benzylic halides under radical conditions.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-3135\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/11044503\/NBSbrominationOfEthylbenzene.png\" alt=\"Ethylbenzene reacts when heated with NBS\/AIBN to give 1-phenyl-1-bromoethane\" width=\"307\" height=\"92\" \/><\/p>\n<\/div>\n<\/div>\n<p>&nbsp;<\/p>\n<div class=\"mt-page-section\">\n<div id=\"section_2\" class=\"mt-section\">\n<div id=\"section_3\" class=\"mt-section\">\n<h4 class=\"editable\">NBS as a Bromine Source<\/h4>\n<p>NBS (N-bromosuccinimide) is the most commonly used reagent to produce low concentrations of bromine. When suspended in tetrachloride (CCl<sub>4<\/sub>), NBS reacts with trace amounts of HBr to produce a low enough concentration of bromine to facilitate the benzylic bromination reaction via a radical process.<\/p>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/26162533\/Slide1_1.jpg\" alt=\"Slide1 (1).jpg\" width=\"307px\" height=\"104px\" \/><\/p>\n<\/div>\n<\/div>\n<\/div>\n<div id=\"section_5\" class=\"mt-section\">\n<h3 class=\"editable\">Exercises<\/h3>\n<div id=\"s61721\" class=\"mt-include\">\n<div id=\"section_34\" class=\"mt-section\">\n<h4 id=\"Questions-61721\">Questions<\/h4>\n<p><strong>Q16.9.1<\/strong><\/p>\n<p><span class=\"mt-font-Times New Roman,serif\"><span class=\"mt-font-size-12.0pt\">Predict the products.<\/span><\/span><\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/26162537\/16-9-1qu.png\" alt=\"\" width=\"311\" height=\"291\" \/><\/p>\n<p><strong>Q16.9.2<\/strong><\/p>\n<p>Consider a benzyl radical. Would it be more stable than an alkyl radical? Explain.<\/p>\n<\/div>\n<div id=\"section_35\" class=\"mt-section\">\n<h4 id=\"Solutions-61721\">Solutions<\/h4>\n<p><strong>S16.9.1<\/strong><\/p>\n<p>The second one leads to no reaction because it requires a hydrogen on the carbon next to the phenyl ring.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/26162541\/16.9.png\" alt=\"\" width=\"503\" height=\"293\" \/><\/p>\n<p><strong>S16.9.2<\/strong><\/p>\n<p><span class=\"mt-font-Times New Roman,serif\"><span class=\"mt-font-size-12.0pt\">Yes it would be more stable than an alkyl radical, consider the pi system able to stabilize through resonance. <\/span><\/span><\/p>\n<\/div>\n<\/div>\n<\/div>\n<div id=\"section_6\" class=\"mt-section\">\n<h3 class=\"editable\">Contributors<\/h3>\n<ul>\n<li><a class=\"external\" title=\"http:\/\/science.athabascau.ca\/staff-pages\/dietmark\" href=\"http:\/\/science.athabascau.ca\/staff-pages\/dietmark\" target=\"_blank\" rel=\"external nofollow noopener\">Dr. Dietmar Kennepohl<\/a> FCIC (Professor of Chemistry, <a class=\"external\" title=\"http:\/\/www.athabascau.ca\/\" href=\"http:\/\/www.athabascau.ca\/\" target=\"_blank\" rel=\"external nofollow noopener\">Athabasca University<\/a>)<\/li>\n<li>Prof. Steven Farmer (<a class=\"external\" title=\"http:\/\/www.sonoma.edu\" href=\"http:\/\/www.sonoma.edu\" target=\"_blank\" rel=\"external nofollow noopener\">Sonoma State University<\/a>)<\/li>\n<\/ul>\n<\/div>\n<\/div>\n<\/section>\n<\/article>\n\n\t\t\t <section class=\"citations-section\" role=\"contentinfo\">\n\t\t\t <h3>Candela Citations<\/h3>\n\t\t\t\t\t <div>\n\t\t\t\t\t\t <div id=\"citation-list-598\">\n\t\t\t\t\t\t\t <div class=\"licensing\"><div class=\"license-attribution-dropdown-subheading\">CC licensed content, Shared previously<\/div><ul class=\"citation-list\"><li>16.9: Oxidation of Aromatic Compounds. <strong>Authored by<\/strong>: Dr. Dietmar Kennepohl FCIC; Prof. Steven Farmer; William Reusch, professor Emeritus. <strong>Provided by<\/strong>: Athabasca University; Sonoma State University; Michigan State. <strong>Located at<\/strong>: <a target=\"_blank\" href=\"https:\/\/chem.libretexts.org\/Textbook_Maps\/Organic_Chemistry\/Map%3A_Organic_Chemistry_(McMurry)\/Chapter_16%3A_Chemistry_of_Benzene_-_Electrophilic_Aromatic_Substitution\/16.09_Oxidation_of_Aromatic_Compounds\">https:\/\/chem.libretexts.org\/Textbook_Maps\/Organic_Chemistry\/Map%3A_Organic_Chemistry_(McMurry)\/Chapter_16%3A_Chemistry_of_Benzene_-_Electrophilic_Aromatic_Substitution\/16.09_Oxidation_of_Aromatic_Compounds<\/a>. <strong>Project<\/strong>: Chemistry LibreTexts . <strong>License<\/strong>: <em><a target=\"_blank\" rel=\"license\" href=\"https:\/\/creativecommons.org\/licenses\/by-nc-sa\/4.0\/\">CC BY-NC-SA: Attribution-NonCommercial-ShareAlike<\/a><\/em><\/li><li>16.9: Oxidation of Aromatic Compounds. <strong>Authored by<\/strong>: Dr. Dietmar Kennepohl FCIC; Prof. Steven Farmer; William Reusch, Professor Emeritus. <strong>Provided by<\/strong>: Athabasca University; Sonoma State University; Michigan State U. <strong>Located at<\/strong>: <a target=\"_blank\" href=\"https:\/\/chem.libretexts.org\/Textbook_Maps\/Organic_Chemistry\/Map%3A_Organic_Chemistry_(McMurry)\/Chapter_16%3A_Chemistry_of_Benzene_-_Electrophilic_Aromatic_Substitution\/16.09_Oxidation_of_Aromatic_Compounds\">https:\/\/chem.libretexts.org\/Textbook_Maps\/Organic_Chemistry\/Map%3A_Organic_Chemistry_(McMurry)\/Chapter_16%3A_Chemistry_of_Benzene_-_Electrophilic_Aromatic_Substitution\/16.09_Oxidation_of_Aromatic_Compounds<\/a>. <strong>Project<\/strong>: Chemistry LibreTexts. <strong>License<\/strong>: <em><a target=\"_blank\" rel=\"license\" href=\"https:\/\/creativecommons.org\/licenses\/by-nc-sa\/4.0\/\">CC BY-NC-SA: Attribution-NonCommercial-ShareAlike<\/a><\/em><\/li><\/ul><\/div>\n\t\t\t\t\t\t <\/div>\n\t\t\t\t\t <\/div>\n\t\t\t <\/section>","protected":false},"author":311,"menu_order":3,"template":"","meta":{"_candela_citation":"[{\"type\":\"cc\",\"description\":\"16.9: Oxidation of Aromatic Compounds\",\"author\":\"Dr. Dietmar Kennepohl FCIC; Prof. Steven Farmer; William Reusch, professor Emeritus\",\"organization\":\"Athabasca University; Sonoma State University; Michigan State\",\"url\":\"https:\/\/chem.libretexts.org\/Textbook_Maps\/Organic_Chemistry\/Map%3A_Organic_Chemistry_(McMurry)\/Chapter_16%3A_Chemistry_of_Benzene_-_Electrophilic_Aromatic_Substitution\/16.09_Oxidation_of_Aromatic_Compounds\",\"project\":\"Chemistry LibreTexts \",\"license\":\"cc-by-nc-sa\",\"license_terms\":\"\"},{\"type\":\"cc\",\"description\":\"16.9: Oxidation of Aromatic Compounds\",\"author\":\"Dr. Dietmar Kennepohl FCIC; Prof. Steven Farmer; William Reusch, Professor Emeritus\",\"organization\":\"Athabasca University; Sonoma State University; Michigan State U\",\"url\":\"https:\/\/chem.libretexts.org\/Textbook_Maps\/Organic_Chemistry\/Map%3A_Organic_Chemistry_(McMurry)\/Chapter_16%3A_Chemistry_of_Benzene_-_Electrophilic_Aromatic_Substitution\/16.09_Oxidation_of_Aromatic_Compounds\",\"project\":\"Chemistry LibreTexts\",\"license\":\"cc-by-nc-sa\",\"license_terms\":\"\"}]","CANDELA_OUTCOMES_GUID":"","pb_show_title":"on","pb_short_title":"","pb_subtitle":"","pb_authors":[],"pb_section_license":""},"chapter-type":[],"contributor":[],"license":[],"class_list":["post-598","chapter","type-chapter","status-publish","hentry"],"part":539,"_links":{"self":[{"href":"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry2\/wp-json\/pressbooks\/v2\/chapters\/598","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry2\/wp-json\/pressbooks\/v2\/chapters"}],"about":[{"href":"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry2\/wp-json\/wp\/v2\/types\/chapter"}],"author":[{"embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry2\/wp-json\/wp\/v2\/users\/311"}],"version-history":[{"count":9,"href":"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry2\/wp-json\/pressbooks\/v2\/chapters\/598\/revisions"}],"predecessor-version":[{"id":3136,"href":"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry2\/wp-json\/pressbooks\/v2\/chapters\/598\/revisions\/3136"}],"part":[{"href":"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry2\/wp-json\/pressbooks\/v2\/parts\/539"}],"metadata":[{"href":"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry2\/wp-json\/pressbooks\/v2\/chapters\/598\/metadata\/"}],"wp:attachment":[{"href":"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry2\/wp-json\/wp\/v2\/media?parent=598"}],"wp:term":[{"taxonomy":"chapter-type","embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry2\/wp-json\/pressbooks\/v2\/chapter-type?post=598"},{"taxonomy":"contributor","embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry2\/wp-json\/wp\/v2\/contributor?post=598"},{"taxonomy":"license","embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry2\/wp-json\/wp\/v2\/license?post=598"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}