{"id":604,"date":"2018-11-26T16:30:28","date_gmt":"2018-11-26T16:30:28","guid":{"rendered":"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry2\/?post_type=chapter&#038;p=604"},"modified":"2019-01-07T18:41:48","modified_gmt":"2019-01-07T18:41:48","slug":"benzylic-carbocation-chemistry-libretexts","status":"publish","type":"chapter","link":"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry2\/chapter\/benzylic-carbocation-chemistry-libretexts\/","title":{"raw":"16.4. The benzyl and related groups","rendered":"16.4. The benzyl and related groups"},"content":{"raw":"<header class=\"elm-header\">\r\n<div class=\"elm-header-custom\">\r\n\r\nThis section gives some examples of benzylic groups, showing the resonance stabilization.\r\n<h2 class=\"mt-container-secondary\"><span style=\"color: #1d1d1d;font-size: 1.5em\">Benzy<\/span><span style=\"color: #1d1d1d;font-size: 1.5em\">lic<\/span><span style=\"color: #1d1d1d;font-size: 1.5em\"> Carbocation<\/span><\/h2>\r\n<\/div>\r\n<\/header><article id=\"elm-main-content\" class=\"elm-content-container\"><section class=\"mt-content-container\">A benzylic carbocation is a resonance-stabilized carbocation in each of the two equally stable major resonance forms of which the formal charge of +1 is on a benzylic carbon.eg:<img class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/26162938\/benzyliccarbocation1.png\" alt=\"\" width=\"600\" height=\"433\" \/>The lightest benzylic carbocation 1 is called the benzyl carbocation.<img class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/26162942\/benzyliccarbocation2.png\" alt=\"\" width=\"600\" height=\"488\" \/>see also\u00a0primary benzylic carbocation, secondary benzylic carbocation, tertiary benzylic carbocation.\r\n<div id=\"section_1\" class=\"mt-section\"><article id=\"elm-main-content\" class=\"elm-content-container\"><header>\r\n<div id=\"flash-messages\">\r\n<h2 class=\"dekiFlash\"><span style=\"color: #1d1d1d;font-size: 1.5em;font-weight: bold\">Benzylic Radical<\/span><\/h2>\r\n<\/div>\r\n<dl class=\"mt-last-updated-container\"><\/dl>\r\n<\/header><section class=\"mt-content-container\">A benzylic radical is a resonance-stabilized radical in each of the two equally stable major resonance forms of which the unpaired electron is on a benzylic carbon.eg:<img class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/26163220\/benzylicradical1.png\" alt=\"\" width=\"572\" height=\"406\" \/>The lightest benzylic radical 1 is called the benzyl radical.<img class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/26163224\/benzylicradical2.png\" alt=\"\" width=\"486\" height=\"472\" \/>see also primary benzylic radical, secondary benzylic radical, tertiary benzylic radical\r\n<div id=\"section_1\" class=\"mt-section\">\r\n<h3 class=\"editable\">Contributors<\/h3>\r\n<ul>\r\n \t<li><a class=\"external\" title=\"http:\/\/www.uvu.edu\/profpages\/profiles\/show\/user_id\/1776\" href=\"http:\/\/www.uvu.edu\/profpages\/profiles\/show\/user_id\/1776\" target=\"_blank\" rel=\"external nofollow noopener\"><span class=\"gD\">Gamini Gunawardena<\/span><\/a> from the <a class=\"external\" title=\"http:\/\/science.uvu.edu\/ochem\/\" href=\"http:\/\/science.uvu.edu\/ochem\/\" target=\"_blank\" rel=\"external nofollow noopener\">OChemPal <\/a>site (<a class=\"external\" title=\"http:\/\/www.uvu.edu\/chemistry\/\" href=\"http:\/\/www.uvu.edu\/chemistry\/\" target=\"_blank\" rel=\"external nofollow noopener\">Utah Valley University<\/a>)<\/li>\r\n<\/ul>\r\n<\/div>\r\n<\/section><\/article><\/div>\r\n<\/section><\/article>","rendered":"<header class=\"elm-header\">\n<div class=\"elm-header-custom\">\n<p>This section gives some examples of benzylic groups, showing the resonance stabilization.<\/p>\n<h2 class=\"mt-container-secondary\"><span style=\"color: #1d1d1d;font-size: 1.5em\">Benzy<\/span><span style=\"color: #1d1d1d;font-size: 1.5em\">lic<\/span><span style=\"color: #1d1d1d;font-size: 1.5em\"> Carbocation<\/span><\/h2>\n<\/div>\n<\/header>\n<article id=\"elm-main-content\" class=\"elm-content-container\">\n<section class=\"mt-content-container\">A benzylic carbocation is a resonance-stabilized carbocation in each of the two equally stable major resonance forms of which the formal charge of +1 is on a benzylic carbon.eg:<img loading=\"lazy\" decoding=\"async\" class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/26162938\/benzyliccarbocation1.png\" alt=\"\" width=\"600\" height=\"433\" \/>The lightest benzylic carbocation 1 is called the benzyl carbocation.<img loading=\"lazy\" decoding=\"async\" class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/26162942\/benzyliccarbocation2.png\" alt=\"\" width=\"600\" height=\"488\" \/>see also\u00a0primary benzylic carbocation, secondary benzylic carbocation, tertiary benzylic carbocation.<\/p>\n<div id=\"section_1\" class=\"mt-section\">\n<article id=\"elm-main-content\" class=\"elm-content-container\">\n<header>\n<div id=\"flash-messages\">\n<h2 class=\"dekiFlash\"><span style=\"color: #1d1d1d;font-size: 1.5em;font-weight: bold\">Benzylic Radical<\/span><\/h2>\n<\/div>\n<dl class=\"mt-last-updated-container\"><\/dl>\n<\/header>\n<section class=\"mt-content-container\">A benzylic radical is a resonance-stabilized radical in each of the two equally stable major resonance forms of which the unpaired electron is on a benzylic carbon.eg:<img loading=\"lazy\" decoding=\"async\" class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/26163220\/benzylicradical1.png\" alt=\"\" width=\"572\" height=\"406\" \/>The lightest benzylic radical 1 is called the benzyl radical.<img loading=\"lazy\" decoding=\"async\" class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/26163224\/benzylicradical2.png\" alt=\"\" width=\"486\" height=\"472\" \/>see also primary benzylic radical, secondary benzylic radical, tertiary benzylic radical<\/p>\n<div id=\"section_1\" class=\"mt-section\">\n<h3 class=\"editable\">Contributors<\/h3>\n<ul>\n<li><a class=\"external\" title=\"http:\/\/www.uvu.edu\/profpages\/profiles\/show\/user_id\/1776\" href=\"http:\/\/www.uvu.edu\/profpages\/profiles\/show\/user_id\/1776\" target=\"_blank\" rel=\"external nofollow noopener\"><span class=\"gD\">Gamini Gunawardena<\/span><\/a> from the <a class=\"external\" title=\"http:\/\/science.uvu.edu\/ochem\/\" href=\"http:\/\/science.uvu.edu\/ochem\/\" target=\"_blank\" rel=\"external nofollow noopener\">OChemPal <\/a>site (<a class=\"external\" title=\"http:\/\/www.uvu.edu\/chemistry\/\" href=\"http:\/\/www.uvu.edu\/chemistry\/\" target=\"_blank\" rel=\"external nofollow noopener\">Utah Valley University<\/a>)<\/li>\n<\/ul>\n<\/div>\n<\/section>\n<\/article>\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-604\">\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>Benzylic Carbocation. <strong>Authored by<\/strong>: Gamini Gunawardena. <strong>Provided by<\/strong>: Utah Valley University. <strong>Located at<\/strong>: <a target=\"_blank\" href=\"https:\/\/chem.libretexts.org\/Ancillary_Materials\/Reference\/Organic_Chemistry_Glossary\/Benzylic_Carbocation\">https:\/\/chem.libretexts.org\/Ancillary_Materials\/Reference\/Organic_Chemistry_Glossary\/Benzylic_Carbocation<\/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>Benzylic Radical. <strong>Authored by<\/strong>: Gamini Gunawardena. <strong>Provided by<\/strong>: Utah Valley University. <strong>Located at<\/strong>: <a target=\"_blank\" href=\"https:\/\/chem.libretexts.org\/Ancillary_Materials\/Reference\/Organic_Chemistry_Glossary\/Benzylic_Radical\">https:\/\/chem.libretexts.org\/Ancillary_Materials\/Reference\/Organic_Chemistry_Glossary\/Benzylic_Radical<\/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":4,"template":"","meta":{"_candela_citation":"[{\"type\":\"cc\",\"description\":\"Benzylic Carbocation\",\"author\":\"Gamini Gunawardena\",\"organization\":\"Utah Valley University\",\"url\":\"https:\/\/chem.libretexts.org\/Ancillary_Materials\/Reference\/Organic_Chemistry_Glossary\/Benzylic_Carbocation\",\"project\":\"Chemistry LibreTexts 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