{"id":373,"date":"2020-02-17T00:19:00","date_gmt":"2020-02-17T00:19:00","guid":{"rendered":"http:\/\/box5250.temp.domains\/~aceorgan\/blog\/?p=373"},"modified":"2020-02-17T20:23:20","modified_gmt":"2020-02-17T20:23:20","slug":"resonance-in-organic-chemistry","status":"publish","type":"post","link":"https:\/\/www.aceorganicchem.com\/blog\/resonance-in-organic-chemistry\/","title":{"rendered":"Resonance between equivalent atoms in organic chemistry means equal bond lengths."},"content":{"rendered":"<h1 style=\"text-align: center;\"><span style=\"font-family: Calibri;\"><span style=\"color: #000000;\">It&#8217;s time for resonance in organic chemistry. \u00a0<\/span><\/span><\/h1>\n<p>Resonance in organic chemistry is one of the most fundamental and useful concepts you will learn in this class. Once most students hear this tip, it makes perfect sense to them, but it isn\u2019t one that you might think of on your own.\u00a0 Take a look at the structure below, and ask yourself: are the two N-O bonds in this molecule the same length?<\/p>\n<p align=\"center\"><a href=\"http:\/\/box5250.temp.domains\/~aceorgan\/blog\/wp-content\/uploads\/2012\/10\/Slide18.png\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone size-medium wp-image-374\" title=\"Slide18\" src=\"http:\/\/box5250.temp.domains\/~aceorgan\/blog\/wp-content\/uploads\/2012\/10\/Slide18-300x181.png\" alt=\"resonance in organic chemistry\" width=\"300\" height=\"181\" srcset=\"https:\/\/www.aceorganicchem.com\/blog\/wp-content\/uploads\/2012\/10\/Slide18-300x181.png 300w, https:\/\/www.aceorganicchem.com\/blog\/wp-content\/uploads\/2012\/10\/Slide18-1024x620.png 1024w\" sizes=\"auto, (max-width: 300px) 100vw, 300px\" \/><\/a><\/p>\n<p>Since freshman chemistry, we have been told that double bonds between two atoms are <em>shorter<\/em> than a single bond between the same two atoms.\u00a0 Hence, the N-O double bond <em>should<\/em> be shorter than the N-O single bond. \u00a0Spoiler: it is not. \u00a0But before we get into that, let\u2019s look at some resonance\u00a0forms of the nitro group at the end of this hydrocarbon:<\/p>\n<p><span style=\"font-family: Calibri;\"><span style=\"color: #000000;\"><a href=\"http:\/\/box5250.temp.domains\/~aceorgan\/blog\/wp-content\/uploads\/2012\/10\/Slide19.png\"><img loading=\"lazy\" decoding=\"async\" class=\"wp-image-375 aligncenter\" title=\"Slide19\" src=\"http:\/\/box5250.temp.domains\/~aceorgan\/blog\/wp-content\/uploads\/2012\/10\/Slide19-1024x244.png\" alt=\"resonance and bond length\" width=\"640\" height=\"152\" srcset=\"https:\/\/www.aceorganicchem.com\/blog\/wp-content\/uploads\/2012\/10\/Slide19-1024x244.png 1024w, https:\/\/www.aceorganicchem.com\/blog\/wp-content\/uploads\/2012\/10\/Slide19-300x71.png 300w\" sizes=\"auto, (max-width: 640px) 100vw, 640px\" \/><\/a><\/span><\/span><\/p>\n<p>Here, we can more clearly see that the nitro group is interconverting between the three resonance\u00a0structures shown above.\u00a0 Structure 3, where the charge is spread evenly between the two oxygens is a valid structure and shows that the bond two oxygen atoms in the molecule are equivalent and have the same bond length (124 pm). \u00a0This is shown here using the dashed bond, which you can think of as &#8220;half of a bond&#8221; for lack of a better term.<\/p>\n<p><a href=\"http:\/\/box5250.temp.domains\/~aceorgan\/blog\/wp-content\/uploads\/2012\/10\/half-of-a-bond.jpg\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter size-medium wp-image-802\" src=\"http:\/\/box5250.temp.domains\/~aceorgan\/blog\/wp-content\/uploads\/2012\/10\/half-of-a-bond-300x300.jpg\" alt=\"\" width=\"300\" height=\"300\" srcset=\"https:\/\/www.aceorganicchem.com\/blog\/wp-content\/uploads\/2012\/10\/half-of-a-bond-300x300.jpg 300w, https:\/\/www.aceorganicchem.com\/blog\/wp-content\/uploads\/2012\/10\/half-of-a-bond-150x150.jpg 150w, https:\/\/www.aceorganicchem.com\/blog\/wp-content\/uploads\/2012\/10\/half-of-a-bond.jpg 426w\" sizes=\"auto, (max-width: 300px) 100vw, 300px\" \/><\/a><\/p>\n<p>\u00a0<\/p>\n<p>We care even more about this principle when it can be applied to more complex organic molecules where it is not obvious that the bonds are equivalent.\u00a0 For example, the cyclopentadiene anion:<\/p>\n<p align=\"center\"><a href=\"http:\/\/box5250.temp.domains\/~aceorgan\/blog\/wp-content\/uploads\/2012\/10\/Slide20.png\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-376\" title=\"Slide20\" src=\"http:\/\/box5250.temp.domains\/~aceorgan\/blog\/wp-content\/uploads\/2012\/10\/Slide20-1024x1008.png\" alt=\"\" width=\"202\" height=\"184\" \/><\/a><\/p>\n<p align=\"center\">\u00a0<\/p>\n<h2><a href=\"http:\/\/www.aceorganicchem.com\/organic-chemistry-ebooks.html\" target=\"_blank\" rel=\"noopener noreferrer\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-869 size-full\" src=\"http:\/\/box5250.temp.domains\/~aceorgan\/blog\/wp-content\/uploads\/2017\/06\/Copy-of-Free-o-chem-study-guides.-Download-now..png\" alt=\"\" width=\"350\" height=\"250\" srcset=\"https:\/\/www.aceorganicchem.com\/blog\/wp-content\/uploads\/2017\/06\/Copy-of-Free-o-chem-study-guides.-Download-now..png 350w, https:\/\/www.aceorganicchem.com\/blog\/wp-content\/uploads\/2017\/06\/Copy-of-Free-o-chem-study-guides.-Download-now.-300x214.png 300w\" sizes=\"auto, (max-width: 350px) 100vw, 350px\" \/><\/a><\/h2>\n<p>At first glance, this appears to have three different carbon atoms.\u00a0 However, once you start looking at resonance\u00a0structures, you can see that the anion can be moved to any of the carbons in the ring.\u00a0 This makes them all equivalent, via resonance.\u00a0 This is confirmed through analytical studies which show that all C-C bonds are <strong><em>approximately 137pm long<\/em><\/strong>.\u00a0 Additionally, as this fits Huckel\u2019s rule\u00a0of 4N+2, the molecule is also aromatic.<\/p>\n<p><span style=\"font-family: Calibri;\"><span style=\"color: #000000;\"><a href=\"http:\/\/box5250.temp.domains\/~aceorgan\/blog\/wp-content\/uploads\/2012\/10\/Slide21.png\"><img loading=\"lazy\" decoding=\"async\" class=\"size-large wp-image-377 aligncenter\" title=\"Slide21\" src=\"http:\/\/box5250.temp.domains\/~aceorgan\/blog\/wp-content\/uploads\/2012\/10\/Slide21-1024x193.png\" alt=\"\" width=\"640\" height=\"120\" srcset=\"https:\/\/www.aceorganicchem.com\/blog\/wp-content\/uploads\/2012\/10\/Slide21-1024x193.png 1024w, https:\/\/www.aceorganicchem.com\/blog\/wp-content\/uploads\/2012\/10\/Slide21-300x56.png 300w\" sizes=\"auto, (max-width: 640px) 100vw, 640px\" \/><\/a><\/span><\/span><\/p>\n<p>One last note on this topic: We showed it above but did not give it a name.\u00a0 When you have two or more bonds, and they have equivalent bond lengths, you can draw dashed bonds to show that the resonance structure is constantly changing and the bonds are constantly moving and interconverting between the two structures.\u00a0 This is referred to as a &#8220;resonance hybrid&#8221;, where the resonance bond is delocalized.\u00a0 What really confuses students about this structure is that it does not make sense with respect to Lewis Dot structures.\u00a0 In fact, resonance hybrids and Lewis Dots are not compatible.\u00a0 So if you are going to use Lewis Dots, make sure you draw double-headed arrows to denote resonance.\u00a0\u00a0<\/p>\n\n\n<div class=\"wp-block-image\"><figure class=\"aligncenter size-large\"><img loading=\"lazy\" decoding=\"async\" width=\"633\" height=\"368\" src=\"http:\/\/box5250.temp.domains\/~aceorgan\/blog\/wp-content\/uploads\/2017\/06\/ozone-resonance-3.jpg\" alt=\"\" class=\"wp-image-1144\" srcset=\"https:\/\/www.aceorganicchem.com\/blog\/wp-content\/uploads\/2017\/06\/ozone-resonance-3.jpg 633w, https:\/\/www.aceorganicchem.com\/blog\/wp-content\/uploads\/2017\/06\/ozone-resonance-3-300x174.jpg 300w\" sizes=\"auto, (max-width: 633px) 100vw, 633px\" \/><figcaption>The top is resonance structures with Lewis Dots, the bottom is a resonance hybrid<\/figcaption><\/figure><\/div>\n\n\n\n<div class=\"wp-block-image is-style-default\"><figure class=\"aligncenter size-large is-resized\"><img loading=\"lazy\" decoding=\"async\" src=\"http:\/\/box5250.temp.domains\/~aceorgan\/blog\/wp-content\/uploads\/2019\/08\/bitmoji-genius.png\" alt=\"\" class=\"wp-image-2849\" width=\"199\" height=\"199\" srcset=\"https:\/\/www.aceorganicchem.com\/blog\/wp-content\/uploads\/2019\/08\/bitmoji-genius.png 398w, https:\/\/www.aceorganicchem.com\/blog\/wp-content\/uploads\/2019\/08\/bitmoji-genius-300x300.png 300w, https:\/\/www.aceorganicchem.com\/blog\/wp-content\/uploads\/2019\/08\/bitmoji-genius-150x150.png 150w\" sizes=\"auto, (max-width: 199px) 100vw, 199px\" \/><\/figure><\/div>\n\n\n\n<p><strong>Take Home Message: If you see symmetry or aromaticity, think equivalent bond lengths<\/strong><\/p>\n\n\n\n<p>&nbsp;For more help with resonance, please see our homepage at <a href=\"https:\/\/www.aceorganicchem.com\" target=\"_blank\" rel=\"noreferrer noopener\">organic chemistry&nbsp;<\/a> &nbsp;it is full of stuff to help you crush organic chemistry fast.&nbsp;<\/p>\n\n\n\n<p><strong>Reference<\/strong>: <a href=\"http:\/\/www.chem.ucalgary.ca\/courses\/350\/Carey5th\/Ch01\/ch1-7.html\">Carey resonance<\/a><\/p>\n\n\n\n<div class=\"wp-block-image\"><figure class=\"aligncenter\"><a href=\"https:\/\/www.aceorganicchem.com\/free.html\" target=\"_blank\" rel=\"noreferrer noopener\"><img loading=\"lazy\" decoding=\"async\" width=\"300\" height=\"214\" src=\"http:\/\/box5250.temp.domains\/~aceorgan\/blog\/wp-content\/uploads\/2017\/06\/Free-o-chem-study-guides.-Download-now.-300x214.jpg\" alt=\"free organic chem study guide\" class=\"wp-image-772\" srcset=\"https:\/\/www.aceorganicchem.com\/blog\/wp-content\/uploads\/2017\/06\/Free-o-chem-study-guides.-Download-now.-300x214.jpg 300w, https:\/\/www.aceorganicchem.com\/blog\/wp-content\/uploads\/2017\/06\/Free-o-chem-study-guides.-Download-now..jpg 350w\" sizes=\"auto, (max-width: 300px) 100vw, 300px\" \/><\/a><\/figure><\/div>\n","protected":false},"excerpt":{"rendered":"<p>It&#8217;s time for resonance in organic chemistry. \u00a0 Resonance in organic chemistry is one of the most fundamental and useful concepts you will learn in this class. Once most students hear this tip, it makes perfect sense to them, but it isn\u2019t one that you might think of on your own.\u00a0 Take a look at [&hellip;]<\/p>\n","protected":false},"author":2,"featured_media":0,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"om_disable_all_campaigns":false,"_monsterinsights_skip_tracking":false,"_monsterinsights_sitenote_active":false,"_monsterinsights_sitenote_note":"","_monsterinsights_sitenote_category":0,"site-sidebar-layout":"default","site-content-layout":"default","ast-site-content-layout":"default","site-content-style":"default","site-sidebar-style":"default","ast-global-header-display":"","ast-banner-title-visibility":"","ast-main-header-display":"","ast-hfb-above-header-display":"","ast-hfb-below-header-display":"","ast-hfb-mobile-header-display":"","site-post-title":"","ast-breadcrumbs-content":"","ast-featured-img":"","footer-sml-layout":"","ast-disable-related-posts":"","theme-transparent-header-meta":"default","adv-header-id-meta":"","stick-header-meta":"","header-above-stick-meta":"","header-main-stick-meta":"","header-below-stick-meta":"","astra-migrate-meta-layouts":"default","ast-page-background-enabled":"default","ast-page-background-meta":{"desktop":{"background-color":"","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-opacity":"","overlay-gradient":""},"tablet":{"background-color":"","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-opacity":"","overlay-gradient":""},"mobile":{"background-color":"","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-opacity":"","overlay-gradient":""}},"ast-content-background-meta":{"desktop":{"background-color":"var(--ast-global-color-5)","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-opacity":"","overlay-gradient":""},"tablet":{"background-color":"var(--ast-global-color-5)","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-opacity":"","overlay-gradient":""},"mobile":{"background-color":"var(--ast-global-color-5)","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-opacity":"","overlay-gradient":""}},"footnotes":""},"categories":[8,9],"tags":[37,46,19,36],"class_list":["post-373","post","type-post","status-publish","format-standard","hentry","category-o-chem-help","category-organic-chemistry","tag-bond-length","tag-organic-chemistry","tag-organic-chemistry-help","tag-resonance"],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.3 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Resonance in organic chemistry and bond length [with examples]<\/title>\n<meta name=\"description\" content=\"This post demonstrates how resonance in organic chemistry makes bond lengths of two equivalent atoms the same length. A free study guide is available too.\" \/>\n<meta name=\"robots\" content=\"index, follow, max-snippet:-1, max-image-preview:large, max-video-preview:-1\" \/>\n<link rel=\"canonical\" href=\"https:\/\/www.aceorganicchem.com\/blog\/resonance-in-organic-chemistry\/\" \/>\n<meta name=\"twitter:label1\" content=\"Written by\" \/>\n\t<meta name=\"twitter:data1\" content=\"Dr. Michael Pa\" \/>\n\t<meta name=\"twitter:label2\" content=\"Est. reading time\" \/>\n\t<meta name=\"twitter:data2\" content=\"2 minutes\" \/>\n<script type=\"application\/ld+json\" class=\"yoast-schema-graph\">{\"@context\":\"https:\\\/\\\/schema.org\",\"@graph\":[{\"@type\":\"Article\",\"@id\":\"https:\\\/\\\/www.aceorganicchem.com\\\/blog\\\/resonance-in-organic-chemistry\\\/#article\",\"isPartOf\":{\"@id\":\"https:\\\/\\\/www.aceorganicchem.com\\\/blog\\\/resonance-in-organic-chemistry\\\/\"},\"author\":{\"name\":\"Dr. Michael Pa\",\"@id\":\"https:\\\/\\\/www.aceorganicchem.com\\\/blog\\\/#\\\/schema\\\/person\\\/854192b6b8f267c7ee95ddba11dcd4b4\"},\"headline\":\"Resonance between equivalent atoms in organic chemistry means equal bond lengths.\",\"datePublished\":\"2020-02-17T00:19:00+00:00\",\"dateModified\":\"2020-02-17T20:23:20+00:00\",\"mainEntityOfPage\":{\"@id\":\"https:\\\/\\\/www.aceorganicchem.com\\\/blog\\\/resonance-in-organic-chemistry\\\/\"},\"wordCount\":507,\"commentCount\":0,\"publisher\":{\"@id\":\"https:\\\/\\\/www.aceorganicchem.com\\\/blog\\\/#organization\"},\"image\":{\"@id\":\"https:\\\/\\\/www.aceorganicchem.com\\\/blog\\\/resonance-in-organic-chemistry\\\/#primaryimage\"},\"thumbnailUrl\":\"http:\\\/\\\/box5250.temp.domains\\\/~aceorgan\\\/blog\\\/wp-content\\\/uploads\\\/2012\\\/10\\\/Slide18-300x181.png\",\"keywords\":[\"bond length\",\"organic chemistry\",\"organic chemistry help\",\"resonance\"],\"articleSection\":[\"o-chem help\",\"organic chemistry\"],\"inLanguage\":\"en-US\",\"potentialAction\":[{\"@type\":\"CommentAction\",\"name\":\"Comment\",\"target\":[\"https:\\\/\\\/www.aceorganicchem.com\\\/blog\\\/resonance-in-organic-chemistry\\\/#respond\"]}]},{\"@type\":\"WebPage\",\"@id\":\"https:\\\/\\\/www.aceorganicchem.com\\\/blog\\\/resonance-in-organic-chemistry\\\/\",\"url\":\"https:\\\/\\\/www.aceorganicchem.com\\\/blog\\\/resonance-in-organic-chemistry\\\/\",\"name\":\"Resonance in organic chemistry and bond length [with examples]\",\"isPartOf\":{\"@id\":\"https:\\\/\\\/www.aceorganicchem.com\\\/blog\\\/#website\"},\"primaryImageOfPage\":{\"@id\":\"https:\\\/\\\/www.aceorganicchem.com\\\/blog\\\/resonance-in-organic-chemistry\\\/#primaryimage\"},\"image\":{\"@id\":\"https:\\\/\\\/www.aceorganicchem.com\\\/blog\\\/resonance-in-organic-chemistry\\\/#primaryimage\"},\"thumbnailUrl\":\"http:\\\/\\\/box5250.temp.domains\\\/~aceorgan\\\/blog\\\/wp-content\\\/uploads\\\/2012\\\/10\\\/Slide18-300x181.png\",\"datePublished\":\"2020-02-17T00:19:00+00:00\",\"dateModified\":\"2020-02-17T20:23:20+00:00\",\"description\":\"This post demonstrates how resonance in organic chemistry makes bond lengths of two equivalent atoms the same length. A free study guide is available too.\",\"breadcrumb\":{\"@id\":\"https:\\\/\\\/www.aceorganicchem.com\\\/blog\\\/resonance-in-organic-chemistry\\\/#breadcrumb\"},\"inLanguage\":\"en-US\",\"potentialAction\":[{\"@type\":\"ReadAction\",\"target\":[\"https:\\\/\\\/www.aceorganicchem.com\\\/blog\\\/resonance-in-organic-chemistry\\\/\"]}]},{\"@type\":\"ImageObject\",\"inLanguage\":\"en-US\",\"@id\":\"https:\\\/\\\/www.aceorganicchem.com\\\/blog\\\/resonance-in-organic-chemistry\\\/#primaryimage\",\"url\":\"http:\\\/\\\/box5250.temp.domains\\\/~aceorgan\\\/blog\\\/wp-content\\\/uploads\\\/2012\\\/10\\\/Slide18-300x181.png\",\"contentUrl\":\"http:\\\/\\\/box5250.temp.domains\\\/~aceorgan\\\/blog\\\/wp-content\\\/uploads\\\/2012\\\/10\\\/Slide18-300x181.png\"},{\"@type\":\"BreadcrumbList\",\"@id\":\"https:\\\/\\\/www.aceorganicchem.com\\\/blog\\\/resonance-in-organic-chemistry\\\/#breadcrumb\",\"itemListElement\":[{\"@type\":\"ListItem\",\"position\":1,\"name\":\"organic chemistry\",\"item\":\"https:\\\/\\\/www.aceorganicchem.com\\\/blog\\\/\"},{\"@type\":\"ListItem\",\"position\":2,\"name\":\"Resonance between equivalent atoms in organic chemistry means equal bond lengths.\"}]},{\"@type\":\"WebSite\",\"@id\":\"https:\\\/\\\/www.aceorganicchem.com\\\/blog\\\/#website\",\"url\":\"https:\\\/\\\/www.aceorganicchem.com\\\/blog\\\/\",\"name\":\"Organic Chemistry Made Easy by AceOrganicChem\",\"description\":\"Teaching organic chemistry hacks since 2006\",\"publisher\":{\"@id\":\"https:\\\/\\\/www.aceorganicchem.com\\\/blog\\\/#organization\"},\"potentialAction\":[{\"@type\":\"SearchAction\",\"target\":{\"@type\":\"EntryPoint\",\"urlTemplate\":\"https:\\\/\\\/www.aceorganicchem.com\\\/blog\\\/?s={search_term_string}\"},\"query-input\":{\"@type\":\"PropertyValueSpecification\",\"valueRequired\":true,\"valueName\":\"search_term_string\"}}],\"inLanguage\":\"en-US\"},{\"@type\":\"Organization\",\"@id\":\"https:\\\/\\\/www.aceorganicchem.com\\\/blog\\\/#organization\",\"name\":\"AceOrganicChem\",\"url\":\"https:\\\/\\\/www.aceorganicchem.com\\\/blog\\\/\",\"logo\":{\"@type\":\"ImageObject\",\"inLanguage\":\"en-US\",\"@id\":\"https:\\\/\\\/www.aceorganicchem.com\\\/blog\\\/#\\\/schema\\\/logo\\\/image\\\/\",\"url\":\"https:\\\/\\\/www.aceorganicchem.com\\\/blog\\\/wp-content\\\/uploads\\\/2020\\\/02\\\/buckyball-AOC-logo-4-clear-background-large-e1641075998975.jpg\",\"contentUrl\":\"https:\\\/\\\/www.aceorganicchem.com\\\/blog\\\/wp-content\\\/uploads\\\/2020\\\/02\\\/buckyball-AOC-logo-4-clear-background-large-e1641075998975.jpg\",\"width\":400,\"height\":400,\"caption\":\"AceOrganicChem\"},\"image\":{\"@id\":\"https:\\\/\\\/www.aceorganicchem.com\\\/blog\\\/#\\\/schema\\\/logo\\\/image\\\/\"},\"sameAs\":[\"https:\\\/\\\/www.facebook.com\\\/Organic-Chemistry-Help-by-AceOrganicChemcom-111153708901583\",\"https:\\\/\\\/www.pinterest.com\\\/drmike0384\\\/_created\\\/\",\"https:\\\/\\\/www.youtube.com\\\/channel\\\/UCyRDzOGwK0LFZPjyCgQXD2Q\"]},{\"@type\":\"Person\",\"@id\":\"https:\\\/\\\/www.aceorganicchem.com\\\/blog\\\/#\\\/schema\\\/person\\\/854192b6b8f267c7ee95ddba11dcd4b4\",\"name\":\"Dr. Michael Pa\",\"image\":{\"@type\":\"ImageObject\",\"inLanguage\":\"en-US\",\"@id\":\"https:\\\/\\\/secure.gravatar.com\\\/avatar\\\/08f5ce8a2d08fcadb6f82a051f85da1ffa9545c9257eaf5e99e7d236b8e1fb93?s=96&d=mm&r=g\",\"url\":\"https:\\\/\\\/secure.gravatar.com\\\/avatar\\\/08f5ce8a2d08fcadb6f82a051f85da1ffa9545c9257eaf5e99e7d236b8e1fb93?s=96&d=mm&r=g\",\"contentUrl\":\"https:\\\/\\\/secure.gravatar.com\\\/avatar\\\/08f5ce8a2d08fcadb6f82a051f85da1ffa9545c9257eaf5e99e7d236b8e1fb93?s=96&d=mm&r=g\",\"caption\":\"Dr. Michael Pa\"},\"description\":\"Dr. Michael Pa got a bachelors degree in chemistry from Binghamton University, a masters degree in organic chemistry from the University of Arizona and a Ph.D. in organic chemistry from the University of Arizona. His research focus was on novel pain killers which were more potent than morphine but designed to have fewer side effects. There may even be a patent or two that came out of it. Prior to all of this, he was a chemist at Procter and Gamble. After all of that, he (briefly) worked as a post-doctoral assistant at Syracuse University, working on novel organic light-emitting diodes (OLEDs). In between, he did NOT compete at the 1996 Olympics, make the Atlanta Braves opening day roster, or become the head coach of the Indiana Pacers, as he had intended. #fail During this entire time, he always loved helping students, especially if they were struggling with organic chemistry. In 2006, Dr. Pa founded AceOrganicChem.com in order to make learning organic chemistry fast and easy. 14 years and about 60,000 students later we are still helping students to learn organic chemistry one reaction at a time at https:\\\/\\\/www.aceorganicchem.com\",\"sameAs\":[\"https:\\\/\\\/www.aceorganicchem.com\",\"https:\\\/\\\/m.facebook.com\\\/pages\\\/category\\\/Science-Website\\\/Organic-Chemistry-Help-by-AceOrganicChemcom-111153708901583\\\/\"],\"url\":\"https:\\\/\\\/www.aceorganicchem.com\\\/blog\\\/author\\\/aceorgan\\\/\"}]}<\/script>\n<!-- \/ Yoast SEO plugin. -->","yoast_head_json":{"title":"Resonance in organic chemistry and bond length [with examples]","description":"This post demonstrates how resonance in organic chemistry makes bond lengths of two equivalent atoms the same length. A free study guide is available too.","robots":{"index":"index","follow":"follow","max-snippet":"max-snippet:-1","max-image-preview":"max-image-preview:large","max-video-preview":"max-video-preview:-1"},"canonical":"https:\/\/www.aceorganicchem.com\/blog\/resonance-in-organic-chemistry\/","twitter_misc":{"Written by":"Dr. Michael Pa","Est. reading time":"2 minutes"},"schema":{"@context":"https:\/\/schema.org","@graph":[{"@type":"Article","@id":"https:\/\/www.aceorganicchem.com\/blog\/resonance-in-organic-chemistry\/#article","isPartOf":{"@id":"https:\/\/www.aceorganicchem.com\/blog\/resonance-in-organic-chemistry\/"},"author":{"name":"Dr. Michael Pa","@id":"https:\/\/www.aceorganicchem.com\/blog\/#\/schema\/person\/854192b6b8f267c7ee95ddba11dcd4b4"},"headline":"Resonance between equivalent atoms in organic chemistry means equal bond lengths.","datePublished":"2020-02-17T00:19:00+00:00","dateModified":"2020-02-17T20:23:20+00:00","mainEntityOfPage":{"@id":"https:\/\/www.aceorganicchem.com\/blog\/resonance-in-organic-chemistry\/"},"wordCount":507,"commentCount":0,"publisher":{"@id":"https:\/\/www.aceorganicchem.com\/blog\/#organization"},"image":{"@id":"https:\/\/www.aceorganicchem.com\/blog\/resonance-in-organic-chemistry\/#primaryimage"},"thumbnailUrl":"http:\/\/box5250.temp.domains\/~aceorgan\/blog\/wp-content\/uploads\/2012\/10\/Slide18-300x181.png","keywords":["bond length","organic chemistry","organic chemistry help","resonance"],"articleSection":["o-chem help","organic chemistry"],"inLanguage":"en-US","potentialAction":[{"@type":"CommentAction","name":"Comment","target":["https:\/\/www.aceorganicchem.com\/blog\/resonance-in-organic-chemistry\/#respond"]}]},{"@type":"WebPage","@id":"https:\/\/www.aceorganicchem.com\/blog\/resonance-in-organic-chemistry\/","url":"https:\/\/www.aceorganicchem.com\/blog\/resonance-in-organic-chemistry\/","name":"Resonance in organic chemistry and bond length [with examples]","isPartOf":{"@id":"https:\/\/www.aceorganicchem.com\/blog\/#website"},"primaryImageOfPage":{"@id":"https:\/\/www.aceorganicchem.com\/blog\/resonance-in-organic-chemistry\/#primaryimage"},"image":{"@id":"https:\/\/www.aceorganicchem.com\/blog\/resonance-in-organic-chemistry\/#primaryimage"},"thumbnailUrl":"http:\/\/box5250.temp.domains\/~aceorgan\/blog\/wp-content\/uploads\/2012\/10\/Slide18-300x181.png","datePublished":"2020-02-17T00:19:00+00:00","dateModified":"2020-02-17T20:23:20+00:00","description":"This post demonstrates how resonance in organic chemistry makes bond lengths of two equivalent atoms the same length. A free study guide is available too.","breadcrumb":{"@id":"https:\/\/www.aceorganicchem.com\/blog\/resonance-in-organic-chemistry\/#breadcrumb"},"inLanguage":"en-US","potentialAction":[{"@type":"ReadAction","target":["https:\/\/www.aceorganicchem.com\/blog\/resonance-in-organic-chemistry\/"]}]},{"@type":"ImageObject","inLanguage":"en-US","@id":"https:\/\/www.aceorganicchem.com\/blog\/resonance-in-organic-chemistry\/#primaryimage","url":"http:\/\/box5250.temp.domains\/~aceorgan\/blog\/wp-content\/uploads\/2012\/10\/Slide18-300x181.png","contentUrl":"http:\/\/box5250.temp.domains\/~aceorgan\/blog\/wp-content\/uploads\/2012\/10\/Slide18-300x181.png"},{"@type":"BreadcrumbList","@id":"https:\/\/www.aceorganicchem.com\/blog\/resonance-in-organic-chemistry\/#breadcrumb","itemListElement":[{"@type":"ListItem","position":1,"name":"organic chemistry","item":"https:\/\/www.aceorganicchem.com\/blog\/"},{"@type":"ListItem","position":2,"name":"Resonance between equivalent atoms in organic chemistry means equal bond lengths."}]},{"@type":"WebSite","@id":"https:\/\/www.aceorganicchem.com\/blog\/#website","url":"https:\/\/www.aceorganicchem.com\/blog\/","name":"Organic Chemistry Made Easy by AceOrganicChem","description":"Teaching organic chemistry hacks since 2006","publisher":{"@id":"https:\/\/www.aceorganicchem.com\/blog\/#organization"},"potentialAction":[{"@type":"SearchAction","target":{"@type":"EntryPoint","urlTemplate":"https:\/\/www.aceorganicchem.com\/blog\/?s={search_term_string}"},"query-input":{"@type":"PropertyValueSpecification","valueRequired":true,"valueName":"search_term_string"}}],"inLanguage":"en-US"},{"@type":"Organization","@id":"https:\/\/www.aceorganicchem.com\/blog\/#organization","name":"AceOrganicChem","url":"https:\/\/www.aceorganicchem.com\/blog\/","logo":{"@type":"ImageObject","inLanguage":"en-US","@id":"https:\/\/www.aceorganicchem.com\/blog\/#\/schema\/logo\/image\/","url":"https:\/\/www.aceorganicchem.com\/blog\/wp-content\/uploads\/2020\/02\/buckyball-AOC-logo-4-clear-background-large-e1641075998975.jpg","contentUrl":"https:\/\/www.aceorganicchem.com\/blog\/wp-content\/uploads\/2020\/02\/buckyball-AOC-logo-4-clear-background-large-e1641075998975.jpg","width":400,"height":400,"caption":"AceOrganicChem"},"image":{"@id":"https:\/\/www.aceorganicchem.com\/blog\/#\/schema\/logo\/image\/"},"sameAs":["https:\/\/www.facebook.com\/Organic-Chemistry-Help-by-AceOrganicChemcom-111153708901583","https:\/\/www.pinterest.com\/drmike0384\/_created\/","https:\/\/www.youtube.com\/channel\/UCyRDzOGwK0LFZPjyCgQXD2Q"]},{"@type":"Person","@id":"https:\/\/www.aceorganicchem.com\/blog\/#\/schema\/person\/854192b6b8f267c7ee95ddba11dcd4b4","name":"Dr. Michael Pa","image":{"@type":"ImageObject","inLanguage":"en-US","@id":"https:\/\/secure.gravatar.com\/avatar\/08f5ce8a2d08fcadb6f82a051f85da1ffa9545c9257eaf5e99e7d236b8e1fb93?s=96&d=mm&r=g","url":"https:\/\/secure.gravatar.com\/avatar\/08f5ce8a2d08fcadb6f82a051f85da1ffa9545c9257eaf5e99e7d236b8e1fb93?s=96&d=mm&r=g","contentUrl":"https:\/\/secure.gravatar.com\/avatar\/08f5ce8a2d08fcadb6f82a051f85da1ffa9545c9257eaf5e99e7d236b8e1fb93?s=96&d=mm&r=g","caption":"Dr. Michael Pa"},"description":"Dr. Michael Pa got a bachelors degree in chemistry from Binghamton University, a masters degree in organic chemistry from the University of Arizona and a Ph.D. in organic chemistry from the University of Arizona. His research focus was on novel pain killers which were more potent than morphine but designed to have fewer side effects. There may even be a patent or two that came out of it. Prior to all of this, he was a chemist at Procter and Gamble. After all of that, he (briefly) worked as a post-doctoral assistant at Syracuse University, working on novel organic light-emitting diodes (OLEDs). In between, he did NOT compete at the 1996 Olympics, make the Atlanta Braves opening day roster, or become the head coach of the Indiana Pacers, as he had intended. #fail During this entire time, he always loved helping students, especially if they were struggling with organic chemistry. In 2006, Dr. Pa founded AceOrganicChem.com in order to make learning organic chemistry fast and easy. 14 years and about 60,000 students later we are still helping students to learn organic chemistry one reaction at a time at https:\/\/www.aceorganicchem.com","sameAs":["https:\/\/www.aceorganicchem.com","https:\/\/m.facebook.com\/pages\/category\/Science-Website\/Organic-Chemistry-Help-by-AceOrganicChemcom-111153708901583\/"],"url":"https:\/\/www.aceorganicchem.com\/blog\/author\/aceorgan\/"}]}},"_links":{"self":[{"href":"https:\/\/www.aceorganicchem.com\/blog\/wp-json\/wp\/v2\/posts\/373","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/www.aceorganicchem.com\/blog\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/www.aceorganicchem.com\/blog\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/www.aceorganicchem.com\/blog\/wp-json\/wp\/v2\/users\/2"}],"replies":[{"embeddable":true,"href":"https:\/\/www.aceorganicchem.com\/blog\/wp-json\/wp\/v2\/comments?post=373"}],"version-history":[{"count":11,"href":"https:\/\/www.aceorganicchem.com\/blog\/wp-json\/wp\/v2\/posts\/373\/revisions"}],"predecessor-version":[{"id":2850,"href":"https:\/\/www.aceorganicchem.com\/blog\/wp-json\/wp\/v2\/posts\/373\/revisions\/2850"}],"wp:attachment":[{"href":"https:\/\/www.aceorganicchem.com\/blog\/wp-json\/wp\/v2\/media?parent=373"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.aceorganicchem.com\/blog\/wp-json\/wp\/v2\/categories?post=373"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.aceorganicchem.com\/blog\/wp-json\/wp\/v2\/tags?post=373"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}