{"id":92,"date":"2023-05-03T13:52:45","date_gmt":"2023-05-03T13:52:45","guid":{"rendered":"http:\/\/organicchemistry.wordpress.com\/?p=92"},"modified":"2023-05-03T13:52:46","modified_gmt":"2023-05-03T13:52:46","slug":"know-the-normal-state-for-common-organic-atoms","status":"publish","type":"post","link":"https:\/\/www.aceorganicchem.com\/blog\/know-the-normal-state-for-common-organic-atoms\/","title":{"rendered":"Know the \u201cnormal\u201d state for common organic atoms  [3 rules to live by]"},"content":{"rendered":"\n<p>Structures of molecules can be difficult to piece together at first when you are just starting in an organic chemistry class. Hopefully you retained some of this knowledge from general chemistry. If not, one of the tricks that can greatly help with this is to know the uncharged or \u201cnormal\u201d state for atoms that are commonly found in organic molecules. &nbsp;&nbsp;Here is a table of the most common of those:<\/p>\n\n\n\n<p><strong>&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; &#8211; C has four bonds and no lone pairs<\/strong><\/p>\n\n\n\n<p><strong>&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; &#8211; N has three bonds and one lone pair<\/strong><\/p>\n\n\n\n<p><strong>&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; &#8211; Halogens (F, Cl, Br, I) have one bond and three lone pairs.&nbsp;<\/strong><\/p>\n\n\n\n<p><strong>&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; &#8211; O has two bonds and two lone pairs<\/strong><\/p>\n\n\n\n<p><strong>&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; &#8211; H has one bond and no lone pairs<\/strong><\/p>\n\n\n\n<p>Three more rules:<\/p>\n\n\n\n<p><strong>&#8211;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; C, N, O are central atoms, meaning that they will always be in the middle of your molecule.<\/strong><\/p>\n\n\n\n<p><strong>&#8211;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; H and halogens are terminal atoms, meaning that they will only have one bond and be at the ends of molecules.<\/strong><\/p>\n\n\n\n<p><strong>&#8211;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; With the exception of H, atoms in group I &amp; group II are only counterions (+1 or +2 and not involved in resonance).<\/strong><\/p>\n\n\n\n<p>Remember, these rules are for when the atom is uncharged; <span style=\"text-decoration: underline;\"><em>this does not apply to charged atoms<\/em><\/span>.&nbsp; For example, a carbocation (a positively charged carbon atom) will have only three bonds with no lone pairs while a carbanion (a negatively charged carbon atom) wlll have three bonds with one lone pair, and a carbene will have two bonds with two lone pairs.<\/p>\n\n\n\n<figure class=\"wp-block-image aligncenter\"><a href=\"http:\/\/box5250.temp.domains\/~aceorgan\/blog\/wp-content\/uploads\/2008\/10\/carbonbonds.jpg\"><img loading=\"lazy\" decoding=\"async\" width=\"300\" height=\"182\" src=\"http:\/\/box5250.temp.domains\/~aceorgan\/blog\/wp-content\/uploads\/2008\/10\/carbonbonds-300x182.jpg\" alt=\"\" class=\"wp-image-808\" srcset=\"https:\/\/www.aceorganicchem.com\/blog\/wp-content\/uploads\/2008\/10\/carbonbonds-300x182.jpg 300w, https:\/\/www.aceorganicchem.com\/blog\/wp-content\/uploads\/2008\/10\/carbonbonds.jpg 500w\" sizes=\"auto, (max-width: 300px) 100vw, 300px\" \/><\/a><\/figure>\n\n\n\n<p>Notice that all of these carbons still follow the octet rule.&nbsp; However, <span style=\"text-decoration: underline;\"><strong>beware of atoms that do not follow the octet rule<\/strong><\/span>, as phosphorus is an example of an atom that can have more than an octet of electrons.&nbsp; Shown below is triphenylphosphine oxide, a byproduct of the Wittig reaction.<\/p>\n\n\n\n<figure class=\"wp-block-image aligncenter\"><a href=\"http:\/\/box5250.temp.domains\/~aceorgan\/blog\/wp-content\/uploads\/2008\/10\/Slide2.png\"><img loading=\"lazy\" decoding=\"async\" width=\"300\" height=\"231\" src=\"http:\/\/box5250.temp.domains\/~aceorgan\/blog\/wp-content\/uploads\/2008\/10\/Slide2-300x231.png\" alt=\"\" class=\"wp-image-809\" srcset=\"https:\/\/www.aceorganicchem.com\/blog\/wp-content\/uploads\/2008\/10\/Slide2-300x231.png 300w, https:\/\/www.aceorganicchem.com\/blog\/wp-content\/uploads\/2008\/10\/Slide2-768x590.png 768w, https:\/\/www.aceorganicchem.com\/blog\/wp-content\/uploads\/2008\/10\/Slide2-1024x787.png 1024w\" sizes=\"auto, (max-width: 300px) 100vw, 300px\" \/><\/a><\/figure>\n\n\n\n<p>Elements with open d-subshells, like phosphorous and sulfur, do not always follow the octet rule.&nbsp; More examples of this are SF<sub>6<\/sub> and PCl<sub>5<\/sub>.&nbsp; However, carbon, nitrogen and oxygen will follow the octet rule.<\/p>\n\n\n\n<figure class=\"wp-block-image aligncenter\"><a href=\"http:\/\/www.aceorganicchem.com\/free.html\" target=\"_blank\" rel=\"noopener noreferrer\"><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>\n","protected":false},"excerpt":{"rendered":"<p>Structures of molecules can be difficult to piece together at first when you are just starting in an organic chemistry class. Hopefully you retained some of this knowledge from general chemistry. If not, one of the tricks that can greatly help with this is to know the uncharged or \u201cnormal\u201d state for atoms that are [&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":"","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":"","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":[4,8,9],"tags":[44,46],"class_list":["post-92","post","type-post","status-publish","format-standard","hentry","category-chemistry","category-o-chem-help","category-organic-chemistry","tag-chemistry","tag-organic-chemistry"],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.3 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Know the \u201cnormal\u201d state for common organic atoms [3 rules to live by]<\/title>\n<meta name=\"description\" content=\"Atoms have a normal or natural state they like to hang out in. If you know these, Lewis dot structures become way easier.\" \/>\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\/know-the-normal-state-for-common-organic-atoms\/\" \/>\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=\"3 minutes\" \/>\n<script type=\"application\/ld+json\" class=\"yoast-schema-graph\">{\"@context\":\"https:\\\/\\\/schema.org\",\"@graph\":[{\"@type\":\"Article\",\"@id\":\"https:\\\/\\\/www.aceorganicchem.com\\\/blog\\\/know-the-normal-state-for-common-organic-atoms\\\/#article\",\"isPartOf\":{\"@id\":\"https:\\\/\\\/www.aceorganicchem.com\\\/blog\\\/know-the-normal-state-for-common-organic-atoms\\\/\"},\"author\":{\"name\":\"Dr. Michael Pa\",\"@id\":\"https:\\\/\\\/www.aceorganicchem.com\\\/blog\\\/#\\\/schema\\\/person\\\/854192b6b8f267c7ee95ddba11dcd4b4\"},\"headline\":\"Know the \u201cnormal\u201d state for common organic atoms [3 rules to live by]\",\"datePublished\":\"2023-05-03T13:52:45+00:00\",\"dateModified\":\"2023-05-03T13:52:46+00:00\",\"mainEntityOfPage\":{\"@id\":\"https:\\\/\\\/www.aceorganicchem.com\\\/blog\\\/know-the-normal-state-for-common-organic-atoms\\\/\"},\"wordCount\":406,\"commentCount\":0,\"publisher\":{\"@id\":\"https:\\\/\\\/www.aceorganicchem.com\\\/blog\\\/#organization\"},\"image\":{\"@id\":\"https:\\\/\\\/www.aceorganicchem.com\\\/blog\\\/know-the-normal-state-for-common-organic-atoms\\\/#primaryimage\"},\"thumbnailUrl\":\"http:\\\/\\\/box5250.temp.domains\\\/~aceorgan\\\/blog\\\/wp-content\\\/uploads\\\/2008\\\/10\\\/carbonbonds-300x182.jpg\",\"keywords\":[\"chemistry\",\"organic chemistry\"],\"articleSection\":[\"chemistry\",\"o-chem help\",\"organic chemistry\"],\"inLanguage\":\"en-US\",\"potentialAction\":[{\"@type\":\"CommentAction\",\"name\":\"Comment\",\"target\":[\"https:\\\/\\\/www.aceorganicchem.com\\\/blog\\\/know-the-normal-state-for-common-organic-atoms\\\/#respond\"]}]},{\"@type\":\"WebPage\",\"@id\":\"https:\\\/\\\/www.aceorganicchem.com\\\/blog\\\/know-the-normal-state-for-common-organic-atoms\\\/\",\"url\":\"https:\\\/\\\/www.aceorganicchem.com\\\/blog\\\/know-the-normal-state-for-common-organic-atoms\\\/\",\"name\":\"Know the \u201cnormal\u201d state for common organic atoms [3 rules to live by]\",\"isPartOf\":{\"@id\":\"https:\\\/\\\/www.aceorganicchem.com\\\/blog\\\/#website\"},\"primaryImageOfPage\":{\"@id\":\"https:\\\/\\\/www.aceorganicchem.com\\\/blog\\\/know-the-normal-state-for-common-organic-atoms\\\/#primaryimage\"},\"image\":{\"@id\":\"https:\\\/\\\/www.aceorganicchem.com\\\/blog\\\/know-the-normal-state-for-common-organic-atoms\\\/#primaryimage\"},\"thumbnailUrl\":\"http:\\\/\\\/box5250.temp.domains\\\/~aceorgan\\\/blog\\\/wp-content\\\/uploads\\\/2008\\\/10\\\/carbonbonds-300x182.jpg\",\"datePublished\":\"2023-05-03T13:52:45+00:00\",\"dateModified\":\"2023-05-03T13:52:46+00:00\",\"description\":\"Atoms have a normal or natural state they like to hang out in. 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