{"id":1632,"date":"2014-11-03T03:38:13","date_gmt":"2014-11-03T03:38:13","guid":{"rendered":"https:\/\/aceorganicchem.com\/Elite\/?p=1632"},"modified":"2014-11-04T15:13:44","modified_gmt":"2014-11-04T15:13:44","slug":"organic-chemistry-trick-8","status":"publish","type":"post","link":"https:\/\/www.aceorganicchem.com\/Elite\/organic-chemistry-trick-8\/","title":{"rendered":"Organic Chemistry Trick #8: Know the “natural state” for common organic atoms"},"content":{"rendered":"

Structures of molecules can be difficult to piece together at first when you are just starting in an organic chemistry class. \u00a0Can hydrogen have 5 bonds?? \u00a0(Hint: the answer is NO) \u00a0Does carbon need to have four bonds, or can it just have one? \u00a0(Again, a resounding no) \u00a0One of the tricks that can greatly help with this is to know the uncharged or \u201cnormal state” for atoms that are commonly found in organic molecules.<\/p>\n

 <\/p>\n

\"Which<\/a>
Which one of these is a “normal state”?<\/figcaption><\/figure>\n

 <\/p>\n

 <\/p>\n

Here is a chart\u00a0of the most common of those, in an UNCHARGED state:<\/strong><\/p>\n

\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0 – C has four bonds (and no lone pairs)<\/strong><\/p>\n

\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0 – N has three bonds (and one lone pair)<\/strong><\/p>\n

\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0 – Halogens have one bond (and three lone pairs)<\/strong><\/p>\n

\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0 – O has two bonds (and two lone pairs)<\/strong><\/p>\n

\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0 – H has one bond (and no lone pairs)<\/strong><\/p>\n

 <\/p>\n

Three more rules:<\/p>\n

–\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0 C, N, O are central atoms, meaning that they will almost always be in the middle of your molecule, never as a terminal atom (IF they are neutral)<\/p>\n

–\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0 H and halogens are almost always terminal atoms, meaning that they will only have one bond and be at the ends of molecules.<\/p>\n

–\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0 With the exception of H, atoms in group I & group II are only counterions (+1 or +2 charge and not involved in resonance).<\/p>\n

 <\/p>\n

Remember, these rules are for when the atom is uncharged; this does not<\/em> apply to charged atoms.\u00a0 For example, a carbocation\u00a0(a positively charged carbon atom) will have only three bonds with no lone pairs while a carbanion (a negatively charged carbon atom) will have three bonds with one lone pair.<\/p>\n

Notice that all of these atoms still follow the octet rule.\u00a0 However, beware of atoms that do not follow the octet rule, as phosphorus is an example of an atom that can have more than an octet of electrons.\u00a0 Shown below is triphenylphosphine oxide, a byproduct of the Wittig\u00a0reaction.<\/p>\n

\"Triphenylphospine<\/a><\/p>\n

 <\/p>\n

Elements with open d-subshells, like phosphorous and sulfur, do not always follow the octet rule.\u00a0 More examples of this are SF6<\/sub> and PCl5<\/sub>.\u00a0 However, carbon, nitrogen and oxygen will follow the octet rule.<\/p>\n","protected":false},"excerpt":{"rendered":"

Structures of molecules can be difficult to piece together at first when you are just starting in an organic chemistry class. \u00a0Can hydrogen have 5 bonds?? \u00a0(Hint: the answer is NO) \u00a0Does carbon need to have four bonds, or can it just have one? \u00a0(Again, a resounding no) \u00a0One of the tricks that can greatly […]<\/p>\n","protected":false},"author":1,"featured_media":0,"comment_status":"closed","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"site-sidebar-layout":"default","site-content-layout":"","ast-site-content-layout":"","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":"","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":"var(--ast-global-color-4)","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":""}},"_jetpack_newsletter_access":"","_jetpack_dont_email_post_to_subs":false,"_jetpack_newsletter_tier_id":0,"_jetpack_memberships_contains_paywalled_content":false,"_jetpack_memberships_contains_paid_content":false,"footnotes":""},"categories":[],"tags":[],"class_list":["post-1632","post","type-post","status-publish","format-standard","hentry"],"jetpack_featured_media_url":"","jetpack_sharing_enabled":true,"jetpack_shortlink":"https:\/\/wp.me\/p4tPTC-qk","_links":{"self":[{"href":"https:\/\/www.aceorganicchem.com\/Elite\/wp-json\/wp\/v2\/posts\/1632","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/www.aceorganicchem.com\/Elite\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/www.aceorganicchem.com\/Elite\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/www.aceorganicchem.com\/Elite\/wp-json\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/www.aceorganicchem.com\/Elite\/wp-json\/wp\/v2\/comments?post=1632"}],"version-history":[{"count":3,"href":"https:\/\/www.aceorganicchem.com\/Elite\/wp-json\/wp\/v2\/posts\/1632\/revisions"}],"predecessor-version":[{"id":1637,"href":"https:\/\/www.aceorganicchem.com\/Elite\/wp-json\/wp\/v2\/posts\/1632\/revisions\/1637"}],"wp:attachment":[{"href":"https:\/\/www.aceorganicchem.com\/Elite\/wp-json\/wp\/v2\/media?parent=1632"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.aceorganicchem.com\/Elite\/wp-json\/wp\/v2\/categories?post=1632"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.aceorganicchem.com\/Elite\/wp-json\/wp\/v2\/tags?post=1632"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}