{"id":29,"date":"2008-09-04T02:25:56","date_gmt":"2008-09-04T09:25:56","guid":{"rendered":"http:\/\/wordpress.reed.edu\/chem201202\/2008\/09\/hyperventilating-about-hypervalent-atoms.html"},"modified":"2014-03-18T10:13:06","modified_gmt":"2014-03-18T17:13:06","slug":"hyperventilating-about-hypervalent-atoms","status":"publish","type":"post","link":"https:\/\/blogs.reed.edu\/chem201202\/2008\/09\/hyperventilating-about-hypervalent-atoms\/","title":{"rendered":"Hyperventilating about hypervalent atoms"},"content":{"rendered":"<p>This question came up after lecture and its one worth bringing to the o chem public: <b>Should sulfuric acid be drawn with double bonds (the way I originally drew it in lecture) or with single bonds+formal charges (the way I subsequently drew it)?<\/b><\/p>\n<p>There is more here than meets the eye.<br \/><!--more-->If you look at Ch 1.6 &#8211; Exceptions to the Octet Rule, you will see that your book recommends the <i>double bond<\/i> formula. It states, &#8220;Elements of the third period and beyond have <i>d<\/i> orbitals that can be used for bonding. These elements can accommodate more than eight electrons in their valence shells.&#8221;<\/p>\n<p>\nI don&#8217;t agree with that statement. To think about how<br \/>\natoms share electrons, we should look at the energies of the orbitals<br \/>\nthat the electrons might occupy. To <i>share<\/i> an electron, two<br \/>\natoms must provide orbitals of similar energy. Otherwise, the electron<br \/>\nwill hang out almost exclusively in the lower energy orbital.<\/p>\n<p>\nAs it happens, the <i>3s, 3p, <\/i>and <i>3d<\/i> orbitals on S and P (the elements we usually think of as &#8220;breaking&#8221; the octet rule) have very different energies. According to <a href=\"http:\/\/www.op.titech.ac.jp\/lab\/mori\/EHTB\/EHTB.html\">one model<\/a>, the energies of these orbitals are -20, -11, and -8 eV for S, and -18.6, -14, and -7 eV for P. Compare the energy of a S <i>3d<\/i> electron (-8 eV) or P <i>3d<\/i> electron (-7 eV) with the energy of an O <i>2p<\/i> electron (-14.8 eV) or a F <i>2p<\/i><br \/>\nelectron (-18.1 eV). An electron that has to choose between S\/P <i>3d<\/i><br \/>\nand O\/F <i>2p<\/i> would have a very strong preference for the low energy<br \/>\norbitals provided by O and F. In fact, the electron might be so<br \/>\npartial to O\/F that we shouldn&#8217;t say the electron is shared, we should<br \/>\nimagine an ionic bond instead.<\/p>\n<p>\nOrbital energies have been known to chemists for decades, yet<br \/>\nmany chemists persist in drawing hypervalent structures. Why? Perhaps because the drawings<br \/>\nare cleaner. Perhaps because certain wrong ideas have so much appeal (the earth is flat, the sun rises, tobacco smoke won&#8217;t harm me because I am young and beautiful) that logic and data no longer matter. If nothing else, this is a nice illustration that scientists are human and science is not always about getting the right answer.<\/p>\n<p>\nHere&#8217;s what I expect you to do on Chem 201 assignments: When I ask<br \/>\nfor a <b>Lewis structure<\/b> drawing, do not draw any exceptions to the octet rule. When <b>any other kind of structural formula<\/b> is needed, you can draw whatever other chemists draw.<\/p>\n<p>\nDoes this make sense? Is there a molecule that&#8217;s bugging you? Am I<br \/>\nforcing you to break a deeply engrained habit? Come see me. Or post a<br \/>\ncomment &#8211; I think I have successfully activated them, but I won&#8217;t know<br \/>\nuntil you try to make a post.<\/p>\n","protected":false},"excerpt":{"rendered":"<p>This question came up after lecture and its one worth bringing to the o chem public: Should sulfuric acid be drawn with double bonds (the way I originally drew it in lecture) or with single bonds+formal charges (the way I&#8230;<\/p>\n","protected":false},"author":55,"featured_media":0,"comment_status":"closed","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[3],"tags":[],"class_list":["post-29","post","type-post","status-publish","format-standard","hentry","category-post-lecture"],"_links":{"self":[{"href":"https:\/\/blogs.reed.edu\/chem201202\/wp-json\/wp\/v2\/posts\/29","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/blogs.reed.edu\/chem201202\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/blogs.reed.edu\/chem201202\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/blogs.reed.edu\/chem201202\/wp-json\/wp\/v2\/users\/55"}],"replies":[{"embeddable":true,"href":"https:\/\/blogs.reed.edu\/chem201202\/wp-json\/wp\/v2\/comments?post=29"}],"version-history":[{"count":2,"href":"https:\/\/blogs.reed.edu\/chem201202\/wp-json\/wp\/v2\/posts\/29\/revisions"}],"predecessor-version":[{"id":5215,"href":"https:\/\/blogs.reed.edu\/chem201202\/wp-json\/wp\/v2\/posts\/29\/revisions\/5215"}],"wp:attachment":[{"href":"https:\/\/blogs.reed.edu\/chem201202\/wp-json\/wp\/v2\/media?parent=29"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/blogs.reed.edu\/chem201202\/wp-json\/wp\/v2\/categories?post=29"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/blogs.reed.edu\/chem201202\/wp-json\/wp\/v2\/tags?post=29"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}