{"id":284,"date":"2017-10-04T15:11:57","date_gmt":"2017-10-04T15:11:57","guid":{"rendered":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/?post_type=chapter&#038;p=284"},"modified":"2017-10-18T19:13:33","modified_gmt":"2017-10-18T19:13:33","slug":"hybridization-structure-of-ethylene","status":"publish","type":"chapter","link":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/chapter\/hybridization-structure-of-ethylene\/","title":{"raw":"Hybridization: Structure of Ethylene","rendered":"Hybridization: Structure of Ethylene"},"content":{"raw":"<div class=\"elm-header\">\r\n<h2 class=\"elm-header-custom\">\u00a0sp^2 Hybrid Orbitals and the Structure of Ethylene<\/h2>\r\n<\/div>\r\n<div id=\"elm-main-content\" class=\"elm-content-container\">\r\n<div>\r\n<div id=\"skills\">\r\n<div class=\"textbox learning-objectives\">\r\n<h3>Objectives<\/h3>\r\n<div id=\"skills\">\r\n\r\nAfter completing this section, you should be able to\r\n<ol>\r\n \t<li>account for the formation of carbon-carbon double bonds using the concept of <em>sp<\/em><sup>2<\/sup> hybridization.<\/li>\r\n \t<li>describe a carbon-carbon double bond as consisting of one \u03c3 bond and one \u03c0 bond.<\/li>\r\n \t<li>explain the difference between a \u03c3 bond and a \u03c0 bond in terms of the way in which <em>p<\/em> orbitals overlap.<\/li>\r\n<\/ol>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<div>\r\n<div class=\"textbox key-takeaways\">\r\n<h3>Key Terms<\/h3>\r\nMake certain that you can define, and use in context, the key terms below.\r\n<ul>\r\n \t<li>pi (\u03c0) bond<\/li>\r\n \t<li><em>sp<\/em><sup>2<\/sup> hybrid<\/li>\r\n<\/ul>\r\n<\/div>\r\n<\/div>\r\n<div id=\"section_1\">\r\n<h3 class=\"editable\">Bonding in Ethene<a title=\"Edit section\" rel=\"broken\"><span class=\"icon\"><\/span><\/a><\/h3>\r\nA key component of using Valence Bond Theory correctly is being able to use the Lewis dot diagram correctly. Ethene\u00a0has a double bond between the carbons and single bonds between each hydrogen and carbon: each bond is represented by a pair of dots, which represent electrons. Each carbon requires a full octet and each\u00a0hydrogen requires a pair of electrons.\u00a0The correct Lewis structure for ethene is shown below:\r\n\r\n<a class=\"external\" title=\"http:\/\/users.stlcc.edu\/gkrishnan\/ethene2dot.gif\" href=\"http:\/\/users.stlcc.edu\/gkrishnan\/ethene2dot.gif\" target=\"_blank\" rel=\"external nofollow noopener\"><img class=\"default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04151128\/ethene2dot.gif\" alt=\"\" \/><\/a>\r\n\r\nIn the molecule ethene, both carbon atoms will be <em>sp<sup>2<\/sup><\/em>hybridized and have one unpaired electron in a non-hybridized p orbital.\r\n<p style=\"text-align: center\"><img class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04151129\/bondin32.gif\" alt=\"\" width=\"484px\" height=\"206px\" \/><\/p>\r\nThese p-orbitals will undergo parallel overlap and form one $$\\sigma$$ bond with bean-shaped probability areas above and below the plane of the six atoms. This pair of bean-shaped probability areas constitutes one $$\\pi$$-bond and the pair of electrons in this bond can be found in either bean-shaped area.\r\n<p style=\"text-align: center\"><img class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04151133\/bondin33.gif\" alt=\"\" width=\"394px\" height=\"125px\" \/><\/p>\r\nThe 3-dimensional model of ethene is therefore planar with H-C-H and H-C-C bond angles of 120o...the <span><span><span><span>\u03c0<\/span><\/span><\/span><\/span>-bond is not shown in this picture.\r\n<p style=\"text-align: center\"><img class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04151135\/bondin34.gif\" alt=\"\" width=\"230px\" height=\"175px\" \/><a title=\"Edit section\" rel=\"broken\"><span class=\"icon\"><\/span><\/a><\/p>\r\n\r\n<div>\r\n\r\nValence Shell Electron Pair Repulsion (VSEPR) Theory is used to predict the bond angles and spatial positions of the carbon and hydrogen atoms of ethene and to determine the bond order of the carbon atoms (the number of bonds formed between them). Each carbon atom\u00a0is of the general\u00a0arrangement\u00a0AX<sub>3<\/sub>, where A is the central atom surrounded by three other atoms (denoted by X); compounds of this form adopt trigonal planar geometry, forming 120 degree bond angles. In order for the unhybridized p orbitals to successfully overlap, the CH<sub>\u200b2<\/sub> must be coplanar: therefore, C<sub>2<\/sub>H<sub>4<\/sub> is a planar molecule and each bond angle is about 120 degrees.\u00a0The diagram below shows the bond lengths and hydrogen-carbon-carbon bond angles of\u00a0ethene:\r\n\r\n<a class=\"external\" title=\"http:\/\/upload.wikimedia.org\/wikipedia\/commons\/3\/3b\/Ethylene-CRC-MW-dimensions-2D.png\" href=\"http:\/\/upload.wikimedia.org\/wikipedia\/commons\/3\/3b\/Ethylene-CRC-MW-dimensions-2D.png\" target=\"_blank\" rel=\"external nofollow noopener\"><img class=\"default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04151137\/Ethylene-CRC-MW-dimensions-2D.png\" alt=\"\" width=\"198\" height=\"124\" \/><\/a>\r\n\r\nAccording to valence bond theory, two atoms form a covalent bond through the overlap of individual half-filled valence atomic orbitals, each containing one unpaired electron. In ethene, each\u00a0hydrogen atom has one unpaired electron and each carbon is sp<sup>2<\/sup> hybridized with one electron each sp<sup>\u200b2<\/sup> orbital. The fourth electron is in the p orbital that will form the pi bond. The bond order for ethene is simply the number of bonds between each atom: the carbon-carbon bond has a bond order of two, and each carbon-hydrogen bond has a bond order of one.\r\n\r\n<\/div>\r\n<\/div>\r\n<div id=\"section_2\">\r\n<div id=\"s61688\">\r\n<div id=\"section_26\">\r\n<div class=\"textbox examples\">\r\n<h3>Example<\/h3>\r\n<div id=\"section_26\">\r\n\r\n<span><span>Consider the following molecule:<\/span><\/span>\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04151139\/1-8-1.png\" alt=\"\" width=\"266\" height=\"152\" \/>\r\n\r\n<span><span>At each atom, what is the hybridization and the bond angle? At atom A draw the molecular orbital.<\/span><\/span>\r\n[reveal-answer q=\"380837\"]Show Answer[\/reveal-answer]\r\n[hidden-answer a=\"380837\"]A - sp2, 120\u00b0 B - sp3, 109\u00b0 C - sp2, 120\u00b0 (with the lone pairs present) D - sp3, 109\u00b0\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04151141\/1-8-1.gif\" alt=\"\" width=\"185\" height=\"161\" \/>\u00a0[\/hidden-answer]\r\n\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<div id=\"section_3\">\r\n<h3 class=\"editable\">Contributors<\/h3>\r\n<ul>\r\n \t<li><a class=\"external\" title=\"http:\/\/science.athabascau.ca\/staff-pages\/dietmark\" href=\"http:\/\/science.athabascau.ca\/staff-pages\/dietmark\" target=\"_blank\" rel=\"external nofollow noopener\">Dr. Dietmar Kennepohl<\/a> FCIC (Professor of Chemistry, <a class=\"external\" title=\"http:\/\/www.athabascau.ca\/\" href=\"http:\/\/www.athabascau.ca\/\" target=\"_blank\" rel=\"external nofollow noopener\">Athabasca University<\/a>)<\/li>\r\n \t<li>Prof. Steven Farmer (<a class=\"external\" title=\"http:\/\/www.sonoma.edu\" href=\"http:\/\/www.sonoma.edu\" target=\"_blank\" rel=\"external nofollow noopener\">Sonoma State University<\/a>)<\/li>\r\n \t<li>William Reusch, Professor Emeritus (<a class=\"external\" title=\"http:\/\/www.msu.edu\/\" href=\"http:\/\/www.msu.edu\/\" target=\"_blank\" rel=\"external nofollow noopener\">Michigan State U.<\/a>), <a class=\"external\" title=\"http:\/\/www.cem.msu.edu\/~reusch\/VirtualText\/intro1.htm\" href=\"http:\/\/www.cem.msu.edu\/%7Ereusch\/VirtualText\/intro1.htm\" target=\"_blank\" rel=\"external nofollow noopener\">Virtual Textbook of\u00a0Organic\u00a0Chemistry<\/a><\/li>\r\n \t<li><a title=\"Organic_Chemistry_With_a_Biological_Emphasis\" href=\"https:\/\/chem.libretexts.org\/Textbook_Maps\/Organic_Chemistry_Textbook_Maps\/Map%3A_Organic_Chemistry_with_a_Biological_Emphasis_(Soderberg)\" rel=\"internal\">Organic Chemistry With a Biological Emphasis <\/a>by\u00a0<a class=\"external\" title=\"http:\/\/facultypages.morris.umn.edu\/~soderbt\/\" href=\"http:\/\/facultypages.morris.umn.edu\/%7Esoderbt\/\" target=\"_blank\" rel=\"external nofollow noopener\">Tim Soderberg<\/a>\u00a0(University of Minnesota, Morris)<\/li>\r\n<\/ul>\r\n<\/div>\r\n<\/div>\r\n<\/div>","rendered":"<div class=\"elm-header\">\n<h2 class=\"elm-header-custom\">\u00a0sp^2 Hybrid Orbitals and the Structure of Ethylene<\/h2>\n<\/div>\n<div id=\"elm-main-content\" class=\"elm-content-container\">\n<div>\n<div id=\"skills\">\n<div class=\"textbox learning-objectives\">\n<h3>Objectives<\/h3>\n<div id=\"skills\">\n<p>After completing this section, you should be able to<\/p>\n<ol>\n<li>account for the formation of carbon-carbon double bonds using the concept of <em>sp<\/em><sup>2<\/sup> hybridization.<\/li>\n<li>describe a carbon-carbon double bond as consisting of one \u03c3 bond and one \u03c0 bond.<\/li>\n<li>explain the difference between a \u03c3 bond and a \u03c0 bond in terms of the way in which <em>p<\/em> orbitals overlap.<\/li>\n<\/ol>\n<\/div>\n<\/div>\n<\/div>\n<div>\n<div class=\"textbox key-takeaways\">\n<h3>Key Terms<\/h3>\n<p>Make certain that you can define, and use in context, the key terms below.<\/p>\n<ul>\n<li>pi (\u03c0) bond<\/li>\n<li><em>sp<\/em><sup>2<\/sup> hybrid<\/li>\n<\/ul>\n<\/div>\n<\/div>\n<div id=\"section_1\">\n<h3 class=\"editable\">Bonding in Ethene<a title=\"Edit section\" rel=\"broken\"><span class=\"icon\"><\/span><\/a><\/h3>\n<p>A key component of using Valence Bond Theory correctly is being able to use the Lewis dot diagram correctly. Ethene\u00a0has a double bond between the carbons and single bonds between each hydrogen and carbon: each bond is represented by a pair of dots, which represent electrons. Each carbon requires a full octet and each\u00a0hydrogen requires a pair of electrons.\u00a0The correct Lewis structure for ethene is shown below:<\/p>\n<p><a class=\"external\" title=\"http:\/\/users.stlcc.edu\/gkrishnan\/ethene2dot.gif\" href=\"http:\/\/users.stlcc.edu\/gkrishnan\/ethene2dot.gif\" target=\"_blank\" rel=\"external nofollow noopener\"><img decoding=\"async\" class=\"default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04151128\/ethene2dot.gif\" alt=\"\" \/><\/a><\/p>\n<p>In the molecule ethene, both carbon atoms will be <em>sp<sup>2<\/sup><\/em>hybridized and have one unpaired electron in a non-hybridized p orbital.<\/p>\n<p style=\"text-align: center\"><img decoding=\"async\" class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04151129\/bondin32.gif\" alt=\"\" width=\"484px\" height=\"206px\" \/><\/p>\n<p>These p-orbitals will undergo parallel overlap and form one $$\\sigma$$ bond with bean-shaped probability areas above and below the plane of the six atoms. This pair of bean-shaped probability areas constitutes one $$\\pi$$-bond and the pair of electrons in this bond can be found in either bean-shaped area.<\/p>\n<p style=\"text-align: center\"><img decoding=\"async\" class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04151133\/bondin33.gif\" alt=\"\" width=\"394px\" height=\"125px\" \/><\/p>\n<p>The 3-dimensional model of ethene is therefore planar with H-C-H and H-C-C bond angles of 120o&#8230;the <span><span><span><span>\u03c0<\/span><\/span><\/span><\/span>-bond is not shown in this picture.<\/p>\n<p style=\"text-align: center\"><img decoding=\"async\" class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04151135\/bondin34.gif\" alt=\"\" width=\"230px\" height=\"175px\" \/><a title=\"Edit section\" rel=\"broken\"><span class=\"icon\"><\/span><\/a><\/p>\n<div>\n<p>Valence Shell Electron Pair Repulsion (VSEPR) Theory is used to predict the bond angles and spatial positions of the carbon and hydrogen atoms of ethene and to determine the bond order of the carbon atoms (the number of bonds formed between them). Each carbon atom\u00a0is of the general\u00a0arrangement\u00a0AX<sub>3<\/sub>, where A is the central atom surrounded by three other atoms (denoted by X); compounds of this form adopt trigonal planar geometry, forming 120 degree bond angles. In order for the unhybridized p orbitals to successfully overlap, the CH<sub>\u200b2<\/sub> must be coplanar: therefore, C<sub>2<\/sub>H<sub>4<\/sub> is a planar molecule and each bond angle is about 120 degrees.\u00a0The diagram below shows the bond lengths and hydrogen-carbon-carbon bond angles of\u00a0ethene:<\/p>\n<p><a class=\"external\" title=\"http:\/\/upload.wikimedia.org\/wikipedia\/commons\/3\/3b\/Ethylene-CRC-MW-dimensions-2D.png\" href=\"http:\/\/upload.wikimedia.org\/wikipedia\/commons\/3\/3b\/Ethylene-CRC-MW-dimensions-2D.png\" target=\"_blank\" rel=\"external nofollow noopener\"><img loading=\"lazy\" decoding=\"async\" class=\"default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04151137\/Ethylene-CRC-MW-dimensions-2D.png\" alt=\"\" width=\"198\" height=\"124\" \/><\/a><\/p>\n<p>According to valence bond theory, two atoms form a covalent bond through the overlap of individual half-filled valence atomic orbitals, each containing one unpaired electron. In ethene, each\u00a0hydrogen atom has one unpaired electron and each carbon is sp<sup>2<\/sup> hybridized with one electron each sp<sup>\u200b2<\/sup> orbital. The fourth electron is in the p orbital that will form the pi bond. The bond order for ethene is simply the number of bonds between each atom: the carbon-carbon bond has a bond order of two, and each carbon-hydrogen bond has a bond order of one.<\/p>\n<\/div>\n<\/div>\n<div id=\"section_2\">\n<div id=\"s61688\">\n<div id=\"section_26\">\n<div class=\"textbox examples\">\n<h3>Example<\/h3>\n<div id=\"section_26\">\n<p><span><span>Consider the following molecule:<\/span><\/span><\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04151139\/1-8-1.png\" alt=\"\" width=\"266\" height=\"152\" \/><\/p>\n<p><span><span>At each atom, what is the hybridization and the bond angle? At atom A draw the molecular orbital.<\/span><\/span><\/p>\n<div class=\"qa-wrapper\" style=\"display: block\"><span class=\"show-answer collapsed\" style=\"cursor: pointer\" data-target=\"q380837\">Show Answer<\/span><\/p>\n<div id=\"q380837\" class=\"hidden-answer\" style=\"display: none\">A &#8211; sp2, 120\u00b0 B &#8211; sp3, 109\u00b0 C &#8211; sp2, 120\u00b0 (with the lone pairs present) D &#8211; sp3, 109\u00b0<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04151141\/1-8-1.gif\" alt=\"\" width=\"185\" height=\"161\" \/>\u00a0<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<div id=\"section_3\">\n<h3 class=\"editable\">Contributors<\/h3>\n<ul>\n<li><a class=\"external\" title=\"http:\/\/science.athabascau.ca\/staff-pages\/dietmark\" href=\"http:\/\/science.athabascau.ca\/staff-pages\/dietmark\" target=\"_blank\" rel=\"external nofollow noopener\">Dr. Dietmar Kennepohl<\/a> FCIC (Professor of Chemistry, <a class=\"external\" title=\"http:\/\/www.athabascau.ca\/\" href=\"http:\/\/www.athabascau.ca\/\" target=\"_blank\" rel=\"external nofollow noopener\">Athabasca University<\/a>)<\/li>\n<li>Prof. Steven Farmer (<a class=\"external\" title=\"http:\/\/www.sonoma.edu\" href=\"http:\/\/www.sonoma.edu\" target=\"_blank\" rel=\"external nofollow noopener\">Sonoma State University<\/a>)<\/li>\n<li>William Reusch, Professor Emeritus (<a class=\"external\" title=\"http:\/\/www.msu.edu\/\" href=\"http:\/\/www.msu.edu\/\" target=\"_blank\" rel=\"external nofollow noopener\">Michigan State U.<\/a>), <a class=\"external\" title=\"http:\/\/www.cem.msu.edu\/~reusch\/VirtualText\/intro1.htm\" href=\"http:\/\/www.cem.msu.edu\/%7Ereusch\/VirtualText\/intro1.htm\" target=\"_blank\" rel=\"external nofollow noopener\">Virtual Textbook of\u00a0Organic\u00a0Chemistry<\/a><\/li>\n<li><a title=\"Organic_Chemistry_With_a_Biological_Emphasis\" href=\"https:\/\/chem.libretexts.org\/Textbook_Maps\/Organic_Chemistry_Textbook_Maps\/Map%3A_Organic_Chemistry_with_a_Biological_Emphasis_(Soderberg)\" rel=\"internal\">Organic Chemistry With a Biological Emphasis <\/a>by\u00a0<a class=\"external\" title=\"http:\/\/facultypages.morris.umn.edu\/~soderbt\/\" href=\"http:\/\/facultypages.morris.umn.edu\/%7Esoderbt\/\" target=\"_blank\" rel=\"external nofollow noopener\">Tim Soderberg<\/a>\u00a0(University of Minnesota, Morris)<\/li>\n<\/ul>\n<\/div>\n<\/div>\n<\/div>\n","protected":false},"author":311,"menu_order":11,"template":"","meta":{"_candela_citation":"[]","CANDELA_OUTCOMES_GUID":"","pb_show_title":"on","pb_short_title":"","pb_subtitle":"","pb_authors":[],"pb_section_license":""},"chapter-type":[],"contributor":[],"license":[],"class_list":["post-284","chapter","type-chapter","status-publish","hentry"],"part":76,"_links":{"self":[{"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapters\/284","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapters"}],"about":[{"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/wp\/v2\/types\/chapter"}],"author":[{"embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/wp\/v2\/users\/311"}],"version-history":[{"count":5,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapters\/284\/revisions"}],"predecessor-version":[{"id":2019,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapters\/284\/revisions\/2019"}],"part":[{"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/parts\/76"}],"metadata":[{"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapters\/284\/metadata\/"}],"wp:attachment":[{"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/wp\/v2\/media?parent=284"}],"wp:term":[{"taxonomy":"chapter-type","embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapter-type?post=284"},{"taxonomy":"contributor","embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/wp\/v2\/contributor?post=284"},{"taxonomy":"license","embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/wp\/v2\/license?post=284"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}