{"id":297,"date":"2017-10-04T15:13:31","date_gmt":"2017-10-04T15:13:31","guid":{"rendered":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/?post_type=chapter&#038;p=297"},"modified":"2018-09-28T20:18:44","modified_gmt":"2018-09-28T20:18:44","slug":"hybridization-of-nitrogen-oxygen-phosphorus-and-sulfur","status":"publish","type":"chapter","link":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/chapter\/hybridization-of-nitrogen-oxygen-phosphorus-and-sulfur\/","title":{"raw":"Hybridization of Nitrogen, Oxygen, Phosphorus and Sulfur","rendered":"Hybridization of Nitrogen, Oxygen, Phosphorus and Sulfur"},"content":{"raw":"<div class=\"elm-header\"><\/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>Objective<\/h3>\r\nAfter completing this section, you should be able to apply the concept of hybridization to atoms such as N, O, P and S explain the structures of simple species containing these atoms.\r\n\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 term below.\r\n<ul>\r\n \t<li>lone pair electrons<\/li>\r\n<\/ul>\r\n<\/div>\r\n<\/div>\r\n<div id=\"note\">\r\n<div class=\"textbox\">\r\n<p class=\"boxtitle\"><strong>Study Notes<\/strong><\/p>\r\nNitrogen is frequently found in organic compounds. As with carbon atoms, nitrogen atoms can be <em>sp<\/em><sup>3<\/sup>-, <em>sp<\/em><sup>2<\/sup>- or sp\u2011hybridized.\r\n\r\nNote that, in this course, the term \u201clone pair\u201d is used to describe an unshared pair of electrons.\r\n\r\n<\/div>\r\n&nbsp;\r\n\r\n<\/div>\r\nThe valence-bond concept of orbital hybridization can be extrapolated to other atoms including nitrogen, oxygen, phosphorus, and sulfur. In other compounds, covalent bonds that are formed can be described using hybrid orbitals.\r\n<div id=\"section_1\">\r\n<h3 class=\"editable\">Methylamine<\/h3>\r\nThe nitrogen is <em>sp<sup>3<\/sup><\/em>hybridized which means that it has four <em>sp<sup>3<\/sup><\/em> hybrid orbitals.\u00a0 Two of the <em>sp<sup>3<\/sup><\/em>hybridized orbitals overlap with s orbitals from hydrogens to form the two N-H sigma bonds.\u00a0 One of the <em>sp3 <\/em>hybridized orbitals overlap with an<em> sp<sup>3<\/sup><\/em> hybridized orbital from carbon to form the C-N sigma bond.\u00a0 The lone pair electrons on the nitrogen are contained in the last <em>sp<sup>3<\/sup><\/em> hybridized orbital.\u00a0 Due to the <em>sp3 <\/em>hybridization the nitrogen has a tetrahedral geometry.\u00a0 However, the H-N-H and H-N-C bonds angles are less than the typical 109.5<sup>o <\/sup>due to compression by the lone pair electrons.\u00a0<img src=\"https:\/\/chem.libretexts.org\/LibreTexts\/Athabasca_University\/Chemistry_350%3A_Organic_Chemistry_I\/Chapter_1%3A_Structure_and_Bonding\/denied:data:image\/png;base64,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#fixme\" alt=\"\" \/>\r\n\r\n<\/div>\r\n<div id=\"section_2\">\r\n\r\n[caption id=\"attachment_2235\" align=\"aligncenter\" width=\"176\"]<img class=\"wp-image-2235 size-full\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/28201414\/download-4.png\" alt=\"\" width=\"176\" height=\"173\" \/> Methylamine[\/caption]\r\n<h3 class=\"editable\">Methanol<\/h3>\r\nThe oxygen is <em>sp<sup>3<\/sup><\/em>hybridized which means that it has four <em>sp<sup>3<\/sup><\/em> hybrid orbitals.\u00a0 One of the <em>sp<sup>3<\/sup><\/em>hybridized orbitals overlap with s orbitals from a hydrogen to form the O-H signma bonds.\u00a0 One of the <em>sp3 <\/em>hybridized orbitals overlap with an<em> sp<sup>3<\/sup><\/em> hybridized orbital from carbon to form the C-O sigma bond.\u00a0 Both the sets of lone pair electrons on the oxygen are contained in the remaining <em>sp<sup>3<\/sup><\/em> hybridized orbital.\u00a0 Due to the <em>sp3<\/em> hybridization the oxygen has a tetrahedral geometry.\u00a0 However, the H-O-C bond angles are less than the typical 109.5<sup>o <\/sup>due to compression by the lone pair electrons.\r\n\r\n[caption id=\"attachment_2240\" align=\"aligncenter\" width=\"169\"]<img class=\"wp-image-2240 size-full\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/28201744\/download-5.png\" alt=\"\" width=\"169\" height=\"142\" \/> Methanol[\/caption]\r\n\r\n<img src=\"https:\/\/chem.libretexts.org\/LibreTexts\/Athabasca_University\/Chemistry_350%3A_Organic_Chemistry_I\/Chapter_1%3A_Structure_and_Bonding\/denied:data:image\/png;base64,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#fixme\" alt=\"\" \/>\r\n\r\n<\/div>\r\n<\/div>\r\n<div id=\"section_3\">\r\n<h3 class=\"editable\">Methyl phosphate<\/h3>\r\nPhosphorus can have have expanded octets because it is in the n = 3 row.\u00a0 Typically, phosphorus forms five covalent bonds.\u00a0 In biological molecules, phosphorusis usually found in organophosphates.\u00a0 Organophosphates are made up of a phosphorus atoms bonded to four oxygens, with one of the oxygens also bonded to a carbon.\u00a0 In methyl phosphate, the phosphorus is <em>sp<sup>3<\/sup><\/em> hybridized and the O-P-O bond angle varying from 110 to 112<sup>o.\u00a0<\/sup>\r\n\r\n<img class=\"size-full wp-image-2233 aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/28200937\/download-1.png\" alt=\"\" width=\"228\" height=\"143\" \/>\r\n\r\n<\/div>\r\n<div id=\"section_4\">\r\n\r\n<img class=\"aligncenter\" src=\"image\/png;base64,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\" alt=\"\" \/>\r\n<h3 class=\"editable\">Methanethiol &amp; Dimethyl Sulfide<\/h3>\r\nIn biological system, sulfur is typically found in molecules called thiols or sulfides. In a thiol, the sulfur atim is conded to one hydrogens and one carbon and is analogous to an alcohol. In a sulfide, the sulfur is bonded to two carbons.\u00a0 In both cases the sulfur is <em>sp<sup>3<\/sup><\/em>hybridized and the bond angles are much less than the typicall 109.5<sup>o<\/sup>.\r\n\r\n[caption id=\"attachment_2238\" align=\"aligncenter\" width=\"189\"]<img class=\"wp-image-2238 size-full\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/28201510\/download-21.png\" alt=\"\" width=\"189\" height=\"158\" \/> Methanethiol[\/caption]\r\n\r\n[caption id=\"attachment_2239\" align=\"aligncenter\" width=\"165\"]<img class=\"wp-image-2239 size-full\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/28201525\/download-3.png\" alt=\"\" width=\"165\" height=\"144\" \/> Dimethyl sulfide[\/caption]\r\n\r\n<\/div>\r\n<div id=\"section_5\">\r\n<div id=\"s61688\">\r\n<div id=\"section_34\">\r\n<div class=\"textbox examples\">\r\n<h3>Example<\/h3>\r\n<div id=\"section_5\">\r\n<div id=\"s61688\">\r\n<div id=\"section_34\">\r\n\r\nIdentify geometry and lone pairs on each heteroatom of the molecules given.\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\/04151318\/1.10_rev.png\" alt=\"\" width=\"474\" height=\"132\" \/>\r\n\r\n<\/div>\r\n<div id=\"section_35\">\r\n\r\n[reveal-answer q=\"679308\"]Show Answer[\/reveal-answer]\r\n[hidden-answer a=\"679308\"]Diethyl ether would have two lone pairs of electrons and would have a bent geometry around the oxygen. Dimethyl amine would have one lone pair and would show a pyramidal geometry around the nitrogen.[\/hidden-answer]\r\n\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<div id=\"section_6\">\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<\/ul>\r\n<\/div>\r\n<\/div>","rendered":"<div class=\"elm-header\"><\/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>Objective<\/h3>\n<p>After completing this section, you should be able to apply the concept of hybridization to atoms such as N, O, P and S explain the structures of simple species containing these atoms.<\/p>\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 term below.<\/p>\n<ul>\n<li>lone pair electrons<\/li>\n<\/ul>\n<\/div>\n<\/div>\n<div id=\"note\">\n<div class=\"textbox\">\n<p class=\"boxtitle\"><strong>Study Notes<\/strong><\/p>\n<p>Nitrogen is frequently found in organic compounds. As with carbon atoms, nitrogen atoms can be <em>sp<\/em><sup>3<\/sup>-, <em>sp<\/em><sup>2<\/sup>&#8211; or sp\u2011hybridized.<\/p>\n<p>Note that, in this course, the term \u201clone pair\u201d is used to describe an unshared pair of electrons.<\/p>\n<\/div>\n<p>&nbsp;<\/p>\n<\/div>\n<p>The valence-bond concept of orbital hybridization can be extrapolated to other atoms including nitrogen, oxygen, phosphorus, and sulfur. In other compounds, covalent bonds that are formed can be described using hybrid orbitals.<\/p>\n<div id=\"section_1\">\n<h3 class=\"editable\">Methylamine<\/h3>\n<p>The nitrogen is <em>sp<sup>3<\/sup><\/em>hybridized which means that it has four <em>sp<sup>3<\/sup><\/em> hybrid orbitals.\u00a0 Two of the <em>sp<sup>3<\/sup><\/em>hybridized orbitals overlap with s orbitals from hydrogens to form the two N-H sigma bonds.\u00a0 One of the <em>sp3 <\/em>hybridized orbitals overlap with an<em> sp<sup>3<\/sup><\/em> hybridized orbital from carbon to form the C-N sigma bond.\u00a0 The lone pair electrons on the nitrogen are contained in the last <em>sp<sup>3<\/sup><\/em> hybridized orbital.\u00a0 Due to the <em>sp3 <\/em>hybridization the nitrogen has a tetrahedral geometry.\u00a0 However, the H-N-H and H-N-C bonds angles are less than the typical 109.5<sup>o <\/sup>due to compression by the lone pair electrons.\u00a0<img decoding=\"async\" src=\"https:\/\/chem.libretexts.org\/LibreTexts\/Athabasca_University\/Chemistry_350%3A_Organic_Chemistry_I\/Chapter_1%3A_Structure_and_Bonding\/denied:data:image\/png;base64,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#fixme\" alt=\"\" \/><\/p>\n<\/div>\n<div id=\"section_2\">\n<div id=\"attachment_2235\" style=\"width: 186px\" class=\"wp-caption aligncenter\"><img loading=\"lazy\" decoding=\"async\" aria-describedby=\"caption-attachment-2235\" class=\"wp-image-2235 size-full\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/28201414\/download-4.png\" alt=\"\" width=\"176\" height=\"173\" \/><\/p>\n<p id=\"caption-attachment-2235\" class=\"wp-caption-text\">Methylamine<\/p>\n<\/div>\n<h3 class=\"editable\">Methanol<\/h3>\n<p>The oxygen is <em>sp<sup>3<\/sup><\/em>hybridized which means that it has four <em>sp<sup>3<\/sup><\/em> hybrid orbitals.\u00a0 One of the <em>sp<sup>3<\/sup><\/em>hybridized orbitals overlap with s orbitals from a hydrogen to form the O-H signma bonds.\u00a0 One of the <em>sp3 <\/em>hybridized orbitals overlap with an<em> sp<sup>3<\/sup><\/em> hybridized orbital from carbon to form the C-O sigma bond.\u00a0 Both the sets of lone pair electrons on the oxygen are contained in the remaining <em>sp<sup>3<\/sup><\/em> hybridized orbital.\u00a0 Due to the <em>sp3<\/em> hybridization the oxygen has a tetrahedral geometry.\u00a0 However, the H-O-C bond angles are less than the typical 109.5<sup>o <\/sup>due to compression by the lone pair electrons.<\/p>\n<div id=\"attachment_2240\" style=\"width: 179px\" class=\"wp-caption aligncenter\"><img loading=\"lazy\" decoding=\"async\" aria-describedby=\"caption-attachment-2240\" class=\"wp-image-2240 size-full\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/28201744\/download-5.png\" alt=\"\" width=\"169\" height=\"142\" \/><\/p>\n<p id=\"caption-attachment-2240\" class=\"wp-caption-text\">Methanol<\/p>\n<\/div>\n<p><img decoding=\"async\" src=\"https:\/\/chem.libretexts.org\/LibreTexts\/Athabasca_University\/Chemistry_350%3A_Organic_Chemistry_I\/Chapter_1%3A_Structure_and_Bonding\/denied:data:image\/png;base64,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#fixme\" alt=\"\" \/><\/p>\n<\/div>\n<\/div>\n<div id=\"section_3\">\n<h3 class=\"editable\">Methyl phosphate<\/h3>\n<p>Phosphorus can have have expanded octets because it is in the n = 3 row.\u00a0 Typically, phosphorus forms five covalent bonds.\u00a0 In biological molecules, phosphorusis usually found in organophosphates.\u00a0 Organophosphates are made up of a phosphorus atoms bonded to four oxygens, with one of the oxygens also bonded to a carbon.\u00a0 In methyl phosphate, the phosphorus is <em>sp<sup>3<\/sup><\/em> hybridized and the O-P-O bond angle varying from 110 to 112<sup>o.\u00a0<\/sup><\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"size-full wp-image-2233 aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/28200937\/download-1.png\" alt=\"\" width=\"228\" height=\"143\" \/><\/p>\n<\/div>\n<div id=\"section_4\">\n<p><img decoding=\"async\" class=\"aligncenter\" src=\"image\/png;base64,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\" alt=\"\" \/><\/p>\n<h3 class=\"editable\">Methanethiol &amp; Dimethyl Sulfide<\/h3>\n<p>In biological system, sulfur is typically found in molecules called thiols or sulfides. In a thiol, the sulfur atim is conded to one hydrogens and one carbon and is analogous to an alcohol. In a sulfide, the sulfur is bonded to two carbons.\u00a0 In both cases the sulfur is <em>sp<sup>3<\/sup><\/em>hybridized and the bond angles are much less than the typicall 109.5<sup>o<\/sup>.<\/p>\n<div id=\"attachment_2238\" style=\"width: 199px\" class=\"wp-caption aligncenter\"><img loading=\"lazy\" decoding=\"async\" aria-describedby=\"caption-attachment-2238\" class=\"wp-image-2238 size-full\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/28201510\/download-21.png\" alt=\"\" width=\"189\" height=\"158\" \/><\/p>\n<p id=\"caption-attachment-2238\" class=\"wp-caption-text\">Methanethiol<\/p>\n<\/div>\n<div id=\"attachment_2239\" style=\"width: 175px\" class=\"wp-caption aligncenter\"><img loading=\"lazy\" decoding=\"async\" aria-describedby=\"caption-attachment-2239\" class=\"wp-image-2239 size-full\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/28201525\/download-3.png\" alt=\"\" width=\"165\" height=\"144\" \/><\/p>\n<p id=\"caption-attachment-2239\" class=\"wp-caption-text\">Dimethyl sulfide<\/p>\n<\/div>\n<\/div>\n<div id=\"section_5\">\n<div id=\"s61688\">\n<div id=\"section_34\">\n<div class=\"textbox examples\">\n<h3>Example<\/h3>\n<div id=\"section_5\">\n<div id=\"s61688\">\n<div id=\"section_34\">\n<p>Identify geometry and lone pairs on each heteroatom of the molecules given.<\/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\/04151318\/1.10_rev.png\" alt=\"\" width=\"474\" height=\"132\" \/><\/p>\n<\/div>\n<div id=\"section_35\">\n<div class=\"qa-wrapper\" style=\"display: block\"><span class=\"show-answer collapsed\" style=\"cursor: pointer\" data-target=\"q679308\">Show Answer<\/span><\/p>\n<div id=\"q679308\" class=\"hidden-answer\" style=\"display: none\">Diethyl ether would have two lone pairs of electrons and would have a bent geometry around the oxygen. Dimethyl amine would have one lone pair and would show a pyramidal geometry around the nitrogen.<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<div id=\"section_6\">\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<\/ul>\n<\/div>\n<\/div>\n","protected":false},"author":311,"menu_order":13,"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-297","chapter","type-chapter","status-publish","hentry"],"part":76,"_links":{"self":[{"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapters\/297","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":7,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapters\/297\/revisions"}],"predecessor-version":[{"id":2241,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapters\/297\/revisions\/2241"}],"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\/297\/metadata\/"}],"wp:attachment":[{"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/wp\/v2\/media?parent=297"}],"wp:term":[{"taxonomy":"chapter-type","embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapter-type?post=297"},{"taxonomy":"contributor","embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/wp\/v2\/contributor?post=297"},{"taxonomy":"license","embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/wp\/v2\/license?post=297"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}