{"id":3169,"date":"2018-06-22T20:11:30","date_gmt":"2018-06-22T20:11:30","guid":{"rendered":"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry\/?post_type=chapter&#038;p=3169"},"modified":"2018-08-06T05:20:40","modified_gmt":"2018-08-06T05:20:40","slug":"2-3-how-to-judge-hybridization-of-an-atom","status":"publish","type":"chapter","link":"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry\/chapter\/2-3-how-to-judge-hybridization-of-an-atom\/","title":{"raw":"2.3. How to judge hybridization of an atom","rendered":"2.3. How to judge hybridization of an atom"},"content":{"raw":"<section class=\"mt-content-container\">\r\n<div class=\"mt-section\">\r\n<h3 class=\"editable\">Hybridization<\/h3>\r\n<a title=\"Hybridization\" href=\"https:\/\/chem.libretexts.org\/Core\/Physical_and_Theoretical_Chemistry\/Chemical_Bonding\/Valence_Bond_Theory\/Hybridization\" rel=\"internal\">Hybridization <\/a>is a simple model that deals with mixing orbitals to from new, hybridized, orbitals. This is part of the valence bond theory and helps explain bonds formed, the length of bonds, and bond energies; however, this does not explain molecular geometry very well.\r\n<ul>\r\n \t<li><u>sp<\/u>\u00a0 An example of this is acetylene (C<sub>2<\/sub>H<sub>2<\/sub>).\u00a0This combines one s orbital with one p orbital. This means that the s and p characteristics are equal.<\/li>\r\n \t<li><u>sp<\/u><sup>2<\/sup> An example of this is ethylene (C<sub>2<\/sub>H<sub>4<\/sub>).\u00a0This\u00a0is the\u00a0combination of one s orbital and two p orbitals.<\/li>\r\n \t<li><u>sp<\/u><sup>3<\/sup>\u00a0An example of this is methane (CH<sub>4<\/sub>). This is the combination of one s orbital and three p orbitals.<\/li>\r\n<\/ul>\r\nIf you add the exponents of the hybridized orbitals, you get the amount of sigma bonds associated with that bond. The sp<sup>2<\/sup> hybridized orbital\u00a0has\u00a0one p orbitals that\u00a0is not hybridized and so\u00a0it can form a pi bond. This means that sp<sup>2<\/sup><sup>\u00a0<\/sup>orbitals allow for the formation of a double bond.\u00a0Also, sp hybridized orbitals form a triple bond.\r\n\r\nThe hybrid orbitals used (and hence the hybridization) depends on how many electron groups are around the atom in question.\u00a0 An electron group can mean either a bonded atom or a lone pair.\u00a0 Examples are shown for carbon; nitrogen and oxygen are similar, with lone pairs taking the place of single bonds:\r\n<table style=\"border-collapse: collapse;width: 100%\" border=\"1\">\r\n<tbody>\r\n<tr>\r\n<td style=\"width: 25%;text-align: center\">No. of electron groups<\/td>\r\n<td style=\"width: 25%;text-align: center\">Hybrid orbital used<\/td>\r\n<td style=\"width: 25%;text-align: center\">Example<\/td>\r\n<td style=\"width: 25%;text-align: center\">Bond angle<\/td>\r\n<\/tr>\r\n<tr>\r\n<td style=\"width: 25%;text-align: center\">2<\/td>\r\n<td style=\"width: 25%;text-align: center\">sp<\/td>\r\n<td style=\"width: 25%;text-align: center\"><img class=\"alignnone wp-image-4740\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3369\/2018\/06\/06051517\/spcarbon.png\" alt=\"\" width=\"58\" height=\"32\" \/><\/td>\r\n<td style=\"width: 25%;text-align: center\">180<sup>o<\/sup><\/td>\r\n<\/tr>\r\n<tr>\r\n<td style=\"width: 25%;text-align: center\">3<\/td>\r\n<td style=\"width: 25%;text-align: center\">sp<sup>2<\/sup><\/td>\r\n<td style=\"width: 25%;text-align: center\"><img class=\"alignnone wp-image-4741\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3369\/2018\/06\/06051549\/sp2carbon.png\" alt=\"\" width=\"57\" height=\"62\" \/><\/td>\r\n<td style=\"width: 25%;text-align: center\">120<sup>o<\/sup><\/td>\r\n<\/tr>\r\n<tr>\r\n<td style=\"width: 25%;text-align: center\">4<\/td>\r\n<td style=\"width: 25%;text-align: center\">sp<sup>3<\/sup><\/td>\r\n<td style=\"width: 25%;text-align: center\"><img class=\"alignnone wp-image-4742\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3369\/2018\/06\/06051624\/sp3carbon.png\" alt=\"\" width=\"60\" height=\"57\" \/><\/td>\r\n<td style=\"width: 25%;text-align: center\">109.5<sup>o<\/sup><\/td>\r\n<\/tr>\r\n<\/tbody>\r\n<\/table>\r\nHowever, there is an even easier way to judge the hybridization:\r\n<div class=\"textbox key-takeaways\">\r\n<h3>SIMPLE WAY to work out hybridization<\/h3>\r\nThis is a simple way to find out the hybridization for an atom of carbon, nitrogen or oxygen.\r\n<ul>\r\n \t<li>All single bonds or lone pairs =&gt; sp<sup>3<\/sup><\/li>\r\n \t<li>One double bond =&gt; sp<sup>2<\/sup><\/li>\r\n \t<li>One triple bond =&gt; sp<\/li>\r\n<\/ul>\r\n<\/div>\r\n<div>\r\n<div class=\"textbox examples\">\r\n<h3>Example<\/h3>\r\nLook at the structure of thiamine diphosphate in the '<a title=\"Structures of common coenzymes\" href=\"https:\/\/chem.libretexts.org\/Textbook_Maps\/Organic_Chemistry_Textbook_Maps\/Map%3A_Organic_Chemistry_with_a_Biological_Emphasis_(Soderberg)\/Reference_Tables\/Structures_of_common_coenzymes\" target=\"_blank\" rel=\"internal noopener\">structures of common coenzymes' table<\/a>.\u00a0 Identify the hybridization of all carbon atoms in the molecule.\r\n[reveal-answer q=\"974002\"]Show Solution[\/reveal-answer]\r\n[hidden-answer a=\"974002\"]\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/107049\/E2-7S.png?revision=1&amp;size=bestfit&amp;width=490&amp;height=227\" alt=\"\" width=\"490\" height=\"227\" \/>\r\n\r\n[\/hidden-answer]\r\n\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<div class=\"textbox examples\">\r\n<h3><a href=\"https:\/\/chem.libretexts.org\/LibreTexts\/Purdue\/Purdue_Chem_26100%3A_Organic_Chemistry_I_(Wenthold)\/Chapter_02._Structures_and_Properties_of_Organic_Molecules\/2.2_Molecular_Shapes_and_Hybridization\/2.2.3._General_Rules_of_Hybridization_and_Geometry\">Useful resources <\/a><\/h3>\r\n<img class=\"size-thumbnail wp-image-4060 alignnone\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3369\/2018\/06\/26154100\/frame-10-150x150.png\" alt=\"\" width=\"150\" height=\"150\" \/>\r\n<h3><a href=\"https:\/\/chem.libretexts.org\/Textbook_Maps\/Physical_and_Theoretical_Chemistry_Textbook_Maps\/Map%3A_Physical_Chemistry_for_the_Biosciences_(Chang)\/12%3A_The_Chemical_Bond\/12.3%3A_Hybridization_of_Atomic_Orbitals\">Further reading<\/a><\/h3>\r\n<img class=\"size-thumbnail wp-image-4059 alignnone\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3369\/2018\/06\/26153944\/frame-9-150x150.png\" alt=\"\" width=\"150\" height=\"150\" \/>\r\n\r\n<\/div>\r\n<h3 class=\"editable\">References<\/h3>\r\n<ol>\r\n \t<li>Chang, Raymond. <u>Physical Chemistry for the Biosciences<\/u>. University Science Books, 2005.<\/li>\r\n<\/ol>\r\n<\/section>","rendered":"<section class=\"mt-content-container\">\n<div class=\"mt-section\">\n<h3 class=\"editable\">Hybridization<\/h3>\n<p><a title=\"Hybridization\" href=\"https:\/\/chem.libretexts.org\/Core\/Physical_and_Theoretical_Chemistry\/Chemical_Bonding\/Valence_Bond_Theory\/Hybridization\" rel=\"internal\">Hybridization <\/a>is a simple model that deals with mixing orbitals to from new, hybridized, orbitals. This is part of the valence bond theory and helps explain bonds formed, the length of bonds, and bond energies; however, this does not explain molecular geometry very well.<\/p>\n<ul>\n<li><u>sp<\/u>\u00a0 An example of this is acetylene (C<sub>2<\/sub>H<sub>2<\/sub>).\u00a0This combines one s orbital with one p orbital. This means that the s and p characteristics are equal.<\/li>\n<li><u>sp<\/u><sup>2<\/sup> An example of this is ethylene (C<sub>2<\/sub>H<sub>4<\/sub>).\u00a0This\u00a0is the\u00a0combination of one s orbital and two p orbitals.<\/li>\n<li><u>sp<\/u><sup>3<\/sup>\u00a0An example of this is methane (CH<sub>4<\/sub>). This is the combination of one s orbital and three p orbitals.<\/li>\n<\/ul>\n<p>If you add the exponents of the hybridized orbitals, you get the amount of sigma bonds associated with that bond. The sp<sup>2<\/sup> hybridized orbital\u00a0has\u00a0one p orbitals that\u00a0is not hybridized and so\u00a0it can form a pi bond. This means that sp<sup>2<\/sup><sup>\u00a0<\/sup>orbitals allow for the formation of a double bond.\u00a0Also, sp hybridized orbitals form a triple bond.<\/p>\n<p>The hybrid orbitals used (and hence the hybridization) depends on how many electron groups are around the atom in question.\u00a0 An electron group can mean either a bonded atom or a lone pair.\u00a0 Examples are shown for carbon; nitrogen and oxygen are similar, with lone pairs taking the place of single bonds:<\/p>\n<table style=\"border-collapse: collapse;width: 100%\">\n<tbody>\n<tr>\n<td style=\"width: 25%;text-align: center\">No. of electron groups<\/td>\n<td style=\"width: 25%;text-align: center\">Hybrid orbital used<\/td>\n<td style=\"width: 25%;text-align: center\">Example<\/td>\n<td style=\"width: 25%;text-align: center\">Bond angle<\/td>\n<\/tr>\n<tr>\n<td style=\"width: 25%;text-align: center\">2<\/td>\n<td style=\"width: 25%;text-align: center\">sp<\/td>\n<td style=\"width: 25%;text-align: center\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-4740\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3369\/2018\/06\/06051517\/spcarbon.png\" alt=\"\" width=\"58\" height=\"32\" \/><\/td>\n<td style=\"width: 25%;text-align: center\">180<sup>o<\/sup><\/td>\n<\/tr>\n<tr>\n<td style=\"width: 25%;text-align: center\">3<\/td>\n<td style=\"width: 25%;text-align: center\">sp<sup>2<\/sup><\/td>\n<td style=\"width: 25%;text-align: center\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-4741\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3369\/2018\/06\/06051549\/sp2carbon.png\" alt=\"\" width=\"57\" height=\"62\" \/><\/td>\n<td style=\"width: 25%;text-align: center\">120<sup>o<\/sup><\/td>\n<\/tr>\n<tr>\n<td style=\"width: 25%;text-align: center\">4<\/td>\n<td style=\"width: 25%;text-align: center\">sp<sup>3<\/sup><\/td>\n<td style=\"width: 25%;text-align: center\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-4742\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3369\/2018\/06\/06051624\/sp3carbon.png\" alt=\"\" width=\"60\" height=\"57\" \/><\/td>\n<td style=\"width: 25%;text-align: center\">109.5<sup>o<\/sup><\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<p>However, there is an even easier way to judge the hybridization:<\/p>\n<div class=\"textbox key-takeaways\">\n<h3>SIMPLE WAY to work out hybridization<\/h3>\n<p>This is a simple way to find out the hybridization for an atom of carbon, nitrogen or oxygen.<\/p>\n<ul>\n<li>All single bonds or lone pairs =&gt; sp<sup>3<\/sup><\/li>\n<li>One double bond =&gt; sp<sup>2<\/sup><\/li>\n<li>One triple bond =&gt; sp<\/li>\n<\/ul>\n<\/div>\n<div>\n<div class=\"textbox examples\">\n<h3>Example<\/h3>\n<p>Look at the structure of thiamine diphosphate in the &#8216;<a title=\"Structures of common coenzymes\" href=\"https:\/\/chem.libretexts.org\/Textbook_Maps\/Organic_Chemistry_Textbook_Maps\/Map%3A_Organic_Chemistry_with_a_Biological_Emphasis_(Soderberg)\/Reference_Tables\/Structures_of_common_coenzymes\" target=\"_blank\" rel=\"internal noopener\">structures of common coenzymes&#8217; table<\/a>.\u00a0 Identify the hybridization of all carbon atoms in the molecule.<\/p>\n<div class=\"qa-wrapper\" style=\"display: block\"><span class=\"show-answer collapsed\" style=\"cursor: pointer\" data-target=\"q974002\">Show Solution<\/span><\/p>\n<div id=\"q974002\" class=\"hidden-answer\" style=\"display: none\">\n<img loading=\"lazy\" decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/107049\/E2-7S.png?revision=1&amp;size=bestfit&amp;width=490&amp;height=227\" alt=\"\" width=\"490\" height=\"227\" \/><\/p>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<div class=\"textbox examples\">\n<h3><a href=\"https:\/\/chem.libretexts.org\/LibreTexts\/Purdue\/Purdue_Chem_26100%3A_Organic_Chemistry_I_(Wenthold)\/Chapter_02._Structures_and_Properties_of_Organic_Molecules\/2.2_Molecular_Shapes_and_Hybridization\/2.2.3._General_Rules_of_Hybridization_and_Geometry\">Useful resources <\/a><\/h3>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"size-thumbnail wp-image-4060 alignnone\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3369\/2018\/06\/26154100\/frame-10-150x150.png\" alt=\"\" width=\"150\" height=\"150\" \/><\/p>\n<h3><a href=\"https:\/\/chem.libretexts.org\/Textbook_Maps\/Physical_and_Theoretical_Chemistry_Textbook_Maps\/Map%3A_Physical_Chemistry_for_the_Biosciences_(Chang)\/12%3A_The_Chemical_Bond\/12.3%3A_Hybridization_of_Atomic_Orbitals\">Further reading<\/a><\/h3>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"size-thumbnail wp-image-4059 alignnone\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3369\/2018\/06\/26153944\/frame-9-150x150.png\" alt=\"\" width=\"150\" height=\"150\" \/><\/p>\n<\/div>\n<h3 class=\"editable\">References<\/h3>\n<ol>\n<li>Chang, Raymond. <u>Physical Chemistry for the Biosciences<\/u>. University Science Books, 2005.<\/li>\n<\/ol>\n<\/section>\n\n\t\t\t <section class=\"citations-section\" role=\"contentinfo\">\n\t\t\t <h3>Candela Citations<\/h3>\n\t\t\t\t\t <div>\n\t\t\t\t\t\t <div id=\"citation-list-3169\">\n\t\t\t\t\t\t\t <div class=\"licensing\"><div class=\"license-attribution-dropdown-subheading\">CC licensed content, Original<\/div><ul class=\"citation-list\"><li>Table and summary of how to judge hybridization. <strong>Authored by<\/strong>: Martin A. Walker. <strong>Provided by<\/strong>: SUNY Potsdam. <strong>Located at<\/strong>: <a target=\"_blank\" href=\"http:\/\/directory.potsdam.edu\/index.pl?function=user=walkerma\">http:\/\/directory.potsdam.edu\/index.pl?function=user=walkerma<\/a>. <strong>License<\/strong>: <em><a target=\"_blank\" rel=\"license\" href=\"https:\/\/creativecommons.org\/licenses\/by-sa\/4.0\/\">CC BY-SA: Attribution-ShareAlike<\/a><\/em><\/li><\/ul><div class=\"license-attribution-dropdown-subheading\">CC licensed content, Shared previously<\/div><ul class=\"citation-list\"><li>Taken from Organic Chemistry with a Biological Emphasis. <strong>Authored by<\/strong>: Tim Soderberg. <strong>Provided by<\/strong>: University of Minnesota, Morris. <strong>Located at<\/strong>: <a target=\"_blank\" href=\"https:\/\/chem.libretexts.org\/Textbook_Maps\/Organic_Chemistry\/Book%3A_Organic_Chemistry_with_a_Biological_Emphasis_(Soderberg)\/Chapter_02%3A_Introduction_to_organic_structure_and_bonding_II\/2.2%3A_Molecular_orbital_theory%3A_conjugation_and_aromaticity\">https:\/\/chem.libretexts.org\/Textbook_Maps\/Organic_Chemistry\/Book%3A_Organic_Chemistry_with_a_Biological_Emphasis_(Soderberg)\/Chapter_02%3A_Introduction_to_organic_structure_and_bonding_II\/2.2%3A_Molecular_orbital_theory%3A_conjugation_and_aromaticity<\/a>. <strong>License<\/strong>: <em><a target=\"_blank\" rel=\"license\" href=\"https:\/\/creativecommons.org\/licenses\/by-nc-sa\/4.0\/\">CC BY-NC-SA: Attribution-NonCommercial-ShareAlike<\/a><\/em><\/li><\/ul><\/div>\n\t\t\t\t\t\t <\/div>\n\t\t\t\t\t <\/div>\n\t\t\t <\/section>","protected":false},"author":311,"menu_order":3,"template":"","meta":{"_candela_citation":"[{\"type\":\"cc\",\"description\":\"Taken from Organic Chemistry with a Biological Emphasis\",\"author\":\"Tim Soderberg\",\"organization\":\"University of Minnesota, Morris\",\"url\":\"https:\/\/chem.libretexts.org\/Textbook_Maps\/Organic_Chemistry\/Book%3A_Organic_Chemistry_with_a_Biological_Emphasis_(Soderberg)\/Chapter_02%3A_Introduction_to_organic_structure_and_bonding_II\/2.2%3A_Molecular_orbital_theory%3A_conjugation_and_aromaticity\",\"project\":\"\",\"license\":\"cc-by-nc-sa\",\"license_terms\":\"\"},{\"type\":\"original\",\"description\":\"Table and summary of how to judge hybridization\",\"author\":\"Martin A. Walker\",\"organization\":\"SUNY Potsdam\",\"url\":\"http:\/\/directory.potsdam.edu\/index.pl?function=user=walkerma\",\"project\":\"\",\"license\":\"cc-by-sa\",\"license_terms\":\"\"}]","CANDELA_OUTCOMES_GUID":"","pb_show_title":"on","pb_short_title":"","pb_subtitle":"","pb_authors":[],"pb_section_license":""},"chapter-type":[],"contributor":[],"license":[],"class_list":["post-3169","chapter","type-chapter","status-publish","hentry"],"part":20,"_links":{"self":[{"href":"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry\/wp-json\/pressbooks\/v2\/chapters\/3169","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry\/wp-json\/pressbooks\/v2\/chapters"}],"about":[{"href":"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry\/wp-json\/wp\/v2\/types\/chapter"}],"author":[{"embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry\/wp-json\/wp\/v2\/users\/311"}],"version-history":[{"count":25,"href":"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry\/wp-json\/pressbooks\/v2\/chapters\/3169\/revisions"}],"predecessor-version":[{"id":4745,"href":"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry\/wp-json\/pressbooks\/v2\/chapters\/3169\/revisions\/4745"}],"part":[{"href":"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry\/wp-json\/pressbooks\/v2\/parts\/20"}],"metadata":[{"href":"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry\/wp-json\/pressbooks\/v2\/chapters\/3169\/metadata\/"}],"wp:attachment":[{"href":"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry\/wp-json\/wp\/v2\/media?parent=3169"}],"wp:term":[{"taxonomy":"chapter-type","embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry\/wp-json\/pressbooks\/v2\/chapter-type?post=3169"},{"taxonomy":"contributor","embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry\/wp-json\/wp\/v2\/contributor?post=3169"},{"taxonomy":"license","embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry\/wp-json\/wp\/v2\/license?post=3169"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}