{"id":836,"date":"2017-10-19T15:30:37","date_gmt":"2017-10-19T15:30:37","guid":{"rendered":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/?post_type=chapter&#038;p=836"},"modified":"2018-10-03T18:10:48","modified_gmt":"2018-10-03T18:10:48","slug":"a-review-of-isomerism","status":"publish","type":"chapter","link":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/chapter\/a-review-of-isomerism\/","title":{"raw":"A Review of Isomerism","rendered":"A Review of Isomerism"},"content":{"raw":"<div class=\"textbox learning-objectives\">\r\n<h3>Objective<\/h3>\r\n<div>\r\n<div id=\"skills\">\r\n\r\nAfter completing this section, you should be able to explain the differences among constitutional (structural) isomers and stereoisomers (geometric isomers).\r\n\r\n<\/div>\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>constitutional<\/li>\r\n \t<li>(structural) isomers<\/li>\r\n \t<li>stereoisomers<\/li>\r\n<\/ul>\r\n<\/div>\r\n<\/div>\r\n\r\n[caption id=\"\" align=\"aligncenter\" width=\"883\"]<img src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05133254\/883px-Isomerism.svg_.png\" alt=\"\" width=\"883\" height=\"558\" \/> Different types of isomers (Vladsinger)[\/caption]\r\n\r\n<div>\r\n<div id=\"section_1\">\r\n<h3 class=\"editable\">Conformational Isomers<\/h3>\r\nThe C\u2013C single bonds in ethane, propane, and other alkanes are formed by the overlap of an sp<sup>3<\/sup> hybrid orbital on one carbon atom with an sp<sup>3<\/sup> hybrid orbital on another carbon atom, forming a \u03c3 bond. Each sp<sup>3<\/sup> hybrid orbital is cylindrically symmetrical (all cross-sections are circles), resulting in a carbon\u2013carbon single bond that is also cylindrically symmetrical about the C\u2013C axis. Because rotation about the carbon\u2013carbon single bond can occur without changing the overlap of the sp<sup>3<\/sup> hybrid orbitals, there is no significant electronic energy barrier to rotation. Consequently, many different arrangements of the atoms are possible, each corresponding to different degrees of rotation. Differences in three-dimensional structure resulting from rotation about a \u03c3 bond are called differences in conformation, and each different arrangement is called a <a>conformational isomer (or conformer)<\/a>.\r\n\r\n<\/div>\r\n<div id=\"section_2\">\r\n<h3 class=\"editable\">Structural Isomers<\/h3>\r\n<\/div>\r\n<\/div>\r\n<div>\r\n\r\nUnlike conformational isomers, which do not differ in connectivity, <a>structural isomers<\/a> differ in connectivity, as illustrated here for 1-propanol and 2-propanol. Although these two alcohols have the same molecular formula (C<sub>3<\/sub>H<sub>8<\/sub>O), the position of the \u2013OH group differs, which leads to differences in their physical and chemical properties.\r\n<div><img class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05133257\/873cac9a3fed64182671c76cf59ceaca.jpg\" alt=\"\" width=\"191\" height=\"310\" \/><\/div>\r\nIn the conversion of one structural isomer to another, at least one bond must be broken and reformed at a different position in the molecule. Consider, for example, the following five structures represented by the formula C<sub>5<\/sub>H<sub>12<\/sub>:\r\n<div><img class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05133259\/93025d394921a7466b995070376f68de.jpg\" alt=\"\" width=\"665\" height=\"122\" \/><\/div>\r\nOf these structures, (a) and (d) represent the same compound, as do (b) and (c). No bonds have been broken and reformed; the molecules are simply rotated about a 180\u00b0 vertical axis. Only three\u2014n-pentane (a) and (d), 2-methylbutane (b) and (c), and 2,2-dimethylpropane (e)\u2014are structural isomers. Because no bonds are broken in going from (a) to (d) or from (b) to (c), these alternative representations are not structural isomers. The three structural isomers\u2014either (a) or (d), either (b) or (c), and (e)\u2014have distinct physical and chemical properties.\r\n\r\n<\/div>\r\n<div id=\"section_3\">\r\n<h3 class=\"editable\">Stereoisomers<\/h3>\r\nMolecules with the same connectivity but different arrangements of the atoms in space are called <a>stereoisomers<\/a>. There are two types of stereoisomers: geometric and optical. Geometric isomers differ in the relative position(s) of substituents in a rigid molecule. Simple rotation about a C\u2013C \u03c3 bond in an alkene, for example, cannot occur because of the presence of the \u03c0 bond. The substituents are therefore rigidly locked into a particular spatial arrangement. Thus a carbon\u2013carbon multiple bond, or in some cases a ring, prevents one geometric isomer from being readily converted to the other. The members of an isomeric pair are identified as either cis or trans, and interconversion between the two forms requires breaking and reforming one or more bonds. Because their structural difference causes them to have different physical and chemical properties, cis and trans isomers are actually two distinct chemical compounds.\r\n<div>\r\n<div id=\"note\">\r\n<blockquote>\r\n<p class=\"boxtitle\">Note<\/p>\r\nStereoisomers have the same connectivity but different arrangements of atoms in space.<\/blockquote>\r\n<\/div>\r\n<\/div>\r\nOptical isomers are molecules whose structures are mirror images but cannot be superimposed on one another in any orientation. Optical isomers have identical physical properties, although their chemical properties may differ in asymmetric environments. Molecules that are nonsuperimposable mirror images of each other are said to be chiral (pronounced \u201cky-ral,\u201d from the Greek cheir, meaning \u201chand\u201d). Examples of some familiar chiral objects are your hands, feet, and ears. As shown in part (a) in Figure 5.9.1, your left and right hands are nonsuperimposable mirror images. (Try putting your right shoe on your left foot\u2014it just doesn\u2019t work.) An achiral object is one that can be superimposed on its mirror image, as shown by the superimposed flasks in part (b) in Figure 5.9.1.\r\n<div>\r\n\r\n[caption id=\"\" align=\"aligncenter\" width=\"399\"]<img class=\"internal\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05133302\/122a3121b7268f235234e7a9091fc4ea.jpg\" alt=\"\" width=\"399\" height=\"393\" \/> Figure 1: Chiral and Achiral Objects\/ (a) Objects that are nonsuperimposable mirror images of each other are chiral, such as the left and the right hand. (b) The unmarked flask is achiral because it can be superimposed on its mirror image.[\/caption]\r\n\r\n<\/div>\r\nMost chiral organic molecules have at least one carbon atom that is bonded to four different groups, as occurs in the bromochlorofluoromethane molecule shown in part (a) in Figure 5.9.2. This carbon, often designated by an asterisk in structural drawings, is called a chiral center or asymmetric carbon atom. If the bromine atom is replaced by another chlorine (part (b) in Figure 5.9.2), the molecule and its mirror image can now be superimposed by simple rotation. Thus the carbon is no longer a chiral center. Asymmetric carbon atoms are found in many naturally occurring molecules, such as lactic acid, which is present in milk and muscles, and nicotine, a component of tobacco. A molecule and its nonsuperimposable mirror image are called enantiomers (from the Greek enantiou, meaning \u201copposite\u201d).\r\n<div>\r\n\r\n[caption id=\"\" align=\"aligncenter\" width=\"461\"]<img class=\"internal\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05133306\/8db206d9deaa4b1b4b4af6260048d343.jpg\" alt=\"\" width=\"461\" height=\"343\" \/> Figure 2: Comparison of Chiral and Achiral Molecules. (a) Bromochlorofluoromethane is a chiral molecule whose stereocenter is designated with an asterisk. Rotation of its mirror image does not generate the original structure. To superimpose the mirror images, bonds must be broken and reformed. (b) In contrast, dichlorofluoromethane and its mirror image can be rotated so they are superimposable.[\/caption]\r\n\r\n<div id=\"section_4\">\r\n<div class=\"textbox exercises\">\r\n<h3>Exercises<\/h3>\r\n<div id=\"section_4\">\r\n<div id=\"s61692\">\r\n<div id=\"section_27\">\r\n<h3 id=\"Questions-61692\">Questions<\/h3>\r\n<strong>1.<\/strong>\r\n\r\nWhat kind of isomers are the following pairs:\r\n\r\nA \u2013 (<em>R<\/em>)-5-chlorohexene and 6-chlorohexene\r\n\r\nB \u2013 (2<em>R<\/em>,3<em>R<\/em>)-dibromohexane and (2<em>R<\/em>,3<em>S<\/em>)-dibromohexan\r\n\r\n<\/div>\r\n<div id=\"section_28\">\r\n<h3 id=\"Solutions-61692\">Solution<\/h3>\r\n<strong>1.<\/strong>\r\n\r\n[reveal-answer q=\"144603\"]Show Answer[\/reveal-answer]\r\n[hidden-answer a=\"144603\"]A = Structural Isomers B = Diastereomers[\/hidden-answer]\r\n\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<div id=\"section_5\">\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<\/ul>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<\/div>","rendered":"<div class=\"textbox learning-objectives\">\n<h3>Objective<\/h3>\n<div>\n<div id=\"skills\">\n<p>After completing this section, you should be able to explain the differences among constitutional (structural) isomers and stereoisomers (geometric isomers).<\/p>\n<\/div>\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>constitutional<\/li>\n<li>(structural) isomers<\/li>\n<li>stereoisomers<\/li>\n<\/ul>\n<\/div>\n<\/div>\n<div style=\"width: 893px\" class=\"wp-caption aligncenter\"><img loading=\"lazy\" decoding=\"async\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05133254\/883px-Isomerism.svg_.png\" alt=\"\" width=\"883\" height=\"558\" \/><\/p>\n<p class=\"wp-caption-text\">Different types of isomers (Vladsinger)<\/p>\n<\/div>\n<div>\n<div id=\"section_1\">\n<h3 class=\"editable\">Conformational Isomers<\/h3>\n<p>The C\u2013C single bonds in ethane, propane, and other alkanes are formed by the overlap of an sp<sup>3<\/sup> hybrid orbital on one carbon atom with an sp<sup>3<\/sup> hybrid orbital on another carbon atom, forming a \u03c3 bond. Each sp<sup>3<\/sup> hybrid orbital is cylindrically symmetrical (all cross-sections are circles), resulting in a carbon\u2013carbon single bond that is also cylindrically symmetrical about the C\u2013C axis. Because rotation about the carbon\u2013carbon single bond can occur without changing the overlap of the sp<sup>3<\/sup> hybrid orbitals, there is no significant electronic energy barrier to rotation. Consequently, many different arrangements of the atoms are possible, each corresponding to different degrees of rotation. Differences in three-dimensional structure resulting from rotation about a \u03c3 bond are called differences in conformation, and each different arrangement is called a <a>conformational isomer (or conformer)<\/a>.<\/p>\n<\/div>\n<div id=\"section_2\">\n<h3 class=\"editable\">Structural Isomers<\/h3>\n<\/div>\n<\/div>\n<div>\n<p>Unlike conformational isomers, which do not differ in connectivity, <a>structural isomers<\/a> differ in connectivity, as illustrated here for 1-propanol and 2-propanol. Although these two alcohols have the same molecular formula (C<sub>3<\/sub>H<sub>8<\/sub>O), the position of the \u2013OH group differs, which leads to differences in their physical and chemical properties.<\/p>\n<div><img loading=\"lazy\" decoding=\"async\" class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05133257\/873cac9a3fed64182671c76cf59ceaca.jpg\" alt=\"\" width=\"191\" height=\"310\" \/><\/div>\n<p>In the conversion of one structural isomer to another, at least one bond must be broken and reformed at a different position in the molecule. Consider, for example, the following five structures represented by the formula C<sub>5<\/sub>H<sub>12<\/sub>:<\/p>\n<div><img loading=\"lazy\" decoding=\"async\" class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05133259\/93025d394921a7466b995070376f68de.jpg\" alt=\"\" width=\"665\" height=\"122\" \/><\/div>\n<p>Of these structures, (a) and (d) represent the same compound, as do (b) and (c). No bonds have been broken and reformed; the molecules are simply rotated about a 180\u00b0 vertical axis. Only three\u2014n-pentane (a) and (d), 2-methylbutane (b) and (c), and 2,2-dimethylpropane (e)\u2014are structural isomers. Because no bonds are broken in going from (a) to (d) or from (b) to (c), these alternative representations are not structural isomers. The three structural isomers\u2014either (a) or (d), either (b) or (c), and (e)\u2014have distinct physical and chemical properties.<\/p>\n<\/div>\n<div id=\"section_3\">\n<h3 class=\"editable\">Stereoisomers<\/h3>\n<p>Molecules with the same connectivity but different arrangements of the atoms in space are called <a>stereoisomers<\/a>. There are two types of stereoisomers: geometric and optical. Geometric isomers differ in the relative position(s) of substituents in a rigid molecule. Simple rotation about a C\u2013C \u03c3 bond in an alkene, for example, cannot occur because of the presence of the \u03c0 bond. The substituents are therefore rigidly locked into a particular spatial arrangement. Thus a carbon\u2013carbon multiple bond, or in some cases a ring, prevents one geometric isomer from being readily converted to the other. The members of an isomeric pair are identified as either cis or trans, and interconversion between the two forms requires breaking and reforming one or more bonds. Because their structural difference causes them to have different physical and chemical properties, cis and trans isomers are actually two distinct chemical compounds.<\/p>\n<div>\n<div id=\"note\">\n<blockquote>\n<p class=\"boxtitle\">Note<\/p>\n<p>Stereoisomers have the same connectivity but different arrangements of atoms in space.<\/p><\/blockquote>\n<\/div>\n<\/div>\n<p>Optical isomers are molecules whose structures are mirror images but cannot be superimposed on one another in any orientation. Optical isomers have identical physical properties, although their chemical properties may differ in asymmetric environments. Molecules that are nonsuperimposable mirror images of each other are said to be chiral (pronounced \u201cky-ral,\u201d from the Greek cheir, meaning \u201chand\u201d). Examples of some familiar chiral objects are your hands, feet, and ears. As shown in part (a) in Figure 5.9.1, your left and right hands are nonsuperimposable mirror images. (Try putting your right shoe on your left foot\u2014it just doesn\u2019t work.) An achiral object is one that can be superimposed on its mirror image, as shown by the superimposed flasks in part (b) in Figure 5.9.1.<\/p>\n<div>\n<div style=\"width: 409px\" class=\"wp-caption aligncenter\"><img loading=\"lazy\" decoding=\"async\" class=\"internal\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05133302\/122a3121b7268f235234e7a9091fc4ea.jpg\" alt=\"\" width=\"399\" height=\"393\" \/><\/p>\n<p class=\"wp-caption-text\">Figure 1: Chiral and Achiral Objects\/ (a) Objects that are nonsuperimposable mirror images of each other are chiral, such as the left and the right hand. (b) The unmarked flask is achiral because it can be superimposed on its mirror image.<\/p>\n<\/div>\n<\/div>\n<p>Most chiral organic molecules have at least one carbon atom that is bonded to four different groups, as occurs in the bromochlorofluoromethane molecule shown in part (a) in Figure 5.9.2. This carbon, often designated by an asterisk in structural drawings, is called a chiral center or asymmetric carbon atom. If the bromine atom is replaced by another chlorine (part (b) in Figure 5.9.2), the molecule and its mirror image can now be superimposed by simple rotation. Thus the carbon is no longer a chiral center. Asymmetric carbon atoms are found in many naturally occurring molecules, such as lactic acid, which is present in milk and muscles, and nicotine, a component of tobacco. A molecule and its nonsuperimposable mirror image are called enantiomers (from the Greek enantiou, meaning \u201copposite\u201d).<\/p>\n<div>\n<div style=\"width: 471px\" class=\"wp-caption aligncenter\"><img loading=\"lazy\" decoding=\"async\" class=\"internal\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05133306\/8db206d9deaa4b1b4b4af6260048d343.jpg\" alt=\"\" width=\"461\" height=\"343\" \/><\/p>\n<p class=\"wp-caption-text\">Figure 2: Comparison of Chiral and Achiral Molecules. (a) Bromochlorofluoromethane is a chiral molecule whose stereocenter is designated with an asterisk. Rotation of its mirror image does not generate the original structure. To superimpose the mirror images, bonds must be broken and reformed. (b) In contrast, dichlorofluoromethane and its mirror image can be rotated so they are superimposable.<\/p>\n<\/div>\n<div id=\"section_4\">\n<div class=\"textbox exercises\">\n<h3>Exercises<\/h3>\n<div id=\"section_4\">\n<div id=\"s61692\">\n<div id=\"section_27\">\n<h3 id=\"Questions-61692\">Questions<\/h3>\n<p><strong>1.<\/strong><\/p>\n<p>What kind of isomers are the following pairs:<\/p>\n<p>A \u2013 (<em>R<\/em>)-5-chlorohexene and 6-chlorohexene<\/p>\n<p>B \u2013 (2<em>R<\/em>,3<em>R<\/em>)-dibromohexane and (2<em>R<\/em>,3<em>S<\/em>)-dibromohexan<\/p>\n<\/div>\n<div id=\"section_28\">\n<h3 id=\"Solutions-61692\">Solution<\/h3>\n<p><strong>1.<\/strong><\/p>\n<div class=\"qa-wrapper\" style=\"display: block\"><span class=\"show-answer collapsed\" style=\"cursor: pointer\" data-target=\"q144603\">Show Answer<\/span><\/p>\n<div id=\"q144603\" class=\"hidden-answer\" style=\"display: none\">A = Structural Isomers B = Diastereomers<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<div id=\"section_5\">\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<\/ul>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n","protected":false},"author":44985,"menu_order":9,"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-836","chapter","type-chapter","status-publish","hentry"],"part":22,"_links":{"self":[{"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapters\/836","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\/44985"}],"version-history":[{"count":5,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapters\/836\/revisions"}],"predecessor-version":[{"id":2267,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapters\/836\/revisions\/2267"}],"part":[{"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/parts\/22"}],"metadata":[{"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapters\/836\/metadata\/"}],"wp:attachment":[{"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/wp\/v2\/media?parent=836"}],"wp:term":[{"taxonomy":"chapter-type","embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapter-type?post=836"},{"taxonomy":"contributor","embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/wp\/v2\/contributor?post=836"},{"taxonomy":"license","embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/wp\/v2\/license?post=836"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}