{"id":611,"date":"2017-10-04T21:06:47","date_gmt":"2017-10-04T21:06:47","guid":{"rendered":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/?post_type=chapter&#038;p=611"},"modified":"2018-10-03T17:33:52","modified_gmt":"2018-10-03T17:33:52","slug":"conformations-of-polycyclic-molecules","status":"publish","type":"chapter","link":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/chapter\/conformations-of-polycyclic-molecules\/","title":{"raw":"Conformations of Polycyclic Molecules","rendered":"Conformations of Polycyclic Molecules"},"content":{"raw":"<div class=\"elm-header\">\r\n<div class=\"elm-header-custom\">\r\n<div class=\"textbox learning-objectives\">\r\n<h3>Objective<\/h3>\r\n<div id=\"elm-main-content\" class=\"elm-content-container\">\r\n<div>\r\n<div id=\"skills\">\r\n\r\nAfter completing this section, you should be able to draw the structures and construct molecular models of <em>cis<\/em>- and <em>trans<\/em>-decalin and of norbornane.\r\n\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\n<div class=\"elm-header\"><\/div>\r\n<div id=\"elm-main-content\" class=\"elm-content-container\">\r\n<div>\r\n<div>\r\n\r\nMake certain that you can define, and use in context, the key terms below.\r\n<ul>\r\n \t<li>bridgehead carbon atom<\/li>\r\n \t<li>polycyclic molecule<\/li>\r\n<\/ul>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<div id=\"elm-main-content\" class=\"elm-content-container\">\r\n<div id=\"note\">\r\n<div class=\"textbox\">\r\n<h3 class=\"boxtitle\">Study Notes<\/h3>\r\nA <em>bridgehead carbon atom<\/em> is a carbon atom which is shared by at least two rings. The hydrogen atom which is attached to a bridgehead carbon may be referred to as a bridgehead hydrogen.\r\n\r\nNote that bicyclo[2.2.1]heptane is the systematic name of norborane. You need not be concerned over the IUPAC name of norbornane. The nomenclature of compounds of this type is beyond the scope of this course.\r\n\r\n<\/div>\r\n<\/div>\r\n<div id=\"section_1\">\r\n<h3 class=\"editable\">Bicyclic\u00a0Ring Systems<\/h3>\r\n<div id=\"section_18\">\r\n\r\nA bridged bicycloalkane is a bicycloalkane whose molecule has two carbon atoms shared by all three rings identifiable in the molecule. \u00a0The two carbon atoms\u00a0shared\u00a0by the three rings are called bridgehead carbon atoms. \u00a0A bond or a chain of bonds connecting the bridgehead carbon atoms is called a bridge.\r\n\r\n<strong>Eg. 1: \u00a0Decalin<\/strong>\r\n\r\n<img class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04210608\/bridgedbicyloalkane1.png\" alt=\"\" width=\"496\" height=\"363\" \/>\r\n\r\n<strong>Eg. 2: \u00a0bicyclo[2.2.1]heptane<\/strong>\r\n\r\n<img class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04210612\/bridgedbicyloalkane2.png\" alt=\"\" width=\"469\" height=\"381\" \/>\r\n\r\nIf in a bridged bicycloalkane, the bridgehead carbons are directly bonded to each other, the compound is called a fused bicycloalkane. In other words, in a fused bicycloalkane, the number of carbon atoms in one of the three bridges is zero. eg: decalin\r\n\r\n<a title=\"Spirobicycloalkane\" href=\"https:\/\/chem.libretexts.org\/Reference\/Organic_Chemistry_Glossary\/Spirobicycloalkane\" rel=\"internal\">see also\u00a0spirobicycloalkane<\/a>\r\n\r\nDecalins can come in two diastereomers, the\u00a0<em>trans<\/em>- or\u00a0<em>cis<\/em>- diastereomer. \u00a0The\u00a0<em>trans<\/em>-diastereomer is a rigid structure which cannot undergo a ring flip. \u00a0The\u00a0<em>cis<\/em>-diastereomer is mobile and can ring flip to allow substituents to sit in the equatorial position.\r\n\r\n<img class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04210615\/decalins.png\" alt=\"\" width=\"602px\" height=\"221px\" \/>\r\n\r\n<\/div>\r\n<\/div>\r\n<div id=\"section_2\">\r\n<h3 class=\"editable\">Steroids<\/h3>\r\nSteroids include such well known compounds as cholesterol, sex hormones, birth control pills, cortisone, and anabolic steroids.\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\/04210617\/556steroid.gif\" alt=\"556steroid.gif\" width=\"154px\" height=\"100px\" \/>\r\n<div>\r\n<div id=\"section_3\">\r\n<h3 class=\"editable\">Cholesterol<\/h3>\r\nThe best known and most abundant steroid in the body is cholesterol. Cholesterol is formed in brain tissue, nerve tissue, and the blood stream. It is the major compound found in gallstones and <a class=\"external\" title=\"http:\/\/www.elmhurst.edu\/~chm\/vchembook\/558detergent.html#bile\" href=\"http:\/\/www.elmhurst.edu\/%7Echm\/vchembook\/558detergent.html#bile\" target=\"_blank\" rel=\"external nofollow noopener\">bile salts<\/a>. Cholesterol also contributes to the formation of deposits on the inner walls of blood vessels. These deposits harden and obstruct the flow of blood. This condition, known as atherosclerosis, results in various heart diseases, strokes, and high blood pressure.\r\n\r\nMuch research is currently underway to determine if a correlation exists between cholesterol levels in the blood and diet. Not only does cholesterol come from the diet, but cholesterol is synthesized in the body from carbohydrates and proteins as well as fat. Therefore, the elimination of cholesterol rich foods from the diet does not necessarily lower blood cholesterol levels. Some studies have found that if certain unsaturated fats and oils are substituted for saturated fats, the blood cholesterol level decreases. The research is incomplete on this problem.\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\/04210619\/556cholesterol.gif\" alt=\"556cholesterol.gif\" width=\"276px\" height=\"290px\" \/>\r\n\r\n<\/div>\r\n<\/div>\r\n<div>\r\n<div id=\"section_4\">\r\n<h3 class=\"editable\">Structures of Sex Hormones<\/h3>\r\nSex hormones are also steroids. The primary male hormone, testosterone, is responsible for the development of secondary sex characteristics. Two female sex hormones, progesterone and estrogen or estradiol control the ovulation cycle. Notice that the male and female hormones have only slight differences in structures, but yet have very different physiological effects.\r\n\r\nTestosterone promotes the normal development of male genital organs ans is synthesized from cholesterol in the testes. It also promotes secondary male sexual characteristics such as deep voice, facial and body hair.\r\n\r\nEstrogen, along with progesterone regulates changes occurring in the uterus and ovaries known as the menstrual cycle. For more details see <a class=\"external\" title=\"http:\/\/www.elmhurst.edu\/~chm\/vchembook\/558birth.html\" href=\"http:\/\/www.elmhurst.edu\/%7Echm\/vchembook\/558birth.html\" target=\"_blank\" rel=\"external nofollow noopener\">Birth Control<\/a>. Estrogen is synthesized from testosterone by making the first ring aromatic which results in mole double bonds, the loss of a methyl group and formation of an alcohol group.\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\/04210622\/556sexhormones.gif\" alt=\"556sexhormones.gif\" width=\"380px\" height=\"256px\" \/>\r\n\r\n<\/div>\r\n<\/div>\r\n<div id=\"section_5\">\r\n<div class=\"textbox exercises\">\r\n<h3>Exercises<\/h3>\r\n<div id=\"section_5\">\r\n<div id=\"s61691\">\r\n<div id=\"section_36\">\r\n<h3 id=\"Questions-61691\">Question<\/h3>\r\nSomeone stated that <em>trans<\/em>-decalin is more stable than <em>cis<\/em>-decalin. Explain why this is incorrect.\r\n\r\n<\/div>\r\n<div id=\"section_37\">\r\n<h3 id=\"Solutions-61691\">Solution<\/h3>\r\n[reveal-answer q=\"869347\"]Show Answer[\/reveal-answer]\r\n[hidden-answer a=\"869347\"]Cis-decalin is flexible and allows for large groups to be axial and therefore reduce strain in the molecule. The rigidity of the trans conformation would not allow it to flip, therefore adding to the intermolecular strain.[\/hidden-answer]\r\n\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:\/\/www.uvu.edu\/profpages\/profiles\/show\/user_id\/1776\" href=\"http:\/\/www.uvu.edu\/profpages\/profiles\/show\/user_id\/1776\" target=\"_blank\" rel=\"external nofollow noopener\"><span class=\"gD\">Gamini Gunawardena<\/span><\/a> from the <a class=\"external\" title=\"http:\/\/science.uvu.edu\/ochem\/\" href=\"http:\/\/science.uvu.edu\/ochem\/\" target=\"_blank\" rel=\"external nofollow noopener\">OChemPal <\/a>site (<a class=\"external\" title=\"http:\/\/www.uvu.edu\/chemistry\/\" href=\"http:\/\/www.uvu.edu\/chemistry\/\" target=\"_blank\" rel=\"external nofollow noopener\">Utah Valley University<\/a>)<\/li>\r\n<\/ul>\r\n<ul>\r\n \t<li><span class=\"person_name\">John D. Robert <\/span>and <span class=\"person_name\">Marjorie C.<\/span> <span class=\"person_name\">Caserio <\/span>(1977) <em>Basic Principles of Organic Chemistry, second edition.<\/em> W. A. Benjamin, Inc. , Menlo Park, CA. ISBN 0-8053-8329-8. This content is copyrighted under the following conditions, \"You are granted permission for individual, educational, research and non-commercial reproduction, distribution, display and performance of this work in any format.\"<\/li>\r\n<\/ul>\r\n<\/div>\r\n<\/div>\r\n<\/div>","rendered":"<div class=\"elm-header\">\n<div class=\"elm-header-custom\">\n<div class=\"textbox learning-objectives\">\n<h3>Objective<\/h3>\n<div id=\"elm-main-content\" class=\"elm-content-container\">\n<div>\n<div id=\"skills\">\n<p>After completing this section, you should be able to draw the structures and construct molecular models of <em>cis<\/em>&#8211; and <em>trans<\/em>-decalin and of norbornane.<\/p>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<div class=\"textbox key-takeaways\">\n<h3>Key TERMS<\/h3>\n<div class=\"elm-header\"><\/div>\n<div id=\"elm-main-content\" class=\"elm-content-container\">\n<div>\n<div>\n<p>Make certain that you can define, and use in context, the key terms below.<\/p>\n<ul>\n<li>bridgehead carbon atom<\/li>\n<li>polycyclic molecule<\/li>\n<\/ul>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<div id=\"elm-main-content\" class=\"elm-content-container\">\n<div id=\"note\">\n<div class=\"textbox\">\n<h3 class=\"boxtitle\">Study Notes<\/h3>\n<p>A <em>bridgehead carbon atom<\/em> is a carbon atom which is shared by at least two rings. The hydrogen atom which is attached to a bridgehead carbon may be referred to as a bridgehead hydrogen.<\/p>\n<p>Note that bicyclo[2.2.1]heptane is the systematic name of norborane. You need not be concerned over the IUPAC name of norbornane. The nomenclature of compounds of this type is beyond the scope of this course.<\/p>\n<\/div>\n<\/div>\n<div id=\"section_1\">\n<h3 class=\"editable\">Bicyclic\u00a0Ring Systems<\/h3>\n<div id=\"section_18\">\n<p>A bridged bicycloalkane is a bicycloalkane whose molecule has two carbon atoms shared by all three rings identifiable in the molecule. \u00a0The two carbon atoms\u00a0shared\u00a0by the three rings are called bridgehead carbon atoms. \u00a0A bond or a chain of bonds connecting the bridgehead carbon atoms is called a bridge.<\/p>\n<p><strong>Eg. 1: \u00a0Decalin<\/strong><\/p>\n<p><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\/04210608\/bridgedbicyloalkane1.png\" alt=\"\" width=\"496\" height=\"363\" \/><\/p>\n<p><strong>Eg. 2: \u00a0bicyclo[2.2.1]heptane<\/strong><\/p>\n<p><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\/04210612\/bridgedbicyloalkane2.png\" alt=\"\" width=\"469\" height=\"381\" \/><\/p>\n<p>If in a bridged bicycloalkane, the bridgehead carbons are directly bonded to each other, the compound is called a fused bicycloalkane. In other words, in a fused bicycloalkane, the number of carbon atoms in one of the three bridges is zero. eg: decalin<\/p>\n<p><a title=\"Spirobicycloalkane\" href=\"https:\/\/chem.libretexts.org\/Reference\/Organic_Chemistry_Glossary\/Spirobicycloalkane\" rel=\"internal\">see also\u00a0spirobicycloalkane<\/a><\/p>\n<p>Decalins can come in two diastereomers, the\u00a0<em>trans<\/em>&#8211; or\u00a0<em>cis<\/em>&#8211; diastereomer. \u00a0The\u00a0<em>trans<\/em>-diastereomer is a rigid structure which cannot undergo a ring flip. \u00a0The\u00a0<em>cis<\/em>-diastereomer is mobile and can ring flip to allow substituents to sit in the equatorial position.<\/p>\n<p><img decoding=\"async\" class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04210615\/decalins.png\" alt=\"\" width=\"602px\" height=\"221px\" \/><\/p>\n<\/div>\n<\/div>\n<div id=\"section_2\">\n<h3 class=\"editable\">Steroids<\/h3>\n<p>Steroids include such well known compounds as cholesterol, sex hormones, birth control pills, cortisone, and anabolic steroids.<\/p>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04210617\/556steroid.gif\" alt=\"556steroid.gif\" width=\"154px\" height=\"100px\" \/><\/p>\n<div>\n<div id=\"section_3\">\n<h3 class=\"editable\">Cholesterol<\/h3>\n<p>The best known and most abundant steroid in the body is cholesterol. Cholesterol is formed in brain tissue, nerve tissue, and the blood stream. It is the major compound found in gallstones and <a class=\"external\" title=\"http:\/\/www.elmhurst.edu\/~chm\/vchembook\/558detergent.html#bile\" href=\"http:\/\/www.elmhurst.edu\/%7Echm\/vchembook\/558detergent.html#bile\" target=\"_blank\" rel=\"external nofollow noopener\">bile salts<\/a>. Cholesterol also contributes to the formation of deposits on the inner walls of blood vessels. These deposits harden and obstruct the flow of blood. This condition, known as atherosclerosis, results in various heart diseases, strokes, and high blood pressure.<\/p>\n<p>Much research is currently underway to determine if a correlation exists between cholesterol levels in the blood and diet. Not only does cholesterol come from the diet, but cholesterol is synthesized in the body from carbohydrates and proteins as well as fat. Therefore, the elimination of cholesterol rich foods from the diet does not necessarily lower blood cholesterol levels. Some studies have found that if certain unsaturated fats and oils are substituted for saturated fats, the blood cholesterol level decreases. The research is incomplete on this problem.<\/p>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04210619\/556cholesterol.gif\" alt=\"556cholesterol.gif\" width=\"276px\" height=\"290px\" \/><\/p>\n<\/div>\n<\/div>\n<div>\n<div id=\"section_4\">\n<h3 class=\"editable\">Structures of Sex Hormones<\/h3>\n<p>Sex hormones are also steroids. The primary male hormone, testosterone, is responsible for the development of secondary sex characteristics. Two female sex hormones, progesterone and estrogen or estradiol control the ovulation cycle. Notice that the male and female hormones have only slight differences in structures, but yet have very different physiological effects.<\/p>\n<p>Testosterone promotes the normal development of male genital organs ans is synthesized from cholesterol in the testes. It also promotes secondary male sexual characteristics such as deep voice, facial and body hair.<\/p>\n<p>Estrogen, along with progesterone regulates changes occurring in the uterus and ovaries known as the menstrual cycle. For more details see <a class=\"external\" title=\"http:\/\/www.elmhurst.edu\/~chm\/vchembook\/558birth.html\" href=\"http:\/\/www.elmhurst.edu\/%7Echm\/vchembook\/558birth.html\" target=\"_blank\" rel=\"external nofollow noopener\">Birth Control<\/a>. Estrogen is synthesized from testosterone by making the first ring aromatic which results in mole double bonds, the loss of a methyl group and formation of an alcohol group.<\/p>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/04210622\/556sexhormones.gif\" alt=\"556sexhormones.gif\" width=\"380px\" height=\"256px\" \/><\/p>\n<\/div>\n<\/div>\n<div id=\"section_5\">\n<div class=\"textbox exercises\">\n<h3>Exercises<\/h3>\n<div id=\"section_5\">\n<div id=\"s61691\">\n<div id=\"section_36\">\n<h3 id=\"Questions-61691\">Question<\/h3>\n<p>Someone stated that <em>trans<\/em>-decalin is more stable than <em>cis<\/em>-decalin. Explain why this is incorrect.<\/p>\n<\/div>\n<div id=\"section_37\">\n<h3 id=\"Solutions-61691\">Solution<\/h3>\n<div class=\"qa-wrapper\" style=\"display: block\"><span class=\"show-answer collapsed\" style=\"cursor: pointer\" data-target=\"q869347\">Show Answer<\/span><\/p>\n<div id=\"q869347\" class=\"hidden-answer\" style=\"display: none\">Cis-decalin is flexible and allows for large groups to be axial and therefore reduce strain in the molecule. The rigidity of the trans conformation would not allow it to flip, therefore adding to the intermolecular strain.<\/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:\/\/www.uvu.edu\/profpages\/profiles\/show\/user_id\/1776\" href=\"http:\/\/www.uvu.edu\/profpages\/profiles\/show\/user_id\/1776\" target=\"_blank\" rel=\"external nofollow noopener\"><span class=\"gD\">Gamini Gunawardena<\/span><\/a> from the <a class=\"external\" title=\"http:\/\/science.uvu.edu\/ochem\/\" href=\"http:\/\/science.uvu.edu\/ochem\/\" target=\"_blank\" rel=\"external nofollow noopener\">OChemPal <\/a>site (<a class=\"external\" title=\"http:\/\/www.uvu.edu\/chemistry\/\" href=\"http:\/\/www.uvu.edu\/chemistry\/\" target=\"_blank\" rel=\"external nofollow noopener\">Utah Valley University<\/a>)<\/li>\n<\/ul>\n<ul>\n<li><span class=\"person_name\">John D. Robert <\/span>and <span class=\"person_name\">Marjorie C.<\/span> <span class=\"person_name\">Caserio <\/span>(1977) <em>Basic Principles of Organic Chemistry, second edition.<\/em> W. A. Benjamin, Inc. , Menlo Park, CA. ISBN 0-8053-8329-8. This content is copyrighted under the following conditions, &#8220;You are granted permission for individual, educational, research and non-commercial reproduction, distribution, display and performance of this work in any format.&#8221;<\/li>\n<\/ul>\n<\/div>\n<\/div>\n<\/div>\n","protected":false},"author":311,"menu_order":16,"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-611","chapter","type-chapter","status-publish","hentry"],"part":21,"_links":{"self":[{"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapters\/611","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\/611\/revisions"}],"predecessor-version":[{"id":2252,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapters\/611\/revisions\/2252"}],"part":[{"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/parts\/21"}],"metadata":[{"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapters\/611\/metadata\/"}],"wp:attachment":[{"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/wp\/v2\/media?parent=611"}],"wp:term":[{"taxonomy":"chapter-type","embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapter-type?post=611"},{"taxonomy":"contributor","embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/wp\/v2\/contributor?post=611"},{"taxonomy":"license","embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/wp\/v2\/license?post=611"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}