{"id":1214,"date":"2017-10-12T15:31:56","date_gmt":"2017-10-12T15:31:56","guid":{"rendered":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/?post_type=chapter&#038;p=1214"},"modified":"2018-10-05T18:26:00","modified_gmt":"2018-10-05T18:26:00","slug":"alkylation-of-acetylide-anions","status":"publish","type":"chapter","link":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/chapter\/alkylation-of-acetylide-anions\/","title":{"raw":"Alkylation of Acetylide Anions","rendered":"Alkylation of Acetylide Anions"},"content":{"raw":"<div class=\"elm-header\">\r\n<div class=\"elm-header-custom\">\r\n<div class=\"textbox learning-objectives\">\r\n<h3>Objectives<\/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\r\n<ol>\r\n \t<li>write an equation to describe the reaction of an acetylide ion with an alkyl halide.<\/li>\r\n \t<li>discuss the importance of the reaction between acetylide ions and alkyl halides as a method of extending a carbon chain.<\/li>\r\n \t<li>identify the alkyne (and hence the acetylide ion) and the alkyl halide needed to synthesize a given alkyne.<\/li>\r\n \t<li>determine whether or not the reaction of an acetylide ion with a given alkyl halide will result in substitution or elimination, and draw the structure of the product formed in either case.<\/li>\r\n<\/ol>\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>\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>alkylation<\/li>\r\n<\/ul>\r\n<\/div>\r\n<div class=\"textbox\">\r\n<div>\r\n<h3>Study Notes<\/h3>\r\n<\/div>\r\n<div id=\"note\">\r\n\r\nThe alkylation of acetylide ions is important in organic synthesis because it is a reaction in which a new carbon-carbon bond is formed; hence, it can be used when an organic chemist is trying to build a complicated molecule from much simpler starting materials.\r\n\r\nThe alkyl halide used in this reaction must be primary. Thus, if you were asked for a suitable synthesis of 2,2-dimethyl-3-hexyne, you would choose to attack iodoethane with the anion of 3,3- dimethyl-1-butyne.<img class=\"aligncenter\" src=\"http:\/\/chem.libretexts.org\/@api\/deki\/files\/86907\/9-8a.png?origin=mt-web\" alt=\"3,3- dimethyl-1-butyne reaction with iodoethane\" \/>\r\n\r\nrather than to attack 2-iodo-2-methylpropane with the anion of 1-butyne.<img class=\"aligncenter\" src=\"http:\/\/chem.libretexts.org\/@api\/deki\/files\/86908\/9-8b.png?origin=mt-web\" alt=\"2-iodo-2-methylpropane reactionwith the anion of 1-butyne\" \/>\r\n\r\nThe reasons will be made clear in Chapter 11.\r\n\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<div id=\"section_1\">\r\n<h3 class=\"editable\">Nucleophilic\u00a0Substitution Reactions of Acetylides<\/h3>\r\nAcetylide\u00a0anions are strong bases and strong <a title=\"Electrophiles &amp; Nucleophiles\" href=\"\/Organic_Chemistry\/Fundamentals\/Acids_and_Bases%3B_Electrophiles_and_Nucleophiles\" rel=\"internal\">nucleophiles<\/a>. Therefore, they are able to displace halides and other leaving groups in substitution reactions. The product is a substituted alkyne.\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\/05144253\/clipboard_1395411301321.png\" alt=\"\" width=\"331px\" height=\"34px\" \/>\r\n\r\nBecause the ion is a very strong base, the substitution reaction is most efficient with methyl or <a title=\"Alkyl Halide Reactions\" href=\"\/Organic_Chemistry\/Alkyl_Halides\/Properties_of_Alkyl_Halides\/Haloalkanes\/Alkyl_Halide_Reactions\" rel=\"internal\">primary halides<\/a> without substitution near the reaction center,\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\/05144254\/clipboard_1395413624963.png\" alt=\"\" width=\"372px\" height=\"35px\" \/>\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\/05144256\/clipboard_1395413388514.png\" alt=\"\" width=\"325px\" height=\"42px\" \/>\r\n\r\nSecondary, tertiary or even bulky primary substrates will give elimination by the E2 mechanism.\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\/05144258\/clipboard_1395413821274.png\" alt=\"\" width=\"413px\" height=\"39px\" \/>\r\n\r\n<\/div>\r\n<div id=\"section_2\">\r\n<h3 class=\"editable\">Nucleophilic\u00a0Addition of Acetylides\u00a0to Carbonyls<\/h3>\r\nAcetylide anions will add to <a title=\"Aldehydes and Ketones\" href=\"https:\/\/chem.libretexts.org\/Core\/Organic_Chemistry\/Aldehydes_and_Ketones\" rel=\"internal\">aldehydes and ketones<\/a> to form <a title=\"Reactions of Alcohols with Base-Preparation of Alkoxides\" rel=\"broken\">alkoxides<\/a>, which, upon protonation, give propargyl alcohols.\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\/05144259\/clipboard_1395414402579.png\" alt=\"\" width=\"432px\" height=\"77px\" \/>\r\n\r\nWith aldehydes\u00a0and non-symmetric ketones, in the absence of chiral\u00a0catalyst, the product will be a racemic mixture of the two enantiomers.\r\n\r\n<\/div>\r\n<div id=\"section_3\">\r\n<div class=\"textbox exercises\">\r\n<h3>Exercise<\/h3>\r\n<div id=\"section_3\">\r\n\r\n1. The pK<sub>a<\/sub>\u200b of ammonia is 35. \u00a0Estimate the equilibrium constant for the deprotonation of pent-1-yne by amide, as shown above.\r\n<h3><strong>Answer<\/strong><\/h3>\r\n[reveal-answer q=\"420273\"]Show Answer[\/reveal-answer]\r\n[hidden-answer a=\"420273\"]\r\n\r\n1. \u00a0Assuming the pK<sub>a<\/sub>\u200b of pent-1-yne is about 25, then the difference in pK<sub>a<\/sub>s is 10. \u00a0Since pentyne is more acidic, the formation of the acetylide will be favored at equilibrium, so the equilibrium constant for the reaction is about 10<sup>1 <\/sup>[\/hidden-answer]\r\n<div id=\"s61714\">\r\n<div id=\"section_24\">\r\n<h3 id=\"Questions-61714\">Questions<\/h3>\r\n<b>1.<\/b>\r\n\r\nGive the possible reactants for the following formations:\r\n\r\n<img class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05144301\/9-8qu.png\" alt=\"\" width=\"395\" height=\"139\" \/>\r\n\r\n<b>2.\u00a0<\/b>\r\n\r\nPropose a synthetic route to produce 2-pentene from propyne and an alkyl halide.\r\n\r\n<\/div>\r\n<div id=\"section_25\">\r\n<h3 id=\"Solutions-61714\">Solutions<\/h3>\r\n[reveal-answer q=\"376891\"]Show Answer[\/reveal-answer]\r\n[hidden-answer a=\"376891\"]\r\n\r\n<b>1.<\/b>\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\/05144304\/9.8.png\" alt=\"\" width=\"503\" height=\"375\" \/>\r\n\r\n<strong>2.<\/strong>\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\/05144308\/9.82.png\" alt=\"\" width=\"519\" height=\"273\" \/>[\/hidden-answer]\r\n\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<div id=\"section_4\">\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<ul>\r\n \t<li><a class=\"external\" title=\"http:\/\/www.chem.purdue.edu\/wenthold\/\" href=\"http:\/\/www.chem.purdue.edu\/wenthold\/\" target=\"_blank\" rel=\"external nofollow noopener\">Prof. Paul G. Wenthold <\/a>(<a class=\"external\" title=\"http:\/\/www.chem.purdue.edu\/\" href=\"http:\/\/www.chem.purdue.edu\/\" target=\"_blank\" rel=\"external nofollow noopener\">Purdue University<\/a>)<\/li>\r\n<\/ul>\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>Objectives<\/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<\/p>\n<ol>\n<li>write an equation to describe the reaction of an acetylide ion with an alkyl halide.<\/li>\n<li>discuss the importance of the reaction between acetylide ions and alkyl halides as a method of extending a carbon chain.<\/li>\n<li>identify the alkyne (and hence the acetylide ion) and the alkyl halide needed to synthesize a given alkyne.<\/li>\n<li>determine whether or not the reaction of an acetylide ion with a given alkyl halide will result in substitution or elimination, and draw the structure of the product formed in either case.<\/li>\n<\/ol>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<div id=\"elm-main-content\" class=\"elm-content-container\">\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>alkylation<\/li>\n<\/ul>\n<\/div>\n<div class=\"textbox\">\n<div>\n<h3>Study Notes<\/h3>\n<\/div>\n<div id=\"note\">\n<p>The alkylation of acetylide ions is important in organic synthesis because it is a reaction in which a new carbon-carbon bond is formed; hence, it can be used when an organic chemist is trying to build a complicated molecule from much simpler starting materials.<\/p>\n<p>The alkyl halide used in this reaction must be primary. Thus, if you were asked for a suitable synthesis of 2,2-dimethyl-3-hexyne, you would choose to attack iodoethane with the anion of 3,3- dimethyl-1-butyne.<img decoding=\"async\" class=\"aligncenter\" src=\"http:\/\/chem.libretexts.org\/@api\/deki\/files\/86907\/9-8a.png?origin=mt-web\" alt=\"3,3- dimethyl-1-butyne reaction with iodoethane\" \/><\/p>\n<p>rather than to attack 2-iodo-2-methylpropane with the anion of 1-butyne.<img decoding=\"async\" class=\"aligncenter\" src=\"http:\/\/chem.libretexts.org\/@api\/deki\/files\/86908\/9-8b.png?origin=mt-web\" alt=\"2-iodo-2-methylpropane reactionwith the anion of 1-butyne\" \/><\/p>\n<p>The reasons will be made clear in Chapter 11.<\/p>\n<\/div>\n<\/div>\n<\/div>\n<div id=\"section_1\">\n<h3 class=\"editable\">Nucleophilic\u00a0Substitution Reactions of Acetylides<\/h3>\n<p>Acetylide\u00a0anions are strong bases and strong <a title=\"Electrophiles &amp; Nucleophiles\" href=\"\/Organic_Chemistry\/Fundamentals\/Acids_and_Bases%3B_Electrophiles_and_Nucleophiles\" rel=\"internal\">nucleophiles<\/a>. Therefore, they are able to displace halides and other leaving groups in substitution reactions. The product is a substituted alkyne.<\/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\/05144253\/clipboard_1395411301321.png\" alt=\"\" width=\"331px\" height=\"34px\" \/><\/p>\n<p>Because the ion is a very strong base, the substitution reaction is most efficient with methyl or <a title=\"Alkyl Halide Reactions\" href=\"\/Organic_Chemistry\/Alkyl_Halides\/Properties_of_Alkyl_Halides\/Haloalkanes\/Alkyl_Halide_Reactions\" rel=\"internal\">primary halides<\/a> without substitution near the reaction center,<\/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\/05144254\/clipboard_1395413624963.png\" alt=\"\" width=\"372px\" height=\"35px\" \/><\/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\/05144256\/clipboard_1395413388514.png\" alt=\"\" width=\"325px\" height=\"42px\" \/><\/p>\n<p>Secondary, tertiary or even bulky primary substrates will give elimination by the E2 mechanism.<\/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\/05144258\/clipboard_1395413821274.png\" alt=\"\" width=\"413px\" height=\"39px\" \/><\/p>\n<\/div>\n<div id=\"section_2\">\n<h3 class=\"editable\">Nucleophilic\u00a0Addition of Acetylides\u00a0to Carbonyls<\/h3>\n<p>Acetylide anions will add to <a title=\"Aldehydes and Ketones\" href=\"https:\/\/chem.libretexts.org\/Core\/Organic_Chemistry\/Aldehydes_and_Ketones\" rel=\"internal\">aldehydes and ketones<\/a> to form <a title=\"Reactions of Alcohols with Base-Preparation of Alkoxides\" rel=\"broken\">alkoxides<\/a>, which, upon protonation, give propargyl alcohols.<\/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\/05144259\/clipboard_1395414402579.png\" alt=\"\" width=\"432px\" height=\"77px\" \/><\/p>\n<p>With aldehydes\u00a0and non-symmetric ketones, in the absence of chiral\u00a0catalyst, the product will be a racemic mixture of the two enantiomers.<\/p>\n<\/div>\n<div id=\"section_3\">\n<div class=\"textbox exercises\">\n<h3>Exercise<\/h3>\n<div id=\"section_3\">\n<p>1. The pK<sub>a<\/sub>\u200b of ammonia is 35. \u00a0Estimate the equilibrium constant for the deprotonation of pent-1-yne by amide, as shown above.<\/p>\n<h3><strong>Answer<\/strong><\/h3>\n<div class=\"qa-wrapper\" style=\"display: block\"><span class=\"show-answer collapsed\" style=\"cursor: pointer\" data-target=\"q420273\">Show Answer<\/span><\/p>\n<div id=\"q420273\" class=\"hidden-answer\" style=\"display: none\">\n<p>1. \u00a0Assuming the pK<sub>a<\/sub>\u200b of pent-1-yne is about 25, then the difference in pK<sub>a<\/sub>s is 10. \u00a0Since pentyne is more acidic, the formation of the acetylide will be favored at equilibrium, so the equilibrium constant for the reaction is about 10<sup>1 <\/sup><\/div>\n<\/div>\n<div id=\"s61714\">\n<div id=\"section_24\">\n<h3 id=\"Questions-61714\">Questions<\/h3>\n<p><b>1.<\/b><\/p>\n<p>Give the possible reactants for the following formations:<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05144301\/9-8qu.png\" alt=\"\" width=\"395\" height=\"139\" \/><\/p>\n<p><b>2.\u00a0<\/b><\/p>\n<p>Propose a synthetic route to produce 2-pentene from propyne and an alkyl halide.<\/p>\n<\/div>\n<div id=\"section_25\">\n<h3 id=\"Solutions-61714\">Solutions<\/h3>\n<div class=\"qa-wrapper\" style=\"display: block\"><span class=\"show-answer collapsed\" style=\"cursor: pointer\" data-target=\"q376891\">Show Answer<\/span><\/p>\n<div id=\"q376891\" class=\"hidden-answer\" style=\"display: none\">\n<p><b>1.<\/b><\/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\/05144304\/9.8.png\" alt=\"\" width=\"503\" height=\"375\" \/><\/p>\n<p><strong>2.<\/strong><\/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\/05144308\/9.82.png\" alt=\"\" width=\"519\" height=\"273\" \/><\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<div id=\"section_4\">\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<ul>\n<li><a class=\"external\" title=\"http:\/\/www.chem.purdue.edu\/wenthold\/\" href=\"http:\/\/www.chem.purdue.edu\/wenthold\/\" target=\"_blank\" rel=\"external nofollow noopener\">Prof. Paul G. Wenthold <\/a>(<a class=\"external\" title=\"http:\/\/www.chem.purdue.edu\/\" href=\"http:\/\/www.chem.purdue.edu\/\" target=\"_blank\" rel=\"external nofollow noopener\">Purdue University<\/a>)<\/li>\n<\/ul>\n<\/div>\n<\/div>\n","protected":false},"author":44985,"menu_order":7,"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-1214","chapter","type-chapter","status-publish","hentry"],"part":25,"_links":{"self":[{"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapters\/1214","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\/1214\/revisions"}],"predecessor-version":[{"id":2324,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapters\/1214\/revisions\/2324"}],"part":[{"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/parts\/25"}],"metadata":[{"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapters\/1214\/metadata\/"}],"wp:attachment":[{"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/wp\/v2\/media?parent=1214"}],"wp:term":[{"taxonomy":"chapter-type","embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapter-type?post=1214"},{"taxonomy":"contributor","embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/wp\/v2\/contributor?post=1214"},{"taxonomy":"license","embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/wp\/v2\/license?post=1214"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}