{"id":1830,"date":"2018-11-29T22:58:22","date_gmt":"2018-11-29T22:58:22","guid":{"rendered":"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry2\/?post_type=chapter&#038;p=1830"},"modified":"2019-01-09T07:11:28","modified_gmt":"2019-01-09T07:11:28","slug":"21-4-imine-formation","status":"publish","type":"chapter","link":"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry2\/chapter\/21-4-imine-formation\/","title":{"raw":"21.4. Imine formation","rendered":"21.4. Imine formation"},"content":{"raw":"<header>\r\n<div>\r\n<h2>Nucleophilic addition of amines: Imine and enamine formation<\/h2>\r\n<\/div>\r\n<\/header><article id=\"elm-main-content\" class=\"elm-content-container\"><header>\r\n<div class=\"textbox learning-objectives\">\r\n<h3>Objectives<\/h3>\r\n<header>\r\n<dl class=\"mt-last-updated-container\"><\/dl>\r\n<\/header><section class=\"mt-content-container\">\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 equations to describe the reactions that occur between aldehydes or ketones and primary or secondary amines.<\/li>\r\n \t<li>identify the product formed from the reaction of a given aldehyde or ketone with a given primary or secondary amine.<\/li>\r\n \t<li>identify the aldehyde or ketone, the amine, or both, required in the synthesis of a given imine or enamine.<\/li>\r\n \t<li>write the detailed mechanism for the reaction of an aldehyde or ketone with a primary amine.<\/li>\r\n \t<li>write the detailed mechanism for the reaction of an aldehyde or ketone with a secondary amine.<\/li>\r\n<\/ol>\r\n<\/div>\r\n<\/section><\/div>\r\n<\/header><section class=\"mt-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 terms below.\r\n<ul>\r\n \t<li>2,4\u2011dinitrophenylhydrazone<\/li>\r\n \t<li>enamine<\/li>\r\n \t<li>imine<\/li>\r\n<\/ul>\r\n<\/div>\r\n<\/div>\r\n<div id=\"note\">\r\n<div class=\"textbox\">\r\n<h3 class=\"boxtitle\">Study Notes<\/h3>\r\nAn imine is a compound that contains the structural unit\r\n<p class=\"max-66\"><img class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/29225614\/19-8a.png\" alt=\"general structure of an imine\" \/><\/p>\r\nAn enamine is a compound that contains the structural unit\r\n<p class=\"max-66\"><img class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/29225615\/19-8b.png\" alt=\"general structure of an enamine\" \/><\/p>\r\nBoth of these types of compound can be prepared through the reaction of an aldehyde or ketone with an amine.\r\n\r\nYou may have the opportunity to observe the reaction of an aldehyde and ketone with 2,4\u2011dinitrophenylhydrazine (Brady\u2019s reagent) to form a 2,4\u2011dinitrophenylhydrozone in the laboratory. This is a classical organic chemistry test to confirm the presence of a carbonyl group. The reaction produces very colourful and bright precipitates of yellow, orange and red.\r\n\r\nIf you can understand why the two reactions of imine and enamine formation are essentially identical, and can write a detailed mechanism for each one, you are well on the way to mastering organic chemistry. If you understand how and why these reactions occur, you can keep the amount of material that you need to memorize to a minimum.\r\n\r\n<\/div>\r\n<\/div>\r\n<div id=\"section_1\" class=\"mt-section\">\r\n<h2 class=\"editable\"><span class=\"title mt-title-edit\">Reaction with primary amines to form imines<\/span><\/h2>\r\n<div id=\"s5825\" class=\"mt-include\">\r\n\r\nThe reaction of <a title=\"Aldehydes &amp; Ketones\" href=\"https:\/\/chem.libretexts.org\/Textbook_Maps\/Organic_Chemistry\/Supplemental_Modules_(Organic_Chemistry)\/Aldehydes_and_Ketones\" rel=\"internal\">aldehydes <\/a>and ketones with ammonia or 1\u00ba-amines forms imine derivatives, also known as Schiff bases (compounds having a C=N function). Water is eliminated in the reaction, which is acid-catalyzed and reversible in the same sense as acetal formation. The pH for reactions which form imine compounds must be carefully controlled. The rate at which these imine compounds are formed is generally greatest near a pH of 5, and drops at higher and lower pH's. At high pH there will not be enough acid to protonate the OH in the intermediate to allow for removal as H<sub>2<\/sub>O. At low pH most of the amine reactant will be tied up as its ammonium conjugate acid and will become non-nucleophilic.\r\n\r\n<img class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/29225616\/1.jpg\" alt=\"1.jpg\" \/>\r\n\r\nConverting reactants to products simply\r\n\r\n<img class=\"internal\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/29225619\/2.jpg\" alt=\"2.jpg\" \/>\r\n<div class=\"mt-section\">\r\n\r\n&nbsp;\r\n<h3 id=\"Examples_of_imine_forming_reactions-5825\">\u00a0Examples of imine forming reactions<\/h3>\r\n<img class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/29225621\/3.jpg\" alt=\"3.jpg\" \/>\r\n\r\n<img class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/29225623\/4.jpg\" alt=\"4.jpg\" \/>\r\n\r\n<\/div>\r\n<div id=\"section_2\" class=\"mt-section\">\r\n\r\n&nbsp;\r\n<h3 id=\"Mechanism_of_imine_formation-5825\">Mechanism of imine formation<\/h3>\r\n1) Nucleophilic addition\r\n\r\n<img class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/29225626\/5.jpg\" alt=\"5.jpg\" width=\"397\" height=\"198\" \/>\r\n\r\n2) Proton transfer\r\n\r\n<img class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/29225628\/6.jpg\" alt=\"6.jpg\" width=\"325\" height=\"161\" \/>\r\n\r\n3)\u00a0 Protonation of OH\r\n\r\n<img class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/29225630\/7.jpg\" alt=\"7.jpg\" width=\"498\" height=\"152\" \/>\r\n\r\n4)\u00a0 Removal of water (nucleophile elimination)\r\n\r\n<img class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/29225634\/8.jpg\" alt=\"8.jpg\" width=\"331\" height=\"169\" \/>\r\n\r\n5)\u00a0 Deprotonation\r\n\r\n<img class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/29225637\/9.jpg\" alt=\"9.jpg\" width=\"509\" height=\"88\" \/>\r\n\r\n<\/div>\r\n<div id=\"section_3\" class=\"mt-section\">\r\n<h3 id=\"Reversibility_of_imine_forming_reactions-5825\">Reversibility of imine forming reactions<\/h3>\r\nImines can be hydrolyzed back to the corresponding primary amine under acidic conditions.\r\n\r\n<img class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/29225639\/10.jpg\" alt=\"10.jpg\" \/>\r\n\r\n<\/div>\r\n<div id=\"section_4\" class=\"mt-section\">\r\n<h3 id=\"Reactions_involving_other_reagents_of_the_type_Y-NH2-5825\">Reactions involving other reagents of the type Y-NH<sub>2<\/sub><\/h3>\r\nImines are sometimes difficult to isolate and purify due to their sensitivity to hydrolysis. Consequently, other reagents of the type Y\u2013NH<sub>2<\/sub> have been studied, and found to give stable products (R<sub>2<\/sub>C=N\u2013Y) useful in characterizing the aldehydes and ketones from which they are prepared. Some of these reagents are listed in the following table, together with the structures and names of their carbonyl reaction products. Hydrazones are used as part of the Wolff-Kishner reduction and will be discussed in more detail in <a href=\"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry2\/chapter\/21-6-wolff-kishner-reduction\/\">section 21.6<\/a>.\r\n\r\n<img class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/29225641\/11.jpg\" alt=\"11.jpg\" \/>\r\n\r\nWith the exception of unsubstituted hydrazones, these derivatives are easily prepared and are often crystalline solids - even when the parent aldehyde or ketone is a liquid. Since melting points can be determined more quickly and precisely than boiling points, derivatives such as these are useful for comparison and identification of carbonyl compounds.\u00a0 It should be noted that although semicarbazide has two amino groups (\u2013NH<sub>2<\/sub>) only one of them is a reactive amine. The other is amide-like and is deactivated by the adjacent carbonyl group.\r\n\r\n<\/div>\r\n<div id=\"section_5\" class=\"mt-section\">\r\n<div class=\"textbox exercises\">\r\n<h3>Exercises<\/h3>\r\n<div id=\"section_5\" class=\"mt-section\">\r\n\r\n1)Please draw the products of the following reactions.\r\n\r\n<img class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/29225644\/12.jpg\" alt=\"12.jpg\" \/>\r\n\r\n2) Please draw the structure of the reactant needed to produce the indicated product.\r\n\r\n<img class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/29225646\/14.jpg\" alt=\"14.jpg\" \/>\r\n\r\n3)\u00a0 Please draw the products of the following reactions.\r\n\r\n<\/div>\r\n<div id=\"section_6\" class=\"mt-section\">\r\n\r\n&nbsp;\r\n<h3 id=\"Answers-5825\">Answers<\/h3>\r\n[reveal-answer q=\"791143\"]Show Answer[\/reveal-answer]\r\n[hidden-answer a=\"791143\"]\r\n\r\n1)\r\n\r\n<img class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/29225648\/15.jpg\" alt=\"15.jpg\" \/>\r\n\r\n2)\r\n\r\n<img class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/29225651\/16.jpg\" alt=\"16.jpg\" \/>\r\n\r\n3)\r\n\r\n<img class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/29225653\/17.jpg\" alt=\"17.jpg\" \/>\r\n\r\n[\/hidden-answer]\r\n\r\n<\/div>\r\n<\/div>\r\n<span style=\"color: #6c64ad;font-size: 1em;font-weight: 600\">Contributors<\/span>\r\n\r\n<\/div>\r\n<div id=\"section_7\" class=\"mt-section\">\r\n\r\nProf. 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>)\r\n\r\nWilliam 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=\"Template:ContribReusch\" href=\"https:\/\/www2.chemistry.msu.edu\/faculty\/reusch\/VirtTxtJml\/intro1.htm\" target=\"_blank\" rel=\"external nofollow noopener\">Virtual Textbook of\u00a0Organic\u00a0Chemistry<\/a>\r\n\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<div class=\"mt-section\">\r\n<h2><\/h2>\r\n<h2 class=\"editable\"><span class=\"title mt-title-edit\">Reaction with secondary amines to form enamines<\/span><\/h2>\r\nMost aldehydes and ketones react with 2\u00ba-amines to give products known as <a title=\"http:\/\/chemwiki.ucdavis.edu\/Organic_Chemistry\/Reactivity_of_Alpha_Hydrogens\/Enamine_Reactions\" href=\"https:\/\/chem.libretexts.org\/Textbook_Maps\/Organic_Chemistry\/Supplemental_Modules_(Organic_Chemistry)\/Reactions\/Reactivity_of_Alpha_Hydrogens\/Enamine_Reactions\" rel=\"internal\"><strong>enamines<\/strong><\/a>. It should be noted that, like acetal formation, these are acid-catalyzed reversible reactions in which water is lost. Consequently, enamines are easily converted back to their carbonyl precursors by acid-catalyzed hydrolysis.\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/29225655\/1a.jpg\" alt=\"1a.jpg\" width=\"467.997161865234px\" height=\"133.991470336914px\" \/>\r\n\r\n&nbsp;\r\n<div class=\"mt-section\">\r\n<h3 class=\"editable\">Mechanism<\/h3>\r\n1) Nucleophilic addition\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/29225658\/3a.jpg\" alt=\"3a.jpg\" \/>\r\n\r\n2) Proton transfer\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/29225700\/4a.jpg\" alt=\"4a.jpg\" \/>\r\n\r\n3)\u00a0 Protonation of OH\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/29225702\/5a.jpg\" alt=\"5a.jpg\" \/>\r\n\r\n4)\u00a0 Removal of water (nucleophile elimination)\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/29225705\/6a.jpg\" alt=\"6a.jpg\" \/>\r\n\r\n5)\u00a0 Deprotonation\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/29225707\/7a.jpg\" alt=\"7a.jpg\" \/>\r\n\r\n&nbsp;\r\n\r\n<\/div>\r\n<div class=\"mt-section\">\r\n\r\n&nbsp;\r\n<h3 class=\"editable\">Reversibility of Enamines<\/h3>\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/29225709\/8a.jpg\" alt=\"8a.jpg\" \/>\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/29225711\/9a.jpg\" alt=\"9a.jpg\" \/>\r\n\r\n<\/div>\r\n<div class=\"mt-section\">\r\n\r\n&nbsp;\r\n<div class=\"textbox exercises\">\r\n<h3>Exercises<\/h3>\r\n<div class=\"mt-section\">\r\n\r\n1) Please draw the products for the following reactions.\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/29225714\/10a.jpg\" alt=\"10a.jpg\" \/>\r\n\r\n2)\u00a0 Please give the structure of the reactant needed to product the following product\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/29225717\/11a.jpg\" alt=\"11a.jpg\" \/>\r\n\r\n<\/div>\r\n<div class=\"mt-section\">\r\n\r\n&nbsp;\r\n<h3 class=\"editable\">Answers<\/h3>\r\n[reveal-answer q=\"813515\"]Show Answer[\/reveal-answer]\r\n[hidden-answer a=\"813515\"]\r\n\r\n1)\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/29225718\/12a.jpg\" alt=\"12a.jpg\" \/>\r\n\r\n2)\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/29225720\/13a.jpg\" alt=\"13a.jpg\" \/>[\/hidden-answer]\r\n\r\n<\/div>\r\n<\/div>\r\n<span style=\"color: #6c64ad;font-size: 1em;font-weight: 600\">Contributors<\/span>\r\n\r\n<\/div>\r\n<div class=\"mt-section\">\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>\r\n<\/section><\/article>","rendered":"<header>\n<div>\n<h2>Nucleophilic addition of amines: Imine and enamine formation<\/h2>\n<\/div>\n<\/header>\n<article id=\"elm-main-content\" class=\"elm-content-container\">\n<header>\n<div class=\"textbox learning-objectives\">\n<h3>Objectives<\/h3>\n<\/div>\n<\/header>\n<header>\n<dl class=\"mt-last-updated-container\"><\/dl>\n<\/header>\n<section class=\"mt-content-container\">\n<div id=\"skills\">\n<p>After completing this section, you should be able to<\/p>\n<ol>\n<li>write equations to describe the reactions that occur between aldehydes or ketones and primary or secondary amines.<\/li>\n<li>identify the product formed from the reaction of a given aldehyde or ketone with a given primary or secondary amine.<\/li>\n<li>identify the aldehyde or ketone, the amine, or both, required in the synthesis of a given imine or enamine.<\/li>\n<li>write the detailed mechanism for the reaction of an aldehyde or ketone with a primary amine.<\/li>\n<li>write the detailed mechanism for the reaction of an aldehyde or ketone with a secondary amine.<\/li>\n<\/ol>\n<\/div>\n<\/section>\n<section class=\"mt-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 terms below.<\/p>\n<ul>\n<li>2,4\u2011dinitrophenylhydrazone<\/li>\n<li>enamine<\/li>\n<li>imine<\/li>\n<\/ul>\n<\/div>\n<\/div>\n<div id=\"note\">\n<div class=\"textbox\">\n<h3 class=\"boxtitle\">Study Notes<\/h3>\n<p>An imine is a compound that contains the structural unit<\/p>\n<p class=\"max-66\"><img decoding=\"async\" class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/29225614\/19-8a.png\" alt=\"general structure of an imine\" \/><\/p>\n<p>An enamine is a compound that contains the structural unit<\/p>\n<p class=\"max-66\"><img decoding=\"async\" class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/29225615\/19-8b.png\" alt=\"general structure of an enamine\" \/><\/p>\n<p>Both of these types of compound can be prepared through the reaction of an aldehyde or ketone with an amine.<\/p>\n<p>You may have the opportunity to observe the reaction of an aldehyde and ketone with 2,4\u2011dinitrophenylhydrazine (Brady\u2019s reagent) to form a 2,4\u2011dinitrophenylhydrozone in the laboratory. This is a classical organic chemistry test to confirm the presence of a carbonyl group. The reaction produces very colourful and bright precipitates of yellow, orange and red.<\/p>\n<p>If you can understand why the two reactions of imine and enamine formation are essentially identical, and can write a detailed mechanism for each one, you are well on the way to mastering organic chemistry. If you understand how and why these reactions occur, you can keep the amount of material that you need to memorize to a minimum.<\/p>\n<\/div>\n<\/div>\n<div id=\"section_1\" class=\"mt-section\">\n<h2 class=\"editable\"><span class=\"title mt-title-edit\">Reaction with primary amines to form imines<\/span><\/h2>\n<div id=\"s5825\" class=\"mt-include\">\n<p>The reaction of <a title=\"Aldehydes &amp; Ketones\" href=\"https:\/\/chem.libretexts.org\/Textbook_Maps\/Organic_Chemistry\/Supplemental_Modules_(Organic_Chemistry)\/Aldehydes_and_Ketones\" rel=\"internal\">aldehydes <\/a>and ketones with ammonia or 1\u00ba-amines forms imine derivatives, also known as Schiff bases (compounds having a C=N function). Water is eliminated in the reaction, which is acid-catalyzed and reversible in the same sense as acetal formation. The pH for reactions which form imine compounds must be carefully controlled. The rate at which these imine compounds are formed is generally greatest near a pH of 5, and drops at higher and lower pH&#8217;s. At high pH there will not be enough acid to protonate the OH in the intermediate to allow for removal as H<sub>2<\/sub>O. At low pH most of the amine reactant will be tied up as its ammonium conjugate acid and will become non-nucleophilic.<\/p>\n<p><img decoding=\"async\" class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/29225616\/1.jpg\" alt=\"1.jpg\" \/><\/p>\n<p>Converting reactants to products simply<\/p>\n<p><img decoding=\"async\" class=\"internal\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/29225619\/2.jpg\" alt=\"2.jpg\" \/><\/p>\n<div class=\"mt-section\">\n<p>&nbsp;<\/p>\n<h3 id=\"Examples_of_imine_forming_reactions-5825\">\u00a0Examples of imine forming reactions<\/h3>\n<p><img decoding=\"async\" class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/29225621\/3.jpg\" alt=\"3.jpg\" \/><\/p>\n<p><img decoding=\"async\" class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/29225623\/4.jpg\" alt=\"4.jpg\" \/><\/p>\n<\/div>\n<div id=\"section_2\" class=\"mt-section\">\n<p>&nbsp;<\/p>\n<h3 id=\"Mechanism_of_imine_formation-5825\">Mechanism of imine formation<\/h3>\n<p>1) Nucleophilic addition<\/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\/3773\/2018\/11\/29225626\/5.jpg\" alt=\"5.jpg\" width=\"397\" height=\"198\" \/><\/p>\n<p>2) Proton transfer<\/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\/3773\/2018\/11\/29225628\/6.jpg\" alt=\"6.jpg\" width=\"325\" height=\"161\" \/><\/p>\n<p>3)\u00a0 Protonation of OH<\/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\/3773\/2018\/11\/29225630\/7.jpg\" alt=\"7.jpg\" width=\"498\" height=\"152\" \/><\/p>\n<p>4)\u00a0 Removal of water (nucleophile elimination)<\/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\/3773\/2018\/11\/29225634\/8.jpg\" alt=\"8.jpg\" width=\"331\" height=\"169\" \/><\/p>\n<p>5)\u00a0 Deprotonation<\/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\/3773\/2018\/11\/29225637\/9.jpg\" alt=\"9.jpg\" width=\"509\" height=\"88\" \/><\/p>\n<\/div>\n<div id=\"section_3\" class=\"mt-section\">\n<h3 id=\"Reversibility_of_imine_forming_reactions-5825\">Reversibility of imine forming reactions<\/h3>\n<p>Imines can be hydrolyzed back to the corresponding primary amine under acidic conditions.<\/p>\n<p><img decoding=\"async\" class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/29225639\/10.jpg\" alt=\"10.jpg\" \/><\/p>\n<\/div>\n<div id=\"section_4\" class=\"mt-section\">\n<h3 id=\"Reactions_involving_other_reagents_of_the_type_Y-NH2-5825\">Reactions involving other reagents of the type Y-NH<sub>2<\/sub><\/h3>\n<p>Imines are sometimes difficult to isolate and purify due to their sensitivity to hydrolysis. Consequently, other reagents of the type Y\u2013NH<sub>2<\/sub> have been studied, and found to give stable products (R<sub>2<\/sub>C=N\u2013Y) useful in characterizing the aldehydes and ketones from which they are prepared. Some of these reagents are listed in the following table, together with the structures and names of their carbonyl reaction products. Hydrazones are used as part of the Wolff-Kishner reduction and will be discussed in more detail in <a href=\"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry2\/chapter\/21-6-wolff-kishner-reduction\/\">section 21.6<\/a>.<\/p>\n<p><img decoding=\"async\" class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/29225641\/11.jpg\" alt=\"11.jpg\" \/><\/p>\n<p>With the exception of unsubstituted hydrazones, these derivatives are easily prepared and are often crystalline solids &#8211; even when the parent aldehyde or ketone is a liquid. Since melting points can be determined more quickly and precisely than boiling points, derivatives such as these are useful for comparison and identification of carbonyl compounds.\u00a0 It should be noted that although semicarbazide has two amino groups (\u2013NH<sub>2<\/sub>) only one of them is a reactive amine. The other is amide-like and is deactivated by the adjacent carbonyl group.<\/p>\n<\/div>\n<div id=\"section_5\" class=\"mt-section\">\n<div class=\"textbox exercises\">\n<h3>Exercises<\/h3>\n<div id=\"section_5\" class=\"mt-section\">\n<p>1)Please draw the products of the following reactions.<\/p>\n<p><img decoding=\"async\" class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/29225644\/12.jpg\" alt=\"12.jpg\" \/><\/p>\n<p>2) Please draw the structure of the reactant needed to produce the indicated product.<\/p>\n<p><img decoding=\"async\" class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/29225646\/14.jpg\" alt=\"14.jpg\" \/><\/p>\n<p>3)\u00a0 Please draw the products of the following reactions.<\/p>\n<\/div>\n<div id=\"section_6\" class=\"mt-section\">\n<p>&nbsp;<\/p>\n<h3 id=\"Answers-5825\">Answers<\/h3>\n<div class=\"qa-wrapper\" style=\"display: block\"><span class=\"show-answer collapsed\" style=\"cursor: pointer\" data-target=\"q791143\">Show Answer<\/span><\/p>\n<div id=\"q791143\" class=\"hidden-answer\" style=\"display: none\">\n<p>1)<\/p>\n<p><img decoding=\"async\" class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/29225648\/15.jpg\" alt=\"15.jpg\" \/><\/p>\n<p>2)<\/p>\n<p><img decoding=\"async\" class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/29225651\/16.jpg\" alt=\"16.jpg\" \/><\/p>\n<p>3)<\/p>\n<p><img decoding=\"async\" class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/29225653\/17.jpg\" alt=\"17.jpg\" \/><\/p>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<p><span style=\"color: #6c64ad;font-size: 1em;font-weight: 600\">Contributors<\/span><\/p>\n<\/div>\n<div id=\"section_7\" class=\"mt-section\">\n<p>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>)<\/p>\n<p>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=\"Template:ContribReusch\" href=\"https:\/\/www2.chemistry.msu.edu\/faculty\/reusch\/VirtTxtJml\/intro1.htm\" target=\"_blank\" rel=\"external nofollow noopener\">Virtual Textbook of\u00a0Organic\u00a0Chemistry<\/a><\/p>\n<\/div>\n<\/div>\n<\/div>\n<div class=\"mt-section\">\n<h2><\/h2>\n<h2 class=\"editable\"><span class=\"title mt-title-edit\">Reaction with secondary amines to form enamines<\/span><\/h2>\n<p>Most aldehydes and ketones react with 2\u00ba-amines to give products known as <a title=\"http:\/\/chemwiki.ucdavis.edu\/Organic_Chemistry\/Reactivity_of_Alpha_Hydrogens\/Enamine_Reactions\" href=\"https:\/\/chem.libretexts.org\/Textbook_Maps\/Organic_Chemistry\/Supplemental_Modules_(Organic_Chemistry)\/Reactions\/Reactivity_of_Alpha_Hydrogens\/Enamine_Reactions\" rel=\"internal\"><strong>enamines<\/strong><\/a>. It should be noted that, like acetal formation, these are acid-catalyzed reversible reactions in which water is lost. Consequently, enamines are easily converted back to their carbonyl precursors by acid-catalyzed hydrolysis.<\/p>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/29225655\/1a.jpg\" alt=\"1a.jpg\" width=\"467.997161865234px\" height=\"133.991470336914px\" \/><\/p>\n<p>&nbsp;<\/p>\n<div class=\"mt-section\">\n<h3 class=\"editable\">Mechanism<\/h3>\n<p>1) Nucleophilic addition<\/p>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/29225658\/3a.jpg\" alt=\"3a.jpg\" \/><\/p>\n<p>2) Proton transfer<\/p>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/29225700\/4a.jpg\" alt=\"4a.jpg\" \/><\/p>\n<p>3)\u00a0 Protonation of OH<\/p>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/29225702\/5a.jpg\" alt=\"5a.jpg\" \/><\/p>\n<p>4)\u00a0 Removal of water (nucleophile elimination)<\/p>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/29225705\/6a.jpg\" alt=\"6a.jpg\" \/><\/p>\n<p>5)\u00a0 Deprotonation<\/p>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/29225707\/7a.jpg\" alt=\"7a.jpg\" \/><\/p>\n<p>&nbsp;<\/p>\n<\/div>\n<div class=\"mt-section\">\n<p>&nbsp;<\/p>\n<h3 class=\"editable\">Reversibility of Enamines<\/h3>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/29225709\/8a.jpg\" alt=\"8a.jpg\" \/><\/p>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/29225711\/9a.jpg\" alt=\"9a.jpg\" \/><\/p>\n<\/div>\n<div class=\"mt-section\">\n<p>&nbsp;<\/p>\n<div class=\"textbox exercises\">\n<h3>Exercises<\/h3>\n<div class=\"mt-section\">\n<p>1) Please draw the products for the following reactions.<\/p>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/29225714\/10a.jpg\" alt=\"10a.jpg\" \/><\/p>\n<p>2)\u00a0 Please give the structure of the reactant needed to product the following product<\/p>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/29225717\/11a.jpg\" alt=\"11a.jpg\" \/><\/p>\n<\/div>\n<div class=\"mt-section\">\n<p>&nbsp;<\/p>\n<h3 class=\"editable\">Answers<\/h3>\n<div class=\"qa-wrapper\" style=\"display: block\"><span class=\"show-answer collapsed\" style=\"cursor: pointer\" data-target=\"q813515\">Show Answer<\/span><\/p>\n<div id=\"q813515\" class=\"hidden-answer\" style=\"display: none\">\n<p>1)<\/p>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/29225718\/12a.jpg\" alt=\"12a.jpg\" \/><\/p>\n<p>2)<\/p>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/29225720\/13a.jpg\" alt=\"13a.jpg\" \/><\/div>\n<\/div>\n<\/div>\n<\/div>\n<p><span style=\"color: #6c64ad;font-size: 1em;font-weight: 600\">Contributors<\/span><\/p>\n<\/div>\n<div class=\"mt-section\">\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<\/section>\n<\/article>\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-1830\">\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>Imine formation. <strong>Authored by<\/strong>: Martin A. Walker. <strong>Provided by<\/strong>: SUNY Potsdam. <strong>Project<\/strong>: Organic chemistry: An open textbook. <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>19.8 Nucleophilic Addition of Amines: Imine and Enamine Formation. <strong>Authored by<\/strong>: Dr. Dietmar Kennepohl and Prof. Steven Farmer . <strong>Provided by<\/strong>: Chemistry LibreTexts. <strong>Located at<\/strong>: <a target=\"_blank\" href=\"https:\/\/chem.libretexts.org\/Textbook_Maps\/Organic_Chemistry\/Map%3A_Organic_Chemistry_(McMurry)\/Chapter_19%3A_Aldehydes_and_Ketones%3A_Nucleophilic_Addition_Reactions\/19.08_Nucleophilic_Addition_of_Amines%3A_Imine_and_Enamine_Formation\">https:\/\/chem.libretexts.org\/Textbook_Maps\/Organic_Chemistry\/Map%3A_Organic_Chemistry_(McMurry)\/Chapter_19%3A_Aldehydes_and_Ketones%3A_Nucleophilic_Addition_Reactions\/19.08_Nucleophilic_Addition_of_Amines%3A_Imine_and_Enamine_Formation<\/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><li>Organic Chemistry With a Biological Emphasis . <strong>Authored by<\/strong>: Tim Soderberg. <strong>Provided by<\/strong>: Chemistry LibreTexts. <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)\">https:\/\/chem.libretexts.org\/Textbook_Maps\/Organic_Chemistry\/Book%3A_Organic_Chemistry_with_a_Biological_Emphasis_(Soderberg)<\/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":4,"template":"","meta":{"_candela_citation":"[{\"type\":\"cc\",\"description\":\"19.8 Nucleophilic Addition of Amines: Imine and Enamine Formation\",\"author\":\"Dr. Dietmar Kennepohl and Prof. Steven Farmer \",\"organization\":\"Chemistry LibreTexts\",\"url\":\"https:\/\/chem.libretexts.org\/Textbook_Maps\/Organic_Chemistry\/Map%3A_Organic_Chemistry_(McMurry)\/Chapter_19%3A_Aldehydes_and_Ketones%3A_Nucleophilic_Addition_Reactions\/19.08_Nucleophilic_Addition_of_Amines%3A_Imine_and_Enamine_Formation\",\"project\":\"\",\"license\":\"cc-by-nc-sa\",\"license_terms\":\"\"},{\"type\":\"cc\",\"description\":\"Organic Chemistry With a Biological Emphasis \",\"author\":\"Tim Soderberg\",\"organization\":\"Chemistry LibreTexts\",\"url\":\"https:\/\/chem.libretexts.org\/Textbook_Maps\/Organic_Chemistry\/Book%3A_Organic_Chemistry_with_a_Biological_Emphasis_(Soderberg)\",\"project\":\"\",\"license\":\"cc-by-nc-sa\",\"license_terms\":\"\"},{\"type\":\"original\",\"description\":\"Imine formation\",\"author\":\"Martin A. Walker\",\"organization\":\"SUNY Potsdam\",\"url\":\"\",\"project\":\"Organic chemistry: An open textbook\",\"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-1830","chapter","type-chapter","status-publish","hentry"],"part":1683,"_links":{"self":[{"href":"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry2\/wp-json\/pressbooks\/v2\/chapters\/1830","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry2\/wp-json\/pressbooks\/v2\/chapters"}],"about":[{"href":"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry2\/wp-json\/wp\/v2\/types\/chapter"}],"author":[{"embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry2\/wp-json\/wp\/v2\/users\/311"}],"version-history":[{"count":10,"href":"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry2\/wp-json\/pressbooks\/v2\/chapters\/1830\/revisions"}],"predecessor-version":[{"id":3057,"href":"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry2\/wp-json\/pressbooks\/v2\/chapters\/1830\/revisions\/3057"}],"part":[{"href":"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry2\/wp-json\/pressbooks\/v2\/parts\/1683"}],"metadata":[{"href":"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry2\/wp-json\/pressbooks\/v2\/chapters\/1830\/metadata\/"}],"wp:attachment":[{"href":"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry2\/wp-json\/wp\/v2\/media?parent=1830"}],"wp:term":[{"taxonomy":"chapter-type","embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry2\/wp-json\/pressbooks\/v2\/chapter-type?post=1830"},{"taxonomy":"contributor","embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry2\/wp-json\/wp\/v2\/contributor?post=1830"},{"taxonomy":"license","embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry2\/wp-json\/wp\/v2\/license?post=1830"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}