{"id":1876,"date":"2018-11-30T15:25:58","date_gmt":"2018-11-30T15:25:58","guid":{"rendered":"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry2\/?post_type=chapter&#038;p=1876"},"modified":"2019-01-09T06:32:05","modified_gmt":"2019-01-09T06:32:05","slug":"21-6-wolff-kishner-reduction","status":"publish","type":"chapter","link":"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry2\/chapter\/21-6-wolff-kishner-reduction\/","title":{"raw":"21.6. Wolff-Kishner reduction","rendered":"21.6. Wolff-Kishner reduction"},"content":{"raw":"<article id=\"elm-main-content\" class=\"elm-content-container\"><header>\r\n<dl class=\"mt-last-updated-container\"><\/dl>\r\n<\/header><section class=\"mt-content-container\">Aldehydes and ketones can be converted to a hydrazine derivative by reaction with hydrazine. These \"hydrazones\" can be further converted to the corresponding alkane by reaction with base and heat. These two steps can be combined into one reaction called the Wolff-Kishner Reduction which represents a general method for converting aldehydes and ketones into alkanes. Typically a high boiling point solvent, such as ethylene glycol, is used to provide the high temperatures needed for this reaction to occur. Note! Nitrogen gas is produced as part of this reaction.\u00a0 Formation of the strong N<span style=\"text-decoration: underline\">=<\/span>N triple bond provides the driving force for the reaction.\r\n<div id=\"section_1\" class=\"mt-section\">\r\n<h3 class=\"editable\">Reaction of Aldehydes or Ketones with Hydrazine Produces a Hydrazone<\/h3>\r\n<img class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30152440\/1.jpg\" alt=\"1.jpg\" width=\"572\" height=\"113\" \/>\r\n\r\n<\/div>\r\n<div id=\"section_2\" class=\"mt-section\">\r\n<h3 class=\"editable\">Reaction with a Base and Heat Converts a Hydrazone to an Alkane<\/h3>\r\n<img class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30152442\/2.jpg\" alt=\"2.jpg\" width=\"468\" height=\"123\" \/>\r\n\r\n<\/div>\r\n<div id=\"section_3\" class=\"mt-section\">\r\n<h3 class=\"editable\">Both Reactions Together Produces the Wolff-Kishner Reduction<\/h3>\r\n<img class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30152445\/3.jpg\" alt=\"3.jpg\" width=\"411\" height=\"130\" \/>\r\n<div class=\"textbox examples\">\r\n<h3>Example<\/h3>\r\n<img class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30152447\/4.jpg\" alt=\"4.jpg\" width=\"288\" height=\"92\" \/>\r\n\r\n<\/div>\r\n<\/div>\r\n<div id=\"section_4\" class=\"mt-section\">\r\n<h3 class=\"editable\">Mechanism of the Wolff-Kishner Reduction<\/h3>\r\n1) Deprotonation of Nitrogen\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\/30152449\/5.jpg\" alt=\"5.jpg\" \/>\r\n\r\n2) Protonation of the Carbon\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\/30152451\/6.jpg\" alt=\"6.jpg\" width=\"421\" height=\"155\" \/>\r\n\r\n3) Deprotonation of Nitrogen\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\/30152453\/7.jpg\" alt=\"7.jpg\" width=\"518\" height=\"85\" \/>\r\n\r\n4)\u00a0 Protonation of Carbon\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\/30152458\/8.jpg\" alt=\"8.jpg\" width=\"470\" height=\"73\" \/>\r\n\r\n<\/div>\r\n<div id=\"section_5\" class=\"mt-section\">\r\n<div class=\"textbox exercises\">\r\n<div id=\"section_5\" class=\"mt-section\">\r\n<h3 class=\"editable\">Problems<\/h3>\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\/30152500\/9.jpg\" alt=\"9.jpg\" width=\"307\" height=\"209\" \/>\r\n\r\n<\/div>\r\n<div id=\"section_6\" class=\"mt-section\">\r\n\r\n&nbsp;\r\n<h3 class=\"editable\">Answers<\/h3>\r\n1)<img class=\" wp-image-2473 aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/07192805\/ans.png\" alt=\"\" width=\"298\" height=\"113\" \/>\r\n\r\n<\/div>\r\n<\/div>\r\n<h3 class=\"editable\">Contributors<\/h3>\r\n<\/div>\r\n<div id=\"section_7\" class=\"mt-section\">\r\n<ul>\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=\"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><\/li>\r\n<\/ul>\r\n<\/div>\r\n<\/section><\/article>","rendered":"<article id=\"elm-main-content\" class=\"elm-content-container\">\n<header>\n<dl class=\"mt-last-updated-container\"><\/dl>\n<\/header>\n<section class=\"mt-content-container\">Aldehydes and ketones can be converted to a hydrazine derivative by reaction with hydrazine. These &#8220;hydrazones&#8221; can be further converted to the corresponding alkane by reaction with base and heat. These two steps can be combined into one reaction called the Wolff-Kishner Reduction which represents a general method for converting aldehydes and ketones into alkanes. Typically a high boiling point solvent, such as ethylene glycol, is used to provide the high temperatures needed for this reaction to occur. Note! Nitrogen gas is produced as part of this reaction.\u00a0 Formation of the strong N<span style=\"text-decoration: underline\">=<\/span>N triple bond provides the driving force for the reaction.<\/p>\n<div id=\"section_1\" class=\"mt-section\">\n<h3 class=\"editable\">Reaction of Aldehydes or Ketones with Hydrazine Produces a Hydrazone<\/h3>\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\/30152440\/1.jpg\" alt=\"1.jpg\" width=\"572\" height=\"113\" \/><\/p>\n<\/div>\n<div id=\"section_2\" class=\"mt-section\">\n<h3 class=\"editable\">Reaction with a Base and Heat Converts a Hydrazone to an Alkane<\/h3>\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\/30152442\/2.jpg\" alt=\"2.jpg\" width=\"468\" height=\"123\" \/><\/p>\n<\/div>\n<div id=\"section_3\" class=\"mt-section\">\n<h3 class=\"editable\">Both Reactions Together Produces the Wolff-Kishner Reduction<\/h3>\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\/30152445\/3.jpg\" alt=\"3.jpg\" width=\"411\" height=\"130\" \/><\/p>\n<div class=\"textbox examples\">\n<h3>Example<\/h3>\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\/30152447\/4.jpg\" alt=\"4.jpg\" width=\"288\" height=\"92\" \/><\/p>\n<\/div>\n<\/div>\n<div id=\"section_4\" class=\"mt-section\">\n<h3 class=\"editable\">Mechanism of the Wolff-Kishner Reduction<\/h3>\n<p>1) Deprotonation of Nitrogen<\/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\/30152449\/5.jpg\" alt=\"5.jpg\" \/><\/p>\n<p>2) Protonation of the Carbon<\/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\/30152451\/6.jpg\" alt=\"6.jpg\" width=\"421\" height=\"155\" \/><\/p>\n<p>3) Deprotonation of Nitrogen<\/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\/30152453\/7.jpg\" alt=\"7.jpg\" width=\"518\" height=\"85\" \/><\/p>\n<p>4)\u00a0 Protonation of Carbon<\/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\/30152458\/8.jpg\" alt=\"8.jpg\" width=\"470\" height=\"73\" \/><\/p>\n<\/div>\n<div id=\"section_5\" class=\"mt-section\">\n<div class=\"textbox exercises\">\n<div id=\"section_5\" class=\"mt-section\">\n<h3 class=\"editable\">Problems<\/h3>\n<p>1) Please draw the products of the following reactions.<\/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\/30152500\/9.jpg\" alt=\"9.jpg\" width=\"307\" height=\"209\" \/><\/p>\n<\/div>\n<div id=\"section_6\" class=\"mt-section\">\n<p>&nbsp;<\/p>\n<h3 class=\"editable\">Answers<\/h3>\n<p>1)<img loading=\"lazy\" decoding=\"async\" class=\"wp-image-2473 aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/07192805\/ans.png\" alt=\"\" width=\"298\" height=\"113\" \/><\/p>\n<\/div>\n<\/div>\n<h3 class=\"editable\">Contributors<\/h3>\n<\/div>\n<div id=\"section_7\" class=\"mt-section\">\n<ul>\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=\"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><\/li>\n<\/ul>\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-1876\">\n\t\t\t\t\t\t\t <div class=\"licensing\"><div class=\"license-attribution-dropdown-subheading\">CC licensed content, Shared previously<\/div><ul class=\"citation-list\"><li>Wolff-Kishner Reduction. <strong>Authored by<\/strong>: Prof. Steven Farmer and William Reusch. <strong>Provided by<\/strong>: Chemistry LibreTexts. <strong>Located at<\/strong>: <a target=\"_blank\" href=\"https:\/\/chem.libretexts.org\/?title=Textbook_Maps\/Organic_Chemistry\/Supplemental_Modules_(Organic_Chemistry)\/Aldehydes_and_Ketones\/Reactivity_of_Aldehydes_%26_Ketones\/Wolff-Kishner_Reduction\">https:\/\/chem.libretexts.org\/?title=Textbook_Maps\/Organic_Chemistry\/Supplemental_Modules_(Organic_Chemistry)\/Aldehydes_and_Ketones\/Reactivity_of_Aldehydes_%26_Ketones\/Wolff-Kishner_Reduction<\/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 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