{"id":161,"date":"2022-01-17T20:24:00","date_gmt":"2022-01-17T20:24:00","guid":{"rendered":"http:\/\/organicchemistry.wordpress.com\/?p=161"},"modified":"2022-02-06T01:49:28","modified_gmt":"2022-02-06T01:49:28","slug":"organic-chemistry-help-symmetric-diols-came-from-the-pinacol-reaction","status":"publish","type":"post","link":"https:\/\/www.aceorganicchem.com\/blog\/organic-chemistry-help-symmetric-diols-came-from-the-pinacol-reaction\/","title":{"rendered":"Organic Chemistry Help: Symmetric diols from the Pinacol reaction"},"content":{"rendered":"\n<p>Some of your professors will try to sneak this one in on you during an exam:\u00a0 Your professor will ask you to synthesize the symmetric diol\u00a0shown below and you will either not know how or you will come up with a convoluted, difficult or wrong answer.\u00a0JUST REMEMBER: Symmetric diols came from the Pinacol reaction.<\/p>\n\n\n\n<div class=\"wp-block-image\"><figure class=\"aligncenter size-full\"><a href=\"http:\/\/box5250.temp.domains\/~aceorgan\/blog\/wp-content\/uploads\/2010\/04\/temp1.jpg\"><img loading=\"lazy\" decoding=\"async\" width=\"388\" height=\"182\" src=\"https:\/\/www.aceorganicchem.com\/blog\/wp-content\/uploads\/2010\/04\/temp1.jpg\" alt=\"\" class=\"wp-image-162\" title=\"temp1\" srcset=\"https:\/\/www.aceorganicchem.com\/blog\/wp-content\/uploads\/2010\/04\/temp1.jpg 388w, https:\/\/www.aceorganicchem.com\/blog\/wp-content\/uploads\/2010\/04\/temp1-300x140.jpg 300w\" sizes=\"auto, (max-width: 388px) 100vw, 388px\" \/><\/a><\/figure><\/div>\n\n\n\n<p>While not obvious, there is a very simple way to create a symmetric diol&nbsp;using the Pinacol reaction.&nbsp; Using a number of reducing agents, ketones and aldehydes can be coupled with themselves to form a symmetric diol, as shown below:<\/p>\n\n\n\n<div class=\"wp-block-image\"><figure class=\"aligncenter size-full\"><a href=\"http:\/\/box5250.temp.domains\/~aceorgan\/blog\/wp-content\/uploads\/2010\/04\/temp11.jpg\"><img loading=\"lazy\" decoding=\"async\" width=\"361\" height=\"321\" src=\"https:\/\/www.aceorganicchem.com\/blog\/wp-content\/uploads\/2010\/04\/temp11.jpg\" alt=\"\" class=\"wp-image-163\" title=\"temp1\" srcset=\"https:\/\/www.aceorganicchem.com\/blog\/wp-content\/uploads\/2010\/04\/temp11.jpg 361w, https:\/\/www.aceorganicchem.com\/blog\/wp-content\/uploads\/2010\/04\/temp11-300x266.jpg 300w, https:\/\/www.aceorganicchem.com\/blog\/wp-content\/uploads\/2010\/04\/temp11-337x300.jpg 337w\" sizes=\"auto, (max-width: 361px) 100vw, 361px\" \/><\/a><\/figure><\/div>\n\n\n\n<p>The reaction is also called the Pinacol Coupling Reaction and can be used on most aldehydes and ketones, but not on acid halides or carboxylic acids.&nbsp; Now to address the original synthetic problem above:<\/p>\n\n\n\n<div class=\"wp-block-image\"><figure class=\"aligncenter size-full\"><a href=\"http:\/\/box5250.temp.domains\/~aceorgan\/blog\/wp-content\/uploads\/2010\/04\/temp12.jpg\"><img loading=\"lazy\" decoding=\"async\" width=\"719\" height=\"84\" src=\"https:\/\/www.aceorganicchem.com\/blog\/wp-content\/uploads\/2010\/04\/temp12.jpg\" alt=\"\" class=\"wp-image-164\" title=\"temp1\" srcset=\"https:\/\/www.aceorganicchem.com\/blog\/wp-content\/uploads\/2010\/04\/temp12.jpg 719w, https:\/\/www.aceorganicchem.com\/blog\/wp-content\/uploads\/2010\/04\/temp12-300x35.jpg 300w, https:\/\/www.aceorganicchem.com\/blog\/wp-content\/uploads\/2010\/04\/temp12-500x58.jpg 500w\" sizes=\"auto, (max-width: 719px) 100vw, 719px\" \/><\/a><\/figure><\/div>\n\n\n\n<p>The first step is reaction of the reaction of ethyl lithium with ethanal to form 2-butanol.&nbsp; This is then oxidized to 2-butanone using Jones\u2019 oxidation.&nbsp; Now, under Pinacol Coupling conditions, 2-butanone is then reacted with itself using magnesium to form the final product.&nbsp;<\/p>\n\n\n\n<p><strong><span style=\"text-decoration: underline;\">Take Home Message<\/span><\/strong><strong>:&nbsp; Symmetric 1,2 diols<\/strong><strong>&nbsp;came from the Pinacol reaction<\/strong><strong>.&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; <\/strong><\/p>\n\n\n\n<p><strong>For more organic chemistry help, go to <a title=\"Organic Chemistry\" href=\"http:\/\/www.aceorganicchem.com\" target=\"_blank\" rel=\"noopener\">organic chemistry<\/a><\/strong><\/p>\n","protected":false},"excerpt":{"rendered":"<p>Some of your professors will try to sneak this one in on you during an exam:\u00a0 Your professor will ask you to synthesize the symmetric diol\u00a0shown below and you will either not know how or you will come up with a convoluted, difficult or wrong answer.\u00a0JUST REMEMBER: Symmetric diols came from the Pinacol reaction. While [&hellip;]<\/p>\n","protected":false},"author":2,"featured_media":0,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"om_disable_all_campaigns":false,"_monsterinsights_skip_tracking":false,"_monsterinsights_sitenote_active":false,"_monsterinsights_sitenote_note":"","_monsterinsights_sitenote_category":0,"site-sidebar-layout":"default","site-content-layout":"","ast-site-content-layout":"default","site-content-style":"default","site-sidebar-style":"default","ast-global-header-display":"","ast-banner-title-visibility":"","ast-main-header-display":"","ast-hfb-above-header-display":"","ast-hfb-below-header-display":"","ast-hfb-mobile-header-display":"","site-post-title":"","ast-breadcrumbs-content":"","ast-featured-img":"","footer-sml-layout":"","ast-disable-related-posts":"","theme-transparent-header-meta":"","adv-header-id-meta":"","stick-header-meta":"","header-above-stick-meta":"","header-main-stick-meta":"","header-below-stick-meta":"","astra-migrate-meta-layouts":"default","ast-page-background-enabled":"default","ast-page-background-meta":{"desktop":{"background-color":"","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-opacity":"","overlay-gradient":""},"tablet":{"background-color":"","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-opacity":"","overlay-gradient":""},"mobile":{"background-color":"","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-opacity":"","overlay-gradient":""}},"ast-content-background-meta":{"desktop":{"background-color":"var(--ast-global-color-5)","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-opacity":"","overlay-gradient":""},"tablet":{"background-color":"var(--ast-global-color-5)","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-opacity":"","overlay-gradient":""},"mobile":{"background-color":"var(--ast-global-color-5)","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-opacity":"","overlay-gradient":""}},"footnotes":""},"categories":[8],"tags":[46,21],"class_list":["post-161","post","type-post","status-publish","format-standard","hentry","category-o-chem-help","tag-organic-chemistry","tag-pinacol-coupling"],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.3 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Organic Chemistry Help: Symmetric diols from the Pinacol reaction<\/title>\n<meta name=\"description\" content=\"Symmetric diols in organic chemistry came from the Pinacol reaction. 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