{"id":434,"date":"2022-01-17T02:00:00","date_gmt":"2022-01-17T02:00:00","guid":{"rendered":"http:\/\/box5250.temp.domains\/~aceorgan\/blog\/?p=434"},"modified":"2022-01-19T01:12:17","modified_gmt":"2022-01-19T01:12:17","slug":"what-is-a-meso-compound","status":"publish","type":"post","link":"https:\/\/www.aceorganicchem.com\/blog\/what-is-a-meso-compound\/","title":{"rendered":"What is a Meso Compound: Surprisingly Not Chiral [with examples]"},"content":{"rendered":"\n<h1 class=\"wp-block-heading\" id=\"h-q-what-is-a-meso-compound\">Q: What is a meso compound?<\/h1>\n\n\n\n<h3 class=\"wp-block-heading\" id=\"h-q-why-should-we-care-about-them-in-our-organic-chemistry-class\">Q: Why should we care about them in our organic&nbsp;chemistry class?<\/h3>\n\n\n\n<h3 class=\"wp-block-heading\" id=\"h-we-care-because-this-is-an-easy-place-for-a-professor-to-try-to-trip-you-up\">We care because this is an easy place for a professor to try to trip you up.<\/h3>\n\n\n\n<p>What is a meso compound? Meso compounds are molecules that have multiple stereocenters but are superimposable&nbsp;on their mirror images. Meso compounds do not have an enantiomer but do have a&nbsp;plane of symmetry. Meso compounds are not optically active but are&nbsp;three-dimensionally shaped. &nbsp;They have dashes\/wedges on stereocenters, but they are not chiral.<\/p>\n\n\n\n<p><span style=\"text-decoration: underline;\"><strong>Test your molecule<\/strong><\/span>: flip all of the chiral centers and check to see if it is the&nbsp;same molecule as you had before you flipped the centers. If the molecule is the&nbsp;same, it is meso. &nbsp;If it is not superimposible on its mirror image, it is chiral. Below is a good example of this.<\/p>\n\n\n\n<p><strong><span style=\"text-decoration: underline;\">Question<\/span><\/strong>: How many forms of tartaric acid are there?<\/p>\n\n\n\n<p>If you use the general rule of 2<sup>N&nbsp;<\/sup>(pronounced &#8220;2 to the n-th power&#8221;)&nbsp;for number of diastereomers, where N is the&nbsp;number of stereocenters, you would be wrong in this case. &nbsp;Here is why: there are three forms of tartaric acid, (R,R), (S,S) and meso&nbsp;tartaric acid. Close examination shows that (R,S) and (S,R) tartaric acid are&nbsp;the same compound, making it meso.<\/p>\n\n\n\n<div class=\"wp-block-image\"><figure class=\"aligncenter size-large\"><a href=\"http:\/\/box5250.temp.domains\/~aceorgan\/blog\/wp-content\/uploads\/2013\/05\/Slide1.jpg\"><img loading=\"lazy\" decoding=\"async\" width=\"1024\" height=\"767\" src=\"https:\/\/www.aceorganicchem.com\/blog\/wp-content\/uploads\/2013\/05\/Slide1-1024x767.jpg\" alt=\"Meso compounds tartaric acid\" class=\"wp-image-435\" srcset=\"https:\/\/www.aceorganicchem.com\/blog\/wp-content\/uploads\/2013\/05\/Slide1-1024x767.jpg 1024w, https:\/\/www.aceorganicchem.com\/blog\/wp-content\/uploads\/2013\/05\/Slide1-300x224.jpg 300w\" sizes=\"auto, (max-width: 1024px) 100vw, 1024px\" \/><\/a><figcaption>(R,R) and (S,S) tartaric acid are on top. Meso tartaric acid is below<\/figcaption><\/figure><\/div>\n\n\n\n<p>You can also look at it as a Fischer projection, which is an even better way to see what is going on here. (Another reason why it pays to know all of the different types of structural representations)<\/p>\n\n\n\n<div class=\"wp-block-image\"><figure class=\"aligncenter size-large\"><a href=\"http:\/\/box5250.temp.domains\/~aceorgan\/blog\/wp-content\/uploads\/2013\/05\/Slide2.jpg\"><img loading=\"lazy\" decoding=\"async\" width=\"1024\" height=\"767\" src=\"https:\/\/www.aceorganicchem.com\/blog\/wp-content\/uploads\/2013\/05\/Slide2-1024x767.jpg\" alt=\"Fischer projections of tartaric acid\" class=\"wp-image-436\" srcset=\"https:\/\/www.aceorganicchem.com\/blog\/wp-content\/uploads\/2013\/05\/Slide2-1024x767.jpg 1024w, https:\/\/www.aceorganicchem.com\/blog\/wp-content\/uploads\/2013\/05\/Slide2-300x224.jpg 300w\" sizes=\"auto, (max-width: 1024px) 100vw, 1024px\" \/><\/a><figcaption>Again, meso tartaric acid has no enantiomer.<\/figcaption><\/figure><\/div>\n\n\n\n<p>This is a trick professors will try to pull in first semester organic chemistry,&nbsp;don&#8217;t get caught by it. Be sure to look for superimposable mirror images (meso&nbsp;compounds) when doing diastereomer problems on exams. Another place this trick&nbsp;will surface is in NMR problems and calculating the number of unique protons,&nbsp;but that is a post for another time.<\/p>\n\n\n\n<p>For more help with meso compounds, or to take advantage of our <a href=\"http:\/\/www.aceorganicchem.com\/organic-chemistry-practice-exams.html\" target=\"_blank\" rel=\"noopener noreferrer\">testbank <\/a>or any of our other free resources, please visit us at <a title=\"organic chemistry\" href=\"http:\/\/www.aceorganicchem.com\">organic chemistry<\/a>.<\/p>\n\n\n\n<div class=\"wp-block-image\"><figure class=\"aligncenter size-full\"><a href=\"https:\/\/www.aceorganicchem.com\/free.html\" target=\"_blank\" rel=\"noopener noreferrer\"><img loading=\"lazy\" decoding=\"async\" width=\"350\" height=\"250\" src=\"https:\/\/www.aceorganicchem.com\/blog\/wp-content\/uploads\/2017\/06\/Free-o-chem-study-guides.-Download-now..jpg\" alt=\"free organic chem study guide\" class=\"wp-image-772\" srcset=\"https:\/\/www.aceorganicchem.com\/blog\/wp-content\/uploads\/2017\/06\/Free-o-chem-study-guides.-Download-now..jpg 350w, https:\/\/www.aceorganicchem.com\/blog\/wp-content\/uploads\/2017\/06\/Free-o-chem-study-guides.-Download-now.-300x214.jpg 300w\" sizes=\"auto, (max-width: 350px) 100vw, 350px\" \/><\/a><\/figure><\/div>\n","protected":false},"excerpt":{"rendered":"<p>Q: What is a meso compound? Q: Why should we care about them in our organic&nbsp;chemistry class? We care because this is an easy place for a professor to try to trip you up. What is a meso compound? Meso compounds are molecules that have multiple stereocenters but are superimposable&nbsp;on their mirror images. Meso compounds [&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":[],"class_list":["post-434","post","type-post","status-publish","format-standard","hentry","category-o-chem-help"],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.4 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>What is a Meso Compound: Surprisingly Not Chiral [with examples]<\/title>\n<meta name=\"description\" content=\"What is a meso compound? 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His research focus was on novel pain killers which were more potent than morphine but designed to have fewer side effects. There may even be a patent or two that came out of it. Prior to all of this, he was a chemist at Procter and Gamble. After all of that, he (briefly) worked as a post-doctoral assistant at Syracuse University, working on novel organic light-emitting diodes (OLEDs). In between, he did NOT compete at the 1996 Olympics, make the Atlanta Braves opening day roster, or become the head coach of the Indiana Pacers, as he had intended. #fail During this entire time, he always loved helping students, especially if they were struggling with organic chemistry. 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