{"id":1263,"date":"2011-01-12T19:48:59","date_gmt":"2011-01-13T00:48:59","guid":{"rendered":"https:\/\/www.masterorganicchemistry.com\/?p=1263"},"modified":"2026-04-18T06:09:03","modified_gmt":"2026-04-18T11:09:03","slug":"the-meso-trap","status":"publish","type":"post","link":"https:\/\/www.masterorganicchemistry.com\/2011\/01\/12\/the-meso-trap\/","title":{"rendered":"The Meso Trap"},"content":{"rendered":"<p><strong>Recognizing Meso Compounds<\/strong><\/p>\n<ul>\n<li>In chemistry, two molecules that are <strong>superimposable\u00a0<\/strong>mirror images are considered to be\u00a0<strong>identical<\/strong> molecules. They will have identical physical properties in all respects.<\/li>\n<li>Two molecules that are\u00a0<strong>non-superimposable<\/strong> mirror images are\u00a0<strong>enantiomers.\u00a0<\/strong>They will have identical physical properties\u00a0<strong>except<\/strong> they rotate plane-polarized light in equal and opposite directions.<\/li>\n<li><strong>Meso compounds<\/strong> contain chiral centers, but these chiral centers are arranged in such a way that the molecule has a\u00a0<strong>mirror plane\u00a0<\/strong>and is therefore\u00a0<strong>achiral\u00a0<\/strong>overall. A meso compound is\u00a0<strong>superimposable<\/strong> on its mirror image.<\/li>\n<li>Watch out for exam questions where two meso compounds are suggestively drawn as mirror images. They are not enantiomers. They are the same molecule, since they are superimposable!<\/li>\n<\/ul>\n<p><img fetchpriority=\"high\" decoding=\"async\" class=\"alignnone wp-image-38601\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2024\/11\/0-summary-of-meso-compounds-and-how-to-tell-if-a-compound-is-meso-update.gif\" alt=\"summary of meso compounds and how to tell if a compound is meso update\" width=\"640\" height=\"639\" \/><\/a><\/p>\n<p><strong>Table of Contents<\/strong><\/p>\n<ol>\n<li style=\"list-style-type: none;\">\n<ol>\n<li><a href=\"#one\">The Meso Trap<\/a><\/li>\n<li><a href=\"#two\">But Clearly There Are No Mirror Planes In\u00a0<em>These<\/em> Molecules&#8230;. (Right?)<\/a><\/li>\n<li><a href=\"#three\">Fischer Projections, Newman Projections, and Cyclohexane Chairs<\/a><\/li>\n<li><a href=\"#four\">Identifying Meso Compounds, Method One: Build A Model<\/a><\/li>\n<li><a href=\"#five\">Identifying Meso Compounds, Method Two: Determine (R,S)<\/a><\/li>\n<li><a href=\"#six\">Reviewing &#8220;Enantiomers, Diastereomers, or The Same&#8221; Questions<\/a><\/li>\n<li><a href=\"#notes\">Notes<\/a><\/li>\n<li><a href=\"#quiz\">Quiz Yourself!<\/a><\/li>\n<li><a href=\"#references\">(Advanced) References and Further Reading<\/a><\/li>\n<\/ol>\n<\/li>\n<\/ol>\n<hr \/>\n<h2><a id=\"one\"><\/a>1. The Meso Trap<\/h2>\n<p>Once you learn about stereochemistry, you&#8217;ll start getting asked to identify whether molecules are enantiomers, diastereomers, constitutional isomers or even identical. (<span style=\"color: #993366;\"><em>See article: <a style=\"color: #993366;\" href=\"https:\/\/www.masterorganicchemistry.com\/2019\/03\/08\/enantiomers-diastereomers-or-the-same-1-using-models\/\">Enantiomers vs. Diastereomers vs. The Same &#8211; Two Methods for Solving Problems<\/a><\/em><\/span>)<\/p>\n<p>Most students by this point have it in their heads that enantiomers are mirror images.<\/p>\n<p>So they are totally ripe for questions like this!<\/p>\n<div class=\"wq-quiz-wrapper\" data-id=\"35699\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"35699\"] {\n--wq-question-width: 100%;\n--wq-question-color: #009cff;\n--wq-question-height: auto;\n--wq-font-color: #444;\n}\n\n\t\t\t.wq-quiz-wrapper[data-id=\"35699\"] {\n\t\t\t\t--wq-question-width: 600px;\n\t\t\t}\n\n\t\t\t@media screen and (max-width: 600px) {\n\t\t\t\t.wq-quiz-wrapper[data-id=\"35699\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-35699\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-35699 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"35699\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-io66s\" data-id=\"io66s\">\n\n\t\n\t<div class=\"item_top\">\n\t\t<div class=\"title_container\">\n\t\t\t<div class=\"wq_questionTextCtr\">\n\t\t\t\t<h4 class=\"wq-question-title\"><\/h4>\n\t\t\t<\/div>\n\t\t<\/div>\n\t<\/div>\n\n\t<div class=\"card \">\n\t\t<div class=\"front\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/2611-Front.gif\" \/>\n\t\t\n\t\t\n\t\n\t\n\t\t\t<span class=\"top-desc\">Click to Flip<\/span>\n\t<\/div>\n\t\t<div class=\"back\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/2611-Reverse.gif\" \/>\n\t\t\n\t\t\n\t\n\t<\/div>\n\t<\/div>\n\n\t\n<\/div>\n<\/div>\n<\/div>\n<!-- \/\/ wp quiz-->\n<\/div><!-- End .wq-quiz-wrapper -->\n<p>Ka-pow! These two molecules are <em>drawn<\/em> like they are mirror images of each other. But they are\u00a0<em>superimposable<\/em> mirror images.<\/p>\n<p>If you rotate the whole molecule on the left around, you can lay it right on top of the molecule on the left.<\/p>\n<p>In organic chemistry, we have a name for two molecules that are superimposable. They are <strong>identical<\/strong> molecules.<\/p>\n<p><span style=\"color: #993366;\"><em>Identical boiling point, freezing point, melting point &#8211; whatever physical property you care to name, they are indistinguishable.\u00a0<\/em><\/span><\/p>\n<p>What make the molecule above particularly tricky is that it\u00a0<em>does<\/em> have two chiral centers. It&#8217;s just that those two chiral centers arranged on the molecule in a way that the molecule itself has an\u00a0<strong>internal mirror plane<\/strong>, which renders the molecule\u00a0<strong>achiral<\/strong> overall.<\/p>\n<p>We call these molecules &#8220;<strong>meso compounds<\/strong>&#8220;.<\/p>\n<p><span style=\"color: #993366;\">[<em>Louis Pasteur noted that there were three stereoisomers of tartaric acid. One rotated plane-polarized light to the left (levorotatory), one rotated plane polarized light to the right (dextrorotatory) and the third did not rotate plane-polarized light at all. This third stereoisomer, what we now call (2S, 3R)-tartaric acid, <\/em><em>was called the &#8220;meso&#8221; (for &#8220;middle&#8221;). [See article &#8211; <a style=\"color: #993366;\" href=\"https:\/\/www.masterorganicchemistry.com\/2017\/02\/07\/optical-rotation-optical-activity-and-specific-rotation\/\">Optical Activity and Optical Rotation<\/a><\/em>]<\/span><\/p>\n<p>So I like to call questions like the one above, &#8220;Meso Traps&#8221;.<\/p>\n<p>Here&#8217;s a similar question in this vein.<\/p>\n<div class=\"wq-quiz-wrapper\" data-id=\"35700\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"35700\"] {\n--wq-question-width: 100%;\n--wq-question-color: #009cff;\n--wq-question-height: auto;\n--wq-font-color: #444;\n}\n\n\t\t\t.wq-quiz-wrapper[data-id=\"35700\"] {\n\t\t\t\t--wq-question-width: 600px;\n\t\t\t}\n\n\t\t\t@media screen and (max-width: 600px) {\n\t\t\t\t.wq-quiz-wrapper[data-id=\"35700\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-35700\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-35700 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"35700\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-0xisr\" data-id=\"0xisr\">\n\n\t\n\t<div class=\"item_top\">\n\t\t<div class=\"title_container\">\n\t\t\t<div class=\"wq_questionTextCtr\">\n\t\t\t\t<h4 class=\"wq-question-title\"><\/h4>\n\t\t\t<\/div>\n\t\t<\/div>\n\t<\/div>\n\n\t<div class=\"card \">\n\t\t<div class=\"front\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/2612-Front.gif\" \/>\n\t\t\n\t\t\n\t\n\t\n\t\t\t<span class=\"top-desc\">Click to Flip<\/span>\n\t<\/div>\n\t\t<div class=\"back\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/2612-Reverse.gif\" \/>\n\t\t\n\t\t\n\t\n\t<\/div>\n\t<\/div>\n\n\t\n<\/div>\n<\/div>\n<\/div>\n<!-- \/\/ wp quiz-->\n<\/div><!-- End .wq-quiz-wrapper -->\n<p>Now that you&#8217;ve done two, try this one.<\/p>\n<p><span style=\"color: #000000; font-family: Calibri; font-size: medium;\"><div class=\"wq-quiz-wrapper\" data-id=\"35701\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"35701\"] {\n--wq-question-width: 100%;\n--wq-question-color: #009cff;\n--wq-question-height: auto;\n--wq-font-color: #444;\n}\n\n\t\t\t.wq-quiz-wrapper[data-id=\"35701\"] {\n\t\t\t\t--wq-question-width: 600px;\n\t\t\t}\n\n\t\t\t@media screen and (max-width: 600px) {\n\t\t\t\t.wq-quiz-wrapper[data-id=\"35701\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-35701\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-35701 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"35701\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-zra0d\" data-id=\"zra0d\">\n\n\t\n\t<div class=\"item_top\">\n\t\t<div class=\"title_container\">\n\t\t\t<div class=\"wq_questionTextCtr\">\n\t\t\t\t<h4 class=\"wq-question-title\"><\/h4>\n\t\t\t<\/div>\n\t\t<\/div>\n\t<\/div>\n\n\t<div class=\"card \">\n\t\t<div class=\"front\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/2613-Front.gif\" \/>\n\t\t\n\t\t\n\t\n\t\n\t\t\t<span class=\"top-desc\">Click to Flip<\/span>\n\t<\/div>\n\t\t<div class=\"back\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/2613-Reverse.gif\" \/>\n\t\t\n\t\t\n\t\n\t<\/div>\n\t<\/div>\n\n\t\n<\/div>\n<\/div>\n<\/div>\n<!-- \/\/ wp quiz-->\n<\/div><!-- End .wq-quiz-wrapper --><\/span><\/p>\n<p>I can&#8217;t give you three Meso Traps in a row!\u00a0 That would make it too easy.<\/p>\n<p>The point is to interleave trick questions with more straightforward ones.<\/p>\n<p>Here&#8217;s another one for you.<\/p>\n<p><span style=\"color: #000000; font-family: Calibri; font-size: medium;\"><div class=\"wq-quiz-wrapper\" data-id=\"35702\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"35702\"] {\n--wq-question-width: 100%;\n--wq-question-color: #009cff;\n--wq-question-height: auto;\n--wq-font-color: #444;\n}\n\n\t\t\t.wq-quiz-wrapper[data-id=\"35702\"] {\n\t\t\t\t--wq-question-width: 600px;\n\t\t\t}\n\n\t\t\t@media screen and (max-width: 600px) {\n\t\t\t\t.wq-quiz-wrapper[data-id=\"35702\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-35702\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-35702 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"35702\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-ojvpb\" data-id=\"ojvpb\">\n\n\t\n\t<div class=\"item_top\">\n\t\t<div class=\"title_container\">\n\t\t\t<div class=\"wq_questionTextCtr\">\n\t\t\t\t<h4 class=\"wq-question-title\"><\/h4>\n\t\t\t<\/div>\n\t\t<\/div>\n\t<\/div>\n\n\t<div class=\"card \">\n\t\t<div class=\"front\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/2614-Front.gif\" \/>\n\t\t\n\t\t\n\t\n\t\n\t\t\t<span class=\"top-desc\">Click to Flip<\/span>\n\t<\/div>\n\t\t<div class=\"back\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/2614-Reverse.gif\" \/>\n\t\t\n\t\t\n\t\n\t<\/div>\n\t<\/div>\n\n\t\n<\/div>\n<\/div>\n<\/div>\n<!-- \/\/ wp quiz-->\n<\/div><!-- End .wq-quiz-wrapper --><\/span><\/p>\n<p>You get the idea. If a molecule has a mirror plane &#8211; and that mirror plane can cut through a <strong>bond<\/strong> or an <strong>atom<\/strong> &#8211; then it is an achiral molecule.<\/p>\n<h2><a id=\"two\"><\/a>2. But Clearly There Are No Mirror Planes In\u00a0<em>These\u00a0<\/em>Molecules&#8230; (Right?)<\/h2>\n<p>Sometimes these questions are asked with a little bit more subtlety.<\/p>\n<p>For example, what about these two molecules? Enantiomers, diastereomers, constitutional isomers, or something else?<\/p>\n<p>Clearly, there&#8217;s no mirror plane in this molecule.<\/p>\n<p><span style=\"color: #000000; font-family: Calibri; font-size: medium;\"><div class=\"wq-quiz-wrapper\" data-id=\"35703\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"35703\"] {\n--wq-question-width: 100%;\n--wq-question-color: #009cff;\n--wq-question-height: auto;\n--wq-font-color: #444;\n}\n\n\t\t\t.wq-quiz-wrapper[data-id=\"35703\"] {\n\t\t\t\t--wq-question-width: 600px;\n\t\t\t}\n\n\t\t\t@media screen and (max-width: 600px) {\n\t\t\t\t.wq-quiz-wrapper[data-id=\"35703\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-35703\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-35703 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"35703\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-kvl1j\" data-id=\"kvl1j\">\n\n\t\n\t<div class=\"item_top\">\n\t\t<div class=\"title_container\">\n\t\t\t<div class=\"wq_questionTextCtr\">\n\t\t\t\t<h4 class=\"wq-question-title\"><\/h4>\n\t\t\t<\/div>\n\t\t<\/div>\n\t<\/div>\n\n\t<div class=\"card \">\n\t\t<div class=\"front\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/2615-Front.gif\" \/>\n\t\t\n\t\t\n\t\n\t\n\t\t\t<span class=\"top-desc\">Click to Flip<\/span>\n\t<\/div>\n\t\t<div class=\"back\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/2615-Reverse.gif\" \/>\n\t\t\n\t\t\n\t\n\t<\/div>\n\t<\/div>\n\n\t\n<\/div>\n<\/div>\n<\/div>\n<!-- \/\/ wp quiz-->\n<\/div><!-- End .wq-quiz-wrapper --><\/span><\/p>\n<p>Or is there?<\/p>\n<p>Don&#8217;t forget that molecules can adopt many different <strong>conformations<\/strong> through rotations about single bonds, and these conformations are all in equilibrium with each other. (<span style=\"color: #993366;\"><em>See article: <a href=\"https:\/\/www.masterorganicchemistry.com\/2020\/05\/29\/newman-projection-of-butane-and-gauche-conformation\/\">Newman Projection of Butane<\/a><\/em><\/span>). So it&#8217;s very possible that you may be given examples where a bond rotation will reveal a plane of symmetry.<\/p>\n<p><strong>If a bond rotation creates a plane of symmetry in a molecule, that molecule is considered achiral.\u00a0<\/strong><\/p>\n<p>In the case above, if you rotate the molecule along the central C-C bond, you&#8217;ll find that these molecules are actually exactly the same as those in the first question. It just takes a little bit more work to see it.<\/p>\n<p>What about this example?<\/p>\n<p><span style=\"color: #000000; font-family: Calibri; font-size: medium;\"><div class=\"wq-quiz-wrapper\" data-id=\"35704\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"35704\"] {\n--wq-question-width: 100%;\n--wq-question-color: #009cff;\n--wq-question-height: auto;\n--wq-font-color: #444;\n}\n\n\t\t\t.wq-quiz-wrapper[data-id=\"35704\"] {\n\t\t\t\t--wq-question-width: 600px;\n\t\t\t}\n\n\t\t\t@media screen and (max-width: 600px) {\n\t\t\t\t.wq-quiz-wrapper[data-id=\"35704\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-35704\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-35704 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"35704\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-y8qiq\" data-id=\"y8qiq\">\n\n\t\n\t<div class=\"item_top\">\n\t\t<div class=\"title_container\">\n\t\t\t<div class=\"wq_questionTextCtr\">\n\t\t\t\t<h4 class=\"wq-question-title\"><\/h4>\n\t\t\t<\/div>\n\t\t<\/div>\n\t<\/div>\n\n\t<div class=\"card \">\n\t\t<div class=\"front\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/2616-Front.gif\" \/>\n\t\t\n\t\t\n\t\n\t\n\t\t\t<span class=\"top-desc\">Click to Flip<\/span>\n\t<\/div>\n\t\t<div class=\"back\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/2616-Reverse.gif\" \/>\n\t\t\n\t\t\n\t\n\t<\/div>\n\t<\/div>\n\n\t\n<\/div>\n<\/div>\n<\/div>\n<!-- \/\/ wp quiz-->\n<\/div><!-- End .wq-quiz-wrapper --><\/span><\/p>\n<p>OK, another change of pace question.\u00a0 Those two <em>are<\/em> actually diastereomers.<\/p>\n<p>What about these?<\/p>\n<p><span style=\"color: #000000; font-family: Calibri; font-size: medium;\"><div class=\"wq-quiz-wrapper\" data-id=\"35705\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"35705\"] {\n--wq-question-width: 100%;\n--wq-question-color: #009cff;\n--wq-question-height: auto;\n--wq-font-color: #444;\n}\n\n\t\t\t.wq-quiz-wrapper[data-id=\"35705\"] {\n\t\t\t\t--wq-question-width: 600px;\n\t\t\t}\n\n\t\t\t@media screen and (max-width: 600px) {\n\t\t\t\t.wq-quiz-wrapper[data-id=\"35705\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-35705\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-35705 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"35705\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-0127b\" data-id=\"0127b\">\n\n\t\n\t<div class=\"item_top\">\n\t\t<div class=\"title_container\">\n\t\t\t<div class=\"wq_questionTextCtr\">\n\t\t\t\t<h4 class=\"wq-question-title\"><\/h4>\n\t\t\t<\/div>\n\t\t<\/div>\n\t<\/div>\n\n\t<div class=\"card \">\n\t\t<div class=\"front\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/2617-Front.gif\" \/>\n\t\t\n\t\t\n\t\n\t\n\t\t\t<span class=\"top-desc\">Click to Flip<\/span>\n\t<\/div>\n\t\t<div class=\"back\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/2617-Reverse.gif\" \/>\n\t\t\n\t\t\n\t\n\t<\/div>\n\t<\/div>\n\n\t\n<\/div>\n<\/div>\n<\/div>\n<!-- \/\/ wp quiz-->\n<\/div><!-- End .wq-quiz-wrapper --><\/span><\/p>\n<h2><a id=\"three\"><\/a>3. Fischer and Newman Projections<\/h2>\n<p>Let&#8217;s look at another set of questions. Remember that molecules won&#8217;t always be helpfully drawn as line diagrams. You can expect to see the full gamut of Newman, Fischer, Sawhorse, and even cyclohexane chair conformations.<\/p>\n<p><span style=\"color: #000000; font-family: Calibri; font-size: medium;\"><div class=\"wq-quiz-wrapper\" data-id=\"35706\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"35706\"] {\n--wq-question-width: 100%;\n--wq-question-color: #009cff;\n--wq-question-height: auto;\n--wq-font-color: #444;\n}\n\n\t\t\t.wq-quiz-wrapper[data-id=\"35706\"] {\n\t\t\t\t--wq-question-width: 600px;\n\t\t\t}\n\n\t\t\t@media screen and (max-width: 600px) {\n\t\t\t\t.wq-quiz-wrapper[data-id=\"35706\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-35706\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-35706 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"35706\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-rqucb\" data-id=\"rqucb\">\n\n\t\n\t<div class=\"item_top\">\n\t\t<div class=\"title_container\">\n\t\t\t<div class=\"wq_questionTextCtr\">\n\t\t\t\t<h4 class=\"wq-question-title\"><\/h4>\n\t\t\t<\/div>\n\t\t<\/div>\n\t<\/div>\n\n\t<div class=\"card \">\n\t\t<div class=\"front\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/2618-Front.gif\" \/>\n\t\t\n\t\t\n\t\n\t\n\t\t\t<span class=\"top-desc\">Click to Flip<\/span>\n\t<\/div>\n\t\t<div class=\"back\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/2618-Reverse.gif\" \/>\n\t\t\n\t\t\n\t\n\t<\/div>\n\t<\/div>\n\n\t\n<\/div>\n<\/div>\n<\/div>\n<!-- \/\/ wp quiz-->\n<\/div><!-- End .wq-quiz-wrapper --><\/span><\/p>\n<p>Sometimes I think that the only reason Fischer projections are still taught is that they give us instructors some variety in asking different stereochemistry questions.<\/p>\n<p>A helpful trick to remember is that <strong>exchanging any three groups on a carbon results in doing a bond rotation.<\/strong><\/p>\n<p><span style=\"color: #993366;\"><em>(Swapping any\u00a0<strong>two\u00a0<\/strong>groups will swap the configuration of a chiral center from\u00a0R to\u00a0S or vice-versa &#8211; see <a style=\"color: #993366;\" href=\"https:\/\/www.masterorganicchemistry.com\/2011\/01\/24\/how-to-draw-enantiomer\/\">The Single Swap Rule<\/a>.\u00a0<\/em><\/span><\/p>\n<p>Let&#8217;s not forget Newman projections!<\/p>\n<p><span style=\"color: #000000; font-family: Calibri; font-size: medium;\"><div class=\"wq-quiz-wrapper\" data-id=\"35707\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"35707\"] {\n--wq-question-width: 100%;\n--wq-question-color: #009cff;\n--wq-question-height: auto;\n--wq-font-color: #444;\n}\n\n\t\t\t.wq-quiz-wrapper[data-id=\"35707\"] {\n\t\t\t\t--wq-question-width: 600px;\n\t\t\t}\n\n\t\t\t@media screen and (max-width: 600px) {\n\t\t\t\t.wq-quiz-wrapper[data-id=\"35707\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-35707\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-35707 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"35707\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-o5aru\" data-id=\"o5aru\">\n\n\t\n\t<div class=\"item_top\">\n\t\t<div class=\"title_container\">\n\t\t\t<div class=\"wq_questionTextCtr\">\n\t\t\t\t<h4 class=\"wq-question-title\"><\/h4>\n\t\t\t<\/div>\n\t\t<\/div>\n\t<\/div>\n\n\t<div class=\"card \">\n\t\t<div class=\"front\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/2619-Front.gif\" \/>\n\t\t\n\t\t\n\t\n\t\n\t\t\t<span class=\"top-desc\">Click to Flip<\/span>\n\t<\/div>\n\t\t<div class=\"back\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/2619-Reverse.gif\" \/>\n\t\t\n\t\t\n\t\n\t<\/div>\n\t<\/div>\n\n\t\n<\/div>\n<\/div>\n<\/div>\n<!-- \/\/ wp quiz-->\n<\/div><!-- End .wq-quiz-wrapper --><\/span><\/p>\n<p>And cyclohexane chairs are also fair game.<\/p>\n<p><span style=\"color: #000000; font-family: Calibri; font-size: medium;\"><div class=\"wq-quiz-wrapper\" data-id=\"35708\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"35708\"] {\n--wq-question-width: 100%;\n--wq-question-color: #009cff;\n--wq-question-height: auto;\n--wq-font-color: #444;\n}\n\n\t\t\t.wq-quiz-wrapper[data-id=\"35708\"] {\n\t\t\t\t--wq-question-width: 600px;\n\t\t\t}\n\n\t\t\t@media screen and (max-width: 600px) {\n\t\t\t\t.wq-quiz-wrapper[data-id=\"35708\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-35708\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-35708 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"35708\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-dxmgp\" data-id=\"dxmgp\">\n\n\t\n\t<div class=\"item_top\">\n\t\t<div class=\"title_container\">\n\t\t\t<div class=\"wq_questionTextCtr\">\n\t\t\t\t<h4 class=\"wq-question-title\"><\/h4>\n\t\t\t<\/div>\n\t\t<\/div>\n\t<\/div>\n\n\t<div class=\"card \">\n\t\t<div class=\"front\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/2620-Front.gif\" \/>\n\t\t\n\t\t\n\t\n\t\n\t\t\t<span class=\"top-desc\">Click to Flip<\/span>\n\t<\/div>\n\t\t<div class=\"back\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/2620-Reverse.gif\" \/>\n\t\t\n\t\t\n\t\n\t<\/div>\n\t<\/div>\n\n\t\n<\/div>\n<\/div>\n<\/div>\n<!-- \/\/ wp quiz-->\n<\/div><!-- End .wq-quiz-wrapper --><\/span><\/p>\n<p>In this case, it helps to imagine what the molecule would look like when looking at it from above.<\/p>\n<p>Remember that molecules are three-dimensional objects just like anything else and can be viewed from a variety of perspectives!<\/p>\n<h2><a id=\"four\"><\/a>4. Identifying Meso Compounds, Method One: Build A Model<\/h2>\n<p>Now that most of\u00a0 the low-hanging fruit of trick questions has been thrown at you, let&#8217;s talk about strategies for identifying meso compounds <em>and<\/em> differentiating different kinds of stereoisomers.<\/p>\n<p>There are two classes of strategies for solving these kinds of problems.<\/p>\n<p>The first involves making a model, and then rotating along C-C bonds to find an axis of symmetry.<\/p>\n<p>Here is an example of doing a bond rotation on a line diagram to reveal a plane of symmetry.<\/p>\n<p><iframe class=\"giphy-embed\" src=\"https:\/\/giphy.com\/embed\/0pmSISIOZGKEzLVy0t\" width=\"270\" height=\"480\" frameborder=\"0\" allowfullscreen=\"allowfullscreen\"><\/iframe><\/p>\n<p><a href=\"https:\/\/giphy.com\/gifs\/meso-organicchemistry-stereochemistry-0pmSISIOZGKEzLVy0t\">via GIPHY<\/a><\/p>\n<p>This also works for Fischer projections. Remember that in a Fischer, the <strong>arms<\/strong> come out to <strong>hug you<\/strong> <span style=\"color: #993366;\"><em>(or strangle you, if you are feeling dark). <\/em><\/span><\/p>\n<p><iframe class=\"giphy-embed\" src=\"https:\/\/giphy.com\/embed\/GHahZSxLiZo3YoFXUd\" width=\"270\" height=\"480\" frameborder=\"0\" allowfullscreen=\"allowfullscreen\"><\/iframe><\/p>\n<p><a href=\"https:\/\/giphy.com\/gifs\/organicchemistry-stereochemistry-mesocompounds-GHahZSxLiZo3YoFXUd\">via GIPHY<\/a><\/p>\n<p>Newman projections can also be rotated, as in the short video below.<\/p>\n<p><iframe class=\"giphy-embed\" src=\"https:\/\/giphy.com\/embed\/Bbayg6W04GOkiZ10Nz\" width=\"270\" height=\"480\" frameborder=\"0\" allowfullscreen=\"allowfullscreen\"><\/iframe><\/p>\n<p><a href=\"https:\/\/giphy.com\/gifs\/organicchemistry-stereochemistry-mesocompounds-Bbayg6W04GOkiZ10Nz\">via GIPHY<\/a><\/p>\n<p>You get the idea. Build the two molecules with your model kit, rotate bonds until you can tell if they are superimposable or not.<\/p>\n<h2><a id=\"five\"><\/a>5.\u00a0 Identifying Meso Compounds, Method Two: Determining Absolute Configuration (<em>R,S<\/em>)<\/h2>\n<p>Generations of students have been told to use model kits to visualize whether molecules are enantiomers, diastereomers, or the same.<\/p>\n<p>And generations of students have rolled their eyes at this advice like they would at a parent admonishing their children to floss their teeth or eat their vegetables.\u00a0 They just don&#8217;t want to do it.<\/p>\n<p>In my opinion, I think this is actually OK not to build models, <strong>provided that\u00a0<\/strong>you practice like hell to get good at determining whether chiral centers are (<em>R<\/em>) or (<em>S<\/em>). Once you master the skill of determining absolute configuration (R\/S), making a model is unnecessary.<\/p>\n<p>That&#8217;s because there&#8217;s One Weird Trick that can help you determine which compounds are meso and which are not. It is also helpful for determining whether molecules are enantiomers, diastereomers, or the same.<\/p>\n<p>Get ready for the One Weird Trick. Here we go.<\/p>\n<p>Look at the <em>R,S<\/em> designations on these meso compounds, compared to their chiral diastereomers. <strong>What do you notice?\u00a0<\/strong><\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-35709\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/10\/14-one-way-to-determine-if-compounds-may-or-may-not-be-meso-is-to-examine-connectivity-and-determine-if-they-are-R-or-S.gif\" alt=\"one way to determine if compounds may or may not be meso is to examine connectivity and determine if they are R or S\" width=\"640\" height=\"485\" \/><\/a><\/p>\n<p><strong>All the meso compounds are (<em>R,S<\/em>) or (<em>S,R<\/em>).\u00a0<\/strong>Furthermore, the compounds that are (<em>S,S)\u00a0<\/em>or (<em>R,R)\u00a0<\/em>are\u00a0<strong>never\u00a0<\/strong>meso. They are chiral.<\/p>\n<p>It makes sense when you think about it!<\/p>\n<p>In a meso compound, the left-hand side of the molecule is the <em>mirror image\u00a0<\/em>of the right hand side. In order for this to be true, a molecule with two chiral centers has to have two chiral centers that have\u00a0<strong>opposite<\/strong> configurations &#8211; (<em>R,S<\/em>) or (<em>S,R<\/em>).<\/p>\n<p>So one way to quickly determine if a compound is meso even if it&#8217;s drawn in a strange conformation is to determine (<em>R,S<\/em>) on each of the chiral centers. <strong>If it&#8217;s (<em>R,S<\/em>) or (<em>S,R<\/em>) your Meso Trap Alarm should be going off.\u00a0<\/strong>[<a href=\"#noteone\">Note 1<\/a>]<\/p>\n<p><span style=\"color: #993366;\"><em>One word of caution: while it&#8217;s a <strong>necessary condition <\/strong>that a meso compound with two chiral centers must have (R,S) or (S,R) configurations it&#8217;s not a <strong>sufficient condition. <\/strong>\u00a0The left-hand half <strong>must<\/strong> have the same\u00a0<strong>connectivity\u00a0<\/strong>as the right hand half.\u00a0<\/em><\/span><\/p>\n<p>You should double check that the molecule has the same connectivity on both sides before declaring it to be meso.<\/p>\n<p>(2<em>S<\/em>, 3<em>R<\/em>)2-bromo-3-methylpentane is clearly not meso, for example, due to the fact that one chiral center has a bromine atom and the other does not.<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-35710\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/10\/15-just-because-two-chiral-centers-are-R-and-S-doesnt-mean-the-molecule-is-meso.gif\" alt=\"just because two chiral centers are R and S doesn't mean the molecule is meso\" width=\"640\" height=\"247\" \/><\/a><\/p>\n<h2><a id=\"six\"><\/a>6. Reviewing &#8220;Enantiomers, Diastereomers, or The Same&#8221; Questions<\/h2>\n<p>In addition to sniffing out meso compounds, determining absolute configuration (R,S) is helpful in determining whether two molecules are enantiomers, diastereomers, or the same.<\/p>\n<p>Just to review what we have covered elsewhere (see <a href=\"https:\/\/www.masterorganicchemistry.com\/2019\/03\/08\/enantiomers-diastereomers-or-the-same-1-using-models\/\"><span style=\"color: #993366;\"><em>Enantiomers, Diastereomers, or the Same &#8211; Two Methods For Solving Problem<\/em><\/span><\/a>s)<\/p>\n<p>For two molecules that have the <strong>same connectivity:\u00a0<\/strong><\/p>\n<ul>\n<li>If they have identical absolute configuration [<em>e..g both (R,R), (S,S), or (S,R)]<\/em>\u00a0then they are considered to be <strong>identical<\/strong>.<\/li>\n<li>If one is (<em>R,R<\/em>) and the other is (<em>S,S<\/em>), they are <strong>enantiomers<\/strong>.<\/li>\n<li>If one is (<em>R,R<\/em>) or (<em>S,S<\/em>) and the other is (<em>R,S<\/em>) or (<em>S,R<\/em>), they are\u00a0<strong>diastereomers<\/strong> since at least one of their chiral centers has an identical configuration.<\/li>\n<li>If one is (<em>R,S<\/em>) and the other is (<em>S,R<\/em>), they\u00a0<em>may<\/em> be enantiomers, but they\u00a0<em>may also be\u00a0<\/em><strong>meso compounds.\u00a0<\/strong>Double check the connectivity to see if a plane of symmetry may be possible. If they are both meso, then they are considered to be\u00a0<strong>identical.\u00a0<\/strong><\/li>\n<\/ul>\n<p>Good luck &#8211; and may you avoid falling into the Meso Trap!<\/p>\n<hr \/>\n<h2><strong><a id=\"notes\"><\/a>Notes<\/strong><\/h2>\n<div class=\"related-articles\"><p><strong>Related Articles<\/strong><\/p><ul><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2017\/02\/07\/optical-rotation-optical-activity-and-specific-rotation\/\" class=\"\"><span>Optical Rotation, Optical Activity, and Specific Rotation<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2017\/02\/24\/optical-purity-and-enantiomeric-excess\/\" class=\"\"><span>Optical Purity and Enantiomeric Excess<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2019\/03\/08\/enantiomers-diastereomers-or-the-same-1-using-models\/\" class=\"\"><span>Enantiomers vs Diastereomers vs The Same? Two Methods For Solving Problems<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2012\/05\/23\/whats-a-racemic-mixture\/\" class=\"\"><span>What\u2019s a Racemic Mixture?<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2019\/05\/21\/how-to-determine-r-and-s-configurations-on-a-fischer-projection\/\" class=\"\"><span>How To Determine R and S Configurations On A Fischer Projection<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2017\/02\/01\/assigning-rs-to-newman-projections-and-converting-newman-to-line-diagrams\/\" class=\"\"><span>Assigning R\/S To Newman Projections (And Converting Newman To Line Diagrams)<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2018\/09\/10\/types-of-isomers\/\" class=\"\"><span>Types of Isomers: Constitutional Isomers, Stereoisomers, Enantiomers, and Diastereomers<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/organic-chemistry-practice-problems\/stereochemistry-practice-problems-and-quizzes\/\" class=\"\"><span>Stereochemistry Practice Problems and Quizzes (MOC Membership)<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/01\/24\/how-to-draw-enantiomer\/\" class=\"\"><span>How To Draw The Enantiomer Of A Chiral Molecule<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2023\/11\/06\/bond-rotation-how-to-draw\/\" class=\"\"><span>How To Draw A Bond Rotation<\/span><\/a><\/li><\/ul><\/div>\n<p><em>Significantly updated Oct 2023 from a previous version<\/em><\/p>\n<p><strong><a id=\"noteone\"><\/a>Note 1.\u00a0<\/strong>This also applies to meso compounds with more than two chiral centers.<\/p>\n<div class=\"wq-quiz-wrapper\" data-id=\"35730\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"35730\"] {\n--wq-question-width: 100%;\n--wq-question-color: #009cff;\n--wq-question-height: auto;\n--wq-font-color: #444;\n}\n\n\t\t\t.wq-quiz-wrapper[data-id=\"35730\"] {\n\t\t\t\t--wq-question-width: 600px;\n\t\t\t}\n\n\t\t\t@media screen and (max-width: 600px) {\n\t\t\t\t.wq-quiz-wrapper[data-id=\"35730\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-35730\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-35730 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"35730\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-k5r29\" data-id=\"k5r29\">\n\n\t\n\t<div class=\"item_top\">\n\t\t<div class=\"title_container\">\n\t\t\t<div class=\"wq_questionTextCtr\">\n\t\t\t\t<h4 class=\"wq-question-title\"><\/h4>\n\t\t\t<\/div>\n\t\t<\/div>\n\t<\/div>\n\n\t<div class=\"card \">\n\t\t<div class=\"front\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/2623-Front.gif\" \/>\n\t\t\n\t\t\n\t\n\t\n\t\t\t<span class=\"top-desc\">Click to Flip<\/span>\n\t<\/div>\n\t\t<div class=\"back\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/2623-Reverse.gif\" \/>\n\t\t\n\t\t\n\t\n\t<\/div>\n\t<\/div>\n\n\t\n<\/div>\n<\/div>\n<\/div>\n<!-- \/\/ wp quiz-->\n<\/div><!-- End .wq-quiz-wrapper -->\n<p>The largest meso compound I am aware of is\u00a0<strong><a href=\"https:\/\/en.wikipedia.org\/wiki\/Nonactin\">nonactin<\/a>.\u00a0<\/strong>Despite having 16 chiral centers, it has a plane of symmetry and is achiral overall.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-35728\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/11\/F1-the-structure-of-nonactin-one-of-the-largest-meso-compounds.gif\" alt=\"the structure of nonactin one of the largest meso compounds\" width=\"640\" height=\"235\" \/><\/a><\/p>\n<p>The assignment of chiral centers in nonactin is (R,R,R,R, S, S, S, S, R, R, R, R, S, S, S, S)\u00a0 &#8211; an equal number of (R) and (S) chiral centers, and the left half is the mirror image of the right half. [<a href=\"https:\/\/www.chemspider.com\/Chemical-Structure.65428.html\">Source<\/a>]<\/p>\n<hr \/>\n<h2><strong><a id=\"quiz\"><\/a>Quiz Yourself!<\/strong><\/h2>\n\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/0837-Front-Image-Only.png\" alt=\"\" width=\"640\" height=\"616\" \/><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a\u00a0 MOC member<\/strong><\/a> to see the clickable quiz with answers on the back. <\/p>\n\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/0843-Front-Image-Only.png\" alt=\"\" width=\"640\" height=\"616\" \/><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a\u00a0 MOC member<\/strong><\/a> to see the clickable quiz with answers on the back. <\/p>\n\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/0847-Front-Image-Only.png\" alt=\"\" width=\"640\" height=\"616\" \/><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a\u00a0 MOC member<\/strong><\/a> to see the clickable quiz with answers on the back. <\/p>\n\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/0850-Front-Image-Only.png\" alt=\"\" width=\"640\" height=\"616\" \/><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a\u00a0 MOC member<\/strong><\/a> to see the clickable quiz with answers on the back. <\/p>\n\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/0859-Front-Image-Only.png\" alt=\"\" width=\"640\" height=\"616\" \/><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a\u00a0 MOC member<\/strong><\/a> to see the clickable quiz with answers on the back. <\/p>\n\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/0899-Front-Image-Only.png\" alt=\"\" width=\"640\" height=\"616\" \/><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a\u00a0 MOC member<\/strong><\/a> to see the clickable quiz with answers on the back. <\/p>\n\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/0905-Front-Image-Only.png\" alt=\"\" width=\"640\" height=\"616\" \/><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a\u00a0 MOC member<\/strong><\/a> to see the clickable quiz with answers on the back. <\/p>\n\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/0911-Front-Image-Only.png\" alt=\"\" width=\"640\" height=\"616\" \/><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a\u00a0 MOC member<\/strong><\/a> to see the clickable quiz with answers on the back. <\/p>\n<hr \/>\n<h2><strong><a id=\"references\"><\/a>(Advanced) References and Further Reading<\/strong><\/h2>\n<p>[references]<\/p>\n","protected":false},"excerpt":{"rendered":"<p>Recognizing Meso Compounds In chemistry, two molecules that are superimposable\u00a0mirror images are considered to be\u00a0identical molecules. They will have identical physical properties in all respects. <\/p>\n","protected":false},"author":1,"featured_media":38601,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[1413],"tags":[197,202,210,211,212,642,640,635,622,641],"post_folder":[],"class_list":["post-1263","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-stereochemistry-chirality","tag-diastereomers","tag-enantiomers","tag-exam-tips","tag-exams","tag-exceptions","tag-fischer-projection","tag-meso","tag-rs","tag-rotations","tag-trick-questions"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.7 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>The Meso Trap &#8211; Master Organic Chemistry<\/title>\n<meta name=\"description\" content=\"Meso compounds contain chiral centers, but these chiral centers are arranged in such a way that the molecule has a\u00a0mirror plane\u00a0and is therefore\u00a0achiral\u00a0overall. 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