{"id":4979,"date":"2012-04-17T15:36:31","date_gmt":"2012-04-17T20:36:31","guid":{"rendered":"https:\/\/www.masterorganicchemistry.com\/?p=4979"},"modified":"2026-02-26T14:32:50","modified_gmt":"2026-02-26T20:32:50","slug":"homotopic-enantiotopic-diastereotopic","status":"publish","type":"post","link":"https:\/\/www.masterorganicchemistry.com\/2012\/04\/17\/homotopic-enantiotopic-diastereotopic\/","title":{"rendered":"Homotopic, Enantiotopic, Diastereotopic"},"content":{"rendered":"<p><strong>Homotopic, Enantiotopic, and Diastereotopic Groups: What Does It Mean?<\/strong><\/p>\n<p>When you have two hydrogens attached to a single carbon, they can have three different types of relationships. We call them &#8220;homotopic&#8221;, &#8220;enantiotopic&#8221;, and &#8220;diastereotopic&#8221;.<\/p>\n<p>To determine these relationships we imagine replacing each hydrogen in turn with a different atom or group, which we can call D.<\/p>\n<ul>\n<li>When replacement of each H with D results in the <strong>same<\/strong> product, we call these hydrogens <strong>homotopic<\/strong>.<\/li>\n<li>When replacement of each H with D results in <strong>enantiomers<\/strong>, we call these hydrogens <strong>enantiotopic<\/strong>.<\/li>\n<li>When replacement of each H with D results in <strong>diastereomers<\/strong>, we call these hydrogens <strong>diastereotopic<\/strong>.<\/li>\n<\/ul>\n<p><img fetchpriority=\"high\" decoding=\"async\" class=\"alignnone wp-image-37379\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2024\/09\/0-Summary-of-homotopic-enantiotopic-diastereotopic-hydrogens.gif\" alt=\"Summary of homotopic enantiotopic diastereotopic hydrogens\" width=\"640\" height=\"582\" \/><\/a><\/p>\n<p><strong>Table of Contents<\/strong><\/p>\n<ol>\n<li><a href=\"#one\">When Is &#8220;Homotopic, Enantiotopic, Diastereotopic&#8221; Important?<\/a><\/li>\n<li><a href=\"#two\">Homotopic Atoms (or Groups)<\/a><\/li>\n<li><a href=\"#three\">Enantiotopic Atoms<\/a><\/li>\n<li><a href=\"#four\">Diastereotopic Atoms<\/a><\/li>\n<li><a href=\"#five\">When Does It Matter?<\/a><\/li>\n<li><a href=\"#notes\">Notes<\/a><\/li>\n<li><a href=\"#quizzes\">Quiz Yourself!<\/a><\/li>\n<\/ol>\n<hr \/>\n<h2><a id=\"one\"><\/a>1. When Is &#8220;Homotopic, Enantiotopic, Diastereotopic&#8221; Important?<\/h2>\n<ul>\n<li>\u00a0Certain reactions directly replace hydrogens with other atoms. For example, free radical chlorination replaces C-H bonds with C-Cl bonds. So understanding these principles help in understanding what potential types of products you could obtain from these reactions.<\/li>\n<li>In Nuclear Magnetic Resonance (NMR) these relationships determine whether or not these hydrogens are in the same &#8220;chemical environment&#8221;. In other words, whether or not they have the same or different signals.<\/li>\n<\/ul>\n<h2><strong><a id=\"two\"><\/a>2.\u00a0 Homotopic Atoms<\/strong><\/h2>\n<p>Take a molecule like ethane. Let&#8217;s label (with color) two different hydrogens, blue and red. Next, let&#8217;s replace each of these hydrogens in turn with a different atom. In this example it could be deuterium (D) but really this can be done with any atom or group (except hydrogen of course).<\/p>\n<p>Replace the red H and the blue H in turn with D and compare the molecules that are formed. Ask: how are these molecules related?<\/p>\n<p>In this case they are both deuterioethane. Since the two molecules are the same, the two hydrogens are said to be &#8220;homotopic&#8221;. Replacement of either gives rise to the same product.<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-15494\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/1-what-is-the-meaning-of-homotopic-example-ethane-replace-any-hydrogen-with-D-and-get-the-exact-same-molecule-homo-equals-the-same.gif\" alt=\"what is the meaning of homotopic example ethane replace any hydrogen with D and get the exact same molecule homo equals the same\" width=\"600\" height=\"264\" \/><\/p>\n<h2><strong><a id=\"three\"><\/a>3. Enantiotopic Atoms<\/strong><\/h2>\n<p>Let&#8217;s look at butane next; specifically, the second carbon of butane. \u00a0Replacement of the red\u00a0 H with D leads to (R)-2-deuteriobutane, while replacement of the blue H with D leads to (S)-2-deuteriobutane. These hydrogens are therefore <strong>not<\/strong> homotopic. Since <strong>enantiomers<\/strong> are obtained here, these two protons are therefore <strong>enantiotopic<\/strong>.<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-18722\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2012\/04\/2-enantiotopic-hydrogen-what-does-it-mean-replace-either-hydrogen-with-d-and-compare-molecules-they-are-enantiomers-this-means-enantiotopic.gif\" alt=\"enantiotopic hydrogen what does it mean replace either hydrogen with d and compare molecules they are enantiomers this means enantiotopic\" width=\"600\" height=\"283\" \/><\/a><\/p>\n<p>Note that the CH<sub>3<\/sub> protons of butane are homotopic; it&#8217;s only the C-2 (and C-3) hydrogens of butane that are enantiotopic.<\/p>\n<h2><strong><a id=\"four\"><\/a>4. Diastereotopic Atoms<\/strong><\/h2>\n<p>It&#8217;s also possible to have diastereotopic protons. Look at the alkene below. Replacement of the red H with D leads to the E-alkene, while replacement of the blue H with D leads to the Z-alkene. What&#8217;s the relationship between these two compounds? They&#8217;re <strong><em>diastereomers<\/em><\/strong> &#8211; stereoisomers, but not mirror images. So the two protons are said to be <strong>diastereotopic.\u00a0<\/strong><\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15496\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/3-example-of-diastereotopic-hydrogens-in-alkene-replace-each-in-turn-with-d-and-obtain-diastereomers-different-nmr-spectra.gif\" alt=\"example of diastereotopic hydrogens in alkene replace each in turn with d and obtain diastereomers different nmr spectra\" width=\"600\" height=\"269\" \/><\/p>\n<p>There&#8217;s another potential situation which can lead to diastereotopic protons. Look at the molecule below &#8211; (R)-butan-2-ol. Replacement of the red H leads to the (<em>R, R<\/em>) product. Replacement of the blue H leads to the (<em>R, S<\/em>) product. Therefore, these two products are <strong>diastereomers<\/strong>, and the two protons are <strong>diastereotopic<\/strong>.<\/p>\n<h2><strong><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15497\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/4-second-example-of-diastereotopic-hydrogens-is-hydrogens-on-carbon-containing-stereocenter-replace-h-with-d-and-obtain-diastereomers-different-nmr-spectra.gif\" alt=\"second example of diastereotopic hydrogens is hydrogens on carbon containing stereocenter replace h with d and obtain diastereomers different nmr spectra\" width=\"600\" height=\"287\" \/><a href=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2012\/04\/3-diastereotopic1.png\"><br \/>\n<\/a><a id=\"five\"><\/a>5. <\/strong><strong>When does it matter?<\/strong><\/h2>\n<p>Two situations:<\/p>\n<ol>\n<li>In free radical chorination &#8211; say, of butane &#8211; on the second carbon (C-2), substitution of C-H with Cl will lead to a mixture of stereocenters. It&#8217;s important to recognize when this can happen.<\/li>\n<li>\u00a0(Most common) &#8211; In NMR spectroscopy:<\/li>\n<\/ol>\n<ul>\n<li><strong>homotopic<\/strong> protons have the exact same chemical shift<\/li>\n<li><strong>enantiotopic<\/strong> protons have the same chemical shift in the vast majority of situations. However, if they are placed in a chiral environment (e.g. a chiral solvent) they will have different chemical shifts.<\/li>\n<li><strong>diastereotopic<\/strong> protons have different chemical shifts in all situations<\/li>\n<\/ul>\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\/2022\/02\/08\/1h-nmr-how-many-signals\/\" class=\"\"><span>1H NMR: How Many Signals?<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2022\/02\/08\/diastereotopic-protons-1h-nmr-examples\/\" class=\"\"><span>Diastereotopic Protons in 1H NMR Spectroscopy: Examples<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2022\/02\/08\/c13-nmr-how-many-signals\/\" class=\"\"><span>C13 NMR \u2013 How Many Signals<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2016\/08\/23\/structure-determination-case-study-deer-tarsal-gland-pheremone\/\" class=\"\"><span>Structure Determination Case Study: Deer Tarsal Gland Pheromone<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2016\/09\/16\/introduction-to-uv-vis-spectroscopy\/\" class=\"\"><span>Introduction To UV-Vis Spectroscopy<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2016\/07\/12\/natural-product-isolation-1-extraction\/\" class=\"\"><span>Natural Product Isolation (1) \u2013 Extraction<\/span><\/a><\/li><\/ul><\/div>\n<hr \/>\n<h2><a id=\"quizzes\"><\/a>Quizzes<\/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\/2876-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. <br \/>\n<\/p>\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/2877-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. <br \/>\n<\/p>\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/2878-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. <br \/>\n<\/p>\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/3052-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. <br \/>\n<\/p>\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/3053-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","protected":false},"excerpt":{"rendered":"<p>Homotopic, Enantiotopic, and Diastereotopic Groups: What Does It Mean? When you have two hydrogens attached to a single carbon, they can have three different types <\/p>\n","protected":false},"author":1,"featured_media":37379,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[386],"tags":[816,815,814,306],"post_folder":[],"class_list":["post-4979","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-spectroscopy-2","tag-diastereotopic","tag-enantiotopic","tag-homotopic","tag-nmr"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.7 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Homotopic, Enantiotopic, Diastereotopic &#8211; Master Organic Chemistry<\/title>\n<meta name=\"description\" content=\"When two or more H are attached to a single carbon, they can have 3 types of relationships. 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