{"id":1353,"date":"2011-02-14T17:22:08","date_gmt":"2011-02-14T22:22:08","guid":{"rendered":"https:\/\/www.masterorganicchemistry.com\/?p=1353"},"modified":"2025-06-12T11:00:34","modified_gmt":"2025-06-12T16:00:34","slug":"table-of-functional-group-priorities-for-nomenclature","status":"publish","type":"post","link":"https:\/\/www.masterorganicchemistry.com\/2011\/02\/14\/table-of-functional-group-priorities-for-nomenclature\/","title":{"rendered":"Table of Functional Group Priorities for Nomenclature"},"content":{"rendered":"<p><strong>How To Determine Which Functional Group Has &#8220;Priority&#8221; For Naming Purposes<\/strong><\/p>\n<ul>\n<li>When a molecule has multiple functional groups, we could potentially run into problems when deciding on how to name it.<\/li>\n<li>For example,\u00a0 does a molecule that contains both a hydroxyl group (-OH) and a carboxylic acid (-COOH) get named as an alcohol (with suffix &#8211;<em>ol<\/em> ) or as a carboxylic acid (with suffix <em>-acid<\/em>) ?<\/li>\n<li>To resolve these questions, a\u00a0<strong>priority sequence\u00a0<\/strong>or hierarchy of functional groups has been established by the international chemistry community (IUPAC, the International Union of Pure and Applied Chemistry).<\/li>\n<li>The key rules are summarized in the article below!<\/li>\n<\/ul>\n<p><strong>Table of Contents<\/strong><\/p>\n<ol>\n<li style=\"list-style-type: none;\">\n<ol>\n<li><a href=\"#one\">A Nomenclature Dilemma<\/a><\/li>\n<li><a href=\"#two\">Highest Priority Groups:\u00a0 Carboxylic Acids, Sulfonic Acids, Esters, Acid Halides, Amides<\/a><\/li>\n<li><a href=\"#three\">Next In Line: Nitrile, Aldehyde, Ketone, Alcohol, Thiol, Amine<\/a><\/li>\n<li><a href=\"#four\">Alkenes and Alkynes<\/a><\/li>\n<li><a href=\"#five\">Alkenes vs. Alkynes: Which\u00a0 Takes &#8220;Priority&#8221;?<\/a><\/li>\n<li><a href=\"#six\">Functional Groups That Are Always Prefixes: Halides, Alkoxides, Azides, Nitro<\/a><\/li>\n<li><a href=\"#seven\">Some Examples With Multiple Functional Groups<\/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><strong><a id=\"one\"><\/a>1. A Nomenclature Dilemma<\/strong><\/h2>\n<p>Here&#8217;s a little nomenclature dilemma.<\/p>\n<p>Let&#8217;s say you&#8217;re trying to name a molecule. You&#8217;re familiar with the familiar naming suffixes like -ol, -ene, -ane, -oic acid and so on. But then you come across a molecule which has\u00a0<strong>multiple<\/strong> functional groups.<\/p>\n<p>What do you do? What suffix do you give the molecule?<\/p>\n<p><img fetchpriority=\"high\" decoding=\"async\" class=\"aligncenter wp-image-14237\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/1-iupac-nomenclature-which-group-takes-priority.gif\" alt=\"iupac-nomenclature-which-group-takes-priority\" width=\"585\" height=\"265\" \/><\/p>\n<p>We need some kind of\u00a0<strong>priority system<\/strong> for nomenclature. And so, IUPAC (think of the &#8220;Ministry\u00a0 of Magic&#8221;, but for chemists) has developed one. If you have a molecule with, say, a carboxylic acid and a ketone you consult the table.<\/p>\n<p>The functional group with the <strong>highest priority<\/strong> will be the one which gives its <strong>suffix<\/strong> to the name of the molecule.<\/p>\n<p>So in example #1 above, the suffix of the molecule will be &#8220;-oic acid&#8221; , not &#8220;-one&#8221;, because <strong>carboxylic acids<\/strong> are given higher priority. However, if a ketone is present with an alcohol (example 3) then we will use the suffix, &#8220;-one&#8221; because ketones have a higher priority for nomenclature than alcohols.<\/p>\n<p><span style=\"color: #993366;\"><em>[You might ask: what is this based on? It&#8217;s an arbitrary agreement by IUPAC [<a style=\"color: #993366;\" href=\"http:\/\/www.acdlabs.com\/iupac\/nomenclature\/93\/r93_326.htm\">source<\/a>], although note that there is some correlation between the oxidation state of the carbon and the priority (more oxidized groups tend to be higher priority). However this really is an example of something you have to either look up , memorize, or have a computer do for you. It&#8217;s not conceptual. ]\u00a0 <\/em><\/span>See\u00a0<strong><a href=\"#noteone\">Note 1<\/a>.\u00a0<\/strong><\/p>\n<h2><strong><a id=\"two\"><\/a>2. Highest Priority Groups:\u00a0 Carboxylic Acids, Sulfonic Acids, Esters, Acid Halides, Amides<\/strong><\/h2>\n<p><img decoding=\"async\" class=\"aligncenter wp-image-14238\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/2-table-of-functional-group-seniority-priority-for-iupac-nomenclature.gif\" alt=\"table-of-functional-group-seniority-priority-for-iupac-nomenclature\" width=\"585\" height=\"674\" \/><\/p>\n<p>Note that with the exception of sulfonic acids, these are all carboxylic acid derivatives. IUPAC goes\u00a0 into way more detail than we need to here.<\/p>\n<p>The &#8220;seniority rules&#8221; continue in the following order, where we are cherry-picking the most common examples. [<a href=\"#notetwo\"><strong>Note 2<\/strong><\/a>]<\/p>\n<h2><a id=\"three\"><\/a>3. Next In Line: Nitrile, Aldehyde, Ketone, Alcohol, Thiol, Amine<\/h2>\n<p><img decoding=\"async\" class=\"aligncenter wp-image-14239\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/3-functional-group-priorities-seniority-for-nomenclature-nitrile-aldehyde-ketone-alcohol-thiol-amine.gif\" alt=\"functional-group-priorities-seniority-for-nomenclature-nitrile-aldehyde-ketone-alcohol-thiol-amine\" width=\"585\" height=\"716\" \/><\/p>\n<p>Again, this is not a complete list &#8211; we&#8217;re cherry picking the most commonly encountered functional groups here.<\/p>\n<h2><a id=\"four\"><\/a>4. Alkenes And Alkynes<\/h2>\n<p>If carbon-carbon multiple bonds are present in the molecule, they are considered as substituents with a priority (or &#8220;seniority&#8221;, according to IUPAC) lower than that of amines.<\/p>\n<p>So for a molecule with an alkene and an\u00a0 <strong>alcohol,<\/strong> the alcohol has priority and the molecule has the suffix, &#8220;-ol&#8221;. The presence of the double bond is noted with the locant followed by the prefix, &#8220;en-&#8220;. For example, pent-4-en-1-ol.<\/p>\n<p>If no higher-priority groups are present, the suffix for a molecule containing an alkene will be &#8220;-ene&#8221;, such as in pent-1-ene.<\/p>\n<p>For an alkyne, the corresponding prefix is &#8220;-yn&#8221; and the suffix is &#8220;yne&#8221;.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-14240\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/4-alkene-alkyne-nomenclature-en-prefix-ene-suffix-yn-prefix-yne-suffix.gif\" alt=\"alkene-alkyne-nomenclature-en-prefix-ene-suffix-yn-prefix-yne-suffix\" width=\"525\" height=\"301\" \/><\/p>\n<p>At this point the methodology for naming molecules changes slightly. In the absence of one of the above functional groups, the suffix will always be &#8220;-ane&#8221;, &#8220;-ene&#8221;, or &#8220;-yne&#8221;, depending on whether any unsaturation is present in the molecule, and any lower-ranked substituents will be prefixes.<\/p>\n<h2><strong><a id=\"five\"><\/a>5. Alkenes vs. Alkynes: Which\u00a0 Takes &#8220;Priority&#8221;?<\/strong><\/h2>\n<p>This brings us to a common source of confusion in nomenclature. When an alkene\u00a0<em>and<\/em> an alkyne are present in a molecule, which takes priority?<\/p>\n<p>It\u00a0 depends on what you mean by &#8220;priority&#8221;.<\/p>\n<p>For the purposes of the\u00a0<em>name<\/em>, &#8220;-ene&#8221; comes before &#8220;-yne&#8221; alphabetically. <strong>So when an alkene and an alkyne are present in\u00a0 the same molecule, the ending will always be &#8220;yne&#8221;.\u00a0<\/strong><\/p>\n<p>For the purposes of\u00a0<strong>numbering<\/strong>, if there is a tie between an alkene and an alkyne for determining the lowest locant, the alkene takes priority.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-14241\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/5-alkene-and-alkyne-naming-which-group-takes-priority.gif\" alt=\"alkene-and-alkyne-naming-which-group-takes-priority\" width=\"585\" height=\"328\" \/><\/p>\n<p>IUPAC says it this way:<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-14242\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/6-iupac-says-that-ene-takes-priority-over-yne-in-the-event-of-a-tie-for-numbering-purposes.gif\" alt=\"iupac-says-that-ene-takes-priority-over-yne-in-the-event-of-a-tie-for-numbering-purposes\" width=\"585\" height=\"108\" \/><\/p>\n<p>Right. Let&#8217;s move along to the other functional groups. Sandwich<\/p>\n<h2><a id=\"six\"><\/a>6. Functional Groups That Are Always Prefixes: Halides, Alkoxides, Azides, Nitro<\/h2>\n<p>Some functional groups have been deemed unworthy of ever getting their own suffixes. For nomenclature purposes, they are forever out of the limelight, subservient to the -ane, -ene, or -yne ending of the parent hydrocarbon\u00a0 (or &#8220;parent hydride&#8221;, as IUPAC calls it).<\/p>\n<p>These groups include the halides (bromo, chloro, fluoro, iodo), ethers (&#8220;alkoxy&#8221;), azide and nitro functional groups. Source: Table 5.1, Section P-59.1.9 of the 2013 Blue Book (Page 630).<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-14243\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/7-functional-groups-that-are-always-prefixes-halides-ethers-azides-nitro.gif\" alt=\"functional-groups-that-are-always-prefixes-halides-ethers-azides-nitro\" width=\"640\" height=\"584\" \/><\/p>\n<h2><a id=\"seven\"><\/a>7. Some Examples With Multiple Functional Groups<\/h2>\n<p>Here are some examples of applying the order of functional group priorities to solve nomenclature problems. The highest ranked functional group becomes the suffix &#8211; it&#8217;s highlighted in red.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"wp-image-14244 aligncenter\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/8-examples-of-applying-iupac-nomenclature-functional-group-priority.gif\" alt=\"examples of applying iupac nomenclature functional group priority\" width=\"640\" height=\"426\" \/><\/a><\/p>\n<p>This covers most of the functional groups you&#8217;ll meet in Org1\/Org2.<\/p>\n<hr \/>\n<h2><a id=\"notes\"><\/a>Notes<\/h2>\n<div class=\"related-articles\"><p><strong>Related Articles<\/strong><\/p><ul><li><a href=\"https:\/\/www.masterorganicchemistry.com\/organic-chemistry-practice-problems\/organic-chemistry-nomenclature-quizzes\/\" class=\"\"><span>Organic Chemistry Nomenclature Quizzes (MOC Membership)<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2014\/10\/21\/organic-chemistry-iupac-nomenclature-demystified-with-a-simple-puzzle-piece-approach\/\" class=\"\"><span>Organic Chemistry IUPAC Nomenclature Demystified With A Simple Puzzle Piece Approach<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2010\/10\/30\/summary-sheet-6-alkane-nomenclature\/\" class=\"\"><span>Summary Sheet \u2013 Alkane Nomenclature<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2010\/10\/06\/functional-groups-organic-chemistry\/\" class=\"\"><span>Meet the (Most Important) Functional Groups<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/11\/10\/dont-be-futyl-learn-the-butyls\/\" class=\"\"><span>Don\u2019t Be Futyl, Learn The Butyls<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2010\/10\/15\/the-many-many-ways-to-draw-butane\/\" class=\"\"><span>The Many, Many Ways of Drawing Butane<\/span><\/a><\/li><\/ul><\/div>\n<p><span style=\"color: #000000;\"><strong><a id=\"noteone\"><\/a>Note 1. <\/strong>This article takes into account the latest recommendations of the <a style=\"color: #000000;\" href=\"https:\/\/pubs.rsc.org\/en\/content\/ebook\/978-0-85404-182-4\"> IUPAC Blue Book\u00a0<\/a> (2013 edition)]\u00a0<\/span><\/p>\n<p><span style=\"color: #000000;\"><strong><a id=\"notetwo\"><\/a>Note 2. <\/strong>. Just for the record these &#8220;rules for\u00a0 seniority&#8221; can\u00a0 be found in section P-41 of the Blue Book, page 428 of the 2013 edition.\u00a0<\/span><\/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\/2986-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\/2987-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\/2988-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\/2989-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\/2990-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<ol>\n<li><strong>IUPAC Blue Book<\/strong>. Nomenclature of Organic Chemistry &#8211; IUPAC Recommendations and Preferred Names 2013<br \/>\nHenri A. Favre; Warren H. Powell<br \/>\n<strong>DOI: <\/strong><a href=\"https:\/\/doi.org\/10.1039\/9781849733069\">doi.org\/10.1039\/9781849733069<\/a><br \/>\nThis book contains IUPAC&#8217;s preferred names for organic compounds, which is not to say that all chemists follow their recommendations unanimously.<br \/>\nSection P-41, page 428 contains the rules for &#8220;seniority&#8221;.<\/li>\n<\/ol>\n","protected":false},"excerpt":{"rendered":"<p>How To Determine Which Functional Group Has &#8220;Priority&#8221; For Naming Purposes When a molecule has multiple functional groups, we could potentially run into problems when <\/p>\n","protected":false},"author":1,"featured_media":14237,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[1408],"tags":[167,209,494,242,504],"post_folder":[],"class_list":["post-1353","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-alkanes-nomenclature","tag-alcohols","tag-esters","tag-functional-groups-2","tag-nomenclature","tag-priorities"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.7 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Table of Functional Group Priorities for Nomenclature &#8211; 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