{"id":5013,"date":"2012-04-27T17:31:42","date_gmt":"2012-04-27T17:31:42","guid":{"rendered":"https:\/\/www.masterorganicchemistry.com\/?p=5013"},"modified":"2026-04-18T06:14:31","modified_gmt":"2026-04-18T11:14:31","slug":"polar-protic-polar-aprotic-nonpolar-all-about-solvents","status":"publish","type":"post","link":"https:\/\/www.masterorganicchemistry.com\/2012\/04\/27\/polar-protic-polar-aprotic-nonpolar-all-about-solvents\/","title":{"rendered":"Polar Protic? Polar Aprotic? Nonpolar? All About Solvents"},"content":{"rendered":"<p><strong>Polar Protic vs Polar Aprotic vs Nonpolar: About Solvents In Organic Chemistry<\/strong><\/p>\n<p>A lot of students I talk to have questions about solvents.<\/p>\n<p>Solvents can cause considerable confusion in reactions, because they&#8217;re listed along with the reagents of a reaction but often don&#8217;t actually participate in the reaction itself. And to be honest, a lot of instructors (myself included) are less than consistent about when to include solvents and when not to. So the whole exercise can come across as somewhat arbitrary: when do you know when to include the solvent?<\/p>\n<p><img fetchpriority=\"high\" decoding=\"async\" class=\"alignnone wp-image-37420\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2024\/10\/0-summary-solvents-polar-protic-polar-aprotic-nonpolar-dielectric-constant-1.gif\" alt=\"summary solvents polar protic polar aprotic nonpolar dielectric constant\" width=\"640\" height=\"667\" \/><\/a><\/p>\n<p><strong>Table Of Contents<\/strong><\/p>\n<ol>\n<li><a href=\"#one\">What Is A Solvent?<\/a><\/li>\n<li><a href=\"#two\">What Does &#8220;Polar&#8221; and &#8220;Non-Polar&#8221; Mean?<\/a><\/li>\n<li><a href=\"#three\">The Distinction Between &#8220;Protic&#8221; And &#8220;Aprotic&#8221; Solvents<\/a><\/li>\n<li><a href=\"#four\">Nonpolar Solvents: A Table<\/a><\/li>\n<li><a href=\"#five\">&#8220;Borderline&#8221; Polar Aprotic Solvents<\/a><\/li>\n<li><a href=\"#six\">Polar Aprotic Solvents: A Table<\/a><\/li>\n<li><a href=\"#seven\">Polar Protic Solvents: A Table<\/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. What Is A Solvent?<\/h2>\n<p>Let&#8217;s back up. What&#8217;s a solvent, anyway?<\/p>\n<p>A solvent is a <strong>liquid<\/strong> that serves as the medium for a reaction. It can serve two major purposes:<\/p>\n<ol>\n<li>(Non-participatory)\u00a0<strong>to dissolve the reactants.<\/strong> Remember &#8220;like dissolves like&#8221; ? Polar solvents are best for dissolving polar reactants (such as ions); nonpolar solvents are best for dissolving nonpolar reactants (such as hydrocarbons).<\/li>\n<li>Participatory: \u00a0as a source of <strong>acid<\/strong> (proton), <strong>base<\/strong> (removing protons), or as a <strong>nucleophile<\/strong> (donating a lone pair of electrons). The only class of solvents for which this is something you generally need to worry about are polar protic solvents (<a href=\"#seven\">see below<\/a>).<\/li>\n<\/ol>\n<h2><a id=\"two\"><\/a>2.\u00a0 Polar Solvents Have Large Dipole Moments. Non-Polar Solvents Have Small Or Zero Dipole Moment<\/h2>\n<p>OK. So what does &#8220;polar&#8221; and &#8220;non-polar&#8221; mean?<\/p>\n<ul>\n<li><strong>Polar solvents<\/strong> have large dipole moments (aka &#8220;partial charges&#8221;); they contain bonds between atoms with very different electronegativities, such as oxygen and hydrogen.<\/li>\n<li><strong>Non polar solvents<\/strong> contain bonds between atoms with similar electronegativities, such as carbon and hydrogen (think hydrocarbons, such as gasoline). \u00a0Bonds between atoms with similar electronegativities will lack partial charges; it&#8217;s this absence of charge which makes these molecules &#8220;non-polar&#8221;.<\/li>\n<\/ul>\n<p>There are two direct ways of measuring polarity. One is through measuring a constant called &#8220;dielectric constant&#8221; or <a href=\"http:\/\/en.wikipedia.org\/wiki\/Relative_permittivity\">permitivity<\/a>. The greater the dielectric constant, the greater the polarity (water = high, gasoline = low). \u00a0A second comes from directly measuring the dipole moment.<\/p>\n<p>Polarity is a <strong>continuum<\/strong>. While we can all agree that pentane is &#8220;non-polar&#8221;, and water is &#8220;polar&#8221;, there are borderline cases like diethyl ether, dichloromethane, and tetrahydrofuran (THF) which have both polar and non-polar characteristics. In a pinch, a good rule-of-thumb dividing line between &#8220;polar&#8221; and &#8220;non-polar&#8221; is miscibility with water. Diethyl ether and dichloromethane don&#8217;t mix with water; THF, DMSO, acetonitrile, DMF, acetone and short-chain alcohols do.<\/p>\n<h2><a id=\"three\"><\/a>3. &#8220;Protic&#8221; Solvents Have O-H or N-H Bonds And Can Hydrogen-Bond With Themselves. &#8220;Aprotic&#8221; Solvents Cannot Be Hydrogen Bond Donors<\/h2>\n<p>There&#8217;s a final distinction to be made and this also causes confusion. Some solvents are called &#8220;protic&#8221; and some are called &#8220;aprotic&#8221;. \u00a0What makes a solvent a &#8220;protic&#8221; solvent, anyway?<\/p>\n<ul>\n<li><strong>Protic solvents<\/strong> have O-H or N-H bonds. Why is this important? Because protic solvents can participate in hydrogen bonding, which is a powerful intermolecular force. Additionally, these O-H or N-H bonds can serve as a source of protons (H+).<\/li>\n<li><strong>Aprotic solvents<\/strong>\u00a0may have hydrogens on them somewhere, but they lack O-H or N-H bonds, and therefore <strong>cannot hydrogen bond <\/strong>with themselves.<\/li>\n<\/ul>\n<div>For the average first semester student, these distinctions come up the most in substitution reactions, where hydrogen bonding solvents tend to decrease the reactivity of nucleophiles; polar aprotic solvents, on the other hand, do not.<\/div>\n<div><\/div>\n<div>There are 3 types of solvents commonly encountered: nonpolar, polar aprotic, and polar protic.<span style=\"color: #993366;\"><em> (There ain&#8217;t such a thing as a non-polar protic solvent).<\/em><\/span><\/div>\n<h2><strong><a id=\"four\"><\/a>4. Nonpolar S<\/strong><strong>olvents Have Little To No Dipole Moment<\/strong><\/h2>\n<p>These solvents have low dielectric constants (&lt;5) and are not good solvents for charged species such as anions. However diethyl ether (Et<sub>2<\/sub>O) is a common solvent for Grignard reactions; its lone pairs are Lewis basic and can help to solvate the Mg cation.<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-14821\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/1-table-of-non-polar-solvents-with-dielectric-constants-and-dipole-moments-for-pentane-benzene-toluene-chloroform-diethyl-ether.gif\" alt=\"table of non polar solvents with dielectric constants and dipole moments for pentane benzene toluene chloroform diethyl ether\" width=\"600\" height=\"862\" \/><\/a><\/p>\n<h2><strong><a id=\"five\"><\/a>5. &#8220;Borderline&#8221; Polar Aprotic Solvents Have Small Dipole Moments And Low (&lt;10) Dielectric Constants<\/strong><\/h2>\n<p>These solvents have moderately higher dielectric constants than the nonpolar solvents (between 5 and 20). Since they have intermediate polarity they are good &#8220;general purpose&#8221; solvents for a wide range of reactions. They are &#8220;aprotic&#8221; because they lack O-H or N-H bonds. For our purposes they don&#8217;t participate in reactions: they serve only as the medium.<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-14822\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/2-borderline-polar-aprotic-solvents-with-dielectric-constants-and-dipole-moments-dichloromethane-thf-ethyl-acetate.gif\" alt=\"borderline polar aprotic solvents with dielectric constants and dipole moments dichloromethane thf ethyl acetate\" width=\"600\" height=\"614\" \/><\/a><\/p>\n<h2><strong><a id=\"six\"><\/a>6. Four Key Polar Aprotic Solvents With Large (&gt;10) Dielectric Constants<\/strong><\/h2>\n<p>These solvents all have large dielectric constants (&gt;20) and large dipole moments, but they do not participate in hydrogen bonding (no O-H or N-H bonds). Their high polarity allows them to dissolve charged species such as various anions used as nucleophiles (e.g. CN(-), HO(-), etc.). The lack of hydrogen bonding in the solvent means that these nucleophiles are relatively &#8220;free&#8221; in solution, making them more reactive. For our purposes these solvents do not participate in reactions.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-14823\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/3-table-of-polar-aprotic-solvents-including-dielectrric-constant-and-dipole-moment-acetone-dmf-dmso-acetonitrile.gif\" alt=\"table of polar aprotic solvents including dielectrric constant and dipole moment acetone dmf dmso acetonitrile\" width=\"600\" height=\"512\" \/><\/a><\/p>\n<h2><strong><a id=\"seven\"><\/a>7. Polar Protic Solvents: A Table<\/strong><\/h2>\n<p>Polar protic solvents tend to have high dielectric constants and high dipole moments. Furthermore, since they possess O-H or N-H bonds, they can also participate in hydrogen bonding. These solvents can also serve as acids (sources of protons) and weak nucleophiles (forming bonds with strong electrophiles).<\/p>\n<p>They are most commonly used as the solvent for their conjugate bases. (e.g. H<sub>2<\/sub>O is used as the solvent for HO(-); EtOH is used as the solvent for EtO(-). )<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-14824\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/4-table-of-polar-protic-solvents-ammonia-and-alcohols-dielectric-constants-and-dipole-moments.gif\" alt=\"table of polar protic solvents ammonia and alcohols dielectric constants and dipole moments\" width=\"600\" height=\"805\" \/><\/a><\/p>\n<p>These types of solvents are by far the most likely to participate in reactions. There are many examples (too many to list) where a polar protic solvent such as water, methanol, or ethanol can serve as the nucleophile in a reaction, often when a strong electrophile (such as an acid) is present. So if you see this type of solvent, be on the lookout.<\/p>\n<p>Source for data: <a href=\"http:\/\/en.wikipedia.org\/wiki\/Solvent\">Wikipedia<\/a><\/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\/2011\/07\/18\/steric-hindrance-is-like-a-fat-goalie\/\" class=\"\"><span>Steric Hindrance is Like a Fat Goalie<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2010\/10\/01\/how-intermolecular-forces-affect-boiling-points\/\" class=\"\"><span>The Four Intermolecular Forces and How They Affect Boiling Points<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2010\/10\/25\/3-trends-that-affect-boiling-points\/\" class=\"\"><span>3 Trends That Affect Boiling Points<\/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><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2016\/01\/29\/gilman-reagents-organocuprates-how-theyre-made\/\" class=\"\"><span>Organocuprates (Gilman Reagents): How They\u2019re Made<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2015\/11\/09\/synthesis-of-grignard-and-organolithium-reagents\/\" class=\"\"><span>Formation of Grignard and Organolithium Reagents<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/organic-chemistry-practice-problems\/substitution-practice-sn1\/\" class=\"\"><span>Substitution Practice \u2013 SN1 (MOC Membership)<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/organic-chemistry-practice-problems\/substitution-practice-sn2\/\" class=\"\"><span>Substitution Practice \u2013 SN2 (MOC Membership)<\/span><\/a><\/li><\/ul><\/div>\n<hr \/>\n<h2><a id=\"quizzes\"><\/a>Quiz Yourself!<\/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\/0147-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\/0159-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\/0163-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\/2691-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\/2692-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>Polar Protic vs Polar Aprotic vs Nonpolar: About Solvents In Organic Chemistry A lot of students I talk to have questions about solvents. Solvents can <\/p>\n","protected":false},"author":1,"featured_media":37420,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[1414],"tags":[819,817,496,820,243,630,629,686,818],"post_folder":[],"class_list":["post-5013","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-substitution-reactions","tag-dmf","tag-dmso","tag-hydrogen-bonding","tag-mecn","tag-nucleophiles","tag-polar-aprotic","tag-polar-protic","tag-solvents","tag-thf"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.7 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Polar Protic? Polar Aprotic? Nonpolar? All About Solvents<\/title>\n<meta name=\"description\" content=\"What&#039;s a polar protic solvent vs a polar aprotic solvent vs a non-polar solvent? 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