{"id":8495,"date":"2014-09-17T15:34:31","date_gmt":"2014-09-17T19:34:31","guid":{"rendered":"https:\/\/www.masterorganicchemistry.com\/?p=8495"},"modified":"2026-05-03T07:45:43","modified_gmt":"2026-05-03T12:45:43","slug":"alcohols-1-nomenclature-and-properties","status":"publish","type":"post","link":"https:\/\/www.masterorganicchemistry.com\/2014\/09\/17\/alcohols-1-nomenclature-and-properties\/","title":{"rendered":"Alcohols &#8211; Nomenclature and Properties"},"content":{"rendered":"<p><strong>Alcohol Nomenclature, Properties, and Structure<\/strong><\/p>\n<p>In this next series of posts we are going to discuss the reactions of <b>alcohols<\/b>.<\/p>\n<p>As a functional group, alcohols are introduced fairly early in organic chemistry. Their reactions, however, are usually not covered until near the end of Org 1 &#8211; at least after subjects like substitution and elimination reactions have been explored. That\u2019s because, as we will see, the reactions of alcohols often fall into these categories.<\/p>\n<p>We\u2019ll cover the reactions of alcohols in due course. But today, let\u2019s just get our feet wet by familiarizing ourselves with their structure, nomenclature and physical properties.<\/p>\n<p><img fetchpriority=\"high\" decoding=\"async\" class=\"alignnone wp-image-35233\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/08\/0-summary-properties-and-nomenclature-of-alcohols.gif\" alt=\"summary-properties and nomenclature of alcohols master organic chemistry\" width=\"640\" height=\"604\" \/><\/a><\/p>\n<p><strong>Table of Contents<\/strong><\/p>\n<ol>\n<li><a href=\"#one\">Structure and Nomenclature of Alcohols: Primary, Secondary, and Tertiary<\/a><\/li>\n<li><a href=\"#two\">Physical Properties of Alcohols: Hydrogen Bonding<\/a><\/li>\n<li><a href=\"#three\">Physical Properties of Alcohols: Boiling Points<\/a><\/li>\n<li><a href=\"#four\">Alcohols Are &#8220;Polar&#8221; And Have Considerable Water Solubility<\/a><\/li>\n<li><a href=\"#quiz\">Quiz Yourself!<\/a><\/li>\n<\/ol>\n<hr \/>\n<h2><b><a id=\"one\"><\/a>1. Structure and Nomenclature Of Alcohols: Primary, Secondary, and Tertiary<\/b><\/h2>\n<p>Alcohols are organic molecules containing the \u201chydroxyl\u201d functional group, \u201cOH\u201d directly bonded to carbon. The carbon directly attached to OH is technically called the \u201ccarbinol\u201d carbon, although this nomenclature is often not introduced in introductory classes. The carbinol carbon (carbon attached to OH), however, is the key to understanding the most common\u00a0classifications\u00a0we use for alcohols, that being \u201cprimary\u201d, \u201csecondary\u201d, and \u201ctertiary\u201d alcohols.<\/p>\n<p>To determine if an alcohol is primary, secondary, or tertiary, <strong>examine the carbon attached to OH<\/strong>. If that carbon is attached to <strong>one<\/strong> carbon, the alcohol is <strong>primary<\/strong>; <strong>two<\/strong>, <strong>secondary<\/strong>; <strong>three<\/strong>, <strong>tertiary<\/strong>. If zero carbons and three hydrogens (a unique situation) it is methanol. Hydroxyl groups attached to aromatic rings are called, \u201cphenols\u201d.<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-15108\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/1-primary-alcohol-secondary-alcohol-tertiary-alcohol-what-does-it-mean-examples-number-of-carbons-attached-to-c-oh-carbon.gif\" alt=\"primary alcohol secondary alcohol tertiary alcohol what does it mean examples number of carbons attached to c-oh carbon\" width=\"630\" height=\"261\" \/><\/p>\n<p>Note that not all functional groups containing OH are alcohols. If the OH is attached to a carbonyl (C=O), that functional group is called a \u201ccarboxylic acid\u201d. OH attached to an alkene is called an \u201cenol\u201d (ene + ol). And there are other funky functional groups such as hydrates (\u201cgeminal diol\u201d) that really belong in a separate category from alcohols themselves.<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-15109\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/2-not-all-functional-groups-with-OH-are-alcohols-example-carboxylic-acid-enol-geminal-diol-or-hydrate.gif\" alt=\"not all functional groups with OH are alcohols example carboxylic acid enol geminal diol or hydrate\" width=\"600\" height=\"159\" \/><\/p>\n<p>The deeper nomenclature of alcohols is not something I\u2019m going to discuss on this blog at the present. There are all kinds of fantastic videos and resources on the internet that describe the naming of alcohols in detail, and I will happily refer you to those for now.<\/p>\n<p>Here\u2019s an example by Leah Fisch, for example.<\/p>\n<p><iframe src=\"\/\/www.youtube.com\/embed\/HuW3Rp1bj2k\" width=\"640\" height=\"360\" frameborder=\"0\" allowfullscreen=\"allowfullscreen\"><\/iframe><\/p>\n<h2><b><a id=\"two\"><\/a>2. Physical Properties of Alcohols: Hydrogen Bonding<\/b><\/h2>\n<p>The key to understanding the physical properties of alcohols &#8211; and as we shall see later, their reactivity &#8211; is to appreciate just how <strong>polarized<\/strong> the hydroxyl group is. Oxygen has an electronegativity of 3.5 and hydrogen 2.2. Oxygen, being \u201cgreedier\u201d for electrons than hydrogen, will have more than its \u201cshare\u201d of the two electrons in the O-H bond.<\/p>\n<p>This means that oxygen will be more \u201celectron rich\u201d (more<strong> negative<\/strong>) and hydrogen more \u201celectron poor\u201d (more <strong>positive<\/strong>) than they would be in a bond where electrons were shared perfectly equally.\u00a0 We say that electron density in the O-H bond is strongly \u201cpolarized\u201d toward oxygen.\u00a0 Another way of saying the same thing is that the O-H bond has a strong \u201cdipole\u201d.<\/p>\n<p>Since opposite charges attract, these partial charges will line up in solution in a way where the partial negative oxygens on one molecule interact with the partially positive hydrogens on another. These interactions between molecules, which we call, \u201c<strong>hydrogen bonds<\/strong>\u201d are about 1\/10 as strong as normal bonds, and are much more transient, lasting only a fraction of a second on average. Still, the effect of hydrogen bonding is to lead molecules to \u201cstick\u201d to one another.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15110\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/4-hydrogen-bonding-in-alcohols-between-partial-negative-oxygen-and-partial-positive-hydrogen-gives-strong-intramolecular-forces-leading-to-high-boiling-points.gif\" alt=\"hydrogen bonding in alcohols between partial negative oxygen and partial positive hydrogen gives strong intramolecular forces leading to high boiling points\" width=\"600\" height=\"258\" \/><\/p>\n<p>&nbsp;<\/p>\n<p>A non-scientific analogy would be to compare the dipoles that lead to hydrogen bonding to the way Velcro &#8220;hooks&#8221; stick to Velcro &#8220;fuzz&#8221;. They&#8217;re not strong bonds, necessarily, but are sticky enough.<\/p>\n<p><iframe src=\"\/\/www.youtube.com\/embed\/-sh-mATW4wQ\" width=\"640\" height=\"360\" frameborder=\"0\" allowfullscreen=\"allowfullscreen\"><\/iframe><\/p>\n<h2><a id=\"three\"><\/a>3. Physical Properties of Alcohols: Boiling Points<\/h2>\n<p>This has two important implications.<\/p>\n<p>First, <strong>hydroxyl groups greatly increase boiling points<\/strong>. Look what happens to the boiling point of propane (an alkane)\u00a0 when a CH<sub>3<\/sub> group is replaced with an OH group &#8211; the molecular weights are the same, but there\u2019s over a 100\u00b0 C difference in boiling point! <span style=\"color: #993366;\"><em>[Why is it important to compare molecules of roughly similar molecular weight? Because boiling points also with increased Van Der Waals interactions, which are roughly proportional to increased surface area. Keeping the molecular weights constant ensures we&#8217;re comparing apples to apples in this respect].<\/em><\/span><\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15111\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/6-alcohols-participate-in-hydrogen-bonding-with-oh-groups-why-does-ethanol-have-higher-boiling-point-than-propane-.gif\" alt=\"alcohols participate in hydrogen bonding with oh groups why does ethanol have higher boiling point than propane\" width=\"600\" height=\"190\" \/><\/p>\n<p>If one is good, then surely more is better? Yes! Replacing a CH<sub>3\u00a0<\/sub>on propanol with an OH group gives us \u201cethylene glycol\u201d, a \u201cdi-ol\u201d (actually called a \u201cvicinal diol\u201d since the alcohols are on adjacent carbons). Having twice as many hydroxyl groups, we would expect it to be even more polar than propanol, and thus have a higher boiling point. This is true &#8211; the boiling point of ethylene glycol is 197\u00b0C.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15112\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/7-why-does-ethylene-glycol-have-higher-boiling-point-than-1-propanol-because-two-oh-groups-means-more-hydrogen-bonding.gif\" alt=\"why does ethylene glycol have higher boiling point than 1 propanol because two oh groups means more hydrogen bonding\" width=\"600\" height=\"164\" \/><\/p>\n<p>The differences in\u00a0boiling point between primary, secondary, and tertiary alcohols can be subtle. Generally, the more \u201cexposed\u201d the hydroxyl group, the more other OH groups it will be able to interact with, and the higher the boiling point.<\/p>\n<p>The isomers of butanol are a perfect example. See how the primary alcohols (1-butanol and 2-methyl-1-propanol) \u00a0have higher boiling points than the secondary alcohol (2-butanol) \u00a0which has a higher boiling point than the tertiary alcohol (t-butanol).<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15113\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/8-examples-of-alcohols-1-butanol-higher-boiling-point-than-isobutyl-alcohol-2-butanol-has-higher-boiling-point-than-t-butanol.gif\" alt=\"examples of alcohols 1 butanol higher boiling point than isobutyl alcohol 2 butanol has higher boiling point than t butanol\" width=\"600\" height=\"197\" \/><\/p>\n<h2><a id=\"four\"><\/a>4. Alcohols Are Polar And Have Considerable Water Solubility<\/h2>\n<p><strong>The second key implication<\/strong> of hydrogen bonding is that the hydroxyl group imparts \u00a0<strong>much greater water solubility<\/strong> upon organic molecules. That&#8217;s because water itself is a hydrogen-bonding solvent, and therefore the dipole of the hydroxyl group can interact favourably with the hydroxyl group of H<sub>2<\/sub>O. Ethanol and water, for example, are mixable (&#8220;miscible&#8221; is the word we actually use) in all proportions.\u00a0 It isn\u2019t until butanol that the greasy alkyl chain starts interfering with water solubility.<\/p>\n<p>We often say that hydroxyl groups are a \u201cpolar\u201d functional group. Solvents containing OH are generally\u00a0considered to be \u00a0&#8220;<strong>polar&#8221;\u00a0<\/strong>solvents because of the large dipole. You may have also heard of alcohols being referred to as &#8220;<strong>polar protic<\/strong>&#8221; solvents. What&#8217;s that about? It has to do with one of the key properties of alcohols &#8211; their ability to participate in acid-base reactions. That&#8217;s the subject of the next post!<\/p>\n<p><strong>Next post &#8211; <a href=\"https:\/\/www.masterorganicchemistry.com\/2014\/10\/06\/how-to-make-alcohols-more-reactive\/\">Alcohols Are Both Acids And Bases<\/a><\/strong><\/p>\n<hr \/>\n<h2>Notes<\/h2>\n<div class=\"related-articles\"><p><strong>Related Articles<\/strong><\/p><ul><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2014\/10\/06\/how-to-make-alcohols-more-reactive\/\" class=\"\"><span>Alcohols Can Act As Acids Or Bases (And Why It Matters)<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2010\/06\/16\/1-2-3-4\/\" class=\"\"><span>Primary, Secondary, Tertiary, Quaternary In Organic Chemistry<\/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\/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\/2012\/04\/27\/polar-protic-polar-aprotic-nonpolar-all-about-solvents\/\" class=\"\"><span>Polar Protic? Polar Aprotic? Nonpolar? All About Solvents<\/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><\/ul><\/div>\n<p><strong>Note 1.\u00a0<\/strong>Some physical properties of alcohols:<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-45810\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2026\/05\/T12-Table-with-physical-properties-of-all-normal-straight-chain-alcohols-from-methanol-to-decanol-density-water-solubility-boiling-melting-point.gif\" alt=\"Table with physical properties of all normal straight chain alcohols from methanol to decanol density water solubility boiling melting point\" width=\"640\" height=\"459\" \/><\/a><\/p>\n<hr \/>\n<h2><a id=\"quiz\"><\/a>Quiz Yourself!<\/h2>\n<p><br \/>\n<img loading=\"lazy\" decoding=\"async\" class=\"wp-image-36214 aligncenter\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/3692-Front-Image-Only.png\" alt=\"\" width=\"600\" height=\"450\" \/><\/a><\/p>\n<p style=\"text-align: center;\"><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a MOC member<\/strong><\/a> to see the clickable quiz with answers on the back.<\/p>\n<p><br \/>\n<br \/>\n<img loading=\"lazy\" decoding=\"async\" class=\"wp-image-36214 aligncenter\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/3693-Front-Image-Only.png\" alt=\"\" width=\"600\" height=\"450\" \/><\/a><\/p>\n<p style=\"text-align: center;\"><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a MOC member<\/strong><\/a> to see the clickable quiz with answers on the back.<\/p>\n<p><br \/>\n<br \/>\n<img loading=\"lazy\" decoding=\"async\" class=\"wp-image-36214 aligncenter\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/0566-Front-Image-Only.png\" alt=\"\" width=\"600\" height=\"450\" \/><\/a><\/p>\n<p style=\"text-align: center;\"><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a MOC member<\/strong><\/a> to see the clickable quiz with answers on the back.<\/p>\n<p><br \/>\n<br \/>\n<img loading=\"lazy\" decoding=\"async\" class=\"wp-image-36214 aligncenter\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/0567-Front-Image-Only.png\" alt=\"\" width=\"600\" height=\"450\" \/><\/a><\/p>\n<p style=\"text-align: center;\"><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a MOC member<\/strong><\/a> to see the clickable quiz with answers on the back.<\/p>\n<p><br \/>\n<br \/>\n<img loading=\"lazy\" decoding=\"async\" class=\"wp-image-36214 aligncenter\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/0568-Front-Image-Only.png\" alt=\"\" width=\"600\" height=\"450\" \/><\/a><\/p>\n<p style=\"text-align: center;\"><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a MOC member<\/strong><\/a> to see the clickable quiz with answers on the back.<\/p>\n<p><br \/>\n<br \/>\n<img loading=\"lazy\" decoding=\"async\" class=\"wp-image-36214 aligncenter\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/0569-Front-Image-Only.png\" alt=\"\" width=\"600\" height=\"450\" \/><\/a><\/p>\n<p style=\"text-align: center;\"><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a MOC member<\/strong><\/a> to see the clickable quiz with answers on the back.<\/p>\n<p><\/p>\n","protected":false},"excerpt":{"rendered":"<p>Alcohol Nomenclature, Properties, and Structure In this next series of posts we are going to discuss the reactions of alcohols. As a functional group, alcohols <\/p>\n","protected":false},"author":1,"featured_media":35233,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[1420],"tags":[167,179,496,242,608,607,606,1017],"post_folder":[],"class_list":["post-8495","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-alcohols-epoxides-ethers","tag-alcohols","tag-boiling-points","tag-hydrogen-bonding","tag-nomenclature","tag-primary","tag-secondary","tag-tertiary","tag-water-solubility"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.7 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Alcohols - Nomenclature and Properties &#8211; Master Organic Chemistry<\/title>\n<meta name=\"description\" content=\"Introduction to alcohol nomenclature: primary, secondary, and tertiary alcohols, hydrogen bonding, boiling points, polarity, and water-solubility.\" \/>\n<meta name=\"robots\" content=\"index, follow, max-snippet:-1, max-image-preview:large, max-video-preview:-1\" \/>\n<link rel=\"canonical\" href=\"https:\/\/www.masterorganicchemistry.com\/2014\/09\/17\/alcohols-1-nomenclature-and-properties\/\" \/>\n<meta property=\"og:locale\" content=\"en_US\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Alcohols - Nomenclature and Properties &#8211; 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