{"id":9020,"date":"2015-07-27T14:41:10","date_gmt":"2015-07-27T19:41:10","guid":{"rendered":"https:\/\/www.masterorganicchemistry.com\/?p=9020"},"modified":"2025-06-05T16:21:32","modified_gmt":"2025-06-05T21:21:32","slug":"synthesis-6-reactions-of-alcohols","status":"publish","type":"post","link":"https:\/\/www.masterorganicchemistry.com\/2015\/07\/27\/synthesis-6-reactions-of-alcohols\/","title":{"rendered":"Alcohol Reactions Roadmap (PDF)"},"content":{"rendered":"<p><strong>The Alcohol Reaction Map<\/strong><\/p>\n<p>Having now finished (at long last) covering the key reactions of alcohols, let&#8217;s stop to put everything in perspective.<\/p>\n<p>Over the past 18 articles (!) in this series on alcohols, we covered reactions such as:<\/p>\n<ul>\n<li>Ether formation via substitution reactions<\/li>\n<li>Elimination of alcohols to form alkenes<\/li>\n<li>Conversion of alcohols to alkyl halides via substitution reactions<\/li>\n<li>Cleavage of ethers<\/li>\n<li>Opening of epoxides<\/li>\n<li>Reactions of thiols<\/li>\n<\/ul>\n<p>In my experience, there&#8217;s nothing that helps doing this like making a &#8220;map&#8221; of reactions. So let&#8217;s put each of these reactions onto a single page, in &#8220;reaction map&#8221; format:<\/p>\n<p><img fetchpriority=\"high\" decoding=\"async\" class=\"alignnone wp-image-16795\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2020\/01\/1-reaction-map-for-alcohols-alkenes-alcohols-ethers-carbonyls-oxidation-formation-of-alkyl-halides-tosylates-elimination-roadmap.gif\" alt=\"reaction-map-for-alcohols-alkenes-alcohols-ethers-carbonyls-oxidation-formation-of-alkyl-halides-tosylates-elimination-roadmap\" width=\"630\" height=\"764\" \/><\/a><\/p>\n<p>It&#8217;s not easy to do this without making some tradeoffs. Here, you&#8217;ll note that &#8220;alcohols&#8221; are all bunched up into a single box, which includes primary, secondary, and tertiary alcohols. As we&#8217;ve stated before, not all reactions work on all types of alcohols (for instance, we can&#8217;t oxidize tertiary alcohols).<\/p>\n<p>Using this map requires some judgement. While it would have been possible to separate the categories, that would have ended up making the map a lot more visually distracting. So in order to use this properly, it&#8217;s up to you to understand which reactions work for each type of alcohol [which is covered in the initial blog posts on each topic, as well as in the notes on the reaction map below].<\/p>\n<p>Similarly, all the &#8220;carbonyls&#8221; (aldehydes, ketones, carboxylic acids, esters) have been grouped together, for now. When we cover future sections we&#8217;ll expand them out, but at this stage I wanted to keep things as simple as possible.<\/p>\n<h2>A Really Big Reaction Map<\/h2>\n<p>You might recall that my previous post on synthesis covered reactions of <a href=\"https:\/\/www.masterorganicchemistry.com\/2014\/01\/29\/synthesis-5-reactions-of-alkynes\/\">alkanes, alkyl halides, alkenes, and alkynes.<\/a> Let&#8217;s now take the same &#8220;map&#8221; and add alcohols. Things are starting to get crowded &#8211; I count 69 different reactions!<\/p>\n<p>This map covers most of the reactions you&#8217;ll see for alcohols, alkenes, alkynes, alkanes, and alkyl halides. One thing it doesn&#8217;t cover is formation of the various conjugate bases and acids from each species.<\/p>\n<p><strong><a href=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2015\/07\/MOC_alcohol-rxn-map_PDF.pdf\">Here is the map in downloadable PDF format<\/a><\/strong><\/p>\n<p>Here&#8217;s the big map.<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-16796\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2020\/01\/2-reaction-map-of-alcohols-comprehensive-about-70-reactions-alcohols-ethers-alkenes-alkynes-various-other-reactions-how-they-all-fit-together-guide-for-synthesis-1-scaled.gif\" alt=\"reaction-map-of-alcohols-comprehensive-about-70-reactions-alcohols-ethers-alkenes-alkynes-various-other-reactions-how-they-all-fit-together-guide-for-synthesis-1-scaled\" width=\"630\" height=\"863\" \/><\/a><\/p>\n<p>I welcome comments and suggestions &#8211; and would even pay for someone who has design skills to make this look better!<\/p>\n<p>In the next series on MOC, we&#8217;ll cover reactions of organometallics. Hopefully this won&#8217;t take nearly a year like this series on alcohols has!<\/p>\n<hr \/>\n<h2>Quiz Yourself!<\/h2>\n\n<p class=\"p1\"><img decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/2714-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\/2715-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\/2718-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\/2723-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\/2726-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>The Alcohol Reaction Map Having now finished (at long last) covering the key reactions of alcohols, let&#8217;s stop to put everything in perspective. Over the <\/p>\n","protected":false},"author":1,"featured_media":16795,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[1420],"tags":[167,954,352],"post_folder":[],"class_list":["post-9020","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-alcohols-epoxides-ethers","tag-alcohols","tag-reaction-map","tag-synthesis"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.7 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Alcohol Reactions [Reaction Map PDF] &#8211; Master Organic Chemistry<\/title>\n<meta name=\"description\" content=\"Let&#039;s summarize the key reactions of alcohols with this big reaction map [PDF] covering 67 reactions of alcohols, alkyl halides, alkenes, alkynes &amp; more.\" \/>\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\/2015\/07\/27\/synthesis-6-reactions-of-alcohols\/\" \/>\n<meta property=\"og:locale\" content=\"en_US\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Alcohol Reactions [Reaction Map PDF] &#8211; Master Organic Chemistry\" \/>\n<meta property=\"og:description\" content=\"Let&#039;s summarize the key reactions of alcohols with this big reaction map [PDF] covering 67 reactions of alcohols, alkyl halides, alkenes, alkynes &amp; more.\" \/>\n<meta property=\"og:url\" content=\"https:\/\/www.masterorganicchemistry.com\/2015\/07\/27\/synthesis-6-reactions-of-alcohols\/\" \/>\n<meta property=\"og:site_name\" content=\"Master Organic Chemistry\" \/>\n<meta property=\"article:publisher\" content=\"https:\/\/www.facebook.com\/Master-Organic-Chemistry-242610599108055\/\" \/>\n<meta property=\"article:published_time\" content=\"2015-07-27T19:41:10+00:00\" \/>\n<meta property=\"article:modified_time\" content=\"2025-06-05T21:21:32+00:00\" \/>\n<meta property=\"og:image\" content=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2020\/01\/1-reaction-map-for-alcohols-alkenes-alcohols-ethers-carbonyls-oxidation-formation-of-alkyl-halides-tosylates-elimination-roadmap.gif\" \/>\n\t<meta property=\"og:image:width\" content=\"1332\" \/>\n\t<meta property=\"og:image:height\" content=\"1616\" \/>\n\t<meta property=\"og:image:type\" content=\"image\/gif\" \/>\n<meta name=\"author\" content=\"James Ashenhurst\" \/>\n<meta name=\"twitter:card\" content=\"summary_large_image\" \/>\n<meta name=\"twitter:label1\" content=\"Written by\" \/>\n\t<meta name=\"twitter:data1\" content=\"James Ashenhurst\" \/>\n\t<meta name=\"twitter:label2\" content=\"Est. reading time\" \/>\n\t<meta name=\"twitter:data2\" content=\"3 minutes\" \/>\n<script type=\"application\/ld+json\" class=\"yoast-schema-graph\">{\"@context\":\"https:\\\/\\\/schema.org\",\"@graph\":[{\"@type\":\"Article\",\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2015\\\/07\\\/27\\\/synthesis-6-reactions-of-alcohols\\\/#article\",\"isPartOf\":{\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2015\\\/07\\\/27\\\/synthesis-6-reactions-of-alcohols\\\/\"},\"author\":{\"name\":\"James Ashenhurst\",\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/#\\\/schema\\\/person\\\/78d83ec7d02b4b7365bade2cedaef80c\"},\"headline\":\"Alcohol Reactions Roadmap (PDF)\",\"datePublished\":\"2015-07-27T19:41:10+00:00\",\"dateModified\":\"2025-06-05T21:21:32+00:00\",\"mainEntityOfPage\":{\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2015\\\/07\\\/27\\\/synthesis-6-reactions-of-alcohols\\\/\"},\"wordCount\":540,\"commentCount\":19,\"publisher\":{\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/#organization\"},\"image\":{\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2015\\\/07\\\/27\\\/synthesis-6-reactions-of-alcohols\\\/#primaryimage\"},\"thumbnailUrl\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/wp-content\\\/uploads\\\/2020\\\/01\\\/1-reaction-map-for-alcohols-alkenes-alcohols-ethers-carbonyls-oxidation-formation-of-alkyl-halides-tosylates-elimination-roadmap.gif\",\"keywords\":[\"alcohols\",\"reaction map\",\"synthesis\"],\"articleSection\":[\"Alcohols, Epoxides and Ethers\"],\"inLanguage\":\"en-US\",\"potentialAction\":[{\"@type\":\"CommentAction\",\"name\":\"Comment\",\"target\":[\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2015\\\/07\\\/27\\\/synthesis-6-reactions-of-alcohols\\\/#respond\"]}]},{\"@type\":\"WebPage\",\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2015\\\/07\\\/27\\\/synthesis-6-reactions-of-alcohols\\\/\",\"url\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2015\\\/07\\\/27\\\/synthesis-6-reactions-of-alcohols\\\/\",\"name\":\"Alcohol Reactions [Reaction Map PDF] &#8211; 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