{"id":708,"date":"2016-02-03T23:37:34","date_gmt":"2016-02-03T23:37:34","guid":{"rendered":"http:\/\/www.studyorgo.com\/blog\/?p=708"},"modified":"2016-02-03T23:37:34","modified_gmt":"2016-02-03T23:37:34","slug":"epoxide-reactions","status":"publish","type":"post","link":"https:\/\/www.studyorgo.com\/blog\/epoxide-reactions\/","title":{"rendered":"Epoxide Reactions"},"content":{"rendered":"<p>Many students taking Orgo 1 have commented there are a few types of reactions the professors save to the end of the semester and cover quickly and \u201cgloss\u201d over or sometimes skip all together in the interest of time.\u00a0 However, in Orgo 2, you will be responsible for all of the reactions necessary for multi-step synthesis (starting product known to get to unknown final product) and retrosynthesis (product known to get to unknown starting material) reactions.\u00a0 We at StudyOrgo don\u2019t want you to get stuck on trying to cram for exams by studying reactions that were poorly covered in your class. \u00a0In this article, we focus on <strong>epoxide formation<\/strong> and <strong>epoxide ring-opening reactions<\/strong> because of their usefulness in synthesis and industrial application.<\/p>\n<p>Epoxide Formation<\/p>\n<p>In order to form an epoxide, a electron-rich reagent is required, such as an alkene.\u00a0 Formation of the epoxide occurs in the presence of a peroxide reactant, such as MCPBA or DET.\u00a0 The choice of reagent depends on the stereo-specificity desired from the reaction.\u00a0 MCPBA is used to <span style=\"text-decoration: underline\">add the epoxide symmetricaly across the double bond<\/span>, so that substituents that are cis- or trans- remain in this configuration.\u00a0 The Sharpless asymmetric addition allows the researcher to choose a stereoisomer of DET, referred to as (+) and (-). \u00a0This reagent allows for the attack of the peroxide intermediate on only one face of the alkene, <span style=\"text-decoration: underline\">allowing for the production of nearly pure enantiomeric excess product<\/span>, generally &gt;98%!<\/p>\n<p><a href=\"http:\/\/www.studyorgo.com\/blog\/wp-content\/uploads\/2016\/02\/epoxides-article-1.gif\" rel=\"attachment wp-att-709\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone size-full wp-image-709\" src=\"http:\/\/www.studyorgo.com\/blog\/wp-content\/uploads\/2016\/02\/epoxides-article-1.gif\" alt=\"epoxides article 1\" width=\"700\" height=\"546\" \/><\/a><\/p>\n<p>Ring-opening Reactions<\/p>\n<p>Many of you have probably hear of epoxy-glue, which is a very strong binding agent.\u00a0 The process usually involves mixing two reagents and you must quickly apply the mixture to the broken items before the expoxy hardens.\u00a0 One tube will contain the resin, or epoxide, while the other contains the \u201chardening\u201d agent, which is the nucleophile that will attack the epoxide.\u00a0 In a ring-opening reaction, a molecule such as TETA, which contains 4 amino groups, will attack 4 equivalents of oxirane to produce a complex polymer, which is the basis for a strong glue.\u00a0 Changing the size and complexity of the epoxide can allow for flexibility of strength, thermostability and rigidity!<\/p>\n<p><a href=\"http:\/\/www.studyorgo.com\/blog\/wp-content\/uploads\/2016\/02\/epoxides-article-2-1.gif\" rel=\"attachment wp-att-711\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone size-full wp-image-711\" src=\"http:\/\/www.studyorgo.com\/blog\/wp-content\/uploads\/2016\/02\/epoxides-article-2-1.gif\" alt=\"epoxides article 2\" width=\"612\" height=\"452\" \/><\/a><\/p>\n<p>We here at StudyOrgo have devoted countless hours to preparing complex reaction mechanisms in simple and easy-to-understand manner to help you maximize your studying. \u00a0Sign up with <a href=\"https:\/\/www.studyorgo.com\/signup.php\">StudyOrgo <\/a>for detailed explanations of epoxide reaction mechanisms and other essential Orgo\u00a02 reactions today!<\/p>\n<p>&nbsp;<\/p>\n","protected":false},"excerpt":{"rendered":"<p>Many students taking Orgo 1 have commented there are a few types of reactions the professors save to the end of the semester and cover quickly and \u201cgloss\u201d over or sometimes skip all together in the interest of time.\u00a0 However, in Orgo 2, you will be responsible for all of the reactions necessary for multi-step [&hellip;]<\/p>\n","protected":false},"author":7,"featured_media":0,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_monsterinsights_skip_tracking":false,"_monsterinsights_sitenote_active":false,"_monsterinsights_sitenote_note":"","_monsterinsights_sitenote_category":0,"footnotes":""},"categories":[1],"tags":[],"class_list":["post-708","post","type-post","status-publish","format-standard","hentry","category-organic-chemistry"],"aioseo_notices":[],"_links":{"self":[{"href":"https:\/\/www.studyorgo.com\/blog\/wp-json\/wp\/v2\/posts\/708","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/www.studyorgo.com\/blog\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/www.studyorgo.com\/blog\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/www.studyorgo.com\/blog\/wp-json\/wp\/v2\/users\/7"}],"replies":[{"embeddable":true,"href":"https:\/\/www.studyorgo.com\/blog\/wp-json\/wp\/v2\/comments?post=708"}],"version-history":[{"count":1,"href":"https:\/\/www.studyorgo.com\/blog\/wp-json\/wp\/v2\/posts\/708\/revisions"}],"predecessor-version":[{"id":712,"href":"https:\/\/www.studyorgo.com\/blog\/wp-json\/wp\/v2\/posts\/708\/revisions\/712"}],"wp:attachment":[{"href":"https:\/\/www.studyorgo.com\/blog\/wp-json\/wp\/v2\/media?parent=708"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.studyorgo.com\/blog\/wp-json\/wp\/v2\/categories?post=708"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.studyorgo.com\/blog\/wp-json\/wp\/v2\/tags?post=708"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}