{"id":1823,"date":"2012-10-23T15:26:43","date_gmt":"2012-10-23T22:26:43","guid":{"rendered":"http:\/\/wordpress.reed.edu\/chem201202\/2012\/10\/day-14---activating-oh-as-a-leaving-group.html"},"modified":"2014-03-18T10:13:01","modified_gmt":"2014-03-18T17:13:01","slug":"day-14-activating-oh-as-a-leaving-group","status":"publish","type":"post","link":"https:\/\/blogs.reed.edu\/chem201202\/2012\/10\/day-14-activating-oh-as-a-leaving-group\/","title":{"rendered":"Day 14 &#8211; Activating OH as a Leaving Group"},"content":{"rendered":"<p>\n\tI&#039;m providing two documents for Day 14 of class: a <a href=\"https:\/\/blogs.reed.edu\/chem201202\/files\/Chem%20201%20-%20Day%2014%202012%20posted%20summary.pdf\" target=\"_blank\"><strong>reaction summary<\/strong><\/a> and my <a href=\"https:\/\/blogs.reed.edu\/chem201202\/files\/Chem%20201%20-%20Day%2014%202012%20posted%20slides.pdf\" target=\"_blank\"><strong>lecture slides<\/strong><\/a>. You can find additional summaries in Sorrell (see p.231-2 &amp; 233-5 near end of chapter) and in my learning objectives. Summaries are highly useful ways of expressing the information that needs to be learned and I recommend that you write your own version. Use the &#039;<em>predict-plan-explain<\/em>&#039; outline in the Day 14-15 learning objectives to guide what you do (and don&#039;t) write down. If your summary takes up more than 1-3 pages, it may be useful, but it isn&#039;t a summary.<\/p>\n<p>\n\t<strong>Mitsunobu reaction alert.<\/strong> I didn&#039;t talk about this reaction in class because I ran out of time, but you need to know the reaction (i.e., know how to &#039;<em>predict-plan-explain<\/em>&#039;) for the next exam, but you don&#039;t need to know all of the subtleties of its mechanism. Just focus on the nucleophilic substitution step: is it SN1 or SN2? what is the ionization state of the Nu? what is the leaving group? There is considerable disagreement about the details of the mechanism. If you&#039;re interested, compare Sorrell&#039;s mechanism with <strong>alternative <\/strong>(and more plausible?) <strong>mechanisms <\/strong>presented in <a href=\"http:\/\/en.wikipedia.org\/wiki\/Mitsunobu_reaction\" target=\"_blank\"><strong>Wikipedia<\/strong><\/a> and at the <a href=\"http:\/\/www.organic-chemistry.org\/namedreactions\/mitsunobu-reaction.shtm\" target=\"_blank\"><strong>Organic Chemistry Portal<\/strong><\/a>.<\/p>\n<p>\n\t<strong>Exam alert.<\/strong> The next exam (Day 16) covers everything presented through Day 14, including the Mitsunobu reaction. The emphasis will be on Ch. 5 (acid-base), Ch. 6 (SNx reactions of alkyl halides), and only part of Ch. 7 (converting ROH into &quot;RLg&quot; and then RNu). The material from Day 15 will not be on the exam.<\/p>\n","protected":false},"excerpt":{"rendered":"<p> I&#039;m providing two documents for Day 14 of class: a reaction summary and my lecture slides. You can find additional summaries in Sorrell (see p.231-2 &amp; 233-5 near end of chapter) and in my learning objectives. Summaries are highly&#8230;<\/p>\n","protected":false},"author":55,"featured_media":0,"comment_status":"closed","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[8,3],"tags":[],"class_list":["post-1823","post","type-post","status-publish","format-standard","hentry","category-exams","category-post-lecture"],"_links":{"self":[{"href":"https:\/\/blogs.reed.edu\/chem201202\/wp-json\/wp\/v2\/posts\/1823","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/blogs.reed.edu\/chem201202\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/blogs.reed.edu\/chem201202\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/blogs.reed.edu\/chem201202\/wp-json\/wp\/v2\/users\/55"}],"replies":[{"embeddable":true,"href":"https:\/\/blogs.reed.edu\/chem201202\/wp-json\/wp\/v2\/comments?post=1823"}],"version-history":[{"count":2,"href":"https:\/\/blogs.reed.edu\/chem201202\/wp-json\/wp\/v2\/posts\/1823\/revisions"}],"predecessor-version":[{"id":5093,"href":"https:\/\/blogs.reed.edu\/chem201202\/wp-json\/wp\/v2\/posts\/1823\/revisions\/5093"}],"wp:attachment":[{"href":"https:\/\/blogs.reed.edu\/chem201202\/wp-json\/wp\/v2\/media?parent=1823"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/blogs.reed.edu\/chem201202\/wp-json\/wp\/v2\/categories?post=1823"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/blogs.reed.edu\/chem201202\/wp-json\/wp\/v2\/tags?post=1823"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}