{"id":1003,"date":"2019-04-16T11:43:19","date_gmt":"2019-04-16T11:43:19","guid":{"rendered":"https:\/\/www.studyorgo.com\/blog\/?p=1003"},"modified":"2019-04-16T11:44:48","modified_gmt":"2019-04-16T11:44:48","slug":"making-new-c-c-bonds-with-alkynes","status":"publish","type":"post","link":"https:\/\/www.studyorgo.com\/blog\/making-new-c-c-bonds-with-alkynes\/","title":{"rendered":"Alkylide Anions: Making new C-C bonds with Alkynes"},"content":{"rendered":"

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Many students taking Orgo 2 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, 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 how to make new C-C bonds using alkenes.<\/b><\/p>\n

Alkynide Anion Formation<\/p>\n

First, the terminal alkyne must be deprotonated with a strong base, such as sodium amide (NaNH2).\u00a0 This proton can be removed because terminal alkyne hydrogens are more “acidic” than alkene or alkane hydrogens.\u00a0 This forms the alkynide anion, which is a great nuleophile.<\/p>\n

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Next, the a alkynide anion must attack a primary or secondary carbon center to perform an Sn2 type reaction. This displaces the leaving group and forms the new C-C triple bond, which has now become an internal alkyne.<\/p>\n

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Once you have the the new alkyne, you can choose to reduce the alkyne to an alkene or alkane, or you can transform the alkyne into many other functional groups, including a ketone\u00a0 or an alcohol by hydration.<\/p>\n

\"\"<\/a><\/p>\n

Remember, alkynes are a great tool to build large carbon skeletons using simple haloalkanes.\u00a0 Remember this reagent for the exam!\u00a0 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 StudyOrgo <\/a>for detailed explanations of epoxide reaction mechanisms and other essential Orgo\u00a02 reactions today!<\/p>\n

 <\/p>\n","protected":false},"excerpt":{"rendered":"

  Many students taking Orgo 2 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, you will be responsible for all of the reactions necessary for multi-step synthesis (starting […]<\/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-1003","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\/1003","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=1003"}],"version-history":[{"count":3,"href":"https:\/\/www.studyorgo.com\/blog\/wp-json\/wp\/v2\/posts\/1003\/revisions"}],"predecessor-version":[{"id":1010,"href":"https:\/\/www.studyorgo.com\/blog\/wp-json\/wp\/v2\/posts\/1003\/revisions\/1010"}],"wp:attachment":[{"href":"https:\/\/www.studyorgo.com\/blog\/wp-json\/wp\/v2\/media?parent=1003"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.studyorgo.com\/blog\/wp-json\/wp\/v2\/categories?post=1003"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.studyorgo.com\/blog\/wp-json\/wp\/v2\/tags?post=1003"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}