{"id":7919,"date":"2014-01-21T15:00:08","date_gmt":"2014-01-21T20:00:08","guid":{"rendered":"https:\/\/www.masterorganicchemistry.com\/?p=7919"},"modified":"2026-04-22T13:20:38","modified_gmt":"2026-04-22T18:20:38","slug":"synthesis-reactions-of-alkenes","status":"publish","type":"post","link":"https:\/\/www.masterorganicchemistry.com\/2014\/01\/21\/synthesis-reactions-of-alkenes\/","title":{"rendered":"Synthesis (4) – Alkene Reaction Map, Including Alkyl Halide Reactions"},"content":{"rendered":"

Reaction Map: Reactions of Alkenes, Alkyl Halides, and Alkanes<\/strong><\/p>\n

In the last post on alkenes we covered the reactions of alkyl halides<\/a> and it made out tiny little reaction map explode into a cascade.<\/p>\n

Here we’re really going to blow up our reaction map, because we’re going to talk about a second very important “hub” for synthesis – alkenes.\u00a0If you haven’t already noticed\u2026. there are a LOT of alkene reactions. Alkenes are a very versatile building block in organic chemistry, as I hope this post will make clear.<\/p>\n

Table of Contents<\/strong><\/p>\n

    \n
  1. The Vast Majority of Alkene Reactions Are Addition Reactions<\/a><\/li>\n
  2. Oxidative Cleavage Reactions of Alkenes<\/a><\/li>\n
  3. A Map of Addition and Oxidative Cleavage Reactions of Alkenes<\/a><\/li>\n
  4. Combined Reaction Map: Reactions of Alkenes and Alkyl Halides<\/a><\/li>\n
  5. Quiz Yourself!\u00a0<\/a><\/li>\n<\/ol>\n
    \n

    <\/a>1. The Vast Majority of Alkene Reactions Are Addition Reactions<\/h2>\n

    This post is going to assume you’re familiar with these reactions and their products. We’re not going to go into mechanisms or other details here. The point is learning how to apply these reactions so that eventually we can plan syntheses that will take us from one functional group to another. If you need more background on these reactions by all means read this series of posts on alkenes<\/a>.<\/p>\n

    As we’ve said many times before, the vast majority of alkene reactions fall into the category of “addition reactions”. That is, we’re breaking a C-C \u03c0\u00a0bond and forming two new bonds to carbon. The new bonds that form, of course, determine the functional group we will be creating. Beneath that, there is a second level of detail – the “regioselectivity” and “stereoselectivity” of the reaction, which you will also need to be familiar with – that will, alas, largely be ignored in our big-picture analysis in this post.<\/p>\n

    <\/a>2. Oxidative Cleavage Reactions of Alkenes<\/h2>\n

    The second category of alkene reactions is “oxidative cleavage”, which involves the cleavage of both C-C bonds and the formation of two new carbonyl [C=O] groups. Depending on conditions, C-H bonds directly attached to the sp2<\/sup> hybridized carbons of the alkene can also be oxidized to C-OH .<\/p>\n

    \"key<\/p>\n

    <\/a>3. A Map of Addition and Oxidative Cleavage Reactions of Alkenes<\/h2>\n

    For the purposes of synthesis, we’ll largely be focusing on the new functional groups that are created in each case. If you look at all the reactions of alkenes, draw the products, and categorize according to functional group, you obtain a diagram which looks something like this:<\/p>\n

    \"map<\/p>\n

    Test Yourself<\/strong><\/p>\n

    Before we go and update the big “reaction map” from previous posts with these alkene reactions, it’s worthwhile to stop for a second and ask yourself a few questions:<\/p>\n