Kinetic vs Thermodynamic Control--Conjugated Systems

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Description

https://joechem.io/videos/122 for video on jOeCHEM and attached worksheet + solution (below video on jOeCHEM aka the link). In this video, we'll take a look at how we can get a mixture of products when doing reactions with conjugated systems that involve carbocation intermediates. We'll dig into how reaction conditions can push a reaction to be under thermodynamic or kinetic control and what that means for predicting products correctly.


Comments:


  • Rachel Frye • 4 years ago
    Why wouldn't the second double bond react? As a thermodynamic product? Because you have a lot of energy wouldn't both react?

    REPLY
    • Joe Del Nano • 4 years ago
      Hey Rachel! So you bring up a good point: In the video with the examples discussed, we start with a reactant that is conjugated. Upon being protonated, for example, we get an intermediate, an intermediate that is resonance stabilized (and then the reaction proceeds and finishes). Once we’ve formed a product, we theoretically have the choice to react with the double bond in that new product, or another fresh conjugated reactant. If we assume we have 1 equivalent of reactant and 1 equivalent of reagent(s), the reagent(s) will react with a fresh reactant that is conjugated because the intermediate produced with be resonance stabilized (as opposed to the newly produced product which will have a carbocation that is not resonance stabilized). Nature does what’s most stable, so the most stable intermediate will be formed. If you have an excess of reagent(s) then every double bond in the original reactant will fully react. But, if you have a 1:1 reactant:reagent ratio, then it will proceed how it is discussed in the video. Does that make sense?

      REPLY
      • Rachel Frye • 4 years ago
        Yes! Thanks so much!

        REPLY