Examples of Choosing Between Sn2, E2, Sn1, and E1 (Part Two)

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Practice Resources:

Guided Worksheet(s) + Solutions:
Worksheet Solutions Walkthrough(s):
-   Identify and Complete the Reaction--More Substitution/Elimination
Series Study Guide:
-   Substitution/Elimination Study Guide
Description

https://joechem.io/videos/113 for video on jOeCHEM and attached worksheet + solution (below video on jOeCHEM aka the link). In this video, we take what we learned in the previous videos and tackle (what I consider) difficult problems and determine which pathway they go through (Sn2, E2, Sn1 or E1) and predict the product.

Tags:  SN2 E2 SN1 E1

Comments:


  • Sharon • 3 years ago
    For the first problem that you did with TsCl, why would the third step also work with DMSO if the product we want involves having CN?

    REPLY
  • Sharon • 3 years ago
    Also, where did the H go when OH left for the problem with TsCl?

    REPLY
    • Joe Del Nano • 3 years ago
      Hi, Sharon! So DMSO is just a solvent (a polar aprotic solvent). It doesn't participate in the reaction (you could also use a solvent like Acetone or DMF or HMPA) and could be left off but is nice to include. And you could assume the H "fell off" and was picked up by something else in the solution--or it could easily stay on (that isn't a super big detail in this problem). Let me know if both of those explanations make sense!

      REPLY
      • Sharon • 3 years ago
        Yes that makes sense for the solvent. For the other question, sorry about that, OH didn’t leave, because O stayed but only the H left, would the H be picked up by a solvent? Thanks so much!

        REPLY
        • Joe Del Nano • 3 years ago
          The H would be picked up by something (could've been the Cl- that was initially part of the Ts-Cl). The fact is, extra H+'s "fall" off in solution all the time, so don't get too hung up about where it went.

          REPLY
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