All About Oxidizing Alcohols

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Practice Resources:

Guided Worksheet(s) + Solutions:
Worksheet Solutions Walkthrough(s):
Series Study Guide:
Description

https://joechem.io/videos/51 for video on jOeCHEM and attached worksheet + solution (below video on jOeCHEM aka the link). In this video, we look at all the ways to take an alcohol (or other carbonyl) and oxidize with PCC or the Jones Regeants (H2SO4 and Na2Cr2O7)


Comments:


  • Emily Miller • 4 years ago
    In the example that you saw a few years ago with the tertiary carbon, why did you not oxidize the lowest or highest carbon? (Low & high as to where they're drawn on the white board not in some other meaning) How do you know which ones to oxidize? Thank you!

    REPLY
    • Joe Del Nano • 4 years ago
      Hey, Emily! I'm assuming you're talking about the problem I start at 6:07 (in red), and in fact, in that problem, I oxidize every -OH I can. To oxidize (whether you're using PCC or H2SO4/Na2Cr2O7), you need at least a C-H bond. Those C-H bonds are replaced with C-O bonds. Since this problem is using the Jones reagents, you can see I oxidized the primary alcohol (bottom right) to be a carboxylic acid, I oxidized the secondary alcohol to be a ketone, but the tertiary alcohol (which has NO C-H bond) remain unchanged since it couldn't be oxidized--there was no C-H bond to replace. Does that make sense? Please let me know if it does or doesn't (also thanks for watching!).

      REPLY
      • Emily Miller • 4 years ago
        Yes that helps, thank you! (& thank you for making these videos!)

        REPLY
        • Joe Del Nano • 4 years ago
          Awesome, I'm glad it makes sense! And thank YOU for watching them.

          REPLY