Lab Notes - Fundamental Mechanistic Insight and New Catalysts for Making Sodium - Nov 30th 2018

I tried that in one of the earlier videos, didn't work very well.

NurdRage

Sure, I mean that avoiding the glassware destruction could possibly be done without any alkali metals and only require preheating of the Mg/alcohol solution. So if the issue is that Na or NaOH attack glassware at temperatures needed to create the Mg alkoxides without a Na/Li jumpstart, why not just heat the solution without Na/NaOH/Li present to create the alkoxides, then let it cool, then add NaOH and avoid the need for raw Na/Li? In other words, don’t introduce any alkali metals or hydroxides until the Mg alkoxides are generated.

Zach Heilman

The jump start was never necessary to begin with. It was already working before with just magnesium, alcohol, sodium hydroxide and mineral oil. The problem was that running without the jump start resulted in glassware getting destroyed as well as lower yields. If you want to run it without the jump start you can, just be aware the glassware is going to be ruined.

NurdRage

Sorry for jumping on an old video but I had a question regarding the three steps of the main reaction - Step 2 happens at lower temperatures, and depends on magnesium alkoxides. Wouldn't it be possible to generate these alkoxides at a high temperature directly by combining the solvent, magnesium, and alcohol and not adding the sodium until the Mg alkoxide had formed and the solution cooled? Then you'd avoid needing to do the sodium (or lithium) jumpstart.

Zach Heilman

i understand your decision. I'm still looking for a patreon alternative and hopefully i can move some members over. Thank you for your patronage.

NurdRage

I'm sorry but I'm stopped my use of the patreon site. I love the work you do and hope you can find another funding platform that isn't censoring people. When Patreon sees reason I will resume my funding.

This is fantastic. I've been following your account but not donating since I'm already donating to a few other channels. But this is so complete, and was such a good video, that it totally changed my mind. Time to become a patron!

Thor Correia

Finally got the chance to become a Patron wooo! It's a shot in the dark but if primary alcohols are being considered, could 2-ethylhexanol be a plausible suggestion to test? It's primary, steric bulk near the hydroxyl isn't much (expected) and that long ranged bulk is kinda present being a branched alkyl compound. Drawbacks would maybe include availability (apart from PVC plasticizer derived sources for the amateur), structurally it's not rigid like the other cyclic alcohols so rotation induced side-reactions could still occur and the bp is 180-186C (wiki) which is a bit short of the new operating temp of 200C but still a good range compared to both t-butyl and t-amyl alcohols.

I have to say this video and your channel has become the height of my YouTube experience. To get to be even a very small part of your exploration into chem has been incredibly interesting, educational, and more fun than I have had on YouTube before thanks =)

i actually tried that but my primary alcohols kept solidifying before i could get to step 2. So i need to find a branched primary alcohol that remains molten.

NurdRage

Assuming primary alcohol fails due to the alcohol/Mg release step on step 3 failed to proceed, can we use equimolar of primary alcohol to just provide sufficient alcohol for step 1 and 2 without completing the catalytic cycle?

Kam chun sing

There might indeed be a difference, its certainly something to try once i try reducing camphor.

NurdRage

Is there a practical difference between the enantiomers of borneol: borneol and isoborneol? Apparently if you start with camphor and reduce it, then which one you get depends on which reductant you use. MPV reduction gives borneol, and NaBH4 gives isoborneol.

I liked the thumbnail with the fighting T-rexes better. :)

Silviu T

It's a shame you don't live in Europe, I would send you hexanol :) Meybe reduction of hexanon?

WOW! A huge step all right. Hope you are able to test your idea shown near end of video.

rolf redford