Thioacetals Explained

joechem.io/vid... for video on jOeCHEM and attached worksheet + solution (below video on jOeCHEM aka the link)
Acetals video:
joechem.io/vid...
Worksheet, Solutions, & Walkthroughs:
worksheets.joec...
worksheets.joec...
joechem.io/vid...
worksheets.joec...
worksheets.joec...
joechem.io/vid...
In this video, we explore thioacetals, what they are, why they are useful, and how they are (basically) the same as acetals, but not quite. We'll step through the forwards and backwards mechanism, as well as do an example where a thioacetal proves useful (and where an acetal would fall short). If you haven't though about acetals in a hot minute, revisiting that video here on jOeCHEM may not be a bad idea (linked below).
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[@life_of_eva]

well explained, thank you! now I finally know how the first step of the Corey-Seebach reaction works

[@scarcety8133]

Just a reminder, the Corey-Seebach is with a 1,3-dithiane and not 1,2. 1,2-dithianes when lithiated typically fragment.

[@steveortega123]

all the homies love Joechem

[@_m_5129]

for the final synthesis. throwing 1 equivalent of an oxydation reagent seems enough to me since the molecule is symetrical

[@micaelaroyo4837]

Oh my goodness I actually understood, I'm so shocked lmao thank you!!

[@jOeCHEM]

I’m so glad, Micaela 🤓 also your profile avi is legendary. Thanks for watching!

[@alexandra95789]

what happened to the CaCO3?

[@mixery_dose5435]

I may be a little influenced by my ochem professor but I actually prefer the deprotection of thioacetals via Hg(OAc)2 Also, the mechanism I designed for my ochem 2 class has the positive charge at the mercury during the step after the Hg-S bond forms. I don't know if that step is long lived enough for the positive charge to go the mercury but it'd be happier there wouldn't it? I also went with a carbokation route. I don't want to say you're wrong, I just wanted to present what I have to spark a discussion and maby learn something new in the process :D

[@adeliebachez4738]

THANK YOU

[@Sprise86]

Thx

[@jOeCHEM]

yw

[@jOeCHEM]

plz lyke nd subscribe

[@michaelspltwrng]

why does the thioacetal not form on both aldehydes?

[@jOeCHEM]

Hi Michael! So since the molecule is symmetrical, and we're throwing in 1 equivalent of the reagents necessary to form the thioacetal, it is safe to (theoretically) assume we'll form the thioacetal on ONE aldehyde in a given molecule. Of course, in practice, some molecules might have both aldehydes react, but the majority of the product will be structures that have one aldehyde undergoing thioacetal formation, and, since we're symmetrical, it doesn't matter which one does so.

[@michaelspltwrng]

@@jOeCHEM Ohh okay i see! thank you :D I was wondering if you plan on doing any asymmetric catalysis soon? i kinda struggle with chiral stuff, stresses me out

[@kushanipanditharathna190]

Can we use HgSO4 instead of HgCl2?

[@jOeCHEM]

Hi, kushani panditharathna! The textbook I'm most familiar with uses HgCl2, which is why I've used it here. If your course uses HgSO4, go with that!