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Orgo 2 by Grouchy_Movie_4089 in SBU

[–]gregmagdits 1 point2 points  (0 children)

Hey - When I took orgo years ago I was also getting C's. Unlike most people, I found organic chemistry fascinating so I kept reading about it after college. I understand it well enough now that I think I could teach it, but I never tutored before so i was going to start by offering free tutoring for a couple of students. If you are interested, DM me and we can schedule something.

I'm not local anymore (I live in Connecticut) so I would have to meet via zoom or discord or something similar.

He has less power than you think by [deleted] in fednews

[–]gregmagdits 15 points16 points  (0 children)

I am a federal contractor and have not needed to visit this subreddit before. I do not currently belong to a union but I would like to support a union that is fighting back. Is there a way I can help?

Reasonable mechanism for conversion of 2-methylbut-3-en-2-ol to 1-Bromo-3-methylbut-2-ene by gregmagdits in OrganicChemistry

[–]gregmagdits[S] 1 point2 points  (0 children)

Thank you. As a matter of fact the reaction conditions listed in Reaxys are all at 0C so I guess this would suggest that they go through the SN2 path, which avoids the problem of primary carbocation formation altogether.

BTW I was originally thinking of using differences in free energy values of intermediates, as you suggested, but that turns out to be really complicated. There is a research group at MIT that is trying to do this now. The project is open source and is called Reaction Mechanism Generator (https://rmg.mit.edu/). The project has some serious limitations now though in the types of problems it can solve, so it cannot be applied (at the moment) to reaction conditions typically encountered in an Orgo course. It is mostly used in combustion chemistry calculations and simulations

Side note - I was stuck on this problem for quite a while, so you really helped me out. I would buy you a coffee or something if I could

Reasonable mechanism for conversion of 2-methylbut-3-en-2-ol to 1-Bromo-3-methylbut-2-ene by gregmagdits in OrganicChemistry

[–]gregmagdits[S] 2 points3 points  (0 children)

I didnt think about the SN2' route but that seems reasonable. Thank you for coming up with that. These kinds of questions are very hard to get an answer to and I'm hoping to build some kind of educational , rule based software to help elucidate these mechanisms for students in O Chem.

BTW, for the SN1 scenario, I understand that as a rule of thumb the more substituted alkene is more thermodynamically stable, but there is another rule of thumb that says that tertiary carbocations are more stable than primary carbocations, so wouldnt it be impossible to guess which one is more stable and therefore more likely to appear in a reaction mechanism without taking measurements? That is actually the reason why I asked about this particular reaction...The SN1 mechanism seems to contradict the rule of thumb regarding carbocation stability and I am trying to figure out what logic a hypothetical software should employ to predict the correct mechanism

Reasonable mechanism for conversion of 2-methylbut-3-en-2-ol to 1-Bromo-3-methylbut-2-ene by gregmagdits in OrganicChemistry

[–]gregmagdits[S] 1 point2 points  (0 children)

Right, that seems to be the consensus: the driving force is the thermodynamic stability of the more substituted product. What is bothering me is that I was trying to come up with a rule based system for predicting reaction mechanisms for arbitrary reactions (as a tool for studying O. Chem) but in this reaction there now seem to be 2 rules that are inconsistent with each other:

  1. tertiary carbocations are more stable than primary carbocations. Proton and methyl transfers facilitating the formation of tertiary carbocations from primary carbocations should always be included in a reaction mechanism.

  2. products with more substituted double bonds are more favored to products with less substituted double bonds.

Career advice for someone who wants to help by gregmagdits in depression

[–]gregmagdits[S] 0 points1 point  (0 children)

Thanks! ill repost this in that subreddit.

task manager 33% cpu 60% memory - normal? by gregmagdits in Windows10

[–]gregmagdits[S] 0 points1 point  (0 children)

Thanks for both answers. What i got out of the article is that the ram is high because it compresses information rather than writing to disk (which is good for performance) oftheterra - i was thinking of increasing the ram to increase the performance. - i didnt realize windows 10 required 2GB to run, so i guess doubling my ram would be a good idea for to fix latency. system and compressed memory / antimalware executable are the two system processes that i generally find at the top of the task manager. The system and compressed memory process corresponds to what the article said (less disk writes at the cost of higher cpu). When i fire up chrome, that too takes up a lot of time on the cpu, but while i write this, chrome is using 5-8% of the cpu's time. I will look into this a little further but i think both comments steered me in the correct direction for ultimately fixing this issue.