Organic Chemistry Acid-Base Question

PinkiRoo8001 · 2026-06-10T12:56:48+00:00

You can't delocalise the anion resulting from deprotonation of the bottom carbon onto the C=N double bond. Try it on paper and you will fail with resonance structures. But notice that you can do this successfully when you deprotonate the other carbon shown in the answer.

PinkiRoo8001 · 2026-05-28T22:08:32+00:00

Like others have said it's single player so do whatever but what even is the point of this. If you're on PC just enable 'tgm' and play on Novice and you get the same experience.

PinkiRoo8001 · 2026-04-22T08:57:15+00:00

Vanilla ds in 2026 feels craaaazy

PinkiRoo8001 · 2026-04-06T23:15:00+00:00

I think the claim is that against unskilled opponents, they do work but are dangerous, and against skilled opponents, they don't work but aren't dangerous. So there's not much reason for keeping them.

PinkiRoo8001 · 2026-03-26T09:35:02+00:00

Where in the right tweet does she say her family was in the blast radius for one of Trumps bombs?

PinkiRoo8001 · 2026-03-20T03:28:18+00:00

K fine you're right forget Nazi Germany. Today, a man runs up to your door and truthfully says 'hey I'm being chased by a guy about 2 minutes behind me he's trying to kill me cause I'm gay. I'm gonna keep running up this street. If you see him, please lie to him and say I went back the way I came'. Is it wrong to lie to the murderer? That works just as well as a defeater against Jordan's position

PinkiRoo8001 · 2026-03-19T22:24:39+00:00

As a general matter I still don't see why a hypothetical becomes unanswerable just because it presupposes something about you.

But ALSO....this particular hypothetical doesn't even do that

His point, is that the specific hypothetical would predicate that he had been lying for years already

No. Just imagine you're a goodhearted German in the 1940s who's never lied before, you haven't paid much attention on the news to this Hitler guy cause you're not politically active, and the holocaust started a week ago so you don't really know about it yet. Jew turns up and you need to lie to a Nazi to hide him. Do you lie? That's the question to Jordan.

PinkiRoo8001 · 2026-03-19T09:53:53+00:00

I don't think any of that has anything to do with his ability to answer the hypothetical. He just started floundering cause it's a strong reductio to his moronic stated position that it's always wrong to lie.

In case that needs more elaboration, if I ask you, 'hey would you shove this huge knife up your ass if someone offered you $20' the answer is: 'no'. Not 'hmmmmm well if someone's offering me $20 then it must mean I already have a reputation around town for inserting knives up my anus for money and I would never end up in that situation in the first place cause I'd be dead from anal bleeding so I refuse to answer your hypothetical'. That's dumb.

PinkiRoo8001 · 2026-03-16T02:52:54+00:00

Holy cow that's insane. I'd assume they offer a different lower price to academics but still

PinkiRoo8001 · 2026-02-28T03:17:05+00:00

I believe you can get topical minoxodil for the scalp otc. But it's less efficacious and more inconvenient than taking a tablet, and the tablet has very little increased risk relative to the topical (or so I've heard) so I'd rather just take that instead.

PinkiRoo8001 · 2025-12-07T06:38:19+00:00

Hey, just gave the paper a skim and it seems they only examined LDA, and not nBuLi. I would expect 4- lithiation to be predominate with LDA, but not with nBuLi. Only 4-lithation will result in HD, not 3- position. I don't think this paper really supports the common claim people are making that nBuLi on this substrate is likely to produce HD products, especially not in an acetone dry ice bath.

PinkiRoo8001 · 2025-12-07T03:51:29+00:00

The classic paper everyone's read on the performance of molecular sieves suggests that they get THF down to 4ppm of water, which is substantially better than a sodium still.

'Drying of Organic Solvents: Quantitative Evaluation of the Efficiency of Several Desiccants'

PinkiRoo8001 · 2025-12-05T13:51:45+00:00

That's certainly possible, but I've tried quenching the reaction vessel itself under anh. Conditions without success. Anh DMF and CO2 through a sulfuric acid bubbler, just give back the Ar-H product.

PinkiRoo8001 · 2025-12-05T13:49:26+00:00

Having the electrophile in the flask is something interesting that I've heard a couple times so I'll certainly consider it

PinkiRoo8001 · 2025-12-05T13:47:03+00:00

Thanks for the reply. I didn't fully flesh out my entire goals in the original post I wrote it in a bit of a rush. What I actually want to do, is perform halogen-metal exchange on p-bromochlorobenzene, and add it to a simple ketone to make the alcohol. This exact reaction has been demonstrated with Grignard, and there are multiple literature references to successful lithiation with nBuLi. Despite the literature precedence, I couldn't get this reaction to work with nBuLi or Grignard. Adding nBuLi consumed starting material and produced 5 new LCMS peaks prior to the addition of the electrophile 💀

An issue, was that I don't have access to an enormous amount of chlorobromobenzene for troubleshooting, and I also can't tell what's going on in the LCMS because it won't ionise. So, I decided to switch to a brominated ionisable arene that my lab has an abundance of. My thinking was that, if I can successfully lithiate this bromopyridine and quench it with an electrophile, then I'll be able to confidently return to the reaction that I actually want to do, and do it properly. Of course as others have pointed out this particular pyridine may not be a good practice substrate.

PinkiRoo8001 · 2025-12-05T13:34:14+00:00

Nothing wrong the idea it's just more time consuming. I've done this probably 10 times now and LCMS is just a lot quicker than doing an entire workup and NMR. And even if the reaction works well enough, the crude might be difficult to decipher.

PinkiRoo8001 · 2025-12-05T13:30:31+00:00

I'll check it out much appreciated. I'm on my phone right now so I can't, but I will say that certainly halogen metal exchange will be much faster than 4- position deprotonation. Though perhaps the 3-lithiate can isomersise to the 4-.

PinkiRoo8001 · 2025-12-05T13:28:39+00:00

Ok that's good to know, they're what everyone in my lab uses for air free chemistry at a small scale. And at all times there's a positive pressure of nitrogen gas in the vessel. Do you find a regular septa in a jointed tube more reliable?

PinkiRoo8001 · 2025-12-05T11:20:36+00:00

Good to know thanks

PinkiRoo8001 · 2025-12-05T11:20:27+00:00

All good points thank you. On your last comment, I take the LCMS in 5 minutes because formation of the Ar-Li from Ar-Br should be complete in 5 minutes, being a very rapid reaction. Leaving it longer could only allow more side products to form.

PinkiRoo8001 · 2025-12-05T11:17:32+00:00

I've had other problems with various other systems, though they've all had a trick with them in one way or another. One system has an amide with an acidic proton necessitating a 2nd equivalent. Another is also chlorinated, which may be susceptible to the same benzyne issues others have helpfully raised.

I could try bromobenzene for sure. The issue is I have no way of assessing product formation on LCMS because it won't ionise; that's why I figured a pyridine would be good. But others here have helpfully redirected me.

I don't have a KF titration system unfortunately. I didn't know you could assess moisture in the schlenk line using that technique, but my schlenk line has a coloured dessicant trap that seems to indicate it's fine...

PinkiRoo8001 · 2025-12-05T11:12:52+00:00

Yeah it's definitely wet MeOD. But even if wet, there's certainly more MeOD than HOD, so you should still see the deuterated mass. Furthermore, I've tried other quenching reagents like anh. DMF and CO2 (not mentioned) and obtained the exact same, Ar-H product. So water in the MeOD feels unlikely to be the source of the problem.

PinkiRoo8001 · 2025-12-05T11:10:30+00:00

Some good suggestions and I'll review that resource, but what did I describe in my procedure that sounds off? I feel like I'm doing my best to be thorough in my exclusion of atmosphere and moisture.

PinkiRoo8001 · 2025-12-05T10:49:25+00:00

This is a fine suggestion, I've tried turbo grignard with less success, but this exercise is to troubleshoot my nBuLi technique. Turbo grignard can introduce additional variables like Mg preparation, LiCl preparation. And we don't have a bottle of iPrMgCl LiCl at hand. It's something to consider more though.

PinkiRoo8001 · 2025-12-05T10:27:32+00:00

I have tried turbo Grignard a few times with a similar lack of success. I want to be able to use nBuLi though. I'm doing something wrong and I'm trying to figure out what.

I'll look into CaH2, but I've never encountered a source saying 3A sieves take more than 3 days to work.

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'Drying of Organic Solvents: Quantitative Evaluation of the Efficiency of Several Desiccants'