Let's do some chemistry Veeky Forums

Tautomerization should be the last step right?
The irony,i have a test in organic chem in two days and i'm browsing 4 chan istead of learning...

So something like this? A bit far fetched but maybe...

Please help, pic related
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Congratulations, you're winner.

Do you even PiHKAL?

Why would you want to make mescaline when something with the magic 2,5-dimethoxy substitution pattern would be about 10x as potent? You need at least half a gram of mescaline to have an interesting time.

Where to learn chemistry to become pro chemist?

uni

Youtube

youtube.com/watch?v=vVbh2HVXEdg

Where did the Cl and the other carbon go? This shit aint even balanced

The Cl- left in when the el pair attacked the carbon and formed a larger ring, the carbon isn't missing it's incorporated into the ring

99% sure OH- initiates it

chemistry brainlet here, what do the + and - signs mean on the structure? for example nexto to the nitrogen and oxygen in OP's picture, does it mean ionic bond?

lmfao underclassman undergraduate detected

charged species

oh wow

electron jacking

>mescaline
Make some fucking 2ce-5eto, and absorb a few chemistry books while on it.

"This was the only compound of the 2CE series evaluated for smart pill activity. It was found to be like its 5-Ethoxy counterpart of the 2CT2 series to be very long acting, about 24 hours with little or no sleep possible without Halcion. Dosages ranged from 5 to 16 mg and it generally took about two hours for the material to become effective after ingestion. In one test three subjects took the material together and read an entire book of over 300 pages, taking turns reading aloud. The following day after a little sleep, they discussed the content of the book and found that they could quote entire paragraphs and their understanding and retention was excellent. All three were quite impressed with the entire test. The feeling was that this would be good for brain-storming or other similar small group activities. They also felt that the material could manifest philosophical overtones during the time the material was active."

Any recommendations for orgochem books? The one I have now is both incredibly slow and boring.

Also, could the reaction in op be performed by methanoic acid?

clayden warren is decent although it misses some stuff and the order is kind of retarded in my opinion

Does anyone have an answer for this one from the other day?

Not really, but I think it's probably via radicals

>it's probably via radicals

If it were radicals, you'd get stereochemical scrambling. This is completely stereospecific for the more hindered product.

I could post the answer but maybe other people want to try.

just chem undergrad here..
Did i don goofed? Not entirely sure about that last Sn(1?) attack

Just post it then and explain it please because I would really like to know and I think nobody is going to get it
And please provide a source

Seems like people have done the original question, how about another one on a related molecule?

Looks good to me, you've even added more detail than most chemists would but I don't see anything wrong.

I want to get good at orgchem but I don’t know how to do this. Maybe use the oxygen double bond for our advatage?

OK fine, I did an answer.

The ring opens with nitrogen elimination to give a sickle-shaped ylid which has a 4-pi delocalised system. So the system has to react antarafacially during ring closure.

Acetic anhydride acting like an electrophile on the double-bonded nitrogen?

Draw us a picture, lazy user

Where would you go after that?

Probably kys myslef

thanks, pretty cool stuff
I figured the sulfur had to be involved for it to be not a radical reaction

You will never become a chemist with that attitude.

Draw the mechanism or everyone in this thread will bully you

I can't, it triggers my PTSD
:(

Yeah, the sulfur lets you get a conjugated system to do it pericyclically.

Interestingly the corresponding case with CH2 instead of S, and Ph instead of tBu, still does the same reaction, but only with 87% retention of stereochemistry, because that molecule does go via a diradical intermediate and some of them have time to invert.

I don't know anymore..
I tried, sorry still brainlet

Bumb

Holy shit user

That's one of the worst mechanisms I've ever seen.

Against all odds, you actually have drawn some part of one critical step, but I'm not going to tell you which part, because you can do better.

Ye, i'm pretty sure i got it right up to the acetic acid part.
After that i'm quite lost, there needs to be way to get rid of the carbonyl oxygen whilst using the two hydrogens next to the imine.
Or i just have this thing all backwards..

You're basically trying to do too much at once, try working it out a bit more stepwise.

Unfortunatelly i have no way to draw the mechanism right now.
But i recon that secondary imine could be created alongside alkene in the next step.
That would unfortunately create formal charge on the other nitrogen which is not possible without counter ion..
I am really uncertain about this, i am looking for ways how to destroy the cyclic comound so that rearrangement might be possible, but i can't see it..

Ok, so this is what i () had in my mind all along..
I just hate seeing carbon with positive charge..
Does this seem ok to you?

You're still not really following the "rules" of drawing mechanisms, and trying to do far too much in each step.

The mechanism does involve a benzylic cation at some point though, they're not so much of a problem as you say.

I think you should stop worrying so much about where the protons go.

I'am still just a pleb, could i see the mechanism atleast?

...

You basically have the right answer but you're drawing the first step in a really awful way, you should divide it into two steps, with a 3-membered ring intermediate.

Don't really have much of a experience with three membered rings..
Always thought they would be unstable due to steric hindrance..

...

There is still alot i need to learn.
Thank you anyways..

Here's one where the focus is less on mechanisms.

This cation is stable at low temperatures. At -90 C, there are different signals for all the inequivalent methyl groups (1&5, 2&4, 3, 6, 7). At -40 C, the signals for methyl groups 1-5 all coalesce into a 15H singlet, but the signals for methyl groups 6 and 7 remain distinct and unchanged. Why?

>[citation needed]

All right I guess mechanism questions are more fun, anyone want to explain how you get to this product?

(I'll give up after this one)

internet

something like this?

I think POCl3 might even give you the geminal dichloride of the acetophenone.

It's a good effort but I should have clarified that the POCl3 and DMF are combined first, as in the Vilsmeier reaction, and then the acetophenone is added. But seeing as I never explicitly said that the first time round, this whole thing has been a disaster.

And there were also no hints for stoechiometrics which was confusing as well