If anyone on here has taken O. Chem/ graduated with a chem degree of some sort please chime in here. I know there are a few RPI, RIT …etc alums/students on here. I have a question regarding what should be a pretty simple reaction and i can photocopy the image with sigma values if need be, but ill try typing my question out first.
Here is why i need your help. My Organic chemistry teacher emailed me asking why me and my friend never are in class and how we have the two highest grades. Class average is a 68 btw lol. So long story short we talked and she wants us to do some independent research with her if we can solve this problem which is yes or no answer (yeah stressful). She only works at at our school for the research grants and has done some top notch stuff. (Cal tech., Berkley, and Johns’ Hopkins). So please do not post any bullshit in this thread and i understand this is a long post but my O chem 1 teacher has no idea neither do either of my Ph.D lab profs.
In Electrophilic aromatic substitutions there are EDG (- sigma) and EWG (+ sigma) that determine the location of the substituent being added.
I know for a fact that friedel-craft alkylation/acylation will not occur if two deactivators are located on the ring. They are electron withdrawing by resonance due to the electronegative atoms location 2 bonds away from the benzene ring. (and we are speaking strictly aromatic rings here)
My question is would say a halogenation/nitration/sulfination reaction (remaining EAS types) occur with two deactivators despite the extremely electron deficient benzene ring?
My thoughts
From a structural point of view it should be possible. Deactivators bind simultaneously and in the meta configuration so say for example the substituent is a nitro group (NO2) x2, an because this group binds simultaneously instead of at once the only possible configuration would be
m-dinitrobenzene. Meaning that the 5 carbon would be open for one more bond because it isn’t stericly inhibited and the “C5” carbon would be meta to both the EWG substituents. So it is likely from a structural look as the product would be 1,3,5 trinitrobenzene and way you look at it.
From a chemical view, which is where i’m the most uncertain. I think the halogenation wouldn’t occur or it would at least occur at such a slow rate that where there would never be a major product. The activation energy would be almost as high as a reaction with a 2+ carbocation meaning the Rate determining step would be long and the entire process slow. On top of that the starting material would be extremely stable and unreactive (sigma values are +0.63 per NO2 if i remember correctly). From an acid base point of view the Ka of the starting material m - dinitrobenzene would be high due to the high sigma values of the of the deactivators which favor the base. Ka = (B)/(A). High Ka means low pKa which means the base is more stable also. Every chemical aspect is leading to this reaction not occurring which is opposite my physical interpretation.
Hey are you set on being an RN? My mom wants to know because there are things you can to do get into her CRNA program sooner. Speaking of i saw Jason Whalen doing his clinical’s last weekend.
Making crystal meth is illegal PJB. That being said it’s much harder to make LSD. Which is why its a schedule one narcotic and you’ll do more time with one LSD capsule than with a pound of cocaine. 90% of the US’ LSD came from 2 chemists shacked up in a bunker. They had been making LSD for almost 40 years when they were caught a couple years back. Net worth 500mill a piece. Sentenced to 2xx years in jail though lol.
I have to do my shadowing of a doctor friday night, work saturday and sunday 7-330 then a physics test on tuesday of next week. You should come chill next wednesday and well go to the bar. Ill have her send me the info next time i talk to her. Mad money in that field man. Plus ill probably be teaching your 1 semester pharmacology class haha
IDFK man. It’s like save lives but sacrifice your entire 20’s or get a job that makes hella good money at 24. Believe it or not its a really tough decision. I’ve been telling myself ill only go to med school if i get into a top 25 med school. If not ill start my own business of some sort right out of pharm school. I wish i was in chucks shoe’s though. High demand for CRNA’s and starting salary at roughly 160k + unlimited overtime all for 6 years and 4 months of school and training.
Where is mike leave for the military already? What about Tungsten? I was relying on these guys mostly to respond lol.
Lol when i read the article online it said that the majority of the primary buyers (dealers who bought by the kilo or so) would all meet at a grateful dead concert and do their dealings. Typical white trash people lol.
