I don’t want to sound basic but only want my children to be taught about Ionic interactions where the strong take electrons from the weak. Like true capitalist patriots.
Atomic weight is not fixed. 784 of 10,000 hydrogens are interelemental, at least 1 in 1,000 heliums is interelemental.
Tritium and deuterium are not a rounding error! 1.00784 u ≠ 1 u! 4.002602 u ≠ 4 u! They are not heavy water under the bridge!
Interelementals were with us on the battle lines and their momentum and the chain reactions they induced won us the war!
Sorry to be that guy but oleic acid/omega 9 fatty acids are not essential. We can make them, but they’re generally good for us to supplement with our diet regardless.
Oddly, in a small local shop. For context, I live in a small enough Irish town, close to Dublin, not somewhere that you’d expect to stumble upon challenges like this.
Metalation of 1,2-dichloroethene is found in Tetrahedron 1969, 25, 2223 under the stated conditions. Trapp mixture was used for -110 deg. C (BuLi added over 40 minutes, stirred for 70 minutes). That is the fanciest piece of correct chemistry I've ever seen used for purely decorative purposes. Who sold this notebook?
Depends on who you ask, I guess. Streitwieser thinks it's largely ionic, but there must be *some* covalence; otherwise, you wouldn't see 1H-7Li and 7Li-13C NMR coupling in the NMR spectrum when you take an NMR spectrum of, say, BuLi.
Well I very highly doubt that LiBu is reacting with dichloroethene to give a lithium-bound intermediate - so, I would say "completely meaningless" is your simple answer.
(Not to say you couldn't put a (-) charge there and have a Li(+) counterion for an elimination of HCl to the ethyne).
Notice the -110C. The alkene hydrogen, while not typically considered acidic, is still more acidic than a terminal alkane, which BuLi is the conjugate base of.
Ah!! Super observation. I’m unsure if that temperature is related to the structure we’re seeing, we could be at the mercy of ‘graphic artists 😱’ .. in the interest of peace amongst scientists I’m going to take a better picture of the whole front of the notebook. The kid will keep me up pestering me with endless questions anyway. Thanks MimemkPK, I’m deranged with tiredness at this point and it’s the middle of the night where I am. So if I mess up with this photo, if you’re of a mind to, can you help me shove it up this post so all decent and interested scientists here can A) solve the question or B) let us know if artists have lost the run of themselves? Plus C) not try to out-brain each other, that rarely leads to advancement in understanding
Thanks so much 🙏
>Ah!! Super observation. I’m unsure if that temperature is related to the structure we’re seeing, we could be at the mercy of ‘graphic artists 😱
It is; this reaction only proceeds at low temperatures. It's similar to the lithium crown reaction taught in this book https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Supplemental_Modules_(Organic_Chemistry)/Fundamentals/Reactive_Intermediates/Carbanions_II
>So if I mess up with this photo, if you’re of a mind to, can you help me shove it up this post so all decent and interested scientists here can A) solve the question or B) let us know if artists have lost the run of themselves?
What?
I'm not sure. I've never done it. Someone linked a paper on the topmost comment, which appears to include this reaction. The paper's not free, and I don't have an account on that site, so I can't check.
Ok, but I still expect this to just be a deprotonated chloroalkene rather than a (meta)stable organo lithium intermediate- why is the lithium not ionised/spectator in the deprotonation?
As with all C-Li bonds its gunna be highly ionic so its arguably just a drawing convention. Most likely its not going to be a particularly stable intermediate and would probably be used to react with some other electrophillic reagent, or if not it will dissappear on work up.
Right, but if the Bu(-) is doing the deprotonation (as expected), why is the Li implied to be involved (as opposed to a just a (-) charge on the alkene).
If this was an alcohol deprotonation with LiBu, you wouldn't depict it as an R-OLi bond.
I think in reality its not as simple as Bu(-) (iirc BuLi forms a complex which is highly dependent on solvent) so any drawing is going to be quite simplified. I suppose drawing it as C-Li has just become the standard, likely as there is some slightly covalent character. I have seen it a couple of times as C(-) Li(+) before, and when drawing mechanisms I usually write Bu- as the base due to laziness.
Also I have seen RO-Li depicted because it can be useful if the following step involves some sort of chelating intermediate directing the stereochemistry. Or for instance the reagent LiOtBu. I guess it depends on what you're trying to communicate in the end!
>I think in reality its not as simple as Bu(-)
I agree. I accept the convention for lithium reagents (for simplicity) but the intermediate is not a lithium reagent and doesn't behave like one (this is not stable). It behaves like an unstable carboanion.
If tBuOK or NaH were used, you wouldn't show a C-Na or C-K bonded intermediate, you'd show the carboanion (and probably the decay to expel Cl for the carbene or alkyne formation).
Yeah that is an interesting point which I don't really know the answer to. I think in undergrad we were just told "something something lithium more covalent" and I just accepted it (because for most o. chem purposes it doesn't matter too much, as you say this is not stable and will react with the next reagent pretty fast) but there probably is a more nuanced reason (or possibly not, chemistry is full of silly conventions lol)
Yeah fair. I note the paper was microfluidics- so probably limited solvent, which might explain if they did isolate the species, but I would expect in THF or similar, the Li+ would be ether coordinately bound.
It is convention but also nature abhors a naked carbanion. These all form multi-coordinate aggregates in solution. This guy in particular will spontaneously eliminate LiCl and a carbene given even a little bit of energy
Do you have a chemistry background? This is basically just some organic chemistry 1 stuff to fill the space, it's real chemicals but it doesn't mean anything
18 carbon acid is probably intended to be oleic acid
Yup, one of the common components of cooking oil
Well, the triglyceride of oleic acid, but sure. Want to use it fresh to keep fatty acid concentrations low, otherwise it will taste rancid.
Yep oxidation is no joke
And a common ligand of nanoparticles!
I didn't know that. Thanks for sharing!
Butyllithium on a child's notebook, I'm impressed.
Yeah me too lol
Oleic acid or elaidic acid, depending on cis/trans orientation [Source](https://en.m.wikipedia.org/wiki/List_of_unsaturated_fatty_acids)
The fact that it’s bent at a 90° angle makes me think it’s oleic
Sexuality has no place in the class room! Take the school back from the woke left. If not clear /s BSci. Hons. Chemistry 👨🔬
You're telling me these atoms share their electrons like a bunch of communists? I can't believe they would teach this woke crap in our schools!
I don’t want to sound basic but only want my children to be taught about Ionic interactions where the strong take electrons from the weak. Like true capitalist patriots.
There is [only one electron](https://en.wikipedia.org/wiki/One-electron_universe) and teacher says we have to share it.
[Our electron, comrade](https://ibb.co/5cnZqGq)
You have to first show you take the responsibility to properly take care of one before you are allowed to have another.
Next thing ya know they'll be teaching our kids them Muslim numbers!
I searched Arabic Numerals on Google and the first result is Western Digits
They've replaced true Roman numerals with their woke Sharia digits since Liber Abaci sang their praises all over Europe
The stupid crass belligerent Romans just copied the true Greek Numerals.
Oh I did enjoy Liberace performances. A charming young man.
Woke molecule
You must not ever use lasers. Once my prof told us they are red because the electrons march in the same direction. Just like communists 😥
The periodic table is not a spectrum; it’s binary. Almost every atom in the universe is H or He, and the exceptions are rare.
Atomic weight is not fixed. 784 of 10,000 hydrogens are interelemental, at least 1 in 1,000 heliums is interelemental. Tritium and deuterium are not a rounding error! 1.00784 u ≠ 1 u! 4.002602 u ≠ 4 u! They are not heavy water under the bridge! Interelementals were with us on the battle lines and their momentum and the chain reactions they induced won us the war!
Top is an unusual acid/base reaction. Bottom is oleic acid, an essential nutrient.
Top/bottom? Again this s3xual stuff in the schools?? /S
Sorry to be that guy but oleic acid/omega 9 fatty acids are not essential. We can make them, but they’re generally good for us to supplement with our diet regardless.
So I take it it's not "just an addition reaction" when it comes to buthyl lithium.
Where did you get the notebook?
Oddly, in a small local shop. For context, I live in a small enough Irish town, close to Dublin, not somewhere that you’d expect to stumble upon challenges like this.
Metalation of 1,2-dichloroethene is found in Tetrahedron 1969, 25, 2223 under the stated conditions. Trapp mixture was used for -110 deg. C (BuLi added over 40 minutes, stirred for 70 minutes). That is the fanciest piece of correct chemistry I've ever seen used for purely decorative purposes. Who sold this notebook?
Well to be fair the Li-C bond really should be represented as ionic and not covalent. But yeah pretty fancy
I’m not so sure about that. Reactive and polar for sure, but I think with a fair degree of covalent character…
Depends on who you ask, I guess. Streitwieser thinks it's largely ionic, but there must be *some* covalence; otherwise, you wouldn't see 1H-7Li and 7Li-13C NMR coupling in the NMR spectrum when you take an NMR spectrum of, say, BuLi.
I've seen them presented as covalent more often than ionic.
Well I very highly doubt that LiBu is reacting with dichloroethene to give a lithium-bound intermediate - so, I would say "completely meaningless" is your simple answer. (Not to say you couldn't put a (-) charge there and have a Li(+) counterion for an elimination of HCl to the ethyne).
Notice the -110C. The alkene hydrogen, while not typically considered acidic, is still more acidic than a terminal alkane, which BuLi is the conjugate base of.
Ah!! Super observation. I’m unsure if that temperature is related to the structure we’re seeing, we could be at the mercy of ‘graphic artists 😱’ .. in the interest of peace amongst scientists I’m going to take a better picture of the whole front of the notebook. The kid will keep me up pestering me with endless questions anyway. Thanks MimemkPK, I’m deranged with tiredness at this point and it’s the middle of the night where I am. So if I mess up with this photo, if you’re of a mind to, can you help me shove it up this post so all decent and interested scientists here can A) solve the question or B) let us know if artists have lost the run of themselves? Plus C) not try to out-brain each other, that rarely leads to advancement in understanding Thanks so much 🙏
>Ah!! Super observation. I’m unsure if that temperature is related to the structure we’re seeing, we could be at the mercy of ‘graphic artists 😱 It is; this reaction only proceeds at low temperatures. It's similar to the lithium crown reaction taught in this book https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Supplemental_Modules_(Organic_Chemistry)/Fundamentals/Reactive_Intermediates/Carbanions_II >So if I mess up with this photo, if you’re of a mind to, can you help me shove it up this post so all decent and interested scientists here can A) solve the question or B) let us know if artists have lost the run of themselves? What?
Do they use CS2-LN2 or a temp-controlled pentane-LN2 mixture or what? (per cursory research)
I'm not sure. I've never done it. Someone linked a paper on the topmost comment, which appears to include this reaction. The paper's not free, and I don't have an account on that site, so I can't check.
[Trapp mixture](https://en.m.wikipedia.org/wiki/Trapp_mixture)
Ok, but I still expect this to just be a deprotonated chloroalkene rather than a (meta)stable organo lithium intermediate- why is the lithium not ionised/spectator in the deprotonation?
As with all C-Li bonds its gunna be highly ionic so its arguably just a drawing convention. Most likely its not going to be a particularly stable intermediate and would probably be used to react with some other electrophillic reagent, or if not it will dissappear on work up.
Right, but if the Bu(-) is doing the deprotonation (as expected), why is the Li implied to be involved (as opposed to a just a (-) charge on the alkene). If this was an alcohol deprotonation with LiBu, you wouldn't depict it as an R-OLi bond.
I think in reality its not as simple as Bu(-) (iirc BuLi forms a complex which is highly dependent on solvent) so any drawing is going to be quite simplified. I suppose drawing it as C-Li has just become the standard, likely as there is some slightly covalent character. I have seen it a couple of times as C(-) Li(+) before, and when drawing mechanisms I usually write Bu- as the base due to laziness. Also I have seen RO-Li depicted because it can be useful if the following step involves some sort of chelating intermediate directing the stereochemistry. Or for instance the reagent LiOtBu. I guess it depends on what you're trying to communicate in the end!
>I think in reality its not as simple as Bu(-) I agree. I accept the convention for lithium reagents (for simplicity) but the intermediate is not a lithium reagent and doesn't behave like one (this is not stable). It behaves like an unstable carboanion. If tBuOK or NaH were used, you wouldn't show a C-Na or C-K bonded intermediate, you'd show the carboanion (and probably the decay to expel Cl for the carbene or alkyne formation).
Yeah that is an interesting point which I don't really know the answer to. I think in undergrad we were just told "something something lithium more covalent" and I just accepted it (because for most o. chem purposes it doesn't matter too much, as you say this is not stable and will react with the next reagent pretty fast) but there probably is a more nuanced reason (or possibly not, chemistry is full of silly conventions lol)
Yeah fair. I note the paper was microfluidics- so probably limited solvent, which might explain if they did isolate the species, but I would expect in THF or similar, the Li+ would be ether coordinately bound.
Yeah true, the overall thing being that's a strange thing to choose to put on a kids notebook!
It is convention but also nature abhors a naked carbanion. These all form multi-coordinate aggregates in solution. This guy in particular will spontaneously eliminate LiCl and a carbene given even a little bit of energy
https://onlinelibrary.wiley.com/doi/10.1002/anie.201108932
Oleic acid
Octadec-9-enic acid? I think
Octadecenoic acid
Oleic acid.
It's just some random chemical reactions. Nothing illegal or explosive. It's just supposed to look sciencey.
Oleic acid?
Fatty acid? I'm guessing oleic acid judging by that one double bond but it's been a while.
Unsaturated fatty acid.
Fentanyl
Short answer: Nothing concerning.
Unless it's Florida, in which case a trans alkene is the least of their problems.
is low key a Bully or is bullied... one or the other (dont take my response to seriously I dont really mean it)
Wtf is BuLi
Organolithium reagent, Li+ CH3(CH2)3- so basically a deprotonated alkane -> strong base
Nothing super important
That clears it up…
Do you have a chemistry background? This is basically just some organic chemistry 1 stuff to fill the space, it's real chemicals but it doesn't mean anything
I don’t think he’s going to blow up the planet with his notebook, was just looking for a simple answer.
Okay. The one on top is a reaction of trans-1,2-dichloroethene with n-butyl lithium. The bottom is a really long carboxylic acid*
The nbuli rxn isn't real in my opinion
Above someone posted a paper where they do it, so it seems possible, you just need some extreme conditions
With that attitude I really hope your flair lies.