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00:38
@Mithoron, interesting link. Sure looks like it should be somewhat water soluble, with half of its non-hydrogen atoms being either hydrogen-bonding acceptors or donors. I'm guessing it bonds with it's partners in some kind of stable layers, making the interior inaccessible to the solvent. But "water solubility:none", quite an oddball.
 
2 hours later…
02:28
-4
A: What is the mechanism for this retro-aldol reaction?

DHMO The condition is assumed to be basic. This is basically a reverse of the aldol condensation reaction. We begin with a molecule of (2E)-5-methyl-4-oxohex-2-enoate $(1)$, which undergoes nucleophilic conjugate addition with hydroxide ion ($\ce{OH-}$) acting as nucleophile to produce 2-hydroxy-5...

What is wrong with my answer?
 
2 hours later…
04:43
how's it going everyone? happy friday
@gannex ^
@DHMO rebuilt my old broken PC, installed some linux, got all my comp chem stuff running. Finally submitted some calculations :-)
I mean
@gannex please chek my above message
oh
I'm tired of thinking lol
you want me to take a look at your answer?
ya sure
04:49
OK
btw @DHMO I've noticed there seem to be two approaches to +repping on this site; answering questions, and editing/moderating things. What is your view on this? I know nothing about the meta, but I wouldn't mind giving back to the website. It's just that I don't have time to be answering a lot of questions these days... should I be editing/meta-ing?
@gannex eh, whatever floats your boat
what do you want me to look at here?
why i got -4
Hello all
@MelanieShebel could you have a look at my question?
04:55
Hi @MelanieShebel !!
Which is that?
@DHMO your mechanism makes no sense.
-4
A: What is the mechanism for this retro-aldol reaction?

DHMO The condition is assumed to be basic. This is basically a reverse of the aldol condensation reaction. We begin with a molecule of (2E)-5-methyl-4-oxohex-2-enoate $(1)$, which undergoes nucleophilic conjugate addition with hydroxide ion ($\ce{OH-}$) acting as nucleophile to produce 2-hydroxy-5...

@gannex would you elaborate?
I'm trying to promote this ochem article I wrote and I have no idea how.
ohh no I was thinking of the beta-enol
that is an alpha, beta-unsaturated
04:56
I never write about science and I'm REALLY trying to, but it's hard promotionally.
Why in step two would the double bond grab the H instead of the O-
...one sec. Just gonna do the mecha myself
@MelanieShebel because later it would have keto-enol tautomerism and go back to the ketone
@DHMO can you get normal chemdraw?
@gannex ?
chemdraw
05:01
it isn't free
instead up having all those C's and H's everywhere, why not just use a default chemdraw theme?
all software is free.
link please?
and please tell me what is wrong with my mechanism
not sure
you had something incorrect written before didn't you?
with a carbocation somewhere
ya
so i got -2
and then i deleted it and fixed it and undeleted it
Pearson HSAB says hydroxyl is a moderately hard nucleophile. Are you sure it attacks at the beta position?
05:04
now i got -4
@gannex i'm just reverse-engineering from the aldol
true alpha attack wouldn't make sense
I mean you did draw the reverse of the aldol
Are we sure that we can actually do a retro-aldol on an alpha, beta-unsaturated though?
I've only heard of this reaction with the beta-hydroxy ketone
From my LinkedIn. I guess I'm not much of a chemist!!!
@MelanieShebel the last step is just keto-enol
@MelanieShebel you do have a hell of a web presence going on there
05:06
I like the social media.
I see that
In my defense, I worked in web development for years before going to school for chemistry. And continue to write articles. so my linkedIn is less chemistry and more social media, haha.
...do you want to web-develop about chemicals?
I would like to write more articles about chemistry.
@DHMO your mechanism is indeed the reverse of the aldol I suppose
05:08
But I an only write general audience type stuff.
I guess that could be interesting
so... what is wrong with it? @gannex
not sure.
Like, "Science Blogs You Should Be Reading" "Unsolved Problems in Chemistry" "Meanings Behind the First 20 Chemical Element Names"
have you checked a textbook to see what the accepted mechanism is?
05:09
That's all I really have the know-how to write.
@MelanieShebel I think even simple things like that would benefit from deeper learning
you're doing a chem degree though right?
@gannex I don't have a textbook
the only mechanism we learn in school is the halogenation of alkanes through free-radicals
Yeah, @gannex I'm nearing the end of my degree and I just don't feel smart enough to try to write about other things.
I would like to do research, particularly computational research before going to graduate school, but I don't think labs really extend out to undergrads so much.
@DHMO what sort of school do you go to?
You can obtain all chemistry textbooks at bookzz DOT org
you can obtain software through various similar methods.
Most schools also offer software packages and have libraries
@gannex sure, I'm too lazy to find a book lol
05:19
@MelanieShebel Don't say that. You've learned all the stuff in your classes right? You probably have the capacity to understand all sorts of things if you go and read about them. I've found that there were some things lacking from my classes, but the main thing was that they taught me that I can learn whatever I want if I put in the effort.
The labs at most universities will do stuff with undergrads who show initiative
2
Yeah, I just lack the confidence, for example, to answer questions on here.
@MelanieShebel then do it. confidence comes from within.
It takes me a lot of time to write out a good answer, so I don't do it much either.
I do research now, but I would like to do other research. I am at a very small university, so there are only three chemists who do research. One has a full lab, one I'm working with, and the other has an interesting project, but it's not really my thing.
but I enjoy looking through the journals and finding good references
05:20
@MelanieShebel you see, you can write good answers:
10
A: How can I draw 2,3-diethylheptane?

Melanie ShebelWhat I usually do when I start numbering is look for branching and start numbering at the end with the closest branch. Also, keep in mind that with branching you'll want to consider numbering from one of the branches (if it'll yield a long chain.) I'm using the structure you made as an example:...

wow, I thought I went to a small university, but 3 chemists???
There are four, but one doesn't do research.
We don't have the chemistry major yet, I'll be the first one.
We have biology, so we always had chemistry classes.
@MelanieShebel hmmm my university is a little similar (although we actually have numerous chem labs) in that they started off with biochemistry and molecular biology programs, and the pure chem program is sort of just a branch of the biochemistry program
I'm looking forward to going to another school for grad. school.
Where would you like to go for grad school?
I want to go to U Pittsburgh, Carnegie Mellon, or Stanford.
well I wanted to go to MIT but now I'm thinking I'm not sure if I'd want to move to the US of A (plus who knows if I can get in there)
I'm looking at UBC and ETHZ
but I have various other ideas. It's dependent on what the lab does. I don't really care where the school is, so long as it's in a decently nice city.
05:34
@MelanieShebel hi
please look at my comment
I'll leave you guys with one important comment: The Simpsons Season 1-10 can simply not be beat. Every episode was gold.
 
1 hour later…
06:55
oooh Gaussian's website is all new
In mathematics, when something is "formal", it is more rigorous. In chemistry, when something is "formal", it is usually wrong.
5
 
1 hour later…
08:12
Well I have got the answer. It's 3.2. I just did not know that policy applies to chemistry stack exchange too coz if u see my maths stack exchange profile, I have asked questions along with my contribution.😒😑 — Lokesh Sangewar 3 hours ago
THEN WHY THE HECK DID YOU NOT EDIT? ಠ_ಠ
Also I'm not sure how the smileys help your case.
@DHMO Some men just want to watch their question burn
08:59
Last night dream (chemistry section):
An organic chemistry lab class involving 3 reagents. One of this is called parathol. I accidentally splashed some parathol into my throat. Moments later, I noticed my mouth is bleeding (at the same time I noticed there's a wound on my right hand).

I then told the class supervisor about it. He then gave me a pack containing 3 things (Beat heat (which are some red pellets), some colorful pellet gums and fly ash). He said I need to chew the gum and the fly ash, then spit out the gum, which will form an inflated cup shaped thing, spit some saliva into the
@Secret I appreciate your courage to share your dreams lol
(more info from the dream): Parathol is known as "caustic alcohol" in the dream. It is implied to be able to dissolve tissues readily like water meeting salt, and thus can cause bleeding. This makes it very dangerous despite not corrode in a manner like acids and bases. It has the same smell as formaldehyde and it is a colorless liquid

Treatment of parathol contamination is also implied to be sophisticated as entire first aid packs are available with specific directions. The packs also implied that some victims of parathol contamination end up losing their thorax completely and had to rely
Meanwhile, if one tries to google parathol, you get a dye company
I am glad not even HF treatment needs such crazy number of first aid steps to handle
Meanwhile, caustic alcohol in reality:
Sodium ethoxide (also is the organic compound with the formula C2H5ONa) is a white to yellowish powder that dissolves in polar solvents such as ethanol. It is commonly used as a strong base. == Preparation == Few procedures have been reported to the anhydrous solid. Instead the material is typically prepared in a solution with ethanol. It is commercially available and as a solution in ethanol. It is easily prepared in the laboratory by treating sodium metal with absolute ethanol: 2 C2H5OH + 2 Na → 2 C2H5ONa + H2 An alternative, cheaper route involves the reaction of sodium hydroxide with anhydrous...
@Secret Best-case scenario: You're a weird person.
@M.A.R. everyone has weird dreams
if you don't, you're a weird person.
09:08
The dream isn't weird.
That's the weird thing about it
To me, a dream is considered weird whenever it involve stuffs that does not exist in reality. But yeah, somehow, my dreams usually have some coherent continuity in it so besides for the nonexistent things, it reads pretty much like a real life event
Time is usually presented correctly in my dreams. however space are usually enlarged to 2 times the real life counterpart of the place it based on
A lot of dream reality check hence fails for my case because clocks in my dream will usually read normally
@M.A.R. ಠ_ಠ
14 mins ago, by M.A.R.
@Secret Best-case scenario: You're a weird person.
 
2 hours later…
 
3 hours later…
14:23
@M.A.R. Guess what I "discovered" today? 3;) ... Hummus goes pretty well with spaghetti :D
@Mithril o/
Also, oregano goes well with hummus ._.
15:00
@paracresol o/
@gannex Alpha attack could happen but it doesn't lead anywhere, so it just falls back off: an "unproductive" route.
@orthocresol can you tell me what is wrong with my mechanism?
15:26
@hBy2Py oh oh oh it took me a while to understand what you said. My thought process was "well, I don't understand the answer to my question, and no one has answered yet...OHHHHHHH"
 
2 hours later…
17:11
@pentavalentcarbon Oh, haha, yeah -- meant that you understand SOC well enough to ask that question. :-)
gah I wish there was a built-in way to turn down sound for specific applications on the Mac
the SE notification sound gives me a heart attack
17:37
Hell
hello*
@DeyanGeorgiev o/
I would like to ask a question here, since I'm not sure that I can open a question for such thing. Is there a way to determine bond type without electronegativity ?
@DeyanGeorgiev no because bond type is defined by electronegativity
in reality, bonds don't care whether you label them as covalent or ionic
Yeah, but my teacher cares :d
your teacher also defined it in terms of electronegativity right
well, usually when metal and non-metal combine, the bond is ionic, and non-metal and non-metal usually forms covalent bonds
but beware that there are a lot of exceptions
17:40
Bond type can't be determined with electronegativity
@Mithoron depends on what "bond type" means here
i think it is referring to covalent vs ionic
Well, we studied a little theory about them, what they are for ionic and covalent(not sure how it's in english but there are two types of covalen)
aa polar and non-polar I think.
polar and non-polar?
sigh And there go lies for students...
@DeyanGeorgiev oh, you're Bulgarian and you speak Bulgarian?
@Mithoron come on
we do live in this education system @Mithoron
like you, i suppose
Кованелнтна полярна и ковалентна неполярна
in Bulgarian
@DeyanGeorgiev you meant Ковалентна not Кованелнтна right
17:44
So the connection of 2NO, will be ionic, right
yes, typo
what is 2NO?
Nitrous oxide
that is N2O
Amm, yeah...
no, it's covalent
17:46
Significant part of what is done here on Chem SE is disproving oversimplifications, deprecated data and such
@Mithoron that's chem.SE, not chatroom
and this person here does indeed have an examination to prepare for
so please
Ok, is there a way to calculate the electronegativity for element, without earning Ph.D in chemistry?
you just recite it
You mean to memories all values for each element?
you won't need to
17:59
I'm pretty sure the teacher won't provide as with one during the exam, nor will allow us to carry one with us.
I mean table
provide us with table...
what do you need it for?
determining the bond type
21 mins ago, by DHMO
well, usually when metal and non-metal combine, the bond is ionic, and non-metal and non-metal usually forms covalent bonds
21 mins ago, by DHMO
but beware that there are a lot of exceptions
I'm keeping this in mind.
the only exceptions that you would be expected to know are compounds containing Li, Be, B, or some complex ions (e.g. chromate)
18:05
so compounds containign Li, Be and B are ionic, all other metal non-metal bonds are ionic, and non-metal non-metal are covalent
well not all, all simple
no that wasn't what I meant
e.g. BeCl2 might be considered covalent
Ahh ok, if I see metal:non-metal I answer ionic and hope for the best covalent otherwise. DHMO I own large beer.
I own you*
you owe me
you should really look at your textbook though
I've done that, some simple definition about what bonds are. Anyway thank you a lot. Wish you good night.
@DeyanGeorgiev Hehe
18:54
@orthocresol I agree. I was just trying to figure out what might've been wrong with DHMO's mechanism
 
5 hours later…
23:30
0
Q: Coordination geometry: why is of Cu(acac)2 square planar?

Alex MayorovWhy is Cu(acac)$_{2}$ square planar, whereas Al(acac)$_{3}$ and Fe(acac)$_{3}$ form octahedral complexes? I see how a similar argument to Pt complexes would apply, i.e. with $d^{9}$, there is only one electron that goes in the very destabilised $2b_{1g}$ (corresp. to $d_{x^2-y^2}$) in the square-...

@Jan There's a distortion named after you. ;)

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