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07:16
I've just solved another problem from the hardest part of the exam set. I wonder if there are really hard problems in that set.
@Hippalectryon (cc @PhMgBr ) Yeah that's one of the potential canon. ones. Even though the question itself is not that awesome written... but if I find the time I would do it ;)
 
4 hours later…
11:25
I see you've been mischievous @Mans.
@PhMgBr yes, 9 shog = 1 centimetre
@Loong Wrong and misleading notation then.
@PhMgBr As if I did it for the first time. :p
@PhMgBr yeah, that's a common problem on all Stackexchange sites. :-(
@Loong What does shog mean?
That joke wasn't intentional.
11:35
shh, don't say his name!
@manshu You'll get perma-banned if you talk about Shog.
You'll get perma-banned if you don't talk about Shog.
So just don't, OK?
ok
my zips are lipped
Although I had a chat with him few hours ago.
 
2 hours later…
13:56
> Alcohols are amphoteric; they can act both as acid or base. The lone pair of electrons on oxygen atom makes the –OH group weakly basic.
But there are two lone pairs, aren't there?
> Thus, in the presence of a strong acid, R—OH acts as a base and protonates into the very acidic alkyloxonium ion +OH2 (The pKa value of a tertiary protonated alcohol can go as low as -3.8).
Wow.
14:19
I don't get it. Why does the OH2(+) group leave? Oxygen exerts a great pull on the neighboring carbon. After all, it has a positive charge now.
And there are H+ floating around that can assume the position instead of the departed H that elopes with HSO4-
@CowperKettle look again. What is the leaving group?
@Loong H2O
aha
Why does it leave... why not just bud away one H+
If I react propanol with H2SO4, I will get 1-propene and water and H2SO4.
Would not propene then react with H2SO4, I wonder.
14:34
@CowperKettle Actually, R-OH2(+) can release one H+, but that just brings us back to the original R-OH. So there is an equilibrium of R-OH + H+ <=> R-OH2(+). Only R-OH2(+) can release H2O, which is a nice stable molecule.
@CowperKettle What reaction of propene with H2SO4 do you expect?
14:59
@Loong - I did not expect any; I was just going through example problems for an exam
(0:
There is a chain of reactions and you have to write down the final product.
Guessing what the intermediate products are.
@CowperKettle Propene is too resilient to be deprotonated with even strong acids.
You'll need some superacid to do it.
SUPERacid
As a rule of thumb, the hydrocarbon won't get protonated.
15:04
@CowperKettle Now consider the boiling points of the reactants and alkenes. How can you perform this reaction in practice in order to get the alkene?
There is a sign saying +180C over the reaction arrow, so I guess I'd have to heat them.
Cook 'em
I don't recall anything about boiling points..
Mhm?
I mean, I don't remember offhand what the boiling points are. (0:
Solving the problems in the list, I revisit pages and reread some stuff
15:08
@CowperKettle Can you compare the boiling points of alcohols and the corresponding alkenes?
e.g. ethanol and ethene?
Ethene: -104C
ethanol: about 350 K
@CowperKettle Not about alcohols. The answerer is a doofus.
15:14
@CowperKettle aha, so it's easy to remove the alkene from the reaction mixture via distillation
It will all bubble out immediately at 180C
So I have "solved" the first step.
Now, propene + HCl
That's easy. I only need to re-read Markovnikov's Mantra
I remember that Cl should attach itself to the least hydrogenated carbon.
I do wonder how he'd feel if he sees this technology.
I guess he would have mastered the technology in a couple of weeks
Yes, I remembered right. Cl will connect to the middle carbon
2-chloropropane
@CowperKettle ok, so why does Markovnikov's rule apply here?
@Loong because we have an alkene as X1, and react it with HCl, which is a hydrogen halide
15:24
Do you know a mechanism for this reaction?
@PhMgBr shouldn't it be "if he saw this technology".. I don't recalll
I read it once, so I hardly recall anything
Because I've read such a heap of stuff O_O
In the Russian texbook, there are no mechanisms at all, only rules
In the USSR, kids had 3 hours a week of chemistry
In specialized schools, 6 hours a week
Now it's only 2 hours a week
And in specialized schools, a whole 3 hours
So the texbooks are not that big
@CowperKettle ok, so it's an electrophilic addition of HCl to the alkene. Thus, what will be added first, the H+ or the Cl− ?
An electrophile craves electrons. That's surely H+
ok
The addition of H+ to the alkene creates a carbocation intermediate.
There are two possible carbocations.
15:31
Which one is better?
I vaguely recall Chemguide's explanation of why the middle one is better
It's more stable, due to some reason
maybe the charge gets diffused both ways
the positive charge
oops, it's the ohter way around
hm? the secondary carbocation is more stable than the primary carbocation
> It is much easier to form the secondary carbocation because it is more energetically stable. The activation energy for the reaction will be less, and so most of the reaction happens via that mechanism.
@CowperKettle about that picture you posted before (about an alcohol reacting with an acid)... Why doesnt a H+ migrate from carbon-2 after H2O leaves so that a more stable alkene can be formed?
So the H+ will attach to the border carbon
@AdityaDev Migrate to where?
> The activation energy for the reaction will be less - but why, I wonder
You've lost me. O_O
Not a H+ transfer.
I haven't read about hydride shifts, sorry.
But if it migrates, won't it leave that C2 atom without hydrogens at all?
No. One hydrogen is left. But a hydride transfer will result in pent-2-ene which is more stable than pent-1-ene
user116211
@cowper @PhMgBr o/
15:42
@AdityaDev But we only have propene, there are not 5 carbons
Good evening, @MAFIA36790!
I was talking about reaction of pentanol
Ah, sorry, I confused the two examples
Frankly, I don't know why it won't migrate.
Maybe it would
Found it. Markovnikov's reaction goes that way because in the secondary ion, the electron-pushing effect from alkyl groups neutralizes the positive charge in the middle.
That calls for some carrot juice
15:47
"Markov" = "carrot" in Russian
Markov+nik+ov
A root and two suffixes
Why would you name someone 'carrot'?
Mark+ov
His name derives from the male name "mark", and "ov" is the suffix
@AdityaDev "Morkovnick" was a nickname for a guy who grew carrots. That was one of his ancient ancestors. That ancestor's kids attached the "ov" suffix and created the surname
"ov" means "belonging to" (belonging to his genus)
Ivan's son =>> Ivanov
Peter's son >> Petrov
A man coming from the Yeltsi village =>> Yeltsin
Russian is interesting. I was learning Japanese because it's script was beautiful. I think I might learn Russian as well.
15:54
Wait. No. "Yeltsin" is from the Turkic word "elchi" meaning "news bearer"
@AdityaDev Good idea!
Forget 'think'. I will learn it. Learning multiple languages is always going to help me
Great!
I mean, "horosho" (good)!
(0:
BBL!
16:41
@CowperKettle Shrug, but I thought the tenses are rather not restricted.
17:01
horosho
horror show
17:52
@Ramanewbie 33%
 
1 hour later…
19:00
Can I directly make propene from 2-propanol?
@CowperKettle yes
19:48
Hi
Hullo
!!greet/@Roscoe
Welcome to The Periodic Table @Roscoe! Here are our chat guidelines and it's recommended that you read them. If you want to turn Mathjax on, follow the instructions in this answer. Happy chatting!
! thanks!
I've got 'chemistry' questions~!
unfortunately, I'm do not even have a baseline advanced enough to know how to ask the questions I'm looking for the answers for.
My background is in Software Engineering, and Computer Science ~
19:51
@roscoe_casita I think you've come to the right place.
I've been working on combinations of compounds for reactions
for close to 2 years, I've been working on the project, the computer science side is satisfied now
Thanks for not going ahead with posting your questions on the main site. You contributed to drama control™.
welcome, I know my limitations
Think of the project as "Find ALL the reactions"
this is a computationally interesting problem
2^60,000 in size
or 60,000! / 128!*(60,000 - 128)!
either way, larger then the universe for practical considerations
(starting database of compounds is around 60k compounds)
i've got a working prototype now
second for image
this is the hypergraph of all reactions, of the compounds {H2,O2,H2O,H2O2,H7O4,H11O8}
@PhMgBr o/
@Mithoron \o
@roscoe_casita H11O8? Woot
19:55
each of the nodes is a reaction, with the balanced coefficients
./shrug, I don't know, I pulled the database from the Material Science project
I've got a high school chemistry background, with some mit open courseware
Yes your nodes look nonsense :(
the compounds? or the coefficients ?
O8 for instance
./nod there are many entries in the database that I know nothing about
19:58
@PhMgBr O_o do you get... what I get ?
project / database source: materialsproject.org
@Hippalectryon Yes
here is the question(s), now that the coefficients are being balanced, what should be calculated in a given reaction?
I heard about O8 but it is exotic allotrope
> INVENT STRUCTURES
Design new compounds with our structure editor and substitution algorithms
@roscoe_casita What do you mean? Chemists calculate a lot of stuff in reactions, for different reasons.
20:00
thats exactly what I suspected @PhMgBr
each reaction has many 'properties'
There is one problem @Roscoe. Those things in your image are mostly theoretical if they exist in some parallel universe.
the question is, what are some 'interesting' properties, to calculate, and how to go about calculating them
fair enough, this is a bad example @PhMgBr, but the vast majority of the database is real compounds
there are some theoretical compounds that I'm more then willing to discard
@roscoe_casita Different reactions are interesting for different reasons. In the explosion of nitroglycerine, the amount of gas released per mole and the heat released are intriguing.
Also sometimes some bizarre things happen in compounds that make them interesting, like that bent benzene Manish had a question about.
(It wasn't bent anyway, but that was a cool complex)
=)
here is a sample entry in the database
those are very real compounds
at least some of them =/
I would like to know how to eliminate non-real ones for sure.
but I digress
@roscoe_casita Unlikely. It should be LiFeO2 I think.
20:06
given the 'magic' numbers in the database, what would be some properties of reactions that would be of interest to a chemist?
NO MORE MAGIC
@roscoe_casita Different chemists find different stuff interesting.
fair enough
A reaction with a surprisingly high equilibrium constant even though it shouldn't according to theory would be interesting.
what is a high equilibrium constant?
20:08
A reaction that leads to a formation of some expensive material in a cheap way is interesting.
that can be a search query to be run over the hypergraph
@roscoe_casita Reactions are at times equilibriums. That means the reactants wouldn't all react to give the products, but some will remain. A way to quantify this is the equilibrium constant, K_eq.
It's a measure of how much the reactants react to give products.
interesting
I was specifically interested in redox reactions I believe
@Chemobot No, his name is @PhMgBr
@Chemobot I'm going to kill you for that one day
20:11
@Chemobot Shut it ._.
@roscoe_casita Oh, electrochemistry is certainly a fancy topic.
looking for reactions to make better batteries
~ but my chemistry is pitiful. I'm seeking to correct this. The computational side is basically complete if I can demonstrate some 'simple' reaction information
I don't know what the field's interest is ATM. Someone else might.
then I can invest time further in the chemistry side to make a viable search engine
@roscoe_casita So maybe you can join @Cowp in his Chemguide journey?
20:13
I think the actual question I'm trying to ask is about a 200 level class question
Chemguide's got some useful tutorials.
thanks, I will research that!
greatly appreciated!
i don't even know what units this database is measured in =/
"energy_per_atom" = ???
"e_above_hull", "energy"
Chemwiki.UCDavis is a nice site too, but sometimes it contains misinformation.
Because many people write it.
awesome, other recommendations?
Including some that might not exactly know what they're talking about.
20:15
it is the internet ~
@roscoe_casita Masterorganicchemistry for organic chemistry.
Depending on how much time you have, I might have recommended some textbooks.
@PhMgBr Isn't it Freemium or something ?
Textbooks are very nice kickstarters, but they consume some time at first and need dedication.
@Hippalectryon Yeah, exam cheat sheets or something like that needed cash.
I also recommend this useful medium.
Make sure you don't interrupt any conversation that's worth having, and someone might be around to help.
Use Quora if you had any trivial questions and Chem.SE if you're sure you have thought enough about your question and researched enough @Roscoe.
@Cowp got started with posting here; he was afraid at first.
But then he ended up with some nice posts.
The level doesn't matter as long as the query is thought-provoking.
BTW I won't be here tomorrow @All.
Rgr. Will do.
I appreciate it.
20:28
@PhMgBr you have job interview tomorrow?
Worse.
I have to study geology.
"Geology" <-------buakh!!
!!gun
( ͝ಠ ʖ ಠ)=ε/̵͇̿̿/’̿’̿ ̿
( ͝ಠ ʖ ಠ)=ε/̵͇̿̿/’̿’̿ ̿ Geology
20:35
I am very weak at chemistry so help me out with this dumb question (very hard for me)
!!(★▼▼)o┳*—————–●));´ロ`))
@Chemobot ?
$\ce{NH(CH_3)_2+BF_4}-$----->?
BF4 doesn't exist.
Chemobot is getting crazy day by day.
20:36
BF4- might.
Hein what is berilium tertraflouride
BeF4?
Berilium =Be , lol i thought 'B'
It again should be BeF4 2-.
Can't we upload photos using iphone
So question is write the acid base reaction of CH3NH and boron tetra fluoride and show electron movements with arrows
20:49
NH(CH3)2 + BF3 would form adduct
Bond between N and B would be created
jealous of the knowledge in this chat room
@Mithoron I thought this too, but nothing would happen with BF4- and BeF4 2-, would it?
Orbitals already filled.
@PhMgBr obviously wrong because of lack of counterion
@Mithoron Ja.
ammonium could be there and it might be salt decomposition
@DeNiSkA But really you need to specify such things exactly
20:55
@DeNiSkA NaBH4?
Ya! Correct
@Mithoron the text i posted that was the question and no more information was given
!!flip/different
(づ๑ʖ๑)┛︵pᴉɟɟǝɹǝuʇ
@DeNiSkA You didn't rewrote such reaction correctly!
21:00
Sorry my bad!
Methanol reacts with BF3---->
I want to ask how do you proceed
I dont need only answer but method also(::*politely*::)
21:27
@DeNiSkA Lewis acid base reaction - on arrow from oxygen lone pair to B with empty orbital
21:41
Huh..! Mithoron is off!
22:05
So they still work.
22:50

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