Merken

Lec. 13. Anions (Pt. II) & Lec. 14. Alkali Organometallics

Zitierlink des Filmsegments
Embed Code

Automatisierte Medienanalyse

Beta
Erkannte Entitäten
Sprachtranskript
In OK we're going to finish up but just that 1 less thing to talk about for elections iron
so we're talking about a bunch of PKA stuff for an alliance armed to the last a cut of about as that called the Alpha effect feisty better once said that whenever so recall something in effective means they don't understand what's going on when you give it a more descriptive name on I sort of feel like maybe we have a better idea of what's going on with the offer Becton relates to this observation that if you look at the stability of a typical immediately readers had an hour group aware he told carbon Hill would normally be you find that there is a header Adam attached to that nitrogen that these tend to be significantly more stable than a regular in the dramatically more stable to the point where you can eat informed them in water and equilibrium favors the inning over the highlights the tells so you already know the Cardinals a stabilizer that this should be so stable towards hydrolysis information the key to this is what we refer to as the album affect the fact that there is an extra hinterland here tends to make this more stable thermodynamic interpretation of the offer effect it has to do with stability ,comma thinks there's also a comedic side to the other affect what you find solution is not only due for more stable outlooks on them and they say are undergoing write this down clear that this is more stable than just and then just a simple either of these 2 derivatives are more stable than a simple on any true we call this a hydra zone and the but these have now become common fixtures in the field of chemical biology because you can form water and we call this other and oxygen system in Oxy and dramatically more stable than me so the Connecticut terpretation is that you have the precursors to these on do what you find is that these are more reactive nucleophilic processes and that's a kinetic effect you get faster rates of reaction from media
attacking some novel allotted minutes until you get faster rates of reaction when there's a header wide on school so there's a
concern there's a thermodynamic stability aspect and then there's the rates of chemical reaction as so defined on this issue that it's faster than just a simple when there's a federal Adamec store for example innocent to the action because let's talk about these these 2 on these 2 aspects of the out of that and I would start by talking about but I feel like is the more obvious aspect that's the thermodynamic aspect and so let's come back to the idea of why is it that something like this should react with water why should water want to attack that Amin the water attacks occur well 1 way to interpret this that reactivity is that we can't think of any sort of an Indian carbon Hill group
kind of like this it maybe there's some partial positive charge for the tone we said there's about a 4th of a positive charge at a Quito carbon so to the extent that
charge matters in nucleophilic attack by water at this center to make it hired realize anything that can stabilize that electron deficiency the hope that system and there's a resonant structure we can draw from this and withdraw that resonance structure and I take that longer on nitrogen or the longer-run oxygenated synopses and I push this over and what I see is well maybe that carbon shouldn't be as electoral Filegate that might otherwise think it to me and that's exactly the case so that you can see how that had just by drawing a simple resonant structure you can see how that handle store helps to make this carbon atom less susceptible to attack by water or hydrolysis and so you can think of this as a way of explaining the preferential stability of
hydrogen and an ox is now the the time thing to explain is the kinetic effect if there's no common Adam here are you explain why the long perilous this this nitrogen and
hydrazine or hydroxyl me why is it kinetically 1 reacted with comeback and interpret that as a was simple :colon skiing farm if you take hydrogen peroxide of draw this out there's hydrogen peroxide we had a base to that with bauxite and iron but the force in the presence of methyl tosser late so what's the product of the reaction because the flat side and that's a good nucleophile governmental Thomas that's a good electrical to reactions no competing lead to elimination match into what you find is you don't get any of this you don't get any of this but dioxide EDS into reactions on the level tirelessly what you see is that the hydro peroxide online is where attacks the metatarsal so it's happening here is there is a very rapid equilibrium we know the proton transferring fast to generate the Hydra proxy in so there is an equilibrium maneuvers Mormon bothers my thoughts either side peroxide and it turns out then peroxides are more acidic than regular calls and maybe you could guess that despite the fact that there is an extra electoral Adams Elektra negative Adam next door here that can help with that negative charge and what you don't know the the numbers it's about PK 12 so peaking at 11 . 6 so somewhere on the order of about 10 thousand times more acidic than a regular alcohol the equilibrium just based on the case on the about 10 thousand times more of this than there is in this president 10
thousand times more peroxide online at equilibrium in dockside for what you could not have guessed that not only is there more of this
is that it's 10 times more nucleophilic and solutions in most cases when you look at simple case if there's 10 thousand times more of something it turned out to be 10 thousand times unless nucleophilic and then you can guess what the product is going to this is a rare case where not only is the 10 thousand times more of this in equilibrium but it's also more nucleophilic and so the effect you see is that it's the hydro proxy and iron that's more abundant and more nucleophilic is is reacting on as the nuclear file this reaction OK and that's the alphabet that's a kinetic effect is very unexpected factor the hydro crop citing online in spite of the fact that that's more
favored more stable also turned out to be more and people argued about this effect 1 should that be why should hydroxy group the effect
this effectively activity of that level minus I'll give you a simple fact it turns out that that is not poorly solvated solvation decreases reactivity when you solvated online with solvent you make it less reactive cancelation of Hydra proxy and I'm on the is less effective but but but but but but but but but if we don't solve Asian of hydroxide which is the corresponding nucleophile without enough
without an effect it was by
21 . 5 cows that's a huge energy difference so he convert that into factors of tend to get a sense that hydroxide is really being solvated you can imagine any respectable solids of forming hydrogen bonds the sodium ions around crowding around that oxygen minus physicians not as effective for how to approximate the height approximately more naked and more nucleophilic even know it's easy to make a height approximately 9 appropriating it turns out that you're you're basically distracting metal minus less with solvation so it's now on generally accepted that this is the kinetic offer effect is the solvation issue has to do with the poor solvation of Alpha affect nuclear files hydroxyl Amin is less effectively solvated hydrazine is less effectively solving these better nuclear files in a simple and counterparts and so you can take advantage that its synthesis
of chemical biology arms the fact is that those have extraordinary nuclear forces
focus so that's it offered for a lecture 31 and irons and analyzes nuclear policy and so now among the switch on over to something closely related I'm basically acknowledging the fact that I've been skimming From the beginning and we're now going to talk about things that are bonded to sodium and lithium and potassium to that 1st column of the periodic table I sketched out a little Periodic table here like this 1 happens when things are bonded to lift and sodium and potassium and cesium not with any of that radioactive it's and things like that so get set to think about Beutel lithium sodium Alcock sides we need to 1st start off by reminding ourselves that we made this claim at the beginning the course and we were going to explain rates of chemical reaction based on 3 different factors 3 different terms and some sort of a hypothetical equation we set the charge is going to matter some things will react faster because minus likes plus or repel because plus seats plus so like charges repel opposite charges attract wizard hysterics this kind of obvious we need to discuss anymore I think on and last we said we were going to use orbital overlap frontier molecular tools to explain things so when you think about the reaction for example of some Alcock side doing units into reaction on methyl toss the reason why this is fast is because there is a large amount of partial positive charge there on that on methyl group that's the effect of the tussling and there is an orbital contribution of this but but colonic attraction plays a big big Wall and why that's a fast reaction that we come over to other reactions were not going to be so adept at using that charge explanation if you look at the reaction and we'll talk about these more later of Antena
means we can't use that charge interpretation to explain why 2 reactions fast here we can't use that they charge interpretation explain why this carbon atom
at the end of the pie bond is so good at attacking methyl iodide community ceasing its very little negative charge at the end of this carbon atom spices this is this is an issue orbital overlap will talk about the means in the late signals more later we need to keep these 2 things separate this issue charge in the comic equation verses orbital overlap filled orbitals the nucleophilic mindful orbitals the electrical 1 thought come down and talk about signal bond is nuclear files so here I do this as a lone pair attacking on that now I want to switch back to just a simple carbon-carbon bond I think you know that anything is not a good nucleophile for attacking things on but that's not very good and so what would you expect if I replaced this carbon atom with a fluorine animal would you expect many winemakers attack things all right he plus electrified so what do you think would happen to the nuclear Felicity this bond if I replaced carbon with the more electoral negative ads now I would expect that in decrees I would expect that I replaced carbon with a more Elektra negative Adam I would expect that to be lower in energy the sigma bond the canonical from 2 orbital focusing on bond on and so I would expect it to drop but what happens if I if I reduced the electoral negativity this other I mean march across to the other end of the periodic table replace covered with lithium another 2nd lack clear on the other side of the periodic table by prediction is and ought to be that I should expect the nuclear Felicity To increase I should expect that this war but always canonical but for a carbon lithium bonds ought to be higher energy the way higher energy than any other type of legislation want we talk of any NEC bond ECC 1 so what we're going to see when we talk about our government of alkali Oregon metallics lithium's predominantly but sodium is that not only do we see an increase in the energies of these these canonical sigma bond warbles we're also going to see an increase in negative charges and there's 2 factors now I play that makers of vastly superior qualified and based anything else we talked about that electrostatic Coloma charge saying and then there's this and things and they're both coming let's talk about alkali again metallics but but but but but but
but but but so if we make bonds between carbon and
lithium or carbon and sodium carbon and potassium what kind of predictions should we have sold on molecular orbital calculations that initial calculations are very powerful they allow you to predict all kinds of things ultimately at the end of this class I hope that you can make all kinds of predictions just by knowing the periodic table that's what we really want to know what you're relying powerful calculations meshes methods to to think about chemistry somewhat to start off by looking at the election negativity of a series of Adams on and sure why organizers I'm going have 3 rows here so not 1 row I talk about the Electra negativity and I have another role where I talk about the covalent character in this bond and then I'll have another role here I talk about ionic character In the
bond and really wanted by ionic character from bond like that and really think about basis at proton
transfer reactions are really driven by charge that kind of telling me about basis to focus on the good and get a list of different dog free-agency here it as I march across this my little table here on and I'm going to start off with the little red salsa operated about a proton not all right magnesium and alright lithium and sodium and potassium and rubidium and cesium and analyze seems like it would make more sense if I into this verdict because we were kind of marching down his 1st row of alkaline earth metals from oblivion to sodium-to-potassium to OK so that's good right out the lecture negativity the lecture negativity of a proton is 2 . 2 carbon is 2 . 5 a Proton is slightly more electoral positive and
carbon if we compare that to magnesium there's a huge jump in electoral positive character so when we think about
that a carbon magnesium bomb so safely -dash draw out some sort of scenario for you to help us think about how I think about a bonds to magnesium more to sodium were 2 potassium there's a resonant structure we can draw a ID card and with an election negativity of 2 . 5 really is more lecture negative in a metal and when I draw resonance structure I shouldn't get the electrons the metal that drove resonance structure of this I should give the electrons to the country and so often it as an undergraduate use this kind of thinking to help you understand the reactivity of organic talents like focus was good and draw out on some of these organic italics if
you and if you look at the electrode negativity story the covalent character so vital bond between carbon and which I had a
similar persons age I would think of that to be the best represented by this a covalent bond an ionic so I look at the Kobe 1 character witnesses at age that you have the most compelling character of any of these but if I replaced the em there with magnesium that should have West Kowloon character and more ionic character and as I dropped down the 1st from lithium to sodium to the task of rebuilding sleazy and what I expect to see is that things become more and more ironic this ridiculous looking picture over here starts to be a better and better representation as I dropped down from Malissia sodium-to-potassium so I expect that we will be less collusion and conversely I expect things to become more ionic so conversely when I got some saying it doesn't matter whether it's apparel wider
chloride on the Vineyard allegiance when I started all these reagents out that what I should expect as these will start to look more and more ionic I'm getting really
and I shouldn't be uncomfortable but I'm going 1 comfortable drawing these sort of covalent bonds to potassium I'm going to skate rubidium it's it's radioactive signals that whatever the hell out of you see what happens in terms of ionic character now will use a different pen color because of crowd to choose now the ionic character is increasing as we go to these lower and lower in the attic table so construction of more like carbon ministers more partial negative charges on March over here to Alcatel potassium species focus let's keep that in mind since the general trend and I expect you to know that things become much more reactive as you go in this
direction and in a way that's not readily controlled so minister of by talking about the simplest kinds of reagents for this class that we can think of that
would be where are as a hydrogen atoms was going to talk about hydride the difference but it was in the 91 draw the the chemical structure for sodium hydride For Your Honor look something like this the you don't have to draw this out but you get the idea this is the chemical structure of a sodium hydride and I'm using dated
bonds here in other words I'm not count these and this is not a Louis structure of I monster so young that they can't have to
charges plus 2 charges so this is a and you have to imagine carrying this out too essentially to infinity but the idea is that each sodium atoms in each hydrogen atoms is locked into a Q cubic Gladys if any of you have ever use sodium hydride or potassium hydroxide lithium hydride life do them but if you sodium hydride a potassium hydride you know it's not soluble in anything the fat-soluble anything just sits there is this great power in the middle of the chemical structure it doesn't look like this not it doesn't go into solution and is all but we can't draw of this every time we do a narrow pushing mechanism so here's what I the validity of this control like this but every time you go at that
you're going to remember that exists is this cubic Gladys and everything is happening on the surface that none of the internal sodium environs are involved in chemical reactivity so true
for sodium hydride potassium hydride lithium hydride sp tended to on many of which arose with this so so if you draw out on sodium hydride so this is not a classical sought more organic chemistry reaction I expect you to know that sodium hydrogen bonds very basic on thermodynamic theory basic kinetically if it's OK for speed as long as you're not trying pull proton off of carbon in the UK get this reaction that will give you a hydrogen gas In all ,comma exciting and that of course the Allcock side is going to want to coordinate to the sodium in 2nd step so it's a good base and as I implied up above here things will become more ironic when I switched to potassium
hydroxide it will become more reactive more ironic this will be much faster I don't think I've
ever worked with potassium drive without having flames somewhere in I'm trying to quench the reagent so if you work was so united of potassium iodide in how the terrorists on a dramatic difference in the activities have never been sorry to testified the story many times to try use the migrant Amedeo sense for relative rates on for these kinds of reactions as you vary the metal and then we'll look at relative rates for D probation nbc's city of Iligan lithium hydride resist sodium hydride persons potassium hydroxide and you look at the relative rates among to assign lithium hydride relatively 1 it's relative to lithium hydride sodium hydride is a thousand times faster Freddie protonation that's why you never use lithium hydride because you don't like reactions that take a thousand days like reactions that occurred right on the time that's like your whole season time is spent in reaction to the good potassium hydroxide This is a recipe if you want your chemistry were quickly if you like reactions that worked well and quickly and you don't like reactions to slow and lousy use potassium iodide hits school reading white-hot aggressive and that's what you want you can always cool things down just quench things carefully on so this is what you want to see to see happening sold it if you wanted to you could and saying that this is a great idea but hypothetically you can use these to decontaminate To the deeper macabre but Unix you should expect because this is a chart-driven reaction it's driven by the amount of negative charge and the proton this might not be very good and because there's very little the less partial positive charge on the proton its attached to carbon get less hydrogen there and I think drop the whole equation OK so potassium hydride when you really want reactions to work fast and well I should switch to potassium doesn't have any usually you usually avoid using word so be careful for what may be greater very reaction you could just suddenly Macon meal of million times faster than an answer is no more 1 of the 2
so what I wanna do that when I look at various organic salad reagents greenery into organic magnesium Brazil Dano sodium which will be in
effect you lithium what happens as we bury the medal when we look at the relative basis city include Felicity Palmer of various again metallic species and want to start off by drawing out a reaction British just imagine and this is 1 of the few where they've actually measured numbers so this is demanding what happened is we take this and we expose it to various different arms fennel organic italics like you can imagine is being fennel magnesium bromides worse than a lithium or fennel sodium takeoff and potassium what happens as we change the we should expect is that we go through this series towards potassium down the product and we should expect rates of that addition to
increase the partial positive charge on the cardinal carbon so you go from lithium sodium 2 potassium you should expect us to get faster and the problem is and that's not the
only reaction against faster there's asserts that the reaction it's that as well as you go as you change that metal and that's the appropriation agreements this is just like the S & tubers 0 2 the attack to make carbon-carbon bonds competes with the permission of protons and elimination reactions to there's 2 possible products that you can get here so you can get the product for additional pies .period but where you attack the carbon yield story get that the productivity probation where you pull a proton often positions around money due them by you have the ratio between these 2 types of products changes hasn't changed so if you have
found magnesium bromide than what you see is a pretty good ratio 97 to 3 for
addition to the car real overdue provocation to make you know and this is why when you look at sought more organic chemistry labs you look at the kinds of reactions they do they do reaction would bring you get relatively good rates of additional carbon he'll versus deprivation the bottom line is the green areas on our own are very nucleophilic on but they're not that base it was switched off and Alethea the it's not quite as good anymore this isn't to say that you can't find conditions to on to get better rates of addiction like switching the solvent anti-Chavez something useful but you can see already is we drive on well let's just stick with the final within important point is what will we do when we stay in
this room so good about living in magnesium different columns but let me stick with this column here as we go from lithium to sodium-to-potassium
because and I think it's clear we're just dropping down in that single column the 1st column the SOS we go from fennel to fennel sodium and I'm getting this job so now things start to look arguably worse if you're trying to make carbon-carbon fundamentally ghetto fennel potassium but we don't see any nucleophilic addition to the cardinal carbon because he's with some the test if you have to make a choice and it's not the reactions are getting faster as you go from fellow magnesium bromide to lithium asserting that doesn't the reactions are giving way way faster but not
the reaction you want to know what's happening is that this is speeding up the deep probe nation is speeding up much more
as you as you switch to the lager of metals the probation is speeding up much more than the addition of cardiovascular that's why you've never made a carbon-carbon bond by adding a metal potassium species testing species to Aqaba he'll never seen anybody do that because they don't wanna get deeper nations and so what have you see people use you see people use green yard reagents and lithium steps which will OK itself this would look at where we get these organic lithium stuff or or Granada reagents I would guess that most of you probably made a greenery agents some of In some undergraduate organic chemistry lab Mennonite everybody but it's it's a very common Labastida I'm guessing
that not many of you have made an Normanna lithium that way from please talk about several ways that you can get your hands on some of the Super reactive again metallic
reagents and won a start off by 1 of the simplest textbook ways to make things arms were you simply add metal just take metal when you mix it with al-Khalayleh so let's just suppose we take sodium and we mix that together with chloride or a bromide tonight I couldn't help feeling like and a look at how the rates vary for this reaction the start of just by considering this reaction of an alkyl chloride plus sodium metal and the ideas that we're going to so sodium chloride is a byproduct of this and the other product that we would get is this alkyl sodium species there's a story geometry takes too silly Institute at the the same thing for lithium before potassium or for other metals and taking sodium sort of prototype example so the 1st thing we have yielded what is that how you draw the mechanism for this reaction and unfortunately we will not be able to draw an arrow pushing mechanism for this action initially had to think about what's going on here 1st thing is where we putting the electrons in this system it involves a radical where's the electrons going What's the nuclear file and what's the electrified Dougal Clyde is clearly electrified and delicious remind ourselves of what is the orbital in the alkyl chloride it's getting attacked followers no Koble Caroline's no interview I don't
see double bonds there's no price what we had was a signal orbital and that his orbital right here there's a seamless orbital where the electrons are
going says Robert and orbital here Sigma star for the common 1 that's where the electrons going and they're going in 1 at a time so sodium is going to dump electron into this war ballistic missile and the sad fact is we have no good way to represent this using Lewis structures so and so and drawing sodium is an electron the Sicilian can so when we do . 1 single electron entered by mortal what happens when we put an electron or 2 electrons into an by more you weaken the bond it's like the duty bonding orbital put to electron we break the bond if we put 1 electron we weaken upon enactment Adrovel Beutel group here and we don't have a little a structure that allows
me to put an extra electron there is that what are we going to put a -dash but that doesn't mean that's not right is not free electrons we don't want to imply that there's 9 electrons on the carbon atoms so we're stuck with this representation of this
all the bonding orbitals down here seem more bottles filled and then 1 extra electron stuck in an antibody moral that makes this bond money linear racism draw this more suggestively makes this bond longer and weaker than extra electron anti-money moral making that bond ready to break and so I knew minus charge here so we don't have a good Louis representation so we can use 0 pushing this site were not Fire-Rescue mechanism involves making again metallic using a metal you won't be able to draw on establishing mechanisms to try new things to make the 1st you have to start with correct Lewis structures and you have to know we lose the chloride ENI and so now long bond weakened it's gotten electron ended on moral that chloride in I'm is going to pop off if we
take these electrons in Galle drawing arrow here for this part of the reaction if I take this pair of electrons in mining and
then get away here the chloride will have the minus all the AA group yeah that's going to have a radical their knew of your chloride over there you can see the effect of weakening the bond that makes it very easy to home lies and want to give a clear idea 9 and radical so now we have this this radical here and I can pick up another electron very fair to hairy very fast to pick up another try by carbon was 7 elections is very unhappy it wants to have another election so then you end up with carbon miners and sodium plus and the C-minus combines with the sort of thing you could you could think of it as factor well if you're jury that away but if you want to think of it as this just forming a bond there you could do that I'm not going to join him for a Gambino habanero pushing away 2 brothers out don't even try so
what you'll find in this in this series is that the rates look like this when you make Oregon metallics and al-Khalayleh simply by mixing in metal
sodium and magnesium alkali guides are better than October faster than outdueled bromides which faster than alkyl Clerides that's the general trend that you you should expect OK so let's talk about the problems with these kinds of reactions I don't think any of you have ever made kill sodium species by adding sodium may have mixed sodium without delay like that you never isolated the Yellville sodium species in waters when I saw this interview is really refer to as Kronos behavior why is it that you never made an Alkol sodium is the
problem but suppose you take some sort of Alcatel chloride Buell chloride and you had some sodium to that stones and chunks of sodium metal
instantly as soon as the reaction starts you got a problem you got this Silber basic Super nucleophilic things floating around in the presence of something that is pretty reactive so the Greek god Kronos was known in mythology for eating his children and that's exactly what happens here I don't know anything about mythology that I'll always remember from because I have no problem with him so as soon as you start doing this you got a problem and look at all about your problem number 1 overall as His problem number tilt I need to and you get both of them are not gonna finish hero 1st official get the
idea is that you certainly get these diners in there and I'm trying to draw a cartons of them as 1 byproduct that you get as you're trying to make it so your hope
is that the alkyl sodium sitting in the part of the anybody impact which you've got is the gas the floated away some on that's just inexpensive we have a special name for this kind of coupling together we call this averts coupling Nunavut name the 2 process that's called its coupling so when NBC organic Alex coupled with each other like that and culinary view was scuffling OK so it is the general trend for how bad this can be how bad is this on the Net drawn under here this this process here How fast is it further but for Donatella to come back and react with its precursor in what you find is the order of rates is it alkyl potassium is the worst to
never seen anybody making out that Garcia because it's so hard to make it past side reactions while you're trying to make them kills sodium very fast
is the side reaction so fast that these 2 are impractical the side reactions were so bad that you just can't make these without super special conditions so people have done it they managed to speak out some kind of local sodium to make this work but that's not a practical way things do become practical by the time you get to lithium and of course you can by tanker train car tankerloads full you lithium so this is practical 10 of course you know it's practical to make green yard regions with magnesium undergraduate students in undergraduate labs OK so it's very hard with sodium and potassium things were so reactive they come back and we really react with the starting material single let's focus on
al-Khalifa himself all faster those side reactions without the lithium In as we varied
daylight Sonoda beer-making inoculate him from Wallaby drop that same scheme that I did before because I think it'll make more sense to and then we have to worry about the side reactions here too the new a mixture of the 2 plus birds coupling the assistant to the how bad is it properly .period sentimentalized how bad these reactions are so it's look at what happened is we vary the daylight idea and will look at the half for the easy to possess into side reactions and 1 of the attention that which feel
like to start with what you buy you let a new users how is that made when you look at the Habur lies
these reactions this is the 1st it's all independent this is eaters Solomon there's a 40 hour half-life for the B-2 innocent side reactions that's slow enough to where you can make the lithium before the war it does this horrible reaction with the starting al-Khalayleh try to make the lithium for Melchior bromide those side reactions are dramatically faster and the fine if you try to make the lithium from you lied side reactions or so fast now the 2 limitations the you'll get just a bunch of octane and butane gas and that sold the bottom line is and the lithium that you buy that they
use in industry is made from local From fuel collided with the car OK so long How
many of you taking lithium wire and use it to make Anelka lithium nobody knows you've ever done that right that's for industry when you go and Lavinie Mitchell advanced intermediate the vinyl Indiana elected you don't use this method so let's talk about the method used to make super complex structures without the lithium bonds this is great for making bombs Beutel lithium set utility and things like that so it when you're in the lab you're not you're not adding lithium wire on snippets of lithium wired to help but what
about the what you're using is an exchange equilibration
reaction there's 1 and 1 member of this class it's not seizing exchange reactions .period by talking about these types of exchange reactions and so it was a good and this is 1 of the most common ways to make Anelka lithium if you've got some advanced intermediate slopes suppose you have you wanna make an error lithium on and others good draw this out it's not interesting is just vandalism making you can buy vandalism but just imagine that that's a more complex aromatic rings in a of the the lives of 5 years something the way he we've sorry I went we start off with a halogen there and how is it that you would convert this into some sort of an error lithium and the way he did simply by
adding you can use other al-Khalifa and speculative
is the cheapest if you just use a simple story geometry analysis is my other product is fennel at the end of the byproduct has to be the elderly so this is a way to make out the things in the lab typically is an important point here is it's it's an equilibrium process if you think of this I will know nobody makes the Bewley they all aspire to be laid in use use that to drive reactions like this so you're all year you can't you
can't you can't have TB ALL a daylight here and get this to work and will talk about that just wasn't equilibrium issues going on here OK so what can exhibition so traditionally in the lab the
betting on Xia just give you the identity of X wide-eyed at the fastest so typically when you see this process of lithium halogen exchange they're using iodized it's much much faster than the next common type which is thank you halogen try muscle tins very fast Middelhoff how to enlist in exchange the look the relative rate rise versus trainable standing it's 80 times faster with the with the wide-eyed than it is with the team and then finally we get down to work ,comma move and I'm not sure why I have this where history
mobility and greater than trim level today so here's what I'm assuming that I on meant to have been adjusted so
OK you may know attitude is very toxic and nobody wants to work with faculty nobody actually does like this Everybody was the tribunal standings and they're less reactive so if you want more reactive 10 reagents yet novels on their armed with the toxic we want less reactive ones used tribunal tendencies and non-toxic but there no less reactive and try muffle standings OK so when you use alkali died at minus 17 it's essentially instantaneous it is fast you're adding even a minor 70 years faster during the view lithium in there you got instant equilibration so just to give you a sense how fast so I don't really kill you to go down the reactivity like this to go instantaneous 2nd or made to use the chair of the 10 is very powerful itself so minus
78 -minus AT those kind at temperatures it's
super-duper cheaper professed to and talk about what's so why would anybody want to do this it turns out that you can you you can have reagents that Havel broader range of substitution of the high-dimensional give you 1 example of something that you can make with 10 and isolated purified that you can make there so here the class of 10 reagents and you couldn't have denied where this changes you can't have an iodide next to the smooth boxy lone pair field alone .period and iodide the local pushed felt the Idaho you'd never be able to isolate them but no problem isolating this and running it on this silicon gel column and you take this new treat this would be lithium N then you can
get very fast rates of exchange the money would draw the United drawing the mechanism for these absolutely comeback over when the finished drawing the mechanism for
this and it's the same as the mechanism for nite I'm not that for years will use the mechanism al-Khalili Missouri nucleophilic it attacks the 10 it doesn't want us into reaction on the test is tax that and surrounded with 10 with 5 firebombs no problem 206 bonds and wouldn't be an issue we call this a standing the world subtext that aid tell you is native to Argentina and Stan 8 we should be thinking every bond to that team is now nucleophilic and so what happens if there's no elective while poised nearby is that that will collide the
manual now convert that into an out him so you couldn't do this with or without with an iodide piano you might like the fast track that I'd I'd faster than reagent this
that at this lithium if this team with him exchange the byproduct that you get in the end this is this is this try methyl spin-off all butane OK so on the powerful about this is the view of a scary eugenics center here would you can tell is that it's a stereo specific trains ventilation but if this team was sticking hollow-eyed this descended this configuration will get retention of configuration for the 10 was the it's not backside attack with the 10th and the OK so it's the same idea if you take
the Bolivians online alive but in other words if I draw the mechanism for this watch this here
we don't freak out over the fact what is that I died with wood to bonds that I can deal with that jury can it's no big deal I don't have 7 bonds no problem this is not an architect will the architect will might is not in the 2nd roles Colvin nitrogen oxygen and lithium and so now that and I O date was that that negative charge they told me a bonded nucleophilic so you shouldn't be surprised that Bonneville now attack and give you a vinyl lithium was wide-eyed OK so we're gonna stop there when we come back we're going to talk about this 3rd common way to make calculate the reagents that's from file fennel compounds through reductive documentation
Organischer Halbleiter
Eisenherstellung
Metallorganische Verbindungen
Chemische Struktur
Dauerwelle
Chemische Forschung
Alkalien
Kalisalze
Peroxyacetylnitrat
Computeranimation
Chemische Biologie
Fülle <Speise>
Oktanzahl
Reaktionsführung
Substrat <Boden>
Verschleiß
Kohlenstofffaser
Permakultur
Besprechung/Interview
Wasser
Zusatzstoff
Alphaspektroskopie
Fleischerin
Stickstoff
Lösung
Präkursor
Derivatisierung
Hydrolyse
Vorlesung/Konferenz
Funktionelle Gruppe
Systemische Therapie <Pharmakologie>
Adamantan
Chemischer Prozess
Sauerstoffverbindungen
Chemische Reaktion
Oktanzahl
Kohlenstofffaser
Reaktivität
Besprechung/Interview
Vorlesung/Konferenz
Funktionelle Gruppe
Wasser
Tank
Zusatzstoff
Enzymkinetik
Hydrierung
Elektron <Legierung>
Wursthülle
Kohlenstofffaser
Besprechung/Interview
Wasser
Tank
Stickstoff
CHARGE-Assoziation
Hydrolyse
Mesomerie
Hope <Diamant>
Vorlesung/Konferenz
Systemische Therapie <Pharmakologie>
Adamantan
Kohlenstoffatom
Alkohol
Wasserstand
Endokrin wirksamer Stoff
Reaktionsführung
Wursthülle
Oxidschicht
Besprechung/Interview
Hydroxyethylcellulosen
Hydrazin
Eliminierungsreaktion <alpha->
Base
Bauxit
Peroxide
Landwirtschaft
Hydroxylierung
Protonierung
Blei-208
Eisenherstellung
Zündholz
Methylgruppe
Wasserstoffperoxid
Elektronegativität
Vorlesung/Konferenz
Adamantan
Hydroxylgruppe
Sonnenschutzmittel
Eisenherstellung
Wursthülle
Besprechung/Interview
Hydroxyethylcellulosen
Vorlesung/Konferenz
Lösung
Wasserstand
Aktivität <Konzentration>
Reaktivität
Besprechung/Interview
Vorlesung/Konferenz
Hydroxide
Chemische Biologie
Enzymkinetik
Sonnenschutzmittel
Destillateur
Digoxigenin
Metallatom
Besprechung/Interview
Entzündung
Hydroxide
Hydrazin
Natrium
Alphaspektroskopie
Sense
Vorlesung/Konferenz
Wasserstoffbrückenbindung
Sauerstoffverbindungen
Biosynthese
Kalium
Sonnenschutzmittel
Fettsäuremethylester
Chemische Reaktion
Oktanzahl
Reaktionsführung
Besprechung/Interview
Natrium
Radioaktiver Stoff
Werkzeugstahl
Cäsium
CHARGE-Assoziation
Eisenherstellung
Lithium
Methylgruppe
Monomolekulare Reaktion
Vorlesung/Konferenz
f-Element
Kohlenstoffatom
Metallatom
Lithiierung
Kohlenstofffaser
Besprechung/Interview
Gewürz
Biogasanlage
Orbital
Fluor
Alkalien
Chemische Bindung
Elektronegativität
Pille
Methyliodid
Vorlesung/Konferenz
f-Element
Sonnenschutzmittel
Einsames Elektronenpaar
Setzen <Verfahrenstechnik>
Entzündung
Natrium
Fruchtmark
Elektronische Zigarette
CHARGE-Assoziation
Bukett <Wein>
Biskalcitratum
Lithium
Elektrostatische Wechselwirkung
Kohlenstoffatom
Adamantan
Chemische Forschung
Kalium
Kohlenstofffaser
Besprechung/Interview
Kaugummi
Ionische Flüssigkeit
Organischer Halbleiter
Konkrement <Innere Medizin>
Protonierung
Elektronische Zigarette
Natriumcarbonat
Chemische Bindung
Lithium
Elektronegativität
Vorlesung/Konferenz
f-Element
Kalium
Reaktionsführung
Kohlenstofffaser
Besprechung/Interview
Erdalkalimetall
Natrium
Magnesium
Protonierung
Cäsium
CHARGE-Assoziation
Rubidium
Sense
Lithium
Elektronegativität
Elektronentransfer
Vorlesung/Konferenz
Kalium
Metallatom
Elektron <Legierung>
Kohlenstofffaser
Reaktivität
Vitalismus
Organischer Halbleiter
Natrium
Magnesium
Chemische Bindung
Mesomerie
Elektronegativität
Vorlesung/Konferenz
Chloride
Altern
Lithium
Atombindung
Vorlesung/Konferenz
Natrium
Magnesium
Kalium
Spezies <Chemie>
Rubidium
Kohlenstofffaser
Farbenindustrie
Besprechung/Interview
Atombindung
Ionische Flüssigkeit
Vorlesung/Konferenz
Penning-Käfig
Fruchtmark
Chemische Struktur
Chemische Bindung
Vorlesung/Konferenz
Natriumhydrid
Hydride
Reglersubstanz
Kalium
Kaliumhydroxid
Potenz <Homöopathie>
Reaktivität
Lithiumhydrid
Entzündung
Natrium
Hydride
Ordnungszahl
Lösung
Kubisches Gitter
Chemische Struktur
CHARGE-Assoziation
Oberflächenchemie
Vorlesung/Konferenz
Natriumhydrid
Kalium
Organischer Stoff
Reaktionsführung
Lithiumhydrid
Kohlenstofffaser
Besprechung/Interview
Gangart <Erzlagerstätte>
Natrium
Hydride
Protonierung
Wasserstoff
Anomalie <Medizin>
Vorlesung/Konferenz
Natriumhydrid
Wasserstoffbrückenbindung
Aminosalicylsäure <para->
Kalium
Chemische Forschung
Metallatom
Hydrierung
Aktivität <Konzentration>
Kaliumhydroxid
Oktanzahl
Reaktionsführung
Kohlenstofffaser
Lithiumhydrid
Organischer Halbleiter
Hydroxide
Natrium
Magnesium
Kaliumiodid
Hydride
Protonierung
Sense
Vorlesung/Konferenz
Natriumhydrid
Flamme
Kalium
Reaktionsführung
Oktanzahl
Kohlenstofffaser
Entzündung
Organischer Halbleiter
Natrium
Magnesium
Spezies <Chemie>
Biskalcitratum
Lithium
Vorlesung/Konferenz
Bromide
Mil
Metallatom
Reaktionsführung
Kohlenstofffaser
Besprechung/Interview
Setzen <Verfahrenstechnik>
Magnesium
Benetzung
Protonierung
Additionsreaktion
Fließgrenze
Chemische Bindung
Vorlesung/Konferenz
Bromide
Eliminierungsreaktion
Additionsreaktion
Organischer Stoff
Reaktionsführung
Oktanzahl
Lithium
Querprofil
Kohlenstofffaser
Kaugummi
Krankheit
Vorlesung/Konferenz
Base
Magnesium
Kalium
Gensonde
Reaktionsführung
Coiled coil
Nucleophile Addition
Kohlenstofffaser
Natrium
Magnesium
Bathygraphie
Bukett <Wein>
Lithium
Vorlesung/Konferenz
Bromide
Chemischer Prozess
Kalium
Metallatom
Trennverfahren
Fülle <Speise>
Organischer Stoff
Reaktivität
Besprechung/Interview
Organischer Halbleiter
Gangart <Erzlagerstätte>
Selenite
Lagerbier
Spezies <Chemie>
Chemische Bindung
Lithium
Vorlesung/Konferenz
Allmende
Kalium
Chloride
Metallatom
Elektron <Legierung>
Oktanzahl
Reaktionsführung
Natriumchlorid
Besprechung/Interview
Natrium
Orbital
Chlororganische Verbindungen
Doppelbindung
Spezies <Chemie>
Metall
Biskalcitratum
Nebenprodukt
Lithium
Vorlesung/Konferenz
Primärelement
Bromide
Alkylierung
Systemische Therapie <Pharmakologie>
Mil
Chemische Struktur
Elektron <Legierung>
Biskalcitratum
Chemische Bindung
Besprechung/Interview
Vorlesung/Konferenz
Natrium
Funktionelle Gruppe
Orbital
Kohlenstoffatom
Chloride
Abfüllverfahren
Chemische Struktur
CHARGE-Assoziation
Metallatom
Elektron <Legierung>
Reaktionsführung
Chemische Bindung
Antikörper
Vorlesung/Konferenz
Ente Nazionale Idrocarburi
Aktives Zentrum
Mineralbildung
Chloride
Sonnenschutzmittel
Metallatom
Elektron <Legierung>
Oktanzahl
Chemische Bindung
Kohlenstofffaser
Vorlesung/Konferenz
Funktionelle Gruppe
Natrium
Chloride
Alkalien
Spezies <Chemie>
Metallatom
Gestein
Reaktionsführung
Sammler <Technik>
Besprechung/Interview
Vorlesung/Konferenz
Bromide
Natrium
Wasser
Magnesium
Oberflächenbehandlung
Reaktionsführung
Nebenprodukt
Umweltkrankheit
Hope <Diamant>
Amrinon
Vorlesung/Konferenz
Base
Medroxyprogesteron
Azokupplung
Kalium
Präparative Chemie
Präkursor
Oktanzahl
Besprechung/Interview
Vorlesung/Konferenz
Paste
Organischer Halbleiter
Natrium
Alkylierung
Chemischer Prozess
Kalium
Präparative Chemie
Lithium
Besprechung/Interview
Krankheit
Vorlesung/Konferenz
Natrium
Magnesium
Selenite
Stratotyp
Azokupplung
Präparative Chemie
Wassertropfen
Sense
Reaktionsführung
Mischen
Besprechung/Interview
Vorlesung/Konferenz
Präparative Chemie
Reaktionsführung
Schönen
Lithium
Besprechung/Interview
Butyraldehyd
Octane
Vorlesung/Konferenz
Bromide
Chemische Struktur
Vinylverbindungen
Chemische Bindung
Lithium
Besprechung/Interview
Vorlesung/Konferenz
Kernreaktionsanalyse
Reaktionsführung
Lithium
Besprechung/Interview
Setzen <Verfahrenstechnik>
Vorlesung/Konferenz
Halogenverbindungen
Aromatizität
Auxine
Elektronische Zigarette
Mannose
Reaktionsführung
Nebenprodukt
Besprechung/Interview
Kaugummi
Vorlesung/Konferenz
Chemischer Prozess
Krankengeschichte
Zinn
Wasserstand
Oktanzahl
Besprechung/Interview
Setzen <Verfahrenstechnik>
Ionenbeweglichkeit
Auxine
Tamoxifen
Mannose
Lithium
Vorlesung/Konferenz
Halogenverbindungen
Chemischer Prozess
Sense
Körpertemperatur
Lithium
Reaktivität
Besprechung/Interview
Toxizität
Vorlesung/Konferenz
Disposition <Medizin>
Ovalbumin
Oktanzahl
Einsames Elektronenpaar
Iodide
Silicone
Lithium
Besprechung/Interview
Vorlesung/Konferenz
Glättung <Oberflächenbehandlung>
Iodide
Reaktionsführung
Chemische Bindung
Mannose
Besprechung/Interview
Vorlesung/Konferenz
ACE
Elektronische Zigarette
Versetzung <Kristallographie>
Nebenprodukt
Lithium
Methylgruppe
Besprechung/Interview
Butyraldehyd
Bewitterung
Vorlesung/Konferenz
Abschrecken
Vinylverbindungen
Chemische Bindung
Lithium
Besprechung/Interview
Mas <Biochemie>
Stickstoff
Sauerstoffverbindungen

Metadaten

Formale Metadaten

Titel Lec. 13. Anions (Pt. II) & Lec. 14. Alkali Organometallics
Alternativer Titel Lec. 14. Pt. 2. Anions (Pt. II) & Alkali Organometallics
Serientitel Chem 201: Organic Reaction Mechanisms I
Teil 19
Anzahl der Teile 26
Autor Vranken, David Van
Lizenz CC-Namensnennung - Weitergabe unter gleichen Bedingungen 3.0 Unported:
Sie dürfen das Werk bzw. den Inhalt zu jedem legalen und nicht-kommerziellen Zweck nutzen, verändern und in unveränderter oder veränderter Form vervielfältigen, verbreiten und öffentlich zugänglich machen, sofern Sie den Namen des Autors/Rechteinhabers in der von ihm festgelegten Weise nennen und das Werk bzw. diesen Inhalt auch in veränderter Form nur unter den Bedingungen dieser Lizenz weitergeben.
DOI 10.5446/19215
Herausgeber University of California Irvine (UCI)
Erscheinungsjahr 2012
Sprache Englisch

Inhaltliche Metadaten

Fachgebiet Chemie
Abstract UCI Chem 201 Organic Reaction Mechanisms I (Fall 2012) Lec 14. Organic Reaction Mechanism -- Anions (Part 2) & Alkali Organometallics Instructor: David Van Vranken, Ph.D. Description: Advanced treatment of basic mechanistic principles of modern organic chemistry. Topics include molecular orbital theory, orbital symmetry control of organic reactions, aromaticity, carbonium ion chemistry, free radical chemistry, the chemistry of carbenes and carbanions, photochemistry, electrophilic substitutions, aromatic chemistry.

Zugehöriges Material

Ähnliche Filme

Loading...