Merken

Lecture 05. Alcohols, Ethers, and Epoxides Part 4.

Zitierlink des Filmsegments
Embed Code

Automatisierte Medienanalyse

Beta
Erkannte Entitäten
Sprachtranskript
so it's time for me not to look at the news a walk in the world around me without seeing someplace organic chemistry doesn't become important I saw this article or a reference to this article in the news Armenian China there was a factories built where I don't know think it is a later .period about using the old on approximately 39 metric tons of Kompong called can only got dumped into a reservoir and ultimately into liver In what comments on the new 39 times something almost inconceivable amount would talk about what analysts and this is the structure of the were going
to talk a lot about handling and benzene ring to it it's a very simple compound on panel is when we get Chapter 18 were going to do a zillion reactions with mainland and when you get to the later chapter on means Chapter 25 and 1051 see you can do is William Morrow reactions all this is the molecule that started the field organic chemistry but 150 years ago in Germany people realize that they can take on a LAN and Lewis a super-secret reaction you'll see in 51 C and make dies prior to their is that they send ships around the world to collect dies from indigo plants in the plantation in here and I want the world to the idea that you could take simple chemicals that come from coal which you burn and make color compounds which were extremely valuable kicked off the field of organic chemistry 150 years ago on 1 of the things that strikes
me when I look at the pictures that were published in multiple news articles from this is that on you look at the safety precautions that people are taking in order to clean up this mess in laying down bags of activated charcoal that's something that absorbs organic compounds on the the main precautions here is to basically wherever hot that and they're waiting around in this CU polluted water 1 of the big problems here is that the water froze over Italy and just having shovel of all decisive was contaminated with England so really heroic work on their part I'm I hope we never had that kind of a problem here ,comma California in the United States is really anywhere in the world it's real disaster "quotation mark the unfortunate is the kind of stuff gives chemistry a bad then I don't like this but his let's return back to where we left off when we left off on on Monday June it is just very powerful reaction is super powerful and I tried to convey with you that this is a money reaction and the mechanism I showed you when I drew the mechanism out there and try to interest will accrue with what I would like you to draw logical back and correct your notes so that you and I are both writing the same book the same mechanism is what's in the book and it's different from the mechanism by which would draw undergraduate class that's what I messed it up sewing class notice appeared I drew the arrow going up to oxygen Toledano minus and then I would say there's other stuff you could go but what I would like to do is draw the mechanism on the bottom where when the chloride and attacks but you use these electrons in this carbon-oxygen volunteer to make as double bond and simultaneously kick out the chloride that's the mechanism of bookshelves and I wanted to try to stick with the book mechanism because the because we'll all be on the same page as long as we stick with the mechanism in the book OK so just try to correct that don't don't let the electrons here just drop on oxygen making associative along the main byproduct that you get here is sulfur dioxide gas and I didn't show that that's not really important for you but the important part here you can convert all calls in the chlorides and that is increased reaction signing the focus of polio once so just that simple correction heroes to correct you know just make sure drawing the mechanism the book and we want to stress just the latest here and right so what if only wants chlorides that Wednesday in chloride so Monday and we're already onto 2 bromides here is a key region with musicals phosphorus try bromide and so I'm going to show you are reagent in case you just happened to not like Clerides you can make out Hillbrow minds and the overall transformation is very similar to that that we deal with vinyl chlorides of we want take some sort of an alcohol and convert that 2 1 help bromide and this is vastly better than just trying dumping HBO massive notice 1st of all that this process leads to inversion of configuration just like vinyl chloride Leuenberger sterigenics center now actually in most cases you hope all's not history an extended but in case it is you'll get inversion and the reagent to use years prosperous try bromide PB yards or that simple and what's different about vinyl chloride if there's no purity based this reaction he generated br is the reaction proceeds don't worry about it and just let the age gobbled up that will accelerate the rate of the reaction actually photo cantilever arm so this is great for primary and secondary substrates that don't generate public and it is very clean conversion to the bromide arm was couldn't talk about the mechanism for this reaction under the mechanism that they show in the book then again this is not the mechanism by which In a graduate class but this is a good mechanism for us in this class for the mechanism they show in the book and loss the hydroxy group directly displacing bromide it's all going draw like that so there's a long pairs on your alcohol hydroxyl group you got this extremely reactive phosphorus try bromide and so now what happens the book shows drawing this and you directly popped out bromide and so now you've made an oxygen phosphorous bombs there already well on the way to making this a fantastic Leading Group it's Analomink this oxygen with this new phosphorus bound to it after 3 months to oxygen but I have 3 months to oxygen without having a positive charge so we don't have positive charges and that means that bromide got popped up somewhere that draw that bromide floating around down here it is my bro 99 cannot draw 1 of the 4 of England's lone pairs on bromide and I'm sad that this good Leading Group and it can simply use that lone pair to of push out this new oxygen phosphorus leaving Group and that's an ascent to reaction that's where you get inversion of configuration so if you want to make an outfield bromides don't just treat our Falls OH with HP are you all kinds of messy side reactions going on PBR 3 is the best way to do that the bromide attacks within version of configuration innocent to process and that's the mechanism for the reaction to the unit dropped for that OK so very cool there's a farm and diligently reagent this is very similar if you were cooking up methamphetamines this weekend but this is very similar probably the method you're using as you know if you go by a thousand little matchbooks scrape off the phosphorus scratching bad many makes with iodine and makes a region P I 3 basically the same as fast as tribal on my arm so what do you want to do and that this incident very interested in yes or you go to the store like 5 thousand matchbooks and they know it you have to stick with the to and then you don't have to show how to make fast track performance in this class used by that if you work in a chemistry OK so OK so if you want me chlorides is finally purity when bromides PBR 3 fastest-rising alive and you don't need that purity into this impact on that period that's not the right set of conditions OK so I just don't step back momentarily it's like Why would you want to make and how and water some issues that come up when you try to make them but ultimately proved to be the reason at least at this stage of the year chemistry training the reason you're being encouraged to make out realizes a convert convert alcohols into good leading groups and money show you just on the kind of thing that often see people doing that this kind of right-thinking but very quickly goes in the wrong place so let's suppose that we wanted to substitute his alcohol on and make it easier had we do that and we substitute alcohol and making open drawing its for comments so we need to do that and maybe there's no 1 step away to do this shall show you I don't want you to do this and you'll be inclined to think that this is possible but I don't want to do is think of Hey I learned in classes that I can prove made out calls and they turn into good leading groups or others that a strong acid like sulfuric acid that converts out calls and Ohio docks only a minor ones like managed to a leading group until he did this which would have floating around some sort of OCS only a minor and then it is then maybe you could add some sort of up and I'm going to abbreviate this fan with pH and then maybe I could throw in some strong nuclear to displace the the leading group and that won't work many show you why this will not work Of this right no here the reason why the workers if you put Knox citing an iron or any outcome exciting and I'm any strong nuclear file it doesn't matter what the strong nuclear in the presence of sulfuric acid you're never going to prove make the alcohol any nucleophile it's nucleophilic enough to attack a carbon-oxygen bond is very rapidly going to displace and is very rapidly going too deep roaming the sulfuric acid and then you don't have sulfuric acid anymore
and you don't have any nuclear file you can't simply add acid and think the proton mistakenly Maine 2 months of street so in other words don't hope that you're going to get that Proton to stick on the substrate like this and then just wait around for a nucleophile maybe you think you'll be clever and Eolande sulfuric acid 1st In in late April May and walked over and bottle of nucleophile and dump in that won't work if you have an oxide and I'm floating around that you have for not citing an iron to an call that's been impregnated it's never going to attack problems it will always be more rapidly deep-rooted nature of this is what's going to happen so if you want to make an alcohol into a leading group don't try just dumping accident you sign your chloride and converted to a chloride or if you want to murder not Hollander leading use phosphorus try bromide and converted into a leading group so the right ways to do this kind of stuff like this I take my house call I use my money reactions final chloride has so Lucille too I always remember to put my purity basin on and then I clean the making of core and now I can't showing any nucleophile I want you get to pick what everyone American leaders oxide online if you want I think you guys are do yes into it's an oxide on islands in in lab not this week I think you doing crystallization this week now makes this nice new carbon oxygen bars so easy and
if you don't like chlorides then you can simply add PBR 3 certainly and then do the displacement with sodium OK so as far as you know now this is the reason to make alcohol because it allows you to make leading groups which control and whatever nuclear file you want but our at and that's not really what could be calculating light in chemistry is a secret reaction you're going to learn it at the start of 1051 super top secret that I'm going to show it to you now and I won't ask you anything because this is 51 the stuff but if you can remember this golden for can 51 C is the super-secret reaction from 1051 see what we're going to show you can take any helpful lied chlorides bromides and Idaho In amid lithium or magnesium to that lithium just store this in the back line after another quarter and soulfully valuable to you and what will happen is that the lithium metal replace the chloride and that is the most powerful nuclear file that we have in 51 as more powerful than our costs either a mine and I know how to live in the carbon lithium bond that I do here is so nucleophilic that were going to be able to use that to attack carbon levels this is All of 1051 seen nutshell don't tell anybody I told you from the intro and that's the best you can't quite tell because it is a bad job of drawing seal double bond but that right there is the best way of forming carbon-carbon bonds it is better than any other method which did you ever saw are more will see throughout this so this is why we're teaching you may help you chlorides you're going to forget about it you know I 51 C and so on just remind it's this ECU bond forming process that you're going to need you there now just can't of forget that are stored in the back of your mind but and this is why do you really need to know how Miguel folkloric and we're going to bring this back to him about 3 months and hit you with a very OK so I while item including moves are our calls and that I'm not a big fan of making out Clerides ineligible lines look is a huge fan of the sampling problems sets the pre-programmed in that I select from seem to be a huge fan that is my favorite leading group 1 that I love you "quotation mark possibly leading groups so if you want the best and easiest way To make leading groups of hydroxyl waiting to be taken out all of your choice and we were going to do is we're going to replace that H with With some special functional group that makes the carbon oxygen binding easy to displace the here's a reagent it's called tussle chloride and we used abbreviation Ts I see and over here you can see abbreviated tussle chloride for you toss corridors a benzene ring with a methyl group on 1 side that's called toluene and on the other side there's this sulfur meal the chloride a little bit like sulfuric acid it turns out that it's very easy for nuclear vows to attack sulfur and displays the chloride so when you treat an alcoholic colossal chloride and a base and the base we use Excuse me is purity so
this is kind of like vinyl chloride in that you had purity will have a lot of reactions use purity base that's why you're going to tend to forget what the fastest tribal mining accident right purity with Foster's try bromide enough to avoid doing that and so when you do that it now create something called the talks group the OTS that entire OTS is called the toss McGowan circle that just years you can see that this whole group top torso and oxygen is called a tosser and how label that has a better word tussling over here there is underlined so that the
toss leading group is now very easy to displace the carbon-oxygen bond what a fantastic leading group we have here and so I can end the nuclear file of my choice just for the sake of having someone will draw very small like sodium meth oxide that very easily do into reaction drostan heroes
here so we can see that as interior there's a mail Koksal animal displays that whole toss business is a fantastically group and usually I don't enjoy all the bond between oxygen and tonsillitis rate OTS but when it is complete ,comma charges here on the Stilian plus and oxygen willingness OK so you can use any nuclear file you want gee what a great way to make a bomb To make a leading group out of oxygen those good talk about the mechanism for this 2nd give you a sense for why this is superior to the final chloride or phosphorus try bromide for making leading groups of oxygen of hydroxyl so the mechanism this reaction you know I'll take my super simple proven all substrate involves the lone pairs on the hydroxyl group attacking from this sulfur new fluoride Leading Group so this this softening chloride sulfur stature he drove it mechanistic Lee that's not important but I just want you to have a sense that the shape of the molecule and so you can imagine the hydroxyl group this is a book mechanism on that I want you to know so you can imagine the hydroxyl group just coming in and doing a displacement that pops up 49 and there we formed an oxygen sulfur bond and hunger that I'm smart enough to draw all the sewage farm because I know I'm going to look that Proton often the next step and I had this very electron withdrawing on an abbreviated that toluene that benzene ring is tall it stands for Stanford tall you can get with the abbreviations just by looking over here to the the left of this now we have this oxygen at 3 bond that better have a positive charge that really wants to be the deep-rooted quickly and what we are to you is that were may seem weird to you is that cheeses chloride their outcome that chloride doesn't do some medicine to reaction and there's no way that's going to happen the period Dean is going to Seoul quickly the programming proton transfer reactions are always faster than reactions comparable reactions that form bonds to carbon it's another period is going to come back in here and deep-rooted mate that Proton and that's it that's how we put the tussle group on this hole this whole time thing is this whole contraption that I have detached here is my tonsils group possibly so this whole thing is a great leaving what's the magic behind this that makes it so much better why is this so much better than the final score because nowhere in this possibly business decorated carbon-oxygen about when you make a movie making out you chloride from alcohol using vinyl chloride yet to do innocent to react with chloride Nowhere in this in this in this bar mechanisms scheme that bring have to break that carbon-oxygen bonds to allows U.S. into reaction this into reactions are lousy Morrison to reactions you have to use to synthesize something the more chances it's going to fail where did you elimination of some kind so the fact that I can convert oxygen into a great leaving group without breaking the carbon-oxygen bond yet means that this is just plain superior to the spinal cord we so later work better in practice maybe when you're just drawn reactions on paper it doesn't matter what you'll find is that on I tend to favor making possibly leaving groups of professional and overcome warned later Chapter 1 and asking you how you synthesizers will not tender pick routes were possibly forming toss leaving groups this is the way to go OK also possibly minister right here because that's 1 your money reactions so remember this make tussling leaving groups in the toughening of an entire chapter to chapters of chloride and bromides could be hard created to steer away from them and get them Money OK so well I should be ways take alcohols and do chemistry with those you figure out calls to Chloride Inge alcohols the bromides you're out calls to toss late so what can you do it in the USA they're nowhere near as reactive but you can break carbon-oxygen bonds was eaters limit take example and there's a strategic thinking here here is an example of an ETA were 1 of the carbons tertiary and the other is primary and I like that distinction because those are hugely different I hate secondary I can never figure out whether its elimination and the substitution what's going on with those in the lab I avoid secondary substrates because the the molecules don't know what to do either so here's 2 years and the 3rd this is TB or methyl ether this carbons tertiary this province primarily so if anything is going to happen so let's suppose I had an accident prone made this he served this there's 2 different things that can happen 1 thing is that the tertiary carbon can pop off the oxygen of former cobbled Caroline stable the other thing that can happen here as the bromide canada Our
substituted this very unhindered carbon and an innocent type reaction without forming the kind in practice you'll see below so and if you had to equivalence of HBO are we'll get this through and 1 reaction and also the mechanism for imminent and you'll get this through innocent to reaction in other words you can clean both of the carbon-oxygen bonds for adding HBO because of stronger mechanism for this for how to think about this and the main thing I want to do is give you a sense for under typical reactions which carbon-oxygen bond breaks 1st under typical reaction conditions so you take HBO are Texas HBO are when you put it in here the 1st thing that's going to happen is that we're going to probe that oxygen HBO is a very powerful acid 3 bonds to oxygen and I wish I had run a bigger bond of more space here from dog but there's long pairs on this oxygen and they're going to pluck a proton off the acid because it's such a strong acid and I'll get this marks only a minor 1 oxygen with 3 bombs that oxygen wants to take its electrons and walk away that's the main thing that you wouldn't know right now there's no way you could notice I have I simply have to tell you otherwise you couldn't know is it under typical concentrations where you would run this reaction this is concentration dependence you got a choice either the bromide with its long years can come in and attacked the method or you could simply ionize out and the oxygen and it depends on the concentration of bromide if I have if I don't in sodium bromide and have 10 times the concentration of bromide bromide will attack them absolutely fantastic but under typical reaction conditions that's not fast enough under typical reaction conditions this bond simply Cleaves before bromide can attack that enough and you could not known that I simply had to tell you that this is Of the 2 possibilities this is the more likely to happen faster she generated generated TB will cobble cast iron 90 people cargo can In byproduct is methanol momentarily and so what happens now is that the bromide 89 that's floating around in there can come in and easily attack let me draw that bromide setting into that that pathetic looking cargo carried and that doesn't have an architect GM and now the about all that America can be prevented by the 2nd equivalent of HBO are so the this equation I showed up above I should to equivalents of HBO and now we simply reprogramming that and now the slower reaction this is not quite as easy and now the waters invoke a a decent enough Leading Group to wear His bromide Canal attack this very unhindered there's no hindrance with a methyl group what social using green areas to be consistent that bromide and I'm now displaced to make the methyl bromide so that's the the mechanism for the reaction it's not a very I would say that's a very interesting action on but we have to show you something you can do with the affairs with super-secret reagents that have involved involves similar mechanisms that are a little bit more efficient for click for cleaning beaches on the won't show you go riding in the lower divisions club something forever prepetition glasses far-right so the sleeping Cleveland you strong acids could provide oxygen make oxygen into a leading group but it's good with HBR NHI Hasbro 99 denied either so nucleophilic it's not quite as good as the CEO of members can't think that I've ever seen my personal focus strong acids including others especially if the tertiary and inform stable of but a huge shift in years now because I wanna talk about Anita that's that that's especially there and that's an epoxy the good and drawn a park site here and I want to admire the ring strain In the epoxy but 1 In all carbon-oxygen 2nd runs typically 150 got for bonds to them typically want 190 rebound angles and that approximates 60 degree barnacles 60 not 109 60 there is a lot of streaming here and that means that we can use nuclear files to a cleaver Parkside majority leaders in ways that we couldn't do any other kind of either social you are a typical I'm sort Our reaction sequence here and what I want you to do 1st is notes that unenumerated my steps and this is something you're going to have to learn how to do I'm going to throw in my nucleophile sodium on the sodium filing nuclear that any plus a C T minus or if you stop them together and did write the plus and minus that's OK so there's of violating an iron there that's a great nucleophile To weighing on equivalent that is based it will draw on a mechanism for this it will glad-handing open up that Parkside and then in step I have to prove maybe all that I generate and so I have to write a step to swim enumerating the step 1 step too if I leave out the 1 in the 2 the enumeration that's wrong I can't simply mix sodium effects you get a poor reaction Iverson was simply mix with sodium a stock citing an iron in the water it would not this good and I walked through the mechanism adjustment to see how made a sulfur carbon bonds and over here with the 0 minus sprung up the point of swamping out the town of water would work up adjustment you shake it with a bunch of water
as the property the online but this was when he dropped that a mechanism for this OK so again we're going to see this a lot this idea of working up reactions Water World Cup excess water and the reason is it's just very hard to isolate in irons and organic chemist always want to convert charged molecules into neutral molecules because then we can extract them and organic solvents so long worker means I was just trying to take all miners and converted into a neutral low-wage so you'll frequently see add water in a way that looks like a reagent I usually write workouts you know I'm simply trying to stick a proton 79 to get an but it's a good draw mechanistic Lee what's happening 1st it is nothing more than a simple lesson to reaction on an I a simple it works because of the rings training so here's my violate an and my file 89 comes in In attacks this very strange system and attacks on the least hindered saw just like all the other into to reactions that you've seen so far it attacks the least he side support if they were both equally hindered you'd probably get a mixture of attack on 1 side plots on the other side but was careful to pick something where the 2 sides are dramatically different in terms of steric hindrance so let's strain is what makes it work we popped this open and we have this all minus floating around and I don't have any good way isolate that in the lab so in the laboratory need to prove me that's why can extract it into an organic solvent and this is why used water it's kind of like the shatter liaise principle if we just had 1 equivalent of water In all ended the one-to-one mixture of hydroxide in iron and my Alcock side yet to use a ton of water to make sure you fully transfer all the protons over to the South outside in order to neutralize them and so the ends and result is either neutral organic molecule that I can isolate they can extracted from organic solvents and then evaporate all the solvent and often I go about pure molecule so that's the point of the work opposite on 1 end up stuck with this this sodium Alcock side trying to isolate the leader of sodium count right here it would be really hard to isolate in the lab on extremely easy nicely neutral organic molecules so there's all kinds of nuclear files that you can use like this to be lesson to reactions on the part that I could have used among dockside an iron I could use a few knocks 89 I could've used in a desire to unite and it's a nucleophile you forgot about them back from Chapter 7 arms sold Parkside have all this training built into them that allows you to to this 2 reactions on OK so let some money just remind you of the distinction between the Parkside witches leaders and typical he fears the ABC oxides socialists should be clear here about what the differences are and I'm going to try to jazz up 1 of these and methyl group his entire drawing the Singapore excited so we have all kinds of reactions were we construe in nuclear files 1 that that violate an iron Allcock citing hands there's just enough rings strain somebody but a lot of re-injuring 26 comes from all but all courtside lousy leaving groups there is just enough to bring strain to allow you to do this on a century action just enough and straight here the reason why didn't you can attack like this is because
of strained but if you had any less rain strains doesn't work anymore so in other words by the four-member ring doesn't work you can do attitude reaction on this kind of four-member bringing with with basically an ionic nucleophile so None of strains so you won't get a to within Alcott citing sold right now don't try to use on this matter there's not strained marriages saying you don't get any 2 a five-member and look at the four-member ring doesn't have enough restraint that of course a five-member doesn't have of French-trained the trade you just a regular a cycling like died at believes there is not enough for instance it's only a part sides that have enough for industry where you can use an ionic nucleophile like Alcock said or style family in order to meet in order to push those open it's just too hard and the other kind the nucleophile so it's the part sides are obviously very special fears and even more special than for memory OK let's say 1 strongly interest but these kinds of basic reaction conditions where the Allcock side irons and Diallo family in irons I those can open up oxides by by attacking the least tended but now that switch gears totally different universes went sides and acidic conditions this is going to be hard straight what is the matter of pop sides and basic conditions of Parkside acidic conditions makes all the difference in the world and I'll show you how there is how the results will differ here I'm going to take exactly the same apart said there should be before and this time I'm going to run reaction in the presence of sulfuric acid and alright catalytic here just so we can remember that the role that is as the catalyst and as you might guess the sulfuric acid is going to probe made the epoxy now I can't strolled with oxide iron in with sulfuric
acid if I throw my thoughts 9 it's simply the the sulfuric acid or simply broke made without citing but I control neutral methanol and I can use that as a solvent cheap solvent and now when we look at the result yes ,comma boxing group is going to attack the substrate let's take a look at the Regio chemistry here In this particular case and when user a color marker years she could see the new bonds that I won the most toxic but attacks had the more substituted position right in in the previous the example that I showed you it was totally expected only on nuclear follows all the time that morning vision and also man showing you that the nuclear file attacking and start with other tech less candid positions now I'm showing you that the nuclear attacked on the more ended positions worsened ,comma nuclear files for for these reactions of a park sites and acidic conditions they just a little listed the common nuclear files 1 would be to have water act a nucleophile where you replace bonds some carbon In other words would be just like I should you hear that alcohol act the nuclear file and then there was another example beating out HP are indeed job not so common with HCl but on the HBO on each I would become a nuclear power and no others were that age wouldn't appear and the bromide would end up there where they train and appearance and that the nucleophile and there buckling walking the mechanism because there's no way in the world on the planet each could guess this so the 1st deputy guests I'm going to abbreviate my acid with the symbol age and the 1st step I think you could guess it's simply that you prove me the epoxy and that converts the alcohol known to have good leading the wide Roberts when I draw this next intermediate purposely going to the store you can get an appreciation for what happens when you probably a strain the parts but I'm going to do them distorted he see that this bonds to the tertiary center is now elongated In a way you can kind of think of this bonds to the tertiary centers kind of pretty broken it's almost like it doesn't pop open and make a tertiary cargo but it's almost as this oxygen is walking away with its electrons already but so this the bond the tertiary centers now it's easier to break and that's what you couldn't have guessed and Saddam going to show you something that should be totally unexpected tea and that is that nuclear files like water like bromide ENI and anything that can can exist without being totally probably in sulfuric acid they don't attack with discharge on here they don't attack the less substituted position they attack at them or substitute positions so if you had some kind of rule in your head that all now you don't do Athens to attack a tertiary said yes you do in the case of strange three-member their positive charges you always attack substituted position so there is no rule that says you can never do anything to tertiary centers this is where you do 3 members reduced was a positive charge on 1 of the Adams in the ring and it's going to be hard to get away from the United 3 chapters telling you never do listen to on tertiary Center who cares so here the next intermediate without got this intermediate Proton sitting there on the nuclear file so let's get rid of history bonds to oxygen there has to be a positive charge on there I still got my A-minus left over from my acid floating around it's my symbol for sulfate online or anything that could that's got a lone parents solution that simply plugs the proton off and gives me my product Indiana OK so do you see how this is totally different from the most oxide under basic conditions with Australian I'm attacked at least 100 side but under acidic conditions I can't have a dark side I have to have methanol oxide would grab the provision of sulfuric acid so under acidic conditions you can't have an ionic nuclear followed thoughts I will simply probe methanol and that attacks at the more substituted position and goal with inversion of configuration it's not obvious what this particular substrate agenda getting inversion of configuration at that center on and that means it's stereos specific OK let me I'll just give you a quick heads up for something you're going to this is the last slide constantly the collection of drawings for institutions I just want you to see in 1 slide this summary of apartheid reactivity so that's good start off if I had any an ionic nucleophile under basic conditions those attack at the less substituted position but if I choose to use acidic conditions and I rely on the proclamation the my Parkside typically don't have proved an ionic nuclear files on litmus dockside yet neutral nuclear files and those attacks have the more substituted position so under basic conditions with my thoughts on things like that would have left the city position With acid catalyst like sulfuric acid you attack more substantive positions so that the important Solomon heroism excels Sony's OK you're going to see stuff like this again later In the next chapter get ready in Chapter 10 I'm going to show you this kind of idea again we're going to have species that you've never seen before cold-call Roney alliance Strange three-member brings where there's a charged added in there and what you're going to see in Chapter 10 is that nuclear files attacked those at the morgue the opposition In the next chapter I'm going to show you the same thing with br ammonium ions that is remembered friends and nucleophile will attack these at the more injured position so you can see the analogy for withdrawal made up oxides this weird thing called for only a minor this freaky thing called of ammonia lines these three-member brings especially and it's only 3 Member brings you attack at the or substituted positions Everything else is the same way you learned it wants their attendants and attacked the the lessons in position which is positive for this method for chapter ,comma Chapter 9 ,comma on Friday
Chapter 10 and you can learn a lot of reactions
Organische Verbindungen
Kohlenlagerstätte
Gangart <Erzlagerstätte>
Chemische Forschung
Stausee
Computeranimation
Chemische Struktur
Fluss
Mannose
Einzugsgebiet
Biskalcitratum
Vancomycin
Anilin
Chemieanlage
Funktionelle Gruppe
Leckage
Periodate
Single electron transfer
Alkohol
Oktanzahl
Wursthülle
VOC <Ökologische Chemie>
Reaktionsmechanismus
Wasser
Zündholzschachtel
Hydrophobe Wechselwirkung
Computeranimation
Doppelbindung
Internationaler Freiname
Fluss
Mannose
Einzugsgebiet
Reaktionsmechanismus
Chemische Bindung
Nebenprodukt
Säure
Verstümmelung
Molekül
Umweltchemikalie
Bromide
Hypobromite
Funktionelle Gruppe
Substrat <Chemie>
Phosphor
Krankengeschichte
Kohlenlagerstätte
Organische Verbindungen
Iod
Elektron <Legierung>
Fülle <Speise>
Holzkohle
Mastzelle
Halogenide
Lammfleisch
Ester
Chloridion
Base
Gekochter Schinken
Kohlenlagerstätte
Benzolring
Krankheit
Anilin
Chemieanlage
Enhancer
Periodate
Chemische Forschung
Hydroxylgruppe
Chloride
Chlorethene
Phosphin
Transformation <Genetik>
Seltenerdverbindungen
Chemische Forschung
Phosphonsäure
Chemische Verbindungen
Indigo
Phosphate
Phosphor
Landwirtschaft
Altern
Wasserfall
Eisenherstellung
Plantagenbesitzer
Teer
Chemieanlage
Funktionelle Gruppe
Gen
Präparative Chemie
Schweflige Säure
Einsames Elektronenpaar
Zigarre
Gangart <Erzlagerstätte>
Tank
Metamfetamin
Gelöster organischer Stoff
Konvertierung
Anomalie <Medizin>
Rubidiumiodid
Biskalcitratum
Vancomycin
Farbenindustrie
Lymphangiomyomatosis
Schwefeldioxid
Leckage
Singulettzustand
Chloride
Tau-Protein
Chemischer Prozess
Sauerstoffverbindungen
Biologisches Material
Chemische Forschung
Chloride
Lithiierung
Alkohol
Kohlenstofffaser
Chemische Forschung
Magnesium
Computeranimation
Doppelbindung
Bindungsenergie
Kristall
Mannose
Eisenherstellung
Chemische Bindung
Querprofil
Methylgruppe
Bromide
Funktionelle Gruppe
Funktionelle Gruppe
Substrat <Chemie>
Sulfur
Insel
Phosphor
Wasserstand
Fülle <Speise>
Schweflige Säure
Etomidat
Einzugsgebiet
Halogenide
Natrium
Tank
Base
Chloridion
Schälgang
Hydrophobe Wechselwirkung
Hydroxylierung
Protonierung
Base
Sekret
Oxide
Biskalcitratum
Vancomycin
Lithium
Benzolring
Tau-Protein
Chemischer Prozess
Sauerstoffverbindungen
Chlorethene
Verschleiß
Besprechung/Interview
Isotopenmarkierung
Base
Natrium
Metamfetamin
Computeranimation
Oxide
Chemische Bindung
Vancomycin
Verstümmelung
Funktionelle Gruppe
Bromide
Einzelmolekülspektroskopie
Funktionelle Gruppe
Haoma
Sauerstoffverbindungen
Veretherung
Methylbromid
Mil
Alkohol
Oktanzahl
Reaktionsmechanismus
Konzentrat
Wasser
Arzneimittel
Computeranimation
Toluol
Geröll
Mannose
Sense
Reaktionsmechanismus
Sterische Hinderung
Chemische Bindung
Wildbach
Nebenprodukt
Säure
Verstümmelung
Methylgruppe
Alkoholgehalt
Molekül
Bromide
Ether
Einzelmolekülspektroskopie
Funktionelle Gruppe
Sulfur
Substrat <Chemie>
Phosphor
Kalbfleisch
Epoxidharz
Medroxyprogesteron
Hydroxylierung
Auxine
Protonierung
Base
Zinnerz
Krankheit
Ermüdung bei hohen Lastspielzahlen
Zellteilung
Periodate
Hydroxylgruppe
Chemische Forschung
Chloride
Mischanlage
Chlorethene
Kohlenstofffaser
Labkäse
Stockfisch
Destillateur
Eisenherstellung
Photosynthese
Natriumbromid
Alkane
Sekundärstruktur
Elektronentransfer
Linker
Abführmittel
En-Synthese
Funktionelle Gruppe
Aktives Zentrum
Sis
Click-Chemie
Einsames Elektronenpaar
Querprofil
Setzen <Verfahrenstechnik>
Ringspannung
Gangart <Erzlagerstätte>
Natrium
Eliminierungsreaktion <alpha->
Krankheit
CHARGE-Assoziation
Biskalcitratum
Grauguss
Oktanzahl
Vancomycin
Dimethylether
Fluoride
Sauerstoffverbindungen
Mineralbildung
Mischgut
Hydroxide
Wasser
Öl
Computeranimation
Calcineurin
Mannose
Eisenherstellung
Sterische Hinderung
Reaktionsmechanismus
Methylgruppe
Molekül
Funktionelle Gruppe
Systemische Therapie <Pharmakologie>
Erholung
Homocystein
Organische Verbindungen
Neutralisation <Chemie>
Lösungsmittel
Mastzelle
Strandsee
Oxidschicht
Aluminiumsalze
Kernreaktionsanalyse
Ringspannung
MO-Theorie
Natrium
Einschluss
Protonierung
Krankheit
Base
Elektronische Zigarette
Chemische Eigenschaft
Anomalie <Medizin>
Biskalcitratum
Mischen
Neprilysin
Vancomycin
Oxidschicht
Gensonde
Alkohol
Memory-Effekt
Wursthülle
Wasser
Peroxyacetylnitrat
Computeranimation
Calcineurin
Spezies <Chemie>
Mannose
Reaktionsmechanismus
Chemische Bindung
Ionenbindung
Säure
Verstümmelung
Amine <primär->
Sulfate
Lactitol
Bromide
Kohlenstoffatom
Krankengeschichte
Fleischersatz
Elektron <Legierung>
Fülle <Speise>
Symptomatologie
Mastzelle
Oxidschicht
Reaktivität
Wachs
Epoxidharz
Base
Auxine
Protonierung
Base
Marker
Mannose
Abflussmenge
Krankheit
Blei-208
Chemische Forschung
ISO-Komplex-Heilweise
Kohlenstofffaser
Ammoniumverbindungen
Disposition <Medizin>
Ente Nazionale Idrocarburi
Lösung
Altern
Ammoniak
Eisenherstellung
Glykosaminoglykane
Exsudat
Sekundärstruktur
Sammler <Technik>
Funktionelle Gruppe
Aktives Zentrum
Schweflige Säure
Einsames Elektronenpaar
Quellgebiet
Gangart <Erzlagerstätte>
Ringspannung
Tank
Ausgangsgestein
Erdrutsch
Krankheit
Säure
Tee
Schwefel
Oxide
Methanol
Anomalie <Medizin>
Biskalcitratum
Vancomycin
Farbenindustrie
Lymphangiomyomatosis
Tee
Chemischer Prozess
Sauerstoffverbindungen

Metadaten

Formale Metadaten

Titel Lecture 05. Alcohols, Ethers, and Epoxides Part 4.
Serientitel Chemistry 51B: Organic Chemistry
Teil 05
Anzahl der Teile 26
Autor Vranken, David Van
Lizenz CC-Namensnennung 3.0 Unported:
Sie dürfen das Werk bzw. den Inhalt zu jedem legalen 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.
DOI 10.5446/19474
Herausgeber University of California Irvine (UCI)
Erscheinungsjahr 2013
Sprache Englisch

Technische Metadaten

Dauer 44:28

Inhaltliche Metadaten

Fachgebiet Chemie
Abstract UCI Chem 51B Organic Chemistry (Winter 2013) Lec 05. Organic Chemistry -- Alcohols, Ethers, and Epoxides -- Part 4 Instructor: David Van Vranken, Ph.D. Description: This is the second quarter of the organic chemistry series. Topics covered include: Fundamental concepts relating to carbon compounds with emphasis on structural theory and the nature of chemical bonding, stereochemistry, reaction mechanisms, and spectroscopic, physical, and chemical properties of the principal classes of carbon compounds. This video is part of a 26-lecture undergraduate-level course titled "Organic Chemistry" taught at UC Irvine by Professor David Van Vranken. Index of Topics: 00:18- Chemical leak into river puts focus on plant 00:53- Structure of Aniline 02:35- 9.12A: SN2 conversion of R-OH to R-Cl with SOCl2 4:03- 9.12B: SN2 conversion of R-OH to R-Br with PBr3 08:51- 9.12C: Why make alkyl halides? 14:57- 9.13: Convert R-O-H to R-O-Ts 22:16- 9.14: Reactions with Ethers with Hl and HBr 28:29- 9.15A: SN2 Reactions of Epoxides Under Basic Conditions 33:29- 9.15A: Reactions of Epoxides Under Basic Conditions 36:00- 9.15B: SN2 Reactions of Epoxides Under Acidic Conditions 41:46- 9.15B: 3-Membreed ring "onium" ions = strange regioselectivity

Zugehöriges Material

Ähnliche Filme

Loading...