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Lecture 04. Alcohols, Ethers, and Epoxides Part 3

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Lecture 04. Alcohols, Ethers, and Epoxides Part 3
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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: 00:17- OLED TV 01:38- OLED explained 03:34- 9.8: E1 Dehydration of tertiary Alcohols via Carbocations 07:00- 9.8: E1 Dehydration of secondary Alcohols via Carbocations 10:28- 9.9: Carbocations rearrange through 1,2 shifts 18:38- 9.9: 1,2 shifts make challenging test questions 26:09- 9.10: Dehydration with POCl3/pyridine 33:35- 9.11: SN1 conversion of tertiary R-OH to tertiary R-X 40:00- 9.11: SN2 conversion of primary R-OH to primary R-Cl with ZnCl2 45:29- 9.12A: Sn2 conversion of R-OH to R-Cl with SOCl2
power mixture organizations Prolin Hausmannit firm man Paste van Computer animation Experiment indoor Inneren screening Filter
bond Sulfate mechanism LSD aluminium potential chemical man molecule age Magnetometer Eliminierungsreaktionen type mixture organizations green concentration Maische Katalase proton chemische Reaktion alcohols end lone pairs van Säuren Computer animation blue function Iron chemical structures Dehydration oxygen stuff
hydrides left Sulfate mechanism hydroxyl groups Salzsäure chloride case man molecule islands age Magnetometer Meeting/Interview temperatures important control localization sulfuric acid Eliminierungsreaktionen Medroxyprogesterone Monoaminoxidase Spektroelektrochemie areas Bromwasserstoffsäure Bromide Double bond ozone Foul Topic carbon valine complexes chemische Reaktion alcohols end water van Drops conditions meso coupling chemical structures substrates Dehydration den sequence
Index Sulfate set molecule hard electron firing Insulin transformations Eliminierungsreaktionen Geröll hydrides steps valine Katalase chemische Reaktion alcohols variety stability firm lone pairs van Säuren coupling compounds migration old penetrative Hab oxygen History form stuff sequence sense bond mechanism hydroxyl groups case conservation methyl man age Magnetometer sulfuric acid parents report level mixture type progress rearrangement carbon Adamantane proton water Wasserstoff Computer animation Iron chemical structures Zigarre den
Index Phosphorsäureester Dehydration phosphorus Aspartate transaminase chloride Salzsäure chlorine electron Coke (fuel) Eliminierungsreaktionen period organizations hydrides Double bond rates steps Foul Katalase chemische Reaktion complexes alcohols van Säuren match coupling Gamma PoC By-product migration oxygen stuff bond Kohlenstoff-14 drug mechanism hydroxyl groups case methyl man Magnetometer important sulfuric acid parents mixture processes oxidation chemical formulae type areas probe nitrogen multiple rearrangement carbon Ethylen-Vinylacetat-Copolymere Adamantane proton hard Combining Drops conditions function Iron chemical structures Dehydration substrates basic den
Index transition metal Sulfate Bohr chloride chlorine Calcium hydroxide solutions chemical molecule enzymes electron conversions benzene rings transformations Eliminierungsreaktionen core Chlorethene oil Double bond alkyl Topic chemische Reaktion solutions alcohols variety firm lone pairs van Säuren Iodide Zink Optische Untersuchungen Gamma Sekundärionen-Massenspektrometrie By-product Alu element oxygen form bottles sequence stuff bond Candy species activities mechanism ZnCl2 HCl hydroxyl groups Lewisite Propionaldehyd man originators specific Chlorkohlenwasserstoffe Magnetometer Common sulfuric acid sore Einschlüssen processes main-group elements metals type probe Alkyl Groups Arginine Bromide Stickstofffixierung carbon proton charge Wasserstoff Combining Computer animation function chemical structures alkali
Digital elevation model Converter Graukäse Bohr secret media chloride Stöße case solutions man electron Eliminierungsreaktionen period processes vinyl sulfur Katalase proton chemische Reaktion end Combining van conditions Computer animation function Sulfite Gamma Iron chemical structures Carboxylierung oxygen den Converter label
every time I have been using it seemed to see some article police in the past week of something called the Consumer Electronics Show on and guess this is 1 of the 2
kinds of devices that they were showing at the CES ,comma and and you're going to see a lot more of this technology is changing this year's things won't be the same anymore so I think a lot of you have heard of this this idea of all LED I mentioned before that many of you have cell phones be Samsung cellphone that a mole ED active-matrix organic light-emitting diode that strict this term right here so but in the future and I'm not sure how far in the future the this is 2 years 3 years instead of having a projector screen like this and a light in the back the the projectors of bright light in the filter the light to make these pictures in future there won't be a projector just be a paper-thin screen here and all the light will come from this screen this will be the source of light there will be any projector in the back with meager shadow like this on and all of that has to do with this idea of organic light-emitting diode arms and sewage is starting to see your new displays the Super Duper thin not quite paper retrieved on clothes and that's all organic chemistry that is making that possible so if you look at the future displays the going to power your television sets the computer monitors yourself owns
this is only possible by organic chemistry so at the same time that making display center what organic chemistry does is it allows you to have flexible displays that can now be bank without breaking not going to have to worry about having a super hard cover for for your iPhone because there's no worry about organic displays shattering online so again that the future of super-thin displays is already here on the future of dependable fast greens on that's already here and it's made possible by organic molecules mention this terrible LED every time I heard the word all LED this is stuff we're teaching you how to do in class the idea behind them organic light-emitting diode take a certain class of organic molecules and you expose them to an electrical potential they start to emit light and these are some of the game-changing types of organic molecules that made by the Red Army green or blue light you can modulate the wavelength by changing the structure of the molecules and I would say this may look a little bit strange every reading in here that's too expensive for for general use right now on but aluminum this is already being used in the displays in yourself in the super-thin TVs more recently people have you moved to polymers and by the end of this quarter we're already going to be able to make things like this to synthesize things like this and particularly by the end of next scoring and 51 C and you just need to get out of here and go do that will make a billion dollars and b the people driving the next generations of display and the next generations of technology and so every time you use your cell phone that's organic chemistry of going to bat for for you the right to pick up
where we left off we left off talking about the 1 dehydration and of tertiary alcohols and I think a lot of people were confused me see if I can find a 10 years so that I can rewrite this stuff on some people out of the there was some confusion over there the way that I drew the molecules that once they start drawing all the hydrogen atoms on the becomes obvious as to what's going on I'm going to take this mechanism that showed you last Friday before left and I'm going to redraw just slightly more clean way and what I showed you with this reaction where and this time I'm going to draw this season the ages for you so you expose an alcohol like this tertiary alcohol CNN just redrawing what I did on Friday hopefully you've already got this in your notes and you expose that 2 a catalytic amount of strong acids usually you know it's catalytic use higher concentrations you can probably make that alcohol and turn it into a good leading group I'm not sure that that's the best way to turn an alcohol into a good leading group but it's certainly a very cheap inexpensive way in the laboratory and so now you you conceded that alcohol as a positive charge OH 2 plus it's synopsis only minor knocks only means oxygen 3 violence that's now the leading and that will leave and so once this that this group pops out here like this it will leave a cobbled cat and when I showed you this mechanism on Friday I did something kind of arms I did something kind of tricky by not drawing on all the hydrogen atoms was just using lines structures so this structure that I do at the bottom where a kindly just throughout the siege for you in line structure looks like this of distraught is equivalent to so I don't draw the pages of the seas for you you might not see that there's an H and actors ages dangling all over this thing and those ages can be deeper made so if I have the counter Orion from my ass and still floating around and it's got its lone pairs of it's not very nucleophilic like sulfate and iron instead of attacking the cotton what you can have is that this thing pulls off a proton and gives you and 1 elimination reactions so in lecture bent the bonds a little bit and I was drawing this season ages for you but had many people come to me and asked what was going on with that I I couldn't always was going on to be a redrawing of all this season the Gators you can see that that we you treat alcohols especially tertiary alcohols armed with acids you get 1 elimination mechanism because tertiary alcohols are so
good at forming cobbled get that wasn't section thousand and just redrawing what I do for you on Friday to clarify that on the case I that complex on a console itself and that's tertiary alcohols tertiary apples from tertiary cobbled can and that's so easy to form tertiary purple Catherine's will love that there's something that's not quite so good that possible it's possible to do that was secondary alcohol and so stridently draw this scenario where instead of having the tertiary alcohol and that a 2nd area images to all the other thing it's attached to this car the cardinal carbon all show that there's a need there so that if I can get that hydroxyl group to leave it's just going to be a secondary cargo can and that's not going to be very easy and it's not going to be very good but you can do it so by treat this alcohol the secondary alcohol with the same reagent that I used before to the church aerial call you can't just let this sit at room temperature yet to heed this is the conditions I found in the literature 150 degrees Celsius unit to remember that I just want you to see that no secondary alcohols calls yet to be on notice to make cargo can that's nothing like so don't you enough have to remember the temperature for that but the book pretends secondary to the same because they don't show that the conditions and I just want to make it clear that anything that requires you to form a cobbled Karin like this I'm not going to draw the mechanism for you that that cover just awful secondary Carvel so ultimately the elimination product that you get out of this will not have a CCW wanted them now and I want to emphasize through the importance of you seeing the hydrogen atoms that we don't draw wise it's so important for you to see the hydrogen atoms that we don't drop so this is the same molecule it is if I eliminated the double bond up above that's the same thing is as this and is reoriented the Markle these are equivalent to each other so the here that we could well many and this is what you don't see if you're not yet practiced in the what we've done is not just create a CC double bomb the important part of this mechanism is that we also removed a if you can see that it's going to burn you later when we get a new chapter 51 seats and so I feel like I'm really harping on this idea that you need to practice on taking line-drawing structures and adding all the ages and because a large fraction of the time those ages are important for the mechanism so we believe it is off the topic at this this structure over here if you pull wages on offer at the bottom of the structure over here on the left and also the same companies rotate the molecule in those identical no human on the planet Earth in the indeed end in there is no ability to distinguish these 2 structures OK so you can duly won eliminations of secondary alcohols the sulfuric acid and you don't use hydrochloric acid a hydrobromic acid because those chloride bromide and alliance floating on those are good nuclear files sulfuric acid because the sulfate 9 is not a good nucleophile on so that's the recipe you need to know for for dehydration reactions for this the 1 reaction and again secondary locals take some hits and heating to make those were not good reactions I don't ever want you to think that secondary couple that islands that would really depressed if you walked away thinking of any time we talk about herbal canines on there is a real lack of control and the lack of control comes from the fact that you can get out shit only just remind you that this is something that you learned about arms Back in Chapter 7 18 and this is just a reminder that those things can occur so we don't substrate this is about the simplest substrate that can undergo a super facile but how people shift so this is a secondary out all it's going to create a very unstable and unhappy couple can I know if I can somehow make the hydroxyl group leave so they take this secondary alcohol and I expose it to sulfuric acid the sulfuric acid and you would have to heed this otherwise it wouldn't work very well and I'm just showing you the temperatures you go Wow 150 degrees that's that's way hotter than boiling water just to reinforce the idea that secondary couple can and do not very good so products that you get out of this reaction look like this the Carter years 1 product and that carbon skeleton is rearranged their that's not the same carbon skeleton news the other products also has a different carbon skeletons so the products
of this reaction on both result from some sort of
a rearrangement has occurred there maybe it looks kind of old that's easy until you sit down and try to figure out what happened in the case was good walk through the mechanism for this reaction just understand that on what's going on of these rearrangements this walked through the mechanism of lot of an ionization reaction that creates an unstable cobble can and I'm not going to show the proclamation of the alcohol just because I want to conserve time and space here I hope that you can draw some mechanism where use the lone pairs on hydroxyl to grab a proton office of the acid that's up to you to go that so this mounted the alcohol to of 1 of those long there's grabs a proton off the sulfuric acid In fire well actually 1 a destroyed it so easy interview that watch this up a notice on depicting at his age I'm not going to drop the entire structure of sulfate an iron on Aero pushing mechanisms I encourage you to use that symbol instead of drawing on acid catalysts so in this oxygen years 3 bonds so it has to have a positive charge we call that not Sony Online of oxygen as 3 bonds there will be a positive charge on and I hope when you see the positive charge an oxygen thinking wasn't very happy the public was act as a leading so to make it actively knew that oxygen skin walk away so it gets the electrons all to itself trade generates waters of leaving you know this is not an easy reaction this step right here is exactly why you have to read it because it's not easy to form secondary Carvel Caroline's not all that secondary couple catalyze the works like this now been whenever I draw cobbled that I'm doing this notice this I take the the time to draw all the things that are attached to the Carbol Caroline Center but there an age there and it's plain as day it's plain as the nose on my face I'm going to drop the decide don't forget adjusting case I needed some time in the mechanism and you don't have to do this century the book doesn't always joy everything attached to the car kind centers but there's a chiropractor and center during underdog on it right now and I always say that there's hydrogen there I'd Raul the hydrogen attached to cover pan and it just reminds me of whether the couple Carolina's primary secondary and tertiary OK secondary cargo can hands so unstable images write this down here secondary couple Cameron it is very fast if you can reduce some hydride or Elk Hills shift to convert a secondary coverage can I'm into a tertiary 1 it will be very very so let's draw that that migration the action there is a very fast migration which 1 of these 3 methyl groups and it doesn't matter which 1 you pick the identical can migrate over Clinton's move over and attach itself to the cargo can find center and when it does that it will create a much more stable and let me draw the ancients we can see that it's still there the move anywhere in I don't have to draw that H but I want to make sure we don't miss it so now it's his other carbon that's lacking in knocked of electrons now there's a tertiary level Caroline and that is definitely a fast car apparently arrangement if you were trying to rearrange a secondary Cobol can to another secondary couple can cut wouldn't be fast at all the fact that would never draw it's when secondary cover parents can rearrange to tertiary those are the fast rearrangements in a case tonight I so in theory you could migrate the methyl group that destroy this tiny little arrow here wants to be but whatever do indicate that in theory it's reversible but you don't want to go from tertiary secondary that's just not summit in Immokalee favorable it's not fast so maybe if you could somehow drawl that the size of an Adam the reversible error than it would be more appropriate OK so the report says whenever you have secondary couple parents the commuter institution would last OK once you've done this and once when she made history Shergar covered chemical valuable it is that I took the time to draw that and if I didn't try out this might be impossible for you to see but I expect you to see every H on every 1 of these Mount line-drawing molecules because you never know when you're going to need those ages watch this but the that each day now I can see how I could easily pull that Proton off in order to give me the more substitutable and generally more substitute films are favored in on the 1 elimination reactions OK so there's another alternative here I'm going to redraw the Seine the same intermediate just so we can draw a 2nd type of mechanism and I won't have a thousand arrows on this 1 mechanism here so there's another way we could eliminate and the other way we could eliminate requires us to see that there are also here and if you're not good at seeing those ages you won't see that there's another way to eliminate so I come in with my counter I'm from sulfuric acid on which abbreviated A-minus now I can eliminate like this and that's what leads to sell the product of the reaction so is to different products the elimination near the major 1 is going to be the 1 that's more substituted on but you can see the impact of Cobble can rearrangement whenever you see herbal parents and especially secondary couple cat eyes but you need to really watch out for what about primary covered forget I'm not going to do anything with you this quarter that leads to a primary couple character doesn't make any sense as far as stability but yet heed to 150 degrees to get a secondary couple Carolina formed amending now how ridiculously an almost impossible it is to generate a primary covered I have seen the book show nonsense like that it just doesn't make any sense I'm not sure why titled slightest 1 2 ships make challenging test questions in winter to galvanize you to pay attention because of that I'm not saying I'm going to put this on the exam but it's the kind of stuff that you'll see on every exam come because it's hard it's 1 of these things where on drawl the hydrogen is and see where they all are located yet it is not yet
known it was it is a but wait the mind of this wait is Saigon to price the prime minister so this data about little symbol up above here that's so that's been secondary with in the lingo secondary not to cry so this is a secondary couple can this is a tertiary Cavalcanti can and these 2 radio the same these the just the same outages we do it again because I did not put extra heroes on this structure I thought about all the arrows on this 1 molecule a little it would get too confusing so I just read through I just redrew the molecule assistance yeah I journalism major progress in this case you'd ever mixture that's close enough to where you see boasts 1 of the slightly Major so usually so I hate that kind of ambiguity and I know that in the book The last few questions like How was I supposed to know I should draw the line of products all usually make the question clear draw all the products you expect the following reactions or I might say draw the May if I know that there might be a mature to products Allstate draw all the major product of the following transformation as a general rule that I want to follow the questions in on problem sets or you know on my
exams if I draw some sort of a reaction out like this and a drop box What do I want to draw on the box I'm on duty out where all of the carbon atoms it up in the product so in other words the product of this reaction might be some sort of innocent 1 process there's also the HCl but I just wanna see where the carbon atoms and up unless I specifically asked you about in organic things that don't contain carbon you don't have to draw that in the box I just want you to show me where these carbon atoms not not not the 2nd proton her that organic ions and stuff like that so I'm trying you to get you to show me where these Adams and of the OMB the carbon atoms because this is an organic chemistry class and so if I if I think there's going to be multiple products I'll usually try to clarify that if I have reasonably that you'll get an equal mixture of 2 are then I'd expect you to draw it I usually class will tell you all you always get 2 things out of this OK so let's Karen rearrangements and keep drawing use of these cargo is an example of once again where I can see that this thing has no choice but to form a secondary cobbled that so they're using my acid for elimination again if I want to do an elimination match and don't use HBO are a irate CEO because he lied minder nuclear files I don't want any nucleophilic attack going on here so the product of this reaction former SEC double bond but it's not even in the same places where the leading group was what's essential here what is it that would make this easy for you to see what's going on well what will make this easy for you to see what's going on is that you know all there's a hydrogen atom here and suddenly there's 2 hydrogen atoms right if you can see those hydrogen atoms if you're not instantaneous and seeing the locations of the hydrogen atoms you're going to miss that will have to somehow get a proton on them the other thing that's important as there used to be a hydrogen atom here and it's no longer there you have an instant clue if you're good at seeing hydrogen atoms yet against include what happened while the hydrogen atoms that used to be here maybe it migrated and something like that my village so that's why it's important to see them on the locations and how many hydrogen atoms of there are win because we're not going to draw them for you anymore with these lines structures we don't do that for you anymore but it's only going draw the cargo can begin on not going to take the time to draw this whole mechanism .period let me draw this couple Caroline intermediate that you again use the couple and I'm going to draw in this on all drawing the hydrogen atom of joining Green just remind you that that's not drawn for you there's that hydrogen atom over there at that tertiary center that really angry and frustrated secondary coke and iron detailing life and wishing he wasn't secondary but so now this hydride just migrate over this Hydeville group can migrate over In can and satisfy the secondary cargo Caroline but leave behind a tertiary it is and I'm going to draw 1 of the hydrogen atoms was already here there was already a hydrogen atom and here's the 1 who migrated overall drawing green and use my tertiary Cobol can and again if you're not good at seeing the locations of the hydrogen and you're going to be stuck solely on abroad for years the other hydrogen atoms we need to know that that's there because the last that this mechanism involves plucking that Proton off To so come along with my symbolic A-minus yeah and I'll simply pull that Proton off to make a double bond so what's the importance of this problem it's once again remind you that when you make unstable secondary ,comma parents to look for for rearrangements and it's to show you the importance of seeing hydrogen atoms line drawn for you the assumption again and very soon I'm going to stop harping on this and just expect you to be fast and good at this it seemed the locations of and nothing short of working lots and lots of problems will help you had the experience and that you need to be fast overseeing those types of deep-rooted nations and hydride migration OK so don't tell you eliminate alcohols without getting secondary Koble constantly arrangement for the secret reagents that I'm going to show you but that allows you to eliminate all calls upon without getting on these kinds of complex rearrangements it's called Foster's Oxy chloride PUC all 3 and you always use it in conjunction with on period leading is a based going to draw the chemical structural rigor in the corner for phosphorus Oxy chloride areas misfired firearms to phosphorus don't freak out about the 5 bonds to the phosphorus is not a 2nd row added 2nd row and can only have 4 bonds but when she dropped to the 3rd role for overthrow unified bonds a is many things you can fit in some cases on do you know this is a phosphorus wide oxidation status by prosperous Indian OK so I I don't actually call the thereby make a mistake in using normal organic lingo forgive me but I call them most organic Enniskillen cockle 3 just as it considers a phosphorus article OK so let's see how users and I'm going to draw 1 structure in the middle and insurance going left and right from the start in the middle of my page here and I'll drawl a secondary alcohol that is just fine for some kind of rearrangement of people to methyl groups here and there we go so I warmed up secondary cattle lickety-split I'm going to have 1 of those methyl groups migrate over and How can we avoid that so In other words if we go back to .period are standard the 1 elimination formula dehydration we call it worries catalytic acid in this case you get to see this of trade heat here just to remind myself that she said that would take some heat when he formed a couple can I just showed you to cases where things can migrate over so 1 of these 2 methyl groups would migrate over and I'm not going to draw that mechanism for you now manager 1 of the methyl groups where it was before the other methyl group drawn have migrated over and end up with the more stable double what so that in this mechanism involves a 1 to shift and I'm not going to draw that up for you but suppose you wanted to eliminate over here to go to the loo ,comma right hand side what
could you do about that this is where you can use this this region combination of POC L-3 again I call that part 3 years Boston sexy chloride when you include period base if you can't remember appeared in his you don't really need to draw out the structure purity we'll see is used as a weak base later in the rest that's period Over here in the corner there's a long-term nitrogen and it's good for plucking not protons so in this particular case POC 3 will efficiently eliminate without generating any kind of cargo can and mechanistic way what's going on Is it this reaction over here on this side and all 1 reactions Koble Caroline's this reaction over here with losses of the quite avoids Koble care information the elimination is need to reaction so let's talk about what's going on with With Foster's article replied OK so that the mechanism for this reaction I'm not going to draw the whole mechanism for him and you don't need to know the truth the mechanism for how you do this but hydroxyl groups nuclear files in this phosphorus adamant Foster's article writers and electrified Legrottaglie will attack the phosphorus and substitute out 1 of the chlorides so let me draw out this this new group we have here which turned out to be a very good leaving where phosphorus is now has all these little negative Adams attached to it but that phosphorus Is that collector of chlorides electronic chloride elected into oxygen it's really going to stabilize and 0 minus if that oxygen can just walk away so this is a very special Leading Group not just write that year this whole Bosphorus with the 2 oxygen and so on it is a good leaving group it is not such a good Leading group but it can just walk away and leave a secondary couple cat it was very carefully chosen not chosen but it was screened on to show that as long you don't this thing of this thing will never walk away the single this P. this this phosphates this coral phosphate ester will never does walk away to leave a cargo carrier and its cargo parents lead to rearrangements like this so you don't have to worry about that happening as just slow don't worry about that that's why we used Foster's Oxy chloride an impurity so under these conditions yeah this time said because purity in his astronomer face would there used to be in a chair on this oxygen purity has a strong hold on to form an OC Sonia mining plus the period will remove that that Proton there but it would it's it's not an issue I mean it that would be so easy to the probe made it would not last a zillion but the 2nd before appearing poised on a lot of purity and is therefore this steps that lead to elimination so this is a need to elimination it's need to elimination here's where the appeared in real Cortinas already removed 1 proton here is where the parity really comes into play it induces the Tuolumne so that's why the Puritan there mainly and so that leads directly to the this is 1 step here that leads directly to the 2 elimination from so again there's no cargo Karen rearrangements because there's no cargo contracts this PO sealed 3 to whatever yes they used to be there are not going to walk through the mechanism you lose here's what you lose you lose this and you lose this and there's a byproduct here that's HCl it's essentially I'm not going to draw the whole mechanism for that because the book gives you an increase mechanism for showing them so you don't have to know the mechanism by which the OH goes to make that oral phosphate ester use need to know that they're going to go to a quarrel fast enough to know the mechanism the important point is this is a need to elimination mechanism and that's why you want to cobble can arrangements and that's what I want you to remember what you remember that you can use this combination to eliminate all calls without getting Carbon Canyon for your freedom to look at what rate they show a mechanism for that I will never ask you that they they show innocent you reaction that's not that that's wonderful if you learn that will fall you later OK so use POC all 3 impurities if you want to eliminate all calls and not out on nite of cargo-carrying arrangements you sulfuric acid if you want something desperately cheap on they don't care about the cost will mainly it's if I ask you I would use it if I want something that's I use sulfuric acid OK let's go back to Haiti lights Chapter 7 and 8 were all about realize how cool he lied to substrates for cargo Carolina formation alkyl the Alliance for 1 innocent 2 reactions and you can make out of the alliance from our calls for example using as and reactions if you take tertiary alcohols and exposes to sulfuric acid I'll get elimination you don't get to choose any kind of acid on the planet if I use another strong acid hydrochloric acid I won't get elimination substitution and here's the difference between HCL and sulfuric acid chloride in irons are good nuclear files sulfate in irons or not so the product of this because chlorine is a that nuclear power is not elimination it's substitution this is nothing more than a run-of-the-mill ISN 1 reaction but it kind of shows you an example of if you prune made out calls you can convert them into believing slip struck the
mechanism here this lone pairs on the alcohol and just like what the sulfuric acid you can't approach mate now use the symbol here then I won't know that there's a chloride I'm floating around so I'm not going to symbolize my answer the just because I want to remember that holders of chloride online including all around in my solution so here is my heart so the oxygen 3 bonds therefore it must have a positive charge and I hope you're not happy when you see oxygen with positive charges it's not a happy situation there's a chloride a nine-foot accuses astronomers chloride and there's the chloride and I'm just waiting to do something yet candy probably 1 of the protons and go backwards but that's totally not interesting that's what must allow the oxygen that is the leading group it's really angry at sharing its electrons and I generated tertiary can and there's all kinds of data hydrogen floating around but because there's chloride floating around in chloride is nucleophilic just like bromide and iodide so this would also you also get as 1 reactions with broad HBR job it's another chloride attacks and this didn't happen with sulfuric acid because the sulfate count is not a good nucleophile core so this is how you get an to redraw the product that's the spinal productivity through OK so again it's the same with Allah be drawn example with HBO are just you can see that these reactions are different from sulfuric acid so they take a tertiary alcohol In a treaty with HBO are going to substitute the alcohol if a sulfuric acid or getting out even if I use hydrology answered on hold get substitution of the hydroxy group realize pH means a fennel group so long as you're going to find me doing this a lot more calls fennel we're going to have an entire chapter chapters on Chapter 18 actually Chapter 17 we're going to talk about the chemistry of benzene rings so don't worry about the structure that fellow group right now I'm just trying to abbreviated make things fit in there and this tertiary are called work in the same way and this is just to show you look HBO are HCl HIV seemed totally different from sulfuric acid which doesn't have a nucleophilic country so in other words when he wanted to an elimination make a double bond don't use HCL and HBO are not in danger you can move mention a little point in the bottom that you could do these reactions with secondary all calls on but you're going to get all these shifts going on and I don't wanna show an example it as more much more cargo can find 1 2 shifts because I typically would go on about 100 run reactions that would give me those kinds of Siberia yet to use hear the word of yes to the question is if you what would you rather use your HCl rated depends on the product that I want on undervalues the higher died at the tertiary alkali died is so sensitive but I it's hard work within the last pops off to get public and so easily that when you try to concentrate your seat folded directions to decomposing because tertiary alkali Dieter so sensitive topic at the that I wanted 1 that's the that's stable enough for me to do high-temperature reactions and go with the chloride because sometimes you going to heed that in some other reaction and you don't want the courts to just about cover so depends on what I want to use the product whether I use HCL HBO your clue when you're doing exams is if I ask you to make the call riders aged fell faster than a tie-dyed newsagent that's the cheerful OK so most of the Super security agents here not that super-secret wouldn't say This is your money reaction but the book seems to love this reaction is actually very old and that's why they love it is because it's confined in textbooks dating back to the interviewed elderlies record any cargo can business with a loss on the primary out of nothing to get any public errands with this in a maybe can you not able industry is with HCL and get them to work so there's a region making use of we want to convert this into an old way over here the little bit of space whatever I wanted convert this into an alkyl chlorides that 3 carbon probe in all and I want to convert this into 3 carbon pro-coal chloride coral propane and so is the reagent that you use use zinc chloride it's a pretty simple looking reagents and reagents the town of zinc chloride loves oxygen into Lewis acid were going to see a lot more reactions of Lewis acids on coming up but Lewis acids In the same way that that the longest oxygen can attack protons the lone pairs on oxygen will also so zinc is the most common transition metal but in the human body if you want to call it a transition metal 2 main group metal on it's the most common metal used by human enzymes in the whole point of activity in your body is this Is it sink forms Ponce de Haro Adams so there's a vast number of zinc producers that that's where the mechanism starts with some oxygen atom coordinating OK so when you when you do that when jobless this intermediate which is going to look very busy to you this is going to bother you because it's got all this stuff on here and I hope you won't be too bothered by this so here's this sank 2 things that have to happen if funding a 3rd behind oxygen I have to put up plus charges that call Nakasone mind we have 3 bonds oxygen you better put up "quotation mark given the choice
navigate a plus in this molecule there must be a minor somewhere because they started with 2 neutral reagents whatever I make has to be neutral because the question is where I put the negative charge will losing just picked up an extra pair of electrons and now has 2 meanings so there's nothing intuitive about yet to you because you're not familiar with looking at zinc once you've looked at 5 thousand zinc's zinc species with 2 bonds it will about you that there's a 3rd bomb and you'll want to put a minus charges but for now I just have to remember that but that zinc as a minus charged if I wanted to be really precise I recall that is engaged to tell you that there's a minus charge Inc OK so now here's what's totally weird so just you have to have some something here for a 2nd there are clawing lines floating around in this solution so 1st is believe me and then I'll show you how I know that so if you want to draw the correct mechanism you have to draw chloride 89 will where's the chloride and I'll show you wouldn't this be patient notion that chloride and it's coming so the cloying signs that a floating around in this solution can come back in and push out this leading you can never guess what would happen with zinc or we have to show you what happens is it were you couldn't have known all this stuff on and you get nascent to substitution totally avoid cargo that I'm formations the same loves oxygen so much grips that oxygen and allows it to turn into a great leaving OK so the byproduct of this reaction Is this species right here here is the byproduct of that zinc species that laughter is the engaged on species that's the byproduct and that's not stable it is suing DuPont that this will start to dissociate and that's where you get the chloride hands from and it's going to seem to you like this chicken problem but where I get the 1st chloride from to get the whole reaction started cannot every bottle of zinc chloride has chloride 89 contaminants in there this is the mechanism for the reaction that and this is the origin of most the chloride you got in a typical reaction you don't have just 1 molecule you get 6 . 0 2 times 10 to the 20 3rd molecules and there's plenty of chloride contaminant floating around so as the reaction goes it generates chloride in I'm that chlorine and serves as the nuclear file to come back in an attack more of these of these of Lewis acids but this is a good example of of how Lewis acids combined oxygen and make them better leaving it's a great example that OK that's not the best way to make a try alkyl chloride let me show you the best way to make a perennial chloride let me show you a money reaction you will use over and over and over and over and over and over again I can't imagine that you will escape this class without me asking you about this region but the Green Canyon that's money and it's not just for this conversion is again Chapter 18 for a similar reaction actually use it over and over and over again the toughest thing about this whole transformation of alcohol Stelco Clerides it's just remembering the name of the reagent SOC Elton we call it the biannual chloride and I'm going to draw on and how cold it has a very specific stereo chemistry justly conceded its intention to reaction because Wilson versions to construe this secondary alcohol and we take this as so sealed to the told by O'Neal chloride this is the best way to make an alkyl caught primary secondary and you could use HCl for tertiary but we don't make tertiary alkyl Clerides super common reaction here and so here's the region combination that we used signing us and purity and I'm not going to draw the structure appeared in we discover that I would that potholes 3 reaction will call this nobody calls the socalled to from recent reduce calls a final chloride so I'm not sure why In other words if you a socalled to and think of like it's your overstretching the lingo OK so here's the products you get a chloride and in the configuration is converted it's now -dash that means it was some sort of MSN to process that occurred in this reaction so would draw part of the mechanism the fact of strong mechanism them ,comma going to be very careful here reasons the recorders and video and people around the world are watching this so I'm going to be very clear this is the mechanism the book shows a teacher graduate class on organic reaction mechanism this is not the mechanism by which oil but this is the mechanism I want you to know because it's the mechanism in the book and I think this will give me a chance to show you the structure of vinyl chloride the misted by drawing alcohol and stuff on the bottom of the apple doesn't matter as much as the lone pairs an oxygen and use the structure of vinyl chloride its parameters there's a lone pair here on this final chloride the lone pair is not involved in any part of this mechanism but it is like to show it there's like see enough vinyl chloride Crandall looks a little bit like potholes read but important point is that it's very easy to attack that's all 10 years I want you to draw all the way the book draws its just because it will make our lives easier the book draws this into reaction that pains me the important point here is that we're going to go from an OH which is a lousy Leading Group and we're going to convert that into a great Leading Group and I have 3 balanced oxygen now that's not happening you can all
draw down here just so we can see the quality behind leading group is floating around someone so now the Puritan based can come in and I didn't leave a whole lot of room for the period in here so the media on distressed squeeze that period unions from using his big fat tends buttress squeeze that appeared in in years so I can use it to pluck the proton that OCS only in my hand so here it appeared in it can come along and pull that Proton off that makes an oxygen a lot happier but that whole group this whole O S O C L thing is a great leaving to drawl the force structure that intermediate but can see all this business attached to them and now here's this leading group here this is called a claw 0 sulfite Esther I will never ask his name for that kind of a functional group just in case you're wondering that Socorro sulfite Esther and that's a great Leading Group and just put a little label great the group who would have thought that it's a great feeling to get the chloride its electron drawing on the sulfur there's another oxygen and sulfur that's electron drawing all that is going to stabilize the buildup of negative charge on this oxygen leaving so you wouldn't you could never known that this would be a great leaving the pressed into action they had to experiment quite a bit venture to stumble onto his right combination that's another chloride come in and do innocent to attack His if you stick with these conditions you get very little heed to elimination who would have thought that you couldn't have guessed that that's why you have to memorize the secret recipe of vinyl chloride and period and so when you attack into innocent reaction is right as into 0 to remind you you get backside attacked an inversion of configuration when the quiet comes in and displaces that leading occasional cargo cat irons so we'll end up with clean version this configuration because it's a mess into process so this is the reaction you should use to make alkyl chlorides and you're going to use it throughout this book there's zillion problems in the back of this chapter on you're going to see a very similar reaction with final collided low-yield nuclear agreement you can convert carboxyl Gastineau wages but that's always
covering for today when we come back to the the middle of Parliament from mines the reaction and