Lecture 11. Alkynes, Part 3

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Lecture 11. Alkynes, 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: 00:29- A Perfect Red 02:42- Cochineal 05:07- 11.7: Best Alkynes for H-X Addition 11:49- 11.7: Worst Alkynes for H-X Addition 15:58- 11.8: Addition of Cl2 and Br2 to Alkynes 21:52- 11.8: Addition of Cl2 and Br2 to Alkynes-Add two equivalents of halogen to generate the tetrahalide 24:58- 11.9: Hydration: Addition of H2O 28:33- 11.9: Initial Product=enol 31:58- 11.9: Mechanism 37:38- 11.9: Keto-Enol Tautomerism
Setzen <Verfahrenstechnik> Lebensmittelfarbstoff Chemical property Spawn (biology) Plasminogen human-Aktivator Chemical reaction Organische Verbindungen Multiple chemical sensitivity Chemistry Molecule Wine tasting descriptors Vancomycin Colourant Substrat <Chemie> Medical history Process (computing)
Dye Aluminium Sea ice Hydrochloric acid Gene Chlorine Chemistry Knot Dreifachbindung Wine tasting descriptors Alkalinity Isomer Colourant Phenol Benzene Cloning Periodate Calcium Alum Substituent Surface science Doppelbindung Walking Chemical reaction Electronic cigarette Systemic therapy Vancomycin Uranhexafluorid Yield (engineering) Powdered milk Chemical compound Stuffing Dietary supplement Kohlenstoff-14 Biosynthesis Calcium Hydrogen chloride Organische Verbindungen Acid Multiple chemical sensitivity Columbia Records Diet food Stereoselectivity Ageing Abbruchreaktion Schweflige Säure Dialysis Explosion Active site Mixture Body weight Silver Chemical reactor Setzen <Verfahrenstechnik> Galactose Alkyne Carbon (fiber) Aluminium Hydrate Water Functional group Salt Body weight Substrat <Chemie> Salt (chemistry)
Diethylstilbestrol Steel Growth medium Chlorine Chemistry Synergy Electron Isomer Colourant Click chemistry Halide Substituent Reaction mechanism Doppelbindung Alkylation Chemical reaction Chronic (medicine) Solution Wine tasting descriptors Reducing agent Vancomycin Yield (engineering) Penning trap Bromine Thermoforming Stereoselectivity Bromine Hydrogen chloride Geochemistry Multiple chemical sensitivity Methylgruppe Ammonium Ageing Lactitol Orange juice Active site International Nonproprietary Name Mixture Halogen Bronze Setzen <Verfahrenstechnik> Molecularity Mixture Bromide Alkyne Carbon (fiber) Chlorine Californium Amrinone Ice Functional group Teilentrahmte Milch National Rifle Association Ammonia
Semiotics Sulfate Steel Chlorine Chemistry Molecule Dreifachbindung Electron Isomer Library (computing) Enone Whitewater Reaction mechanism Doppelbindung Patent Octane rating Mineral hydration Vinylverbindungen Walking Sulfur Katalase Chemical reaction River source Electronic cigarette Wine tasting descriptors Neoteny Vancomycin Stream gauge Acid Attachment theory Stripping (chemistry) Isomer Zellmigration Bromine Medical history Cobaltoxide Stereoselectivity Pipette Stuffing Isotopenmarkierung Kohlenstoff-14 Bromine Species Ketone Alchemy Hydroxyl Wursthülle Multiple chemical sensitivity Columbia Records Methylgruppe Reactivity (chemistry) Origin of replication Mercury (element) Solvent Ageing Enol Abbruchreaktion Lactitol Common land Schweflige Säure Faserplatte Elektronentransfer Translation <Genetik> Sea level Halogen Process (computing) Setzen <Verfahrenstechnik> Malt Molecularity Alkyne Carbon (fiber) Protonation Natriumglutamat <Natrium-L-glutamat> Water Hydrate Hydrogen Kalisalze Drop (liquid) Functional group Proton-pump inhibitor Storage tank Salt Chemical structure Butcher Substrat <Chemie> Base (chemistry) Halogen
Semiotics Sulfate Chloride Tautomer Polyvinyl chloride Wine tasting descriptors Shear strength Isomer Fackel Till Vinyl chloride Trauma (medicine) Reaction mechanism Vinylverbindungen Solution Chemical reaction Alcohol Vancomycin Plastic Chemical compound Isomer Acetone Aage Cobaltoxide Stuffing Pipette Kohlenstoff-14 Ionenbindung Species Ketone Lead Enol Tachyphylaxie International Nonproprietary Name Conjugated system Chemical formula Setzen <Verfahrenstechnik> Tumor Bromide Meat Carbon (fiber) Protonation Amrinone Water Hydrate Hydrogen Functional group Proton-pump inhibitor Storage tank Blind experiment Carbon dioxide Base (chemistry)
Vancomycin Isomer Ketone Lactitol Resonance (chemistry) Proton-pump inhibitor Chemical structure Tautomer Memory-Effekt Chemical reaction Columbia Records Process (computing)
they started back in the middle of absorbing new industry also so we just had a exam on Friday and it was a tough examined and you guys did fantastic the on out 130 the 125 and the average was 74 . 5 7 5 on us those great there's always room to improve and the trendy so what is it that makes can fit in 1 the 2nd quarter of organic chemistry so challenging it's different from the challenges he faced in chemistry 51 a you have to change the way you study change the way you absorb the material is about learning lots and lots of new reactions to real focal point for this quarter and I'm going to continue to give you lots and lots of new reactions to learn and yet to master those yet to practice them on as early in different substrates universities and continue to do that job continue working the happened problems that's great job on just the key challenging yourself with questioned you've never seen before because my exams will consist of questions you've never seen before but seoul been denied usually start off by talking about something that I've seen somewhere and I ran into this some mention of this textbook just a popular book on about the color red and specifically about a certain type of guy that the coloreds so I had to read this book on many issues but on my list it's called a perfect red and specifically it is about the history of a guy called coaching and you may have heard of this died last year there was all this break is about Starbucks taking some guy out of their strawberry getting a lot of heat for that they were putting the unnatural color into their properties are and the natural coloring using the cost of the unit told was this guy coaching .period about coaching what the molecule behind this entire book and behind that Starbucks strawberry from the coaching he
was indicted comes from both specifically these kinds of insects he sometimes you on the indebted flip over at Cactus League you'll see this stuff where it looks like just white powder flake fungus white fungus going on on the leaves you never know that under system white fluffy surface but you dig actual blows underneath this typically looks like this and if you pinch 1 of those gloves on people exploded in prepared explosion of color on at all it is amazing about these blows is the certainty if you drive announced 17 to 24 per cent of the insects weight on it is this substance called ,comma gas that's astounding that's a difficult 1 of them is your weight was final for some organic compounds but that's just absolutely stunning and this is indeed a brilliant red color reddish purplish color and is commonly used for dialysis South American trade that the Europeans borrowed and is now used worldwide on typically Diez became just expose call off to college ,comma to mix it with something called a mordant compound that really causes the diced stick like glue to arms to "quotation mark cloth the fabric on so so usually to make community useful as a diet mixing with an aluminum salts calcium salt and helps the compound to grip onto the fabric on and that's what used to to Diamond traditional actually modern fabrics not just in South America OK so I think it decided whether it bugs me sorry about whether it bothers me to drink a lot where they have lot you Senate arm in arm ,comma chemical compounds are chemical compounds what I feel better than this and that and on and on they get bothered me OK so when I'm talking about this chemistry today were getting back onto Elkind instances Chapter 11 in the book sold the Sapling problems it was nonetheless I extended that to Wednesday because we have 2 more lectures on how kind Monday and now on Wednesday and the intent is that the Dow kind of problems that online will be due on Wednesday nite some major work on but occasionally left off
remember the replied reactions from Chapter 10 Whittaker managing different regions and we had endowed genes inside AGR yeah Saudis he's chlorine sealed to we added that outlines of sulfuric acid in water and hydration about the size of orations stuff like that but we're doing 4 of those reactions in Chapter 11 exhibiting trip along the lines on and we spent when we left off before that example I gave you we talked over and over about the intricacies of adding agency each sale across an kind soul finished that up and try to make more headway in covering those other reactions all of these reactions were the inside the Alpine access the nuclear plant look at the numbers and on 1 of would be examples of about kind and that would be good for efficiently N HCl across the aisle and there are 2 types of all kinds they give you a position on the official results we get 1 major product in high yield on and usually you might have noticed in the last thing the exam I say on introduced story material efficiently converted into lot of some products on new show the regions chemical reagents and the steps in other words don't show the worst alkaline and try to figure out a way to synthesize things using the best of times the European example of an outcome that I know will officially not give 1 product and have a mixture of rejoices so they take it out and I have not just 1 equivalent of that of hydrochloric acid but to equivalents of HCl so to with on remembers accuse the abbreviation for equations so I tend to use the full abbreviation quick on the 1st day of the 1st equivalent of HCl had an iconic off on fashion as will the 2nd equivalent important point is that it specifically puts the chlorine and Morrison Institute Jakarta and again in a knot but obviously you mean you can't see it but there is an age that got added to that terminal carbon on and it's 1 of those 2 wages you can't tell after the reactions over which of those 2 regions came from Europe Silver 1 of and if I had to clones of each year will continue and that will add yet another equivalent of HCl registered 1 equivalent Rachel I could start in the middle with that little intermediate but now With that 2nd equivalent we had steal again and so this will be an official reaction in other words you don't get the ,comma competition you don't get additional chlorine into both sides of the of the triple bond because the trip alone is not symmetrically substituted on 1 side and H and that's the site it's going to that's the carbon and at the end it's going to provide needed on the other side it's more substituted for Watson another example however a type of substrate that will efficiently on 1 type of product and only 1 type product moving in and out all this had mentioned before that I tend to use abbreviations for functional groups just makes for a cleaner lectures you'll find organic chemists published papers and give lectures and use abbreviations pH means fan it's an appreciation for a benzene ring and you know I don't really want you to worry about the fact that the double bonds and benzene ring and they're not reactive in Iraq policy anyway to make those reactors double bonds in a benzene ring react but until we get to Chapter 18 and cannot show you a million ways that the double bonds and and sometimes things we have to worry about but for now just assume the double bonds benzene rings are not reacted so if I want to add the HCl today I cannot either 1 of those to equivalents and on miniature chosen to draw additional to calls of HCl so now that AP substituent on both sides of the alkaline and so now I have to hypothetically you would have to worry about Regio chemistry which side gets th which gets the the CEO the notice how clever I was to choose the substrate here is symmetrical and substituted since I got the same group of both sides of the Alpine it doesn't matter which side gets the region which side gets the so Sony dropped initial intermediate but that was that now that on this particular isomer has phenol and chlorine on the same side but this particular intermediate on because these are ones Zain's that's a whole new monarch device that sea ice in the HM the other side is the low priority group I'm just taking the 2 highest priority groups chlorine on 1 of the carbon atoms and on the other carbon and finalize the higher priority so this is an initial intermediate you also get the yesterday so this right must be down below if I had only 1 equivalent on it divided only 1 upon which the old stuff .period MCI centers of the reaction that's not very good was like to get mixtures of isomers and that means different compounds to the boiling point you have had to use different techniques to purify the soul by adding a 2nd equivalent of HCl this intermediate goes further this period the NCI isomers added another equivalent of HCL and so the end result is that you've lost this double bond geometries is no more double wanting their season after worries about the UCI summaries on right there is no easy there is no sterigenics centers product this would be an example of a substrate that would be very efficiently 1 product and only 1 product of the reaction you wouldn't get mixtures of isomers a scary Westerners so you know when I draw questions on my problem sets reminds on-site tend to drop supplements where you draw 1 product in the into box I do not want them great problems where you draw 50 inches in the answer box on and I don't want you to design syntheses were where your reactions can potentially lead to 2 50 different products and so much to take note of when these reactions will work well and this would be an example OK so the contract about things that would not work well In the premier example of how to take
Elkind reactions where the region's engaging in some kind of mechanical suffering from chronic cough regional selectivity clear examples would be an on symmetrically substituted alkyl so we take an example of an kind that has 2 types of different substituent on each side of the all kinds of this kind of methyl groups taking off on the left-hand side and on the right hand side opened Ethel group but it doesn't matter what the 2 groups are just the bad part is that they're different on each side so now when if I had just 1 equivalent of HCl now I have to worry about which side gets the age in which said gets this year this go next to the methyl group for the Attleboro as the Corning go next and this is you'll get both From the start of the year so the drummer product where because of Madeleine afternoon significantly different in terms of Moore ,comma coverage of selected someone going to start up a drawing of the product with each goes next to the affable drawl that each year that my tiny little pen on so that's 1 product and of course this will give me a mixture of the MCI so so is this the EDI synergies yesterday so I started on this current at the red dot world and how well the reductions where I'm pointing and the highest priority to his effort and I am aware the other carbonized been was calling the 2 high-priority groups on the losing side that is busy I said and you also get the out of that as well she mixture that's not so bad but the worst thing is but the prime-time doesn't know whether it should next to the affluent muscle groups and so will also get his other product out of their out of this reaction through the coroner's down here and where the Proton has initially headed over here next to the methyl group and look at this massive products that were getting in this reaction that's horrible and Polonius and of course we're going to get a mixture I have chosen to draw the CEI summer on I'm not going to label it is the youngest answers indirect plus the search for products you get out of this additional HCl this would be a lousy way did you chemistry nobody likes to do chemistry we get lots and lots of products you may feel very productive because you don't need so many things you've got to separate those see all these if I had a 2nd equivalent of HCl all of these isomers will continue to react and so what will happen as just noted all get mark ,comma competition of another equivalent of HCl to my top products on at a 2nd each with the same place for the 1st 100 that and this is kind of nice because of sea and the isomers of that time the content of the boat will give the same product action here and in the bottom of this bomb intermediate the next time I had HCl across the double bond H will also add in the same position and so get this product as well and those are not the same sort of any and all I won't have to worry if I had to columns of HCl wanted for products that I wanted to completely different products this reaction and that's not sufficient I would not consider that to be an efficient reaction if you're yield is going to be 50 per cent at best of either of those 2 things you want and there is no situation where you want can it's not it's not a realistic situation OK so From Hell kinds just like LPG have to worry about the GIO selected it's important issue OK so protagonist for reactions this that we'd already talked about last chapter additional paychecks each orange CL so we're done talking about missionary zeal and HBO so now it's switched gears and talk about a different reaction this is our 2nd reaction was going to talk about where we had electrified calls to help companies instead about teens on Wednesday announced talk about additional bromine and chlorine your too and sealed but I hope you're really familiar with that as a reagent just not in the context of all kinds and so now to take that same on symmetrical teenagers showed before me line it's not a disaster when I had either in the yard to oversee all too the reason why this is easier years on to use as a reaction is because you don't have to worry about real geochemistry when you're adding to be yards into seals so good going to start by talking about additional bromine molecular bromine br 2 and so when you add molecular bromine since both of the cartons of milk and both get a bromine there is no issue of Regio selected you don't worry about me just selectively if both carbons on the al-Qaida getting a bronze and moreover in this reaction gives you the and believes that the relative relationship of these 2 halogen is handy to each other so you know so that the word this and all because the bromine join neighboring province and on the same carbon say trans isomer so there's a strange relationship very using high-tech nomenclature I would refer to this as the we in italics ice and content beginning to opposite sides it's not this year so With with the addition of HP are you have to be really careful about using and symmetrical all kinds but I don't see can be careless but when you're having your exterior steel to on direct worry about that OK so it's good to talk about the mechanism for this reaction it's the same mechanism that we saw Keen's bullets could walk through them because it also helps to reinforce those notions on of electrify reacted important point here that there is no problem can if you remember way back to almost 5 days ago showed you a mechanism for HBR edition and when you probably kind generate of final cargo can of final very weird thing that you've never seen before so but there's no apparent in this mechanism that the point behind this mechanism is that broke media to such a powerful electrified that the AL climaxes in nucleophile the whole kind type no we don't want to since there's lot that the the closer and closer that does bromine gets to outline the closer and closer to those of appears Getty all kinds of ways you start to take electrons away from kind 1 of the longer version is bromine gives back the electrons to you never have a cargo can intermediate this read this this reaction proceeds via a site click bemoaning a minor canceling the draw that cycle
for ammonia lines but it looks kind of painful actually if you haven't seen this before I say it's got this renumbered rename and moreover there a double bond that range no problem bromine is such a powerful electrified the readily forms this intermediate so I think it's of ammonium ion because there's 2 monster bromine but the weird thing is that remembered during and the important thing for you to remember is there's no cargo catamarans in this mechanism so what about the bromide and I'm leading group and floating around here you can imagine wandering around in your solution and so now they can attack at 1 side or the other and it doesn't make any difference I'm going to draw the although attacking down here so it matches the product the way I do it up above there we go like that and that generated in the the depiction I have above if I took that April 1999 attacked the other ,comma that you'll get the same product you get the same product and I'm a little bit reluctant to draw media using different and color that that would be exciting in a good way to do that only the same and others won't happen if the bromide attacked other carbon the Ethel group on that happening
this reaction 50 % the molecules are heading this way and when it ended this way what would happen to know how the bromine is going to be pointing down and but I don't want to be going this way and this burning the nor the Red Arrows now that remind us to be pointing out that they always end up friends to each other and look at that that's exactly the same molecule Liberia about flew around it's the same thing that's why doesn't matter this whole Regio chemistry so just in case it's not out of this rates scene as well but he just flip that over where there's no sterigenics centers you can put structure over without inverted thing that's the same translates that I do about the same on according to the idea that nomenclature OK so because there's no cobbled apparently convenient east of relationships between the 2 bromine and if it's if you seal to it's the same deal with the addition of chlorine you get the chance that OK so let's talk about in the previous example book and I guess the thing that I noticed she that there is a double bond there maybe we can do another edition of an electrified and so let's talk about that in true equivalents on hand to equivalents of halogen across the board on a double 1 that's going to take on a substrate and again I don't have to worry about whether it's symmetrically substituted enough when I had chlorine or bromine the cases might help kind of methyl group on 1 side Scott and isopropyl group on the other side and I'll show the addition of 2 equivalents the chlorine you know I ask you to draw the productivity don't have to draw the intermediate and I'm just show the intermediate to help you see what's going on in this reaction so not only will a chlorine to each side of the double want and my initial intermediate that our 2nd equivalent of scoring all dropped the final product for you here so you can see there's no sterigenics centers when had to colds and halogen and each 1 of these carvings that's not actually on as as To the same groups and on the cards which can be stages so of dropping the intermediate again you don't have to draw the intermediate and this reaction but we just remind you that this reaction does not proceed through I through cargo can I answer to vinyl can intermediates the intermediate that this proceeds to the 1st product to generate you led the 1st equivalent of chlorine will add chlorine come across the the double once they end up with a trans relationship and that 2nd of chlorine that adds again crossed the double bond In others having these 2 Korans on their core intellectual negative this lots of little bit less nucleophilic than than the original triple bond on but chlorine is such an aggressive nuclear of electrified the can readily add across the double bond even to coins attached to OK so but again for its shares I said to equivalents of age of C O 2 and because we don't have to worry about sister trains on relationships it's nice to have 2 equals HCl and articles young generation history Janik centers around the story about that OK so that's is the number 1 morning and say about edition of steel to the Arctic you've you've mastered that now without teens here's reactions without without kinds on and so it's going look at another reaction so we're not talking about originated beyond Cl we talk about additional of chlorine and bromine C O 2 and to but other about condoms and in this particular case it's just slightly different from the hydration recipe that we showed in the last chapter Chapter 2 and here's a little tricks that you need to remember that in order to make this work is you need some kind of mercury in salt to sprinkling just a little danger of mercury salts to meet the hydration all kinds work stations so good insurance and I'm only going to show you 1 type of mercury salts this class so that's manageable memorize that specific sold the case you're drawn up my In my alkaline and while I do when that symmetrically substituted which means probably there's some issue and trying to avoid with mechanical things in common :colon looking wants a recipe for adoration him on you do if you had in water across double bond your best you best got furious reaction out the water is your solvent lots of water used part of his recipes were going to include catalytic sulfuric acid if you don't write catalytic still come to correct on if you if you leave afterward catalytic in you got from equivalent in the reaction still work at its if you're telling me you added a tonnage of sulfuric acid said a pinch well OK that works you don't have to buy a reagents for the exam OK so here's what's different this wouldn't the reaction would work like this we get some sort of mercury salts and here's the mercury salt did did she do remember and will be hard to remember and here's why it's hard to remember it's because the mercury we show you looks so much like sulfuric acid all I've done is taken substituted replaced it with G energy is symbol of america mercury sulfate is is the the catalyst that you have to have been in addition to sulfuric acid and if you leave that all this will work if you leave out the sulfuric acid this will work you don't have to say Qatar catalytic abbreviation on but I would recommend that you do just emphasize that those are catalysts for the reaction to the end product of this reaction is going to be is going to require us to do some explaining and and I will explain it to you shore so is 1 of the Commentary on financial literacy so it's clear there's the other prominent al-Qaida and so immediately evangelical hole With this is nothing like I the reaction of teams candidates but will get to to that OK so there's no OH-group laments what happened to that I want to talk about that at that moment OK see needed mercury to make this work otherwise the reaction doesn't but that's where the wages of American from the hydration reaction and I'm trying emphasized to you on I read somewhere that the discovery of the Of the accelerating effect of Mercury came from the thermometer somebody was using to run migration reactions before they knew about this broke and I was like the best reaction they had ever run so they explain happened found that you know if you literally don't Mercury uncle these actions were fantastically so another words don't forget the mercury or your reaction what lousy and you will get full credit for any such reaction of the outcome
additional OK so I'm not sure that it what's with that carbon the key to business in that state and talk about the intermediate it's forming in his reaction this time I'm going to start the 9th symmetrical all terminal how come they all kinds at the end of a carbon chain and then you draw my and my secret recipe now were do hydration water and water across the double bond and catalytic sulfuric acid cat that's what we did for hydration of Keane's but because it's an al-Qaida remembering to throw in the Mercury sold there's McCarrick sulfur and is not Mercury with the substrate to his no subscript to Mercury because of mercury to as a charge of plus to maturity in my book into the end product of this reaction will look like this and just in case you're wondering what happened here did I started off with 5 carbons and my substrate I've got 5 carbons in my product and so the carbon indicates the Cardinals Israeli here already gets oxygen it's the more substituted top getting back out at the Patent Directive so another reactions Regio selective obeys ,comma selectively just like hydrogen Malkin's does and the more substituted carbon atoms of the pipe bomb gets the oxygen out just like hydration announce that struck the intermediate you don't see this as an intermediate goods forming this reaction is related to the mechanism and wants see this intermediate maybe you can take a deep breath and some of it that is like on that is like the height of the hydration out a little bit so there is a major part of my head you get to this intermediate John chat on here it is that that lady so just like hydration announced the United 1808 across highway yet H and OH across a pipe bomb and that the thing that you could not have known yet because we have covered here is that this type of hydroxy out where the need for that type of species with there's a hydroxy group attachment he we call that Indian all and what you will learn is that also are surrounding manically unstable but I sometimes and you cannot stop them from summarizing if you shrunk assert itself down to the molecular level in grad H and the OED it would still find a way to wiggle its way away from you and I sometimes to get this and so will talk about this process of isomerization originals into Cardinals like don't analyze .period about that no way you could have guessed that that was too so again it is it's very much like like hydrogen and yet a across a double life but what you didn't know was that this scene all product is not stable and we're going to see it twice in this chapter that's going to be the most starts in this chapter and then we're going to hit you with it over and over and over again in Chapter 24 125 you can fit 1 scene when we talk about Karniol on reactivity INA lates stuff you know you're not ready for yet so the Texas in all businesses important concept we have a title here it's not really is not really relevant Proton catalyze mechanism understand scratched out and wouldn't really need a Sears the mechanism the book shows for this reaction a from tenants would like you to know you can show your lot face your more correct version admitted graduate class eventually know that for now going to try to stick with the things about this thing OK location would start the substrate I got an hour on 1 side of the alchemy and then a chat and that I didn't draw on the other side of the aisle come in but the 1st step for this hydration mechanism involves the sulfuric acid when you're putting sulfuric acid into a reaction the duty of really powerful as this would draw our artists to the universal symbol for error pushing age before doing a proton transfer case Olson said that a strong acid in their sulfuric acid I'm looking for what in my molecule can act as a base that pipeline looks to me like the best thing that the base there we go and you can't tell where 1 think that Proton at that narrow question I showed you start from the very center of perfect center of the Strip can't tell at 1st sight to where I'm going to stick that Proton and Solomon you will see that until his next intermediate and of course it's had told I guess I told above its mark on a confrontation so the proton goes to the least substituted carbon so legal drop that intermediate and here's the protons and there's another Proton below you can actually tell whether I added the proton on top of the proton but was to protons are identical and if I'm taking electrons away from the more substituted carbon I'm going to get another 1 of these final 10 intermediates just like when we added HCl reached across the globe so there's my final have time intermediate now there's all kinds of stuff floating around in here there's a minus but there's also this sea of water they were reminiscent of using water as our solvent or at least as Arkansas there's lots of water that makes it very likely that this water will come attack that that pitiful cargo carrier that only has 6 electric the 2nd row Adams demanded octave electrons carbons really unhappy there is a line of cars and we've already seen vinyl headlines Canada's label here so we can remember 0 yeah we've seen vinyl cat before and the vinyl had the whole species of their medal winner
was chloride bromide present but no water chloride bromide added focus the next intermediate regenerate this starting to look like hydration products except it's got the Sox only a minor here 3 advanced oxygen you better have a positive charge on that I would call that OCS box only in that species industry bounced oxygen so I can come in with mine but with the conjugate base my answer this symbol a mine is really in this solution you don't really know whether it's water :colon Proton or the excess sulfate and I am calling the proton off that's where the similarities of the A-minus so useful so just pluck at protons and this is what leads to that you know all intermediate that unstable and all I think it's a reaction stopped here if for whatever reason who knows what that would be true if he always stable than this reaction would look so much like Al-Qaeda hydration life would be easy but I just want to remind you this and all right here the casino His unstable you couldn't isolate them and you couldn't come up with the quality of the no isolated really quickly knowing what it's going like you cannot isolate that will will be unstable no amount of speed that you would have had lot isolate that product and reaction to it what is the definition of a minority of final group means this group great here so summers as what is the definition of mine this is vital he calls vinyl when they put a big long bond here and you'll hear is a word vinyl to mean SEC government its old nomenclature it's archaic but still used on you go to the hardware store to buy some white plastic pipes it's called PVC piping means poly vinyl chloride on so vinyl is now stuck in our common vernacular on so if you hear me use with vinyl today I wish I could escape that focus on vinyl means RCC double-blind healthy OK let's talk about the malls and again we're going to once we believe this chapter there on and you know kind of forget his whole in all business I promise you if you could just hang on the lead all by some concept that I'm going to show you contribute immensely valuable when you get to the next quarter immense value so let's talk about Renault's every time I see him you all the good draw this all year amendment to draw the Proton because that Proton doesn't want to stay there all draw 1 of the 2 carbon atoms there so this is that all direction acetone and if I put this in all solution I cannot stop it from equilibrating to generate this place American compound with exactly the same number of cartons and oxygen and hydrogen this is we're going to win although that's included in the book is that acetone 3 cartons and Keaton waiting so mean also taught Tom arise they II sunrise this these 2 types of a murderous special Titleist and when I really nice in to license the differ only in the position of protons right lifted up a proton in the summer of those kinds of isomers that seen molecular formula oracle torturers so these 2 top tumors all I've done you can kind of see here is I have taken this H off the oxygen and had moved it down to the carbon atoms and the bonds we draw differently but the important point is that literally and Adam has changed its position so here whenever we have these 2 toddlers on really attached to his name is called what's that's none of that and so the time to know that :colon being all talk and it's colony all because it's an Al-Qaeda it's an alcohol also kind of an obvious name and we call this the Quito Tottenham come but you could call it a key Bill sometimes you say Oh that's an example of the total he'd always summaries you might be wondering why did he say Quito but it is a key and I didn't invent the language say it's just I don't know why they call Quito gene-altered traumas in Quito altered times so whenever you make any knowledge about what the mechanism as it I sometimes to give heater and conceptually the reason is that in terms of bond strength that you don't really learn about it in 1051 carbon wheels are massively more stable than CCW wants time you'll see lots of reactions that result in the formation of criminal groups and that's because the thermodynamic sinks the carbon-dioxide global warming on carbon dioxide is burn things everything tends to form carbon-dioxide OK so these are examples of tolerance and that's going to talk about it it's going to talk about what other kind of tolerating won't see this quarter but see you can extend this idea and better understand the concept of a torch is another kind of the story here has an keen and as an enemy on their hands it's kind of like this now but this is :colon lean and mean Tottenham and you'll get to this Chapter 27 tons and tons and tons of that stuff "quotation mark tortoise now that even the very very rapidly equilibrated with the and doubled counterpart of the differences the thermodynamic difference in instabilities is not as dramatic Ferdinand so get ready when you get take to the next quarter both of these
processes of isomerization her going to become super super importance so I lived at proton office here and I put it down here where the 2 protons on and it was 3 so the partners of each other so you won't see means in this chapter you won't see innings in this chapter just stored that the back of your RAM memory here and will dissuade Chapter 27 I'm not going to ask you about that I just want to come with another example of here's to isomers the partners of each other no notice these are nonresidents structures resonance structures don't have Adams in different positions such as the bombing this changed on these adjusted I suppose there's a a two-step mechanism that I will show you as soon as we come back on Wednesday I will show you the mechanism for this reaction to step in August will start their own comeback on Monday will pick up on all issues including our carbon-carbon longingly at the morning how


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