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Lecture 13. Reduction and Oxidation, Part 1

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Lecture 13. Reduction and Oxidation, Part 1
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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: 00:10- Imitation Vanilla 01:13- 'Vanilla Extract' produced in Mexico is no bargain 02:09- The Tonka Bean 03:30- Structure of Vanillin vs. Coumarin CHAPTER 12-Oxidation and Reduction 05:52- 12.1: Introduction 12:42- 12.2: Secret "Hydride" Reducing Agents from Ch 20 15:54- 12.2: Other Reducing Agents 19:20- 12.3,12.4: Hydrogenation of Alkenes 25:12- 12.3,12.4: Hydrogenation of Alkenes-Benzene rings, C=C bonds 29:37- 12.5A,B: Partial Hydrogenation of Alkynes 32:20- 12.5 A,B: Hydrogenation of Alkynes 37:17- 12.5C: Partial Hydrogenation of Alkynes to Alkenes 42:57- 12.5C: Dissolving metal reduction
Mashing Differential calculus Deep sea Man page Alcohol Extract Molecule Agriculture Vancomycin Mur, Switzerland Drop (liquid) Electron Meeting/Interview Azo coupling Lactitol Chemical compound Extract Stuffing
Cumarin Fermium Chemical plant Institute of National Remembrance Toll-like receptor Wursthülle Columbia Records Extract Molecule Lone pair Table wine Nomifensine Chemical plant Ingredient Cell growth Concentrate Proline Action potential Food River source Toxicity Vancomycin Computer animation Chemical compound ISO-Komplex-Heilweise Extract Bottling line National Rifle Association Pill (pharmacy) Isotopenmarkierung
Hydride Chain (unit) Aluminium Portable Document Format Molecule Altbier Click chemistry Data conversion Transformation <Genetik> Aluminium hydride Lethal dose Organische Chemie Hydride Redox Concentrate Ene reaction Gas Valine Chemical reaction River source Alcohol Anomalie <Medizin> Wine tasting descriptors Electronic cigarette Death Toxicity Mill (grinding) Vancomycin Chemical compound Arzneimitteldosis Pharmaceutics Cobaltoxide Lymphangioleiomyomatosis Biomolecular structure Stuffing Vanillin Ionenbindung Biosynthesis Reaction mechanism Cumarin Chemical plant Dörren Crevasse Columbia Records Man page Functional group Sand Redox International Nonproprietary Name Lithium Ligand Katalytische Hydrierung Process (computing) Naturstoff Setzen <Verfahrenstechnik> Area Grading (tumors) Rubidium iodide Hydrogen bond Carbon (fiber) Molecular beam Spawn (biology) Chemistry Water Sodium Drop (liquid) Curing (food preservation) Initiation (chemistry) Radical (chemistry) Functional group Chemical structure Ion channel Carboxylierung
Mechanically separated meat Secretion Solution Hydrierung Chemistry Block (periodic table) Molecule Isomer Transformation <Genetik> Aluminium hydride Coordinating European Council for the Development of Performance Tests for Transportation Fuels, Lubricants and Other Fluids Alum Surface science Redox Doppelbindung Katalase Cadmium sulfide Chemical reaction River source Ash (analytical chemistry) Vancomycin Collecting Tiermodell Dominican Republic Chemical compound Aage Cobaltoxide Stuffing Pipette Ethylene Ionenbindung Recreational drug use Atom probe Reaction mechanism Wursthülle Columbia Records Methylgruppe Man page Ham Solvent Functional group Redox Active site Lithium Nanoparticle Sea level Katalytische Hydrierung Palladium Cell cycle Katalytische Hydrierung Setzen <Verfahrenstechnik> Metal Area Potenz <Homöopathie> Tumor Phase (waves) Galactose Nitrogen fixation Hydrogen bond Deposition (phase transition) Carbon (fiber) Ice front Kohlenstoff-14 Biodiesel Sodium Combine harvester Hydrogen Computer animation Diatomics-in-molecules-Methode Solvent Drowning Butcher Substrat <Chemie> Base (chemistry) Ammonia
Semiotics Katalase Alcohol Hydrierung Molecule Dreifachbindung Alkalinity Meeting/Interview Ale Municipality Benzene Periodate Doppelbindung Calcium carbonate Katalase Chemical reaction Alcohol Stockfish Systemic therapy Neoteny Vancomycin Penning trap Stuffing Ethylene Biosynthesis Ionenbindung Alkali Spawn (biology) Copper Ion transporter Wursthülle Columbia Records Man page Reactivity (chemistry) Hydrogen Adversary Functional group Human subject research Redox Nanoparticle Song of Songs Halogen Katalytische Hydrierung Palladium Katalytische Hydrierung Hydrocarboxylierung Setzen <Verfahrenstechnik> Potenz <Homöopathie> Stop codon Galactose Alkyne Carbon (fiber) Hydro Tasmania Hydrogen Ingredient Gesundheitsstörung Computer animation Functional group Blind experiment Chemical structure Benzene
Übergangszustand Left-wing politics Memory-Effekt Set (abstract data type) Hydrierung Molecule Dreifachbindung Wine tasting descriptors Electric arc furnace Lake Transformation <Genetik> Elimination reaction Medroxyprogesterone Periodate Base (chemistry) Trauma (medicine) Doppelbindung Chemical reaction Trockeneis Stockfish Food additive Systemic therapy Vancomycin Thermoforming Ethylene Stop codon Biosynthesis Ionenbindung Weinfehler Reaction mechanism Action potential Gold Man page Ring strain Inflammation Stress (mechanics) Abbruchreaktion Redox Storage tank Mineral Katalytische Hydrierung Process (computing) Metal Setzen <Verfahrenstechnik> Carbon (fiber) CHARGE syndrome Synthetic oil Hydrogen Sodium Combine harvester Gesundheitsstörung Salt Deception Substrat <Chemie> ISO-Komplex-Heilweise Satellite DNA Ammonia
so was mine looking for something and Albertson's supermarket a couple of days ago and I thought it is just go dragged out of an electron was aware that there are different the prices are between actual wielding a abstracted imitation vanilla flavors it's not obvious to me while 1 ounce of the natural stuff call 6 dollars 8 ounces of imitation vanilla flavor should concentrate on its huge price differentials and deep down inside I know they just take a vanilla bean and put it in alcohol here they take the actual manual flavor compounds and few drops in alcohol and it's not that big a difference except for the Sony wants it extracted out of the military and I'm not sure I can tell those differences on everything in here is natural traditional of maybe except for the final molecules itself but would serve so I want to go online and find out what's important in a extracts and what else is in these farm what else is in these
bottles and remembrance of doing interesting article about the FDA warning people about what kinds of cheap the military might sometimes find produced in Mexico on what they warn you against sometimes when you go by and not in every case and not supermarket brand I just showed you but there have been cases where you go to buy vanilla extract its label is natural extract to be like you or something like that and they warn you that it's not actually even know what they say is that these are actually tonka being extracts that contain the compound from where I was immediately interested that they know is not quite as interesting crewman is very interesting because I happened to be that the selling these unsettling extracts of completion of plant and never heard of the contain compromise .period about that on what I quickly
realized is that if you can find these extracts of tonka beans that's actually phenomenal I want to get my hands on some of this because it turns out that all of the avant-garde checks out there are using talk of peace and it turns out that there are legal is no longer allowed by the FDA for you to use tonka beans is flavors on and autonomic got chapter trying to impress people you would use shadings of this very subtle shadings of these tonka beans but to try get superb players on and it turns out that these taste very much like Miller and the French have known this for a long time and again in this article it reinforces this idea that tonka beans are a major source of humor and so was the author of this article pretty impressed by the chemical sophisticated because Kumaratunga's high concentrations of the toxic and I'll address that focused solely on what this With this author was clever enough to point out is that we would have to be completely insane amounts greater normally just shaking off a little bit and we have to literally swallow on the municipal many handfuls of the Legion of Merit toxic effects this will take a look at the molecules that underlie what is inside a vanilla bean and what find inside the trunk of the I
take the bit of a tree dry out the reason why so fantastic in your bait for the junta has this wonderful analysts smell and flavor to it is because of the small called so this molecule represents about 2 per cent of the vanilla beans easily prevented alcohol the mill and it's extracted and has this wonderful flavor if you take the tonka bean different plant different tree given everything that he put these in alcohol let them so you also get to know and I don't know if that's even present in these tonka beans with yourself out is a completely different multiple called Kumar that as the wonderful smells like vanilla and again this is about 2 per cent of the tonka beans circuits extracted out on so I you know not so sure had comfortable ingesting that on purpose but I'm going to do it through the for whatever reason and looked at the LD 50 is it turns out for every compound and look at the lethal dose what's the dosage of which 50 per cent of the animals who take a diving course they never mentions for humans you can suggest you it but they know the numbers for mouse yet to subject yourself to about at least if you're about to about books for the going for a kilo of rattle mouse with the words out of 70 kilogrammes person you can imagine I would have to take a spoon spoonfuls of pure Kumar before it started have those kinds of toxic effects but no 1 was also toxic great everything is toxic if you are in a concentration sand is toxic eagle-eyed concentration and that significantly less toxic at about 5 times less toxic than I think encumbrance so you can claim that no 1 is nontoxic so you have to be careful about what about what you say about toxicity so I'd love to get my hands on some tonka beans it's fascinating on there are many many natural products and pharmaceuticals that help cure intake structures in them and what I'm going to talk about those in this chapter on but it's fascinating to me can't say that the FDA has decided to make that legal on the was evidence and the big time shift to using bogus amounts could go back to Chapter 12 stuff on and we're undergoing a major
shift in years when he mentioned the same last Friday on those announcements the Indian received the files yesterday I immediately uploaded them the drop box so you can now go to the Web site and going drop boxes and somewhere on I can't look at you don't know what you see when you log the jovial click on the file to bring up the PDF version of your standing example never see your original exam again on but there's a good quality scanning so the questions about the great if you feel that was a mistake in the grading you can e-mail me the instructions on their we've already given partial credit did not send e-mails fishing for extra points because we've already given you partial credit the points but if you think something was amiss created on Intel arrived didn't let me know and again instructions and when you look at you when you look at your exams OK so Chapter 12 we just want to finish on various recovered from his 9th and 10th 9 10 11 suggestion result calls but U.S. and 1 assent to anyone 2 reactions of alcohols but chapter in injected 10 we talked about all these different regions you can hand out things that need be RBI to seal the and we just finished Chapter 11 which is basically the same agents it's reapplied and out and one-trick relearning Chapter 11 as you can probably tell constantly constantly evolves so this chapter rather to talk about oxidation and reduction reactions the essential functional group transformations for organic synthesis and you'll be using these kinds of reactions to the very end of Of the the of the conflicting ones you can say the same for S N 1 s and 2 in the morning to actions with these reactions can be very useful cemented the view definition that's that's not a perfect definition is a functional definition is probably the most useful to use the most useful definition you you are certainly for this chapter for the 1051 series and that is that we consider the reduction of an organic molecules are too to correlate with the formation or the presence of more ch bonds now I'm sure you guys did reduction oxidation and bouncing equations we don't do anything like that in organic chemistry that you did freshman intends to make good on a series of molecules you can see more clearly this pattern of oxidation reduction this year draw series of molecules and as a drawing molecules of you up he drove molecules that are consistently more oxidized so there's a molecule wherever they stick in oxygen atom in there and the only difference now is that I have more oxygen carbon bonds more oxygen Vermont squeeze more oxygen more carbon hydrogen bonds means more reduced so this compound with the new oxygen carbon budget I would consider to be oxidize relative to the personal I can join molecule hearing held now I have to oxygen carbon bonds that's even more oxidized and the alcohol so if I show you always got along well reagent you need to use to convert that to another and you need a region that has oxidation that's why it's useful to distinguish the oxidation state of things and the highest typical oxidation state for organic molecules and that the carboxyl gasses that I had 3 oxygen carbon bonds the carboxyl death so you could see that this pattern of oxidation and 10 to cover area as a drawn series here going in this direction that oxidation things are becoming more oxidized it will be the reagents for doing those transformations not not this first one Morgan and wait until a chapter on radicals and that's Chapter 15 will show you how to do that today that 1st transformation but will show you how to transform how calls and allied in comics of gasses check so the reverse this process would be reduction I'm going in the other direction that those are all require reductive processes they will require reductive reagents reducing reagents and will show you some of those probably the most useful reactions from Finland transformation calls endowed hides and back and we're only going to show you have heard this during this chapter begins with about all carbon compounds that have no oxygen and because we can draw a similar sort of sequences similar shows a pattern so we are just going to draw a simple Al Kane and it doesn't matter that it's at the end of an outlaw chain I just wanna contrasted this with a CCD singalong along with a very similar molecule that as the CCW the important point here is that even with the same number of carbons because I have more cotton and cotton garments in this genius double long-haul kill that's considered to be more right here there's a single carbon-carbon bond now the statute carbon-carbon bonds so that Keane is more oxidized and a molecule that has more on carbon is more reduced and I think you can see where this is headed if I dropped an alkaline that's even more consider to be more oxidized in either of the 2 so again is pattern that as we reduce the number of CH bonds those are becoming more oxidized and as we as as we increase the number of C bonds becoming martyrs and the reversed and calls the converse is true as you reduce the number of is you increase the number of seats bonds and this involves some sort of reduction initiatives and reduction of about the change my verbiage he said reductions OK so oxidation in this direction reduction in in the opposite direction and knowing those patterns yes no absence of Bush's oxidation of only to carbon-monoxide monster they could also requirement for advance 1 unconditionally reagents in this chapter that it do that yet again that's chapter on radicals will will show that stuff so don't worry about that just worry about carbon-oxygen finale carbon-carbon that's that's really need to organic chemistry right there until the focus of attention focused so the draft starts off with the powerful set of reducing agents so right here in Chapter 12 . channel and it's wonderful they showed he's right I feel that on among the most useful regions in this chapter taking every new areas it feels like so I'm just gonna show you how to a preview of what these allegiances for its sodium lauryl hydride and lithium aluminum hydride and other items packed tightly into those 10 tribal warriors attacked tried regularly so here's what you will see that it's not until Chapter 21 initially this top-secret reaction they they don't show you this yet because your head will explode I'm willing to risk that say here is that the amendment hydride lithium and had tried to remain in again you don't need to know this and is hoping you'll store that in your brain somewhere and then when Chapter 20 comes along going all over that stuff and then you always follow these reactions of nature to a worker but does the work that I do on the other hand before individual worker watching dozens of Staples hydrated group of carbon hydrogen bomb right there with the Cardinals used to be see that ch bond that's what that lithium aluminum hydride does and this is among the most important reactions the chain will learn and can 51 seats so the book shows you the reagents but they don't show you what you're going to do it but I don't know why that is and look at them you have to dump a bunch of water on their error-prone the alcohol and you've reduced the to alcohol at a reduction process I just feels so good to see that and why isn't so good because you know as a zillion reactions you can do without I didn't want to know how to convert carbon no doubt poses not thousand things that you can do with that are in terms of chemical reactions and further transformations so that won't show that and just to give you a further heads up the year totally ready to kick but you get into 1051 Sears the mechanism for a for a hydra reagent the book will show you and has sent you type reaction and utterly pathetic destined to take reaction to hear that I drill illuminate for bonds to aluminum conventional weirdly sold aluminum things we to you and so you have to attach a hydrant eliminates PCs and the negative charge on aluminum tells me that all the bonds to aluminum nucleophilic so I should be at all surprised that it's going to do this and then we go that's that's what's going on here so I'm big
point here is remember this this region regularly eliminate hold onto until Chapter 20 and 21 and 22 23 and 24 you're going to be using that over and over and over again very powerful stuff but I'm never going to have this reaction ,comma
because the book doesn't show in this chapter looking so well that's 1 reducing agent which took a look at some other types of reducing agents ones that they do show you in this chapter ones that they ask you questions about this chapter and ones that are left with questions about again at the time of reducing duty is hydrogen gas if I want to increase the number of carbon hydrogen bonds it kind of makes sense hiding against might be a region for doing that prompts me to ensure they were on a transformation is now keen In hydrogen into this hydrogen gas registered things under whom under the little flask under atmosphere of hydrogen gas and the products no longer has a double bomb that's what a 90 person might see as OCC don't want is gone is what I see where CDs to carbon hydrogen bonds that's what I see you know they're not drawn for you that's what it's there was not just the CEC demand is missing the to part no-smoking Irish now the make it taken out he makes with hydrogen gas and nothing will happen on the timescale of your word of the times here your undergraduate career you have to have a catalyst to this from an old hotel you about those catalysts secret constitutes secret traditionally right now but I'll show you just a little bit actually lots of catalysts that will do the things I will talk about that should look at the data received hydrogen gas very useful reducing easygoing wants the museum to another type of reducing agent it's come to this conclusion different but the question was can you use this victory belongs that the hydrogenation of talk about that later OK so that if you want to reducing our kind 1 of those who don't want to know what kinds we have a religion can do that region combination that's very different from this this hydrogen bombs and it looks like this it's sodium and I'm going to show you still geometry at least 2 soldiers but to make this work and sometimes I get little 0 here indicate that it's in a 0 oxidation states sometimes only that off important part is it's not to sodium plus cash to so impressed can I wouldn't do anything was not toxic and it's the reason this works because sodium metal wants to be Sicilian town and there's 1 and only 1 solid continues this and that ammonia yet of tons of excess among you there because they're is the source of the new dangers again added there OK it's in all talk about the actual shortly so here's 2 types of reducing agents were showing you and we use those throughout this chapter over and over and over again hydrogen gas and sodium and liquid ammonia and unfortunately we're not really going to use that lithium aluminum hydride on successful and interaction and look there was talk about this hydrogenation that's only call hydrogenation is the addition of hydrogen across a pipe sorry secret catalysts that was used to hydrogenation reactions on his palladium 1 carbon and firstly that out and then I'll explain to you what that is also the daughter of molecules and Ltd but is my molecules and the Euro draw my reagent usually of the hero in this case of distrust side side next to my house she conceded those 2 hydrogen ,comma cat across the CDC global bond and cash was used this we write like this we write ,comma palladium on carbon and I I like to write word catalytic there are want Street which things are catalysts in which things are still connected reagents you don't happen that the book doesn't do that this doesn't always do that on but I like to do that elected to always keep straight in my mind what's what's the reagent versus what's the cash because the region has been incorporated in the molecules OK so the product of this reaction looks like this and what's the important feature of of what has happened here it's not the 2 methods went out it's that the 2 hydrogen got added from the same fate unknown words this reaction involves a C in addition of hydrogen atoms it involves a situation so because the 2 hydrogen .period added from 1 phase and the 2 medals both have to be going in the opposite direction direction this is Amesville compound so if I drop I'm in the mirror images is identical so that the 2 levels going up and up to items going on that's the same model because it's means so worried I purposely chose this because I knew would give an a Cairo molecules hundreds of OK so what is Palladium on carbon if you just take charcoal in mind out just takes some charcoal and winding up teeny-tiny little particles with mass surface area and so the abductors pictures on a carbon particles and I took this off the Web conceded page there's massive surface area it's not just like us square blocks and all that service area provide sites for chemical reactions some very clever persevered out on deposits palladium all over the this these men surfaces of each carbon particle and that's what used for hydrogenation has so much surface area everything is occurring once on the surface of palladium and the common underneath is not really consequential just the high surface area particles what's essential is that its palladium is acting as the catalyst for action we will never talk about the mechanism for this reaction don't worry about the mechanism for candidates hydrogenation by police you don't need to know OK so let's go and talk about a different kind of substrate where we will great not every case gives you a diesel product so that draw attention accessory here that would not give your product for just a single oxygen atom that substance and I'll remove 1 of 1 of the 2 methyl groups and so and and on hydrogen across this it's not going to give me a means of product and this will give you date a chance to see how I would typically draw out my regions regions above the here and I put solvents below there so typically are married hydrogen about the euro another great catalytic palladium on carbon and again the book all right catalytic but what I do that I hope you do that but I would catch along did OK solicitude different faces of the soul of Sony would try to help you imagine edge on which and see if you're looking down at the 2 faces of old and new director of this this kind of fancy John version here in years you might find going back and then I had these bonds going forward and there's a siege to regroup this is what I would see something like this the point is if I were to look at substrate edge on there's 2 different faces that easy double off and so the hydrogen gas skinhead from either the top leaders of the bottom and so you will get both products of this reaction you get appeared in tumors you get the product for the hydrogen headed from the top face and you get beginning anti-American where the hiding had from the bottom yeah None of the drug so that should be siege so I'm not going to draw with other hybrid yes there's another hydrogen the guide added that the hydrogen that added to this bottom carbon it doesn't create a student centers focus focus just important when you hydrogenated and has 2 faces to the double bond deal hydrogenated both bases and you have to know what the security chemical consequences of that we we ask you want the exams are clearly indicates there chemistry in the presence of stereo isomers at the front page of arguments that this is an example of world where you will have to pay attention to those still of the potential formation sterilized OK to top and bottom face on where you can manage to just look at him and I think actor chapters especially after chapter tenure to be good at thinking about addition to top and bottom faces double ones
let's talk about something I'm not sure that's a limitation on but some things that you need to remember about hydrogenation and the 1st thing that I want to emphasize is the unique lack of reactivity of the double bonds and benzene ring I ask a question on the last examined where I had a halogen on the benzene ring and aren't you were supposed to recognize that no no colleges scoring a run on benzene rings never reacted very interiors and wanted to know and some people made a mistake of trying to do stuff with colleges on benzene rings will start doing Jesus into someone tell me actions the double wasn't benzene also don't hydrogenated under any conditions that we show those double bonds on reacted to hydrogenation some of the words I take this molecule might treat with hydrogen and catalytically human cargo then the only don't belong it's going to get produced here that will be reduced as the government's taken off of the bench in the 3 don't along inside engineering they just laugh at double bonds and benzene rings are super happy if you want double bonds their hearings to react to something unique super-duper powerful electoral files and will show you would electrify housing Chapter 18 but were not going to show super reacted regions until that so far you know nothing reacts with the double bonds of and we have to wait till chatted Tennessee anything different about them OK and there's 1 more there's 1 more issue I want you to look out for and that is Cardinal groups so I'm using pH is an abbreviation for a for a family group benzene ring on remembered the double bonds in the final group don't react with the hydrogenation conditions so that the treaty is hydrogen gas and catalytically Amon Carter In will end up having to wages across that and I'm not going to draw the beaches here on that I eventually just not cross poem crossed the double bond the is this is the main product it should get out of this reaction but you also get an additional product you it under certain conditions and this is not a reliable reaction you will reduce carbon young groups stand alcohols and it's not very efficient I don't want you to try to use hydrogenation of cardinals and so in other words all draw this general use this sort of theater and music can see another other words in addition to the addition of hydrogen gas across the city double-blind you're also going to start season edition the hydrogen gas across the sealed double about and that's not as easy it's not reliable you can reliably used that and that's why I don't want you to use it in a synthesis because you cannot possibly predict when that's going to be efficient enough to remind you that action on bill so you have to be careful there's choral groups in a molecule because those might get reduced by hydrogen including 1 ,comma I'm interested is because the book mentions this and I wish they hadn't mentioned by writing so much easier because I'm almost always it's possible to carry out selective hydrogenation now that the book is brought that up on and let you in on and that the capriciousness of carbonyl reduction by hydrogenation OK so benzene rings don't hydrogenated and worry about the disclosed double bonds super happy and superstition currently offers on the care and hydrogenation I'm going to be super careful when asking questions of the super careful when I ask you questions because I know you can't predict when current overdue when choose my questions for the exams and problems that wouldn't be super careful about which questions we ask that was not the joint position to try to decide whether Kerviel going to be reduced OK so CC double-entendre communication let's talk about your belongings and I am going to show 2 different recipes for the hydrogenated triple Lawrence and this good start off with a secret catalyst here Linda Canada you could also say Lindh Lawrence catalyst that to some but this year reaction and if we take is this alkaline here and we had to let my pen is running out of steam when just don't drawings on Soviet hydrogen again after this instead of writing catalytically among Moncada I'm on the right Lynne lot catalyst and this is the way I expect you to write cat list I suppose if you move cat period I would know that the creation of an underwriter catalytic than lot catalyst that's kind of redundancy people destroyed the like what is the lockout is actually a type played catch somebody found this you don't do some extra ingredients when you're coding little particles it's not carbon particles but but basically seashell calcium carbonate particles so found only in Queen and there also and other stuff that you can you can deactivate partially in Larkana so that it no longer is capable of producing simple CCW CIS this landmark catalyst can't produce easy double bonds look at that it's still there the product but it can reduce triple bonds and moreover it produces triple bonds so that you get a scene addition of hydrogen so that the 2 hydrogen and end up on the same side so if you want a generator system will want they use this landmark and I'll show you another reducing agent gives you the transdermal double the CIA important this is because was Canada's double bonds and stocks at the CCW want it never touches of the CC belong in there that doesn't react so the account of special for that don't worry about the structure of the analysts I will never that be used if he wants it but you can get through members it's a special type of palladium on particles In all you have to do is right and like this To get what happens if you take hydrogen in realistically carbon because you're going to have a hard time keeping the straight this is going to seem like the hottest thing in the world hydrogen plating on carbon political icon remember those 2 yes he can remember those still you'll be able to do it but it's going to be very confusing at 1st all you'll see the hydrogen gas and that looks that's the same reagent for the lockout was completely copper let me show you what happens if you take an all kinds and treat with hydrogen and palladium and copper so alcohol doesn't matter here I'm just trying to make an interesting subject so many very clear what happens if they had to equivalents of hydrogen gas and I throw and catch palladium cotton To
equivalent sliding and yes the trip along all the way down to a cane there's nothing to worry about that seen because it was his rotational bond will have mysterious centers there and because red into hydrogen which comes just in case you can see years those 202 is 1 pair guidance but there and then there's another on the same there's no I didn't the sold the light to to convert kind when I came on this is a great way to do just said to to call of hydrogen or excess hydrogen on and catalytic Moncada this is going to kill you because in the back of the people in the back of the chapter the going of all kinds of questions they ask you how to make this annually 1 such that I don't know
how to make Carter Carter lines like that will you do not encourage everyone's like these you know how to make the current ones like that and you know how having carbon-carbon bonds like that you take manage the premier announced kind and the you had some sort out poorly aligned units into action and so you know how to make those and once you want Israel know-how to make security not to make these kinds of bonds once you hydrogenated goes down and nobody can tell which bonds it hides it sort of it's sort of mosques which bonds you actually made new synthesizers molecule that's going to make it very difficult for you to do retro synthetic analysis and fear he how would I synthesized them so the hydrogenation makes the trip bond disappear and that sort of Wilhite this potential CC bond forming reactions were looking so frequently you're going to be asked to elegant problems said 1 exam I want to do the following transformation knowledge you do this and you won't be able to remember the lockout it hydrogen in some hydrogen is something and I can't remember what all I can remember is playing on carbon and what would happen maybe I could just use 1 equivalent I know just joined 1 equivalent of hydrogen and analysts all that that's not going to work you have to remember that a lot has estimated work here is what happens if you put collect candidate and cards and you don't put a lot of catalyst did not put landmark status here the problem is that midway through your reaction yes the candidate .period among companies start to do this this hydrogenation but midway in the reaction of playing ,comma will see a lot there's more centuries and will start to further reduce this as fast or faster than reducing the outcome sold stock to further reduce this all the way down to the arcane but now you're going to run out of hydrogen gas could only put into equivalents but this words are usually put in 1 of 100 guests at the opening of hydrogen gas then you're going to have left kinds starting material so this is what happens if you joined as 1 equivalent Hi it won't allow you to officially make it won't allow you to officially meet reality there's 1 in only 1 way to make that sets out the answers England lock out so you have to remember those 2 catalyst for hydrogenation of triple bonds and double bonds so I didn't reduces all CCW doubled tripled bonds Roslin .period countless only reduces triple bonds partly hydrogenated Street OK so what if you don't want to sit down I'll show you another region combination continues to get the trends capital want the system the other half the time when the trends of and so it could take an example that memory traitorous ensued between the looking substrate here because I'm bored with singing all kinds but the important point here is that have a system that is now being here and I'm going to show you a set of conditions that doesn't touch with regular out scenes from just like lockout doesn't touch regular outings this is a region combination the only hydrogenation that's the only hydrogenated all kinds and you don't have the book doesn't fault still accounted for the sodium but it takes 2 to Adams of Soviet medal for every trip along the tree-lined right and years something hydrogenation but there's no hydrogen gas and usually see reduction the important point is limited to hide regions across the triple what it will reliably give us the transit of on so this this double bond over your left side doesn't get touched this triple bond is now a training and have a lot and the 2 hydrogen is just that is 1 of news too so if you want the system 1 use hydrogen and a lockout if you want the transit of bond is Sylvia pandemonium and Keane's don't reacted stops once you get to the Al-Qaeda it won't touch sulking further never touches you don't now there's going to be a problem you and I promise you this will be a problem and that is that sodium and liquid ammonia this actually is the solvent for the reaction you normally among with a gas so you when these reactions in the hall this huge tank of ammonia over until his gold miners 83 dry ice back and you blow gas in it starts to condense to make this on this basically to make liquid ammonia as your solvent on it so in years but this looks so much like so you may you already know what so may might do this outcome might take this whole community treat this here's reaction learned the last chapter if I'd taken out climbing a tree that was Soviet-made mind that's going to be probably that To make a nucleophile that I can use stress injury actions enjoyed long periods minus charges here so you can find floating around sodium and liquid ammonia looks very similar especially because the book frequently draws sodium /slash along icy solely matter as United unanimously some majors then righted look so similar so you have to keep the straight "quotation mark I draw was joined the sodium is Regent above the air and the ammonia as a solvent because it is the solvent for this reaction so you have to get to work very hard to keep the so remember I just told you what happens with sodium ammonia and the book will always raise the number to geometry to next to the Soviet Union and that's required but and this gives you the transition on border of course only and it doesn't really matter that the 2 majors and treatments because there's teenagers on their red itself and so you could get the same product to hydrogen and then lockout since there's no there is no existence of system trans isomers eternal so struggle taking the strain sodium and liquid ammonia is completely different from sodium mind OK let's talk about how the mechanism for this reaction yet on the you need to know that this is the interrelated the stability the CDC travel warrant home on the low-level statistics now was not so the question is why SEC double not reacted somewhat on the purpose of the on so we have a lot out could you sitting there in the let yet that so the question is when this when the sodium being mindful that often becomes ammonia and so doesn't do this and the answer is no because it noted .period we have metallic sodium but many combat and totals EUR here to make it clear that this is solely a matter on and it is in the lab the sodium metal you know it's nothing like it's this is so soft metal were so you can are like so you for a table salt lake sodium plus and no point in time this reaction is there is the metallic sodium floating around but committed hold off on this mechanism and I want to clarify 1 initiated it that it's come up on the last problems the meeting this time instead of giving you anything new to try to clarify something that came up already the mendacity was something from the last chapter solely from Chapter 11 and it has to do with the hydroelectric nations concerning my hand is running out of steam of terminal to give terminal outcome so you have a system that looks like this and you treaties with 2 equivalent of so may not like that what happens typically under these conditions is as you generate a product which is in Hong Kong because sodium in mind is also a reagent for appropriation of this you're going to have problems with the silly and I never talk was very maybe I was lucky you very clever I never talked about turning while commendation internal kind but when you apply this double-elimination reaction to the eternal coming you have to worry that the solely in mind can come back and indeed deep-rooted this tournament ,comma and that's something she was 1 your equivalent of your sodium and you won't have enough left over to do the tunnel reductions so if you really want to do this if you really want to effectively convert this into this other kind which need to do is this you need to take account of the life style up and throwing 3 equivalents of sodium in mind To equivalents will Bolton the double-elimination and the 3rd equivalent will focus form and this a satellite and then you have to have a lot of work to be done and there were some problems I think on this happened about this that relate to this if you want you can also use this furnace and you reaction when soldiers right so I never talked about terminal out kinds installation process by election so that they can you want to do double elimination Jamaica longtime he needed 3 equivalents of sodium in mind and improving productivity and ended data that also gives you the option of using that terminals deficit life in August when we come back or not .period when you come back from Monday will talk about the mechanism for the dissolving of reduction but then will launch into some other types of I think oxidation reactions .period the Cumberland Center