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Lecture 14. Reduction and Oxidation, Part 2


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OK so I'm just over coal so you may hear me the noises election to and point out that the exam 1 regrade deadline is today I extend it until today at 5 PM so if you believe we made a mistake grading examined by who can follow the instructions on the drop box he log into drop box to look at your exam this instructions there on sewer I it's good start off just talking about so I got onto the 1051 on the website many of taking at the same time this I think most of you are taking the same time laboratory class compared to 1 of the and I saw that you guys were doing thin layer chromatography were TLC and ending opportunity to say something of more about the military did not get a chance to talk about during the this little but pretty lectures that I had on Friday so In this came from a blog that that I was looking at last week on written by a professor at the Denmark Daniel Sager and stick it in this body was talking about the generally talks about stuff that's going on and Latvia mentions that militants staying at this stage you may get a vanilla of the same kind of the military used putting your cupcakes the sugar cookies in your baking on and if you did to you then layer chromatography in the land use you put some little spots of compounds mixtures of compounds until the plate and then you did did it was all that about a year and as the solvent moved up the
plate carried compounds of the with it and the problem is you can't see most organic compounds they they don't absorb light the invisible to you need some way to visualize the spots that appear under TLC plates you can count on 2 of the 3 things in my mixture for things and I mixture so 1 of the common things we do is we visualize the TLC plates under a fluorescent lamp or a dip into an iodine chamber but by far the most common way that we visualize the compounds until the plates we take our Teal c plates this is not trying to scale the TLC plates smaller than this job and you did the Teal c played into this liquid and then you set on a hot plate to let it make a little bit in the solvent evaporates off in the heat causes the chemicals the spots to react at all they don't diffuse outer deplored the stay in place but if you're using a good thing you don't turn different colors and so if you want to make a deep stain that's very common in organic chemistry is a typical recipes take 6 grams of Milan's most labs have visited the lab yes it's exactly the same stuff you you mix it up with some ethanol and the thing that distinguishes this from the flavoring agent that you put in your food when you're cooking is that we had just a catalytic amount of sulfuric acid that this thing was not exactly the kind of no 1 could your food because of the acid catalyst on the list also but show what's going on with that With these tips things
so here the results of common dip stains I also founder of the Web some some pictures of dead stains this is serious cerium ammonium will date and it's usually used to oxidize alcohol concede there were 5 spots in Teal played around the mountains you can clearly see that right here this is composed of 3 different compounds and that mixture makes super-easy to see possible melodic acid is another common did disdain Diana true final Hydra zone is really most sensitive of aikido Donaldo hides and I don't see any yellow spots here's the public know about the key towns here that the militants staying right here and you can see just barely that some of the spots have different colors and I can tell the staying was old 1 of the big problems with the stain is that it goes bad very quickly your job liquid starts to get Brown over about a month and then you have to make a new batch so the wonderful thing about the nonsense the whole lab smells like you just pulled out on a dozen sugar cookies from the oven smells wonderful news no 1 staying on but nobody likes to remake this stuff every month so in practice very few people use understand because it's a pain to make over and over again is up potassium for magnate it's not sedated state it's very easy to see because the contrast by far the most organic chemistry laboratories this is the most common did stating that we use for TLC plates it's peer and seldom and the reason is it doesn't go bad as quickly as as Finland's smells kind of like almonds or amaretto on stilts in that way it's kind of fun to use for the 1st 4 years until you get tired of smelling a bigger is an example of a Teal c plate that was stained with the that hasn't gone bad debt so you can see the whole Teal c plate is not all brown it wasn't over developed and what somebody did as they took some essential oils from Cedar plants from orange lines from pine oil from spring soil and the spotted those oils on the TLC played and then eluded and then we did this in the tournament staying and warmed it up a little bit on a hot plate and you could see the wonderful different colors to see those different colors make it very easy to tell that for example here in on some says India Moyal you can see that there's really just 2 major chemical compounds in there if you go to some incense shop and buy diesel oils these are not filled with mysterious chemicals is revealed with chemicals that you can identify more for the most part you could re-create these oils in the lab using chemical compounds that you can buy on his pure flavoring agents you know there's nothing this mysterious about the kinds of chemicals that you find in during flavoring agents and fragrance companies in the same chemical compounds that we can draw structures of Einstein's smells wonderful spots turned very different colors makes it very easy to distinguish TLC plates I don't know if you need abstains in the camp 51 I'll be lab but he didn't you missed an opportunity to have the whole smelling like these wonderful cupcakes and cookies and stuff like that OK that's good enough to get back to our lecture because we've been talking about oxidation and reduction reactions which is actually kind of cool all the stains here oxidation Zurich ammonium litigators oxidative possible aghast oxidative potassium manganese and oxidative stains and so let's talk about reduction oxidation reactions on In the context of mostly of seasoned loans but they may try to pick up where we left
off on on Friday we were
talking and so this is just a reminder of the last thing we talked about on on Friday "quotation mark took off so you might remember that I showed you this method for an end to wages across an al-Qaida 1982 different methods for hydrogenated in our time actually 3 so he won over enough but now kind of all the way down to mail came and use hydrogen and played in the car but if you just want to ages to an alkaline and stop at the Albertine the media's Lindh large catalyst h hydrogen gas and large catalyst to have the 2 agencies but if you want to have to adjust trillions to each other so the 2 regions you have any antique relationships and know this empty relationship yet use other recipes sodium in liquid ammonia the literally use on low-temperature ammonia as a liquid solvent for this reaction and so the book typically draws up like this OMB which makes it very easy to confuse with sodium a mine that super base sodium and liquid ammonia is nothing like Sony in a mine sodium in liquid ammonia is for hydrogenation reactions and specifically hydrogenation all kinds it's too and talk about a mechanism because I don't want this to be a mysterious as to what's happening with the sodium in liquid ammonia so we can see that it's utterly different from sodium in light so the mechanism for that sodium and liquid ammonia production in order to appreciate what's going on with the solely in the government when do something very very strange that I don't really expect you come to appreciate until we get chapter 15 some going to alkaline here and what's important in order to make it understandable what's going on with this summer With this al-Qaida reduction I'm going to a resonance structure of alkaline I'm going to take 1 of these bombs 1 of these pipelines in mail coming and going Split that bond and give each 1 of these carbon atoms 1 of those electrons so called 1 of the electrons from 1 of the triple once here in another 1 that's a resident structure didn't move any of the Adams all I did was partitioned the electrons in 1 of Alonso each carbon gets 1 the electrons so now that you can see that each carbon in this residents depiction each carbon army has a single electron you can see where I'm going to put the electrons when add sodium today since you been chunks of sodium metal Interior Interior very cold ammonia solutions will all go and psyllium here 1 when I'm talking know like a little 0 year usually to distinguish them from sodium plus I noticed a lot of of were not super religious about putting those plus charges on sodium atoms were lithium atoms when you draw mechanisms and I want you to all put charges on metals so in this case there is no charge means sodium has a single electron it's trying to get rid of sodium wants to be sodium plus it's desperate to get rid of these electrons and so it doesn't dumps its electron and there's no error wishing I can use to show this we don't have In in our area pushing formalism we don't have a way to depict electron jumps Sicilian onto 1 of these carbon atoms and so you simply have to imagine how that happens so the redraw on my story material here and what I'll do is I'll drop 1 of the electrons that was on this that spare electronic the sodium all parable over for years and as soon as I have a little here on a carbon atom that has had a negative charge it's not clear and it doesn't really matter here which of these 2 carbon atoms Stickley electron so here's my negative charge a year In my sodium Cat Island will be floating around here is an A-plus would like to keep track of that now because carbon ions are Super Duper basic super powerfully basis they will reap a profit of ammonia nothing but a Caribbean and I can do that so here's my ammonia solvent liquid ammonia floating around now and I can use their pushing for this because this is to electron chemistry is just another nothing but an acid-base reaction so deep-rooted made that the Crotona this allows only 1 of my 2 carbon atoms now so this is now just a regular help the carbon and up above my head is very strange still looking carbon with a single electron is desperate to get a hold of another Elektra write those that carbon atom now only has 7 electrons so it's missing in action so we continue the mechanisms along comes another sodium atoms it would really love to get rid of its it's extra electron that's supposed to be a little 0 superscript there to indicate that the charge on that sodium atom 0 arms it's carrying an extra electron to dumps its electronic international air operations can depict for this it dumps its actual electron right there so the cardinal it's another Sakaba online car and skis beat and another picks up an extra protons so carbon I'm just super basic nothing else can rebut program of Vermont the Socialist proton transfer reaction and it always promenades so that you get the Trinian's double-blind Falwell's because no exceptions to that this is a complex mechanism him in it we're going to cover radicals in significant detail only get Chapter 15 not out so the everywhere you see these unpaired electron just single electrons on that radical chemistry and we'll get to that end in a 2 chapters from now OK the main point here is sodium in liquid ammonia is nothing like sodium mainline sodium a mind when you put that in reactions related you're using it as a base to rip a proton off of something no 1 cautionary note that I'm giving you hear is that the sodium liquid ammonia reactions are not compatible with carbonyl groups the benzene rings so if you're
trying to do some sort of a synthesis of ask you how do you take the starting material and synthesizers other things don't use sodium liquid ammonia their affair carbonyl groups of benzene rings it in your substrate Tom because it will destroy them and I'm not going to show you what happens to them it's not only in the context of course genius for this so dissolving metal reduction that's if you want to try and out Keane from Malcolm it's talk about lithium aluminum hydride lithium Tetra 100 aluminum was a reagent that I mentioned you're going to use to add ages to carbonyl groups when we get to Chapter 20 you do that over and over and over again it's going to be very powerful there is 1 reason that they show you this far reaction because really all you know is there someone 1 innocent you have now and if they show you this reaction of S 2 with lithium aluminum hydride This is not really the most common way that it's used on but because the book uses this reaction so much over uses that I'm going to talk about it so here's the way you use lithium aluminum hydride I'm going to enumerate the steps because the last thing in the world I would ever want to do His makes for water directly with my lithium aluminum hydrate so step 1 is you and lithium aluminum hydride the the intact 100 eliminate 20 oxide if you want a cleaver carbon-oxygen bond with a hydride ENI and this is the region that you use and then stepped to we have to prove me Carol Cox online and on brought a mechanism shortly by dumping in a town of water if you leave the numbers out the numbers 1 and 2 it doesn't matter that he's kind of Roman numeral numbers or Arabic numbers either way that's fine and I usually use a little Roman numeral numbers from when the intention is not to isolate after the 1st step so the product of this reaction the threat deceptive here and why it's deceptive because you can't see what has just happened in this reaction I just made a I don't know what you see when you look at this maybe you see that there is a carbon-oxygen bonds missing that's totally obvious but what you can't see it maybe not so obvious is that I just added a new carbon hydrogen bonds a little .period hydrogen that I just threw came from the lithium aluminum hydride it is essential that you're able to see hydrogen atoms that are drawn for you so let's talk about the mechanism wanted this lithium aluminum hydrate is doing so good draw attention hydrate illuminate counters and I'm here to take traded for bonds to aluminum and negative charge so there's might have tried to we'll talk about as much more in Chapter 20 when you get to camp 51 C and there's a lithium Carolina's floating around totally inconsequential for this on the court-appointed that negative charge the aluminum and the long bonds to aluminum aluminum is a those long bombs to an ionic aluminum and make those bonds nucleophilic so this is looking for something to attack industry member during the just-ended not just barely landed enough 2 elected to innocent to reaction and it always react similarly stated position it's just barely reacted enough to pop that opened by attacking on the lease ended position and there's no way whatever attack at the more hindered position so the intermediate that can generate and Allcock signed and once we get electrons that oxygen and notice how it doesn't touch this other either normally Thursday would never reacted to the the loan hydrologists estranged remembered really is the only country just barely has enough bring straight through yet the carbon-oxygen money was there before the changes scarier chemistry or break that carbon-oxygen bond and I've added a new ch fond of it can't resist drawing out here you know I would typically never drop you still have your lithium can and floating around so distraught that you can see how the charges bounced out so now after this reaction has been stirring for a few hours sometimes you have to heed these and great reactions but after your reaction is and for a while now you can come along and do your work and you have to somehow neutralize this seeking extracted into organic solvents and so that's when we come along with that an excess of water just off the town of water in there and at that point it's just on a proton transfer reaction is nothing spectacular on about this so normally with the Proton would be from passed back and forth but if there is an excess of water principal tells you that is pushing the 2 bp dump a ton of water in there all the protons and upon on alcohol OK so just remember Europeans Cleve normal carbon-oxygen bonds with lithium aluminum hydride is just a part sites and ads in the least hundreds of this OK so we're done talking about reduction reactions and for the rest Of this lecture in the next lecturer talk of oxidation reactions and it's killing me because the book starts with the maybe not totally most boring ones but it saves the best for last nite I feel kind of Nancy because I want to get to these chromium chromium observations with most useful oxidation reactions you'll see in this chapter they say that for the end but keep talking about double bonds are going I'm going to talk about some important features here and the women going to start off for use of start by drawing out a very typical reaction here where they take on some sort of an Al-Qaeda like this and then I'll draw this the way the book draws in the book is going to give you a reagent looks like this and it looks so seductively similar to something that you've seen before which is a carboxyl gasses that you might not notice what's going on here and so I want to talk about what is this bars C O 3 business we've never seen anything like that nothing universities like pretzels talk about that and the way by introducing the idea of compounds that have oxygen oxygen bonds you seen those before casinos in the case of of hydrogen peroxide which was used as a work of art form from boring reductions so I would call this functional group break here some anything with this week oxygen oxygen radical peroxide as soon as I see it come around with the week oxygen oxymoron my 1st thought is Oh my God it's going to explode that's what carbon that's what compounds with oxygen oxygen months do but there are a lot of explosive and dangerous explosive compound used by terrorists that have oxygen option bonds oxygen does not like sharing with other oxygen OK so let's talk about the R A C O 3 business right here this is called a proxy acid so this is the basic structure for for a carboxyl aghast if I put a proton on there that's just a simple carboxyl gasses but they do there's a 3rd oxygen atom in a proxy it looks like this and that is now very unusual you haven't seen anything like this so proxy acid region specifically the specifically that we use for making peroxide upon oxides so you you know already 1 reaction from making up oxides that's taking a hybrids and treating them as sodium hydride learned that back in Chapter 10 and obvious and new reaction that it once did allegedly taken out Keane's Stanley Cup oxides of next very powerful this is called a proxy acid a proxy also knows that little 3 there and watch out for that when you see somebody use that is region on a proxy as it has this very a mysterious sucking oxygen margin now I'm not going to draw sealed 3 h you are couldn't theory be all kinds of different functional groups it could be a methyl group in other words proxy a seedy gas there's 1 and only 1 common proxy acid that you will be exposed to this quarter and really and this is the most common regional using organic synthesis and Marlatt another so it's not
just any old all born there it's a benzene ring the panel ruled on whether chlorine atoms in a very special position and I think we were not ready yet to talk about the naming system used to this I'm simply going to have to tell you that this is called Little and I italics CPB madam quarrel proxy benzoate gasses if you're desperate to know that I'm not going to write that down because I am not ready to tell you what Medellin's I'm simply going to tell you the abbreviation for that particular proxy as citizens PBA so in other words up on top here you don't necessarily have to draw ROC 318 factor that don't think I will ever do that again from now on I'm going to simply write a little and I italics CPB as my abbreviation for a for a proxy access and I expect you to know that that's useful for 1 thing in this course and that's to make oxides talking just need to remember that talk about on some reactions because I don't talk about the stereo chemistry I totally ignored that in this simplistic example and we need to talk about the stereo chemical implications of this of oxidation reactions using MCP so I'm going to start off by drawing this very simple helping right there you can see that it's got to substitutes an Al-Qaeda fennel group and methyl Rubin Eritreans to each other and if the transit to each other the the starting material when I epoxy rises with MCP like that they'll still be trained to each other when you look at the new Wilcox entering its form to his manual Parkside rate and if the family group was going up this is somewhat arbitrary then the method of testing going down they were on opposite sides of the double bond on behalf on opposite sides of the three-member group now you get the into chairman that already last fall actually draw for you book threatened to draw dashed and then the other product and you get an equal amount is Indian into psychologist written plus here OK so in both of those in anti-American products the fennel and Amapola are hands to each other just like they were in the starting material so that we call these reactions stereo specific 1 1 isomer like Sister transited gives you very specifically a certain kind of isomers surgery so if I take this is a summary of the same starting material noticed the metal in the final on the same side as ages here I have drawn those on the same side of the treat this with the same reagent and CPB the only products that I get the tumor they only get the product where the metal in the fans are on the same side of the three-member epoxy great multitude plus just I'm not going to write the hatched with a final on the floor hatched good OK so it's very specific sought by asking how to make this a part said to substituent from the same side I expect you to know that the starting material has to the panel and the methyl group on the same side England a practice that has to be good with that kind of scary specific transformation thank you in order to help us see the consequences of this mysterious chemical consequences of this approximation I find that it's always helpful for me but especially at this stage of your career in organic chemistry To help me see all the hydrogen that are attached To the Commons that form bonds sometimes it will really help to explicitly draw those in so I treat this with them CPB I expect you to account for scarier licenses I say that under instructions to my exams clearly indicate stereo isomers and the formation strategic centers things instructions like that so in order to clearly indicate history chemistry what I want to notice that there was a hydrogen atom over here at the beginning and I hadn't drawn out in and might help you to draw those and what I want to know is is that the family nature on the same face since I just don't want therefore they have to still be in the same faces the loss inside the epoxy until the product begins this but the encourages created 2 new sterigenics centers and I expect you to draw stares chemistry that the excuse me so that the point is that I can tell mounted by drawing like this what the stereo you may want to draw this oxygen atom here with adapted from going down or going down you don't have to do that good job that more ingenuity there go but just by having the agency found out that ambiguous because the Parkside ring defines a plane in in my sheet of paper case was good talk about another way to oxidize double bonds see in all kinds of well you know too the main types of reactions for reducing double bonds hydrogenation reactions in that liquid ammonia reaction for all kinds of but we have many ways to oxidize double once there's actually a larger number of different regions this could talk about a completely different type of transformation and this is similar to a kind of transformation you can accomplish using on bromine probiotic concealed to a actually oxidizing regions you know we didn't put them in this chapter to good start off by talking about this transformation and that is how is it that you might get from this outside Qaeda and I put a bold area this is not necessarily 1 step it could be multiple steps in fact you only know multiple steps ways to do this and so how do you get to this so the way this is were oxides can be really valuable and you know a way to make an epoxy intermediate would allow him to get to this In 1 and DVDs kinds of synthesis problems small potentially multistep said problems there's no 1 step away that you have to have to do this reaction and so the challenge here is to ask yourself how many different reactions joined could put 2 oxygen is next to each other and so 1 reaction that you might know is that you can take up and treat them with nucleophilic hydroxide and this this particular epoxy had chosen this century because the Parkside is Meza so it doesn't matter where they draw the oxygen hatched going back or wedged In going for the same molecule the mirror images so you treat this with hydroxide ENI after solvent or you you can enumerate the steps is 1 and 2 that would give you the same result in this particular case so if you treat this with sodium hydroxide and open this up so in this case it would give this question getting into added this reaction you would then need to figure out how I to make the Parkside and this is where the MCP PBA really become valuable In other words you don't have to make a run and treat the Bromo with sodium hydride in a single step you can make that up oxide so I expect you to know that we take a pox you treat them with hydroxide and this particular this 1 specific reaction you can draw this either way because it's OK to have water water doesn't decompose so he might drop side if hydroxide calls a program of water you get back another hydroxide if you'd like to enumerate this the way we've been doing that would also be but for sodium hydroxide he then in water won't have to enumerate
those 2 regions that the substrate for you could write like that OK see you need to know that when you open up oxides with hydroxide and you get trans 1 2 dials and the reason why it's important to focus in on a functional group transformation is I'm getting ready to show you how to put to and to our calls to a drug-treatment system each other With assist relationships when you start with the double 1 1st talk about that because it's a completely different type of transformation to end up with the 2 hydroxyl groups history
this 1 and so here's my super-secret reagent that we're going to use it's called Bosnian Ted trioxide and in practice we really only use this in catalytic amounts here's a recipe catalytic oxide and Eindhoven animal you don't even need to know what animal with and that more fully an oxide spelled it out for you but I'm not going to draw the structure you need another structure because I'm not going to show the mechanism for animal does reaction this is the single most common way to effect this transformation and when you apply this reaction against in 1 step not to step so it adds both hydroxyl groups system each other and that's magnificent a single
status symbols pair of regions just 1 recipe and you can add to a drug so if you need to make the trains dialog with the 2 hydroxyl groups on opposite sides you have to make the approximate 1st and then open the apart so if you want to make a sister died at all then use this recipe catalytic housing and Tektronix I come in it with within an and knuckle more fleeing an oxide history I think we all agree that it's easier to write and I know that future squeeze in and Nestle more an oxide underneath underneath the USM 2 trucks so they could draw Marshall mechanism for years and really I'm only going to show you a mechanism for the formation of carbon-oxygen bonds because that's the bottom lead you to desist stereo and configuration of the 2 new oxygen atoms and where to start out by attempting to draw that Al Keenan said or any help he said John for a look at that keen so the stand on the edge those 2 carbons will be going back more and more and sticking out forward out of these 2 hydrogen Adams that I'd never drew on my substrate that would be a Cissell keen and you come in with us trackside boy had made a lot of room soldiers squeeze stuff in here I drugs looks like this is Bosnia and there's so as news operators transition metal so obviously there's no architectural for on I can have 8 Bronze stars mean easily in years those oxygen atoms the before oxygen announcement to drugs and they're all double bond in oxygen and I have no simple way to represent this but its territory he dropped and so it is I mean to track saying goes flying around in your reaction Neuchatel eventually land on top of on your Al-Qaeda substrates and you'll get a concerted cycle addition reaction that nucleophilic CCW tax 1 of these weak housing oxygen substrates were words the oxygen bonds that breaks and goes down as there's no way you could have guessed that and then there's other oxygen attacks the leftover carbon that's that's now losing part of its CC don't want but the cycle additional actions of five-member during the transition state and the product that you get before the animal comes along I guess I should call it an intermediate intermediate is something called an Osmond Esther will never see this again it's not really important I just want to show you why you always end up with this CIS relationship so the intermediate could you get still has been ages system each other because that's where they were in the substrate and because there are groups were system each other in the substrate the and the like that these are the 2 means oxygen double bonds still there so this is an that forms in the reaction call this size meet yesterday no that's not the final product in reaction to the final product inaction has to hydroxy groups where there was a where there no helping before that and I'm not going to talk about the mechanism for how animal does this animal replaces the Bosnian oxygen bonds with the wages that's what the animal does while the reaction is going into regenerates asylum in Jeddah oxides we can go back to his more substrates and salute the important point is that relative to where the double 1 of the 2 hydroxyl groups and up on the same face of the double bond with 1 so you don't need to know the mechanism not to say don't worry about this and don't worry about that mechanism about the mechanism for to trucks OK very powerful and very powerful transformation and again if you want to if you want to get the trains style with the 2 hydroxyl groups trains to each other you have to go through a two-step procedure where you make your pots and then see PDA and then you open that up with sodium hydroxide but OK let's let's talk about stereo chemistry here because 1 double bonds have 2 different to them we have to pay attention hysteria chemical consequences of reactions that form on potentially to history Janik centers so it's very carefully measles substrates and I'm going to continue Johnny's of substrate here but in this case the top and bottom face because I put the Neville group on top now the top and bottom faces the wonder no longer equivalent the top faces the same phase where the metal group sticking up from the bottom phase this double bond From doesn't have enough of groups sticking up on their face so fine .period my reaction conditions for you here for a diet hydroxyl Asian catalytic Osmond at trackside my real oxidant and that's the way we draw line it's not step 1 instead to it's just all mixed together I have to pay attention to the fact that there's 2 different faces to the soul of the 2 hydroxyl groups will add both from the top place from the bottom place so 1 product altogether the 2 hydroxyl groups and from the top place just like the methyl group is on the top face but you also get a 2nd product out of this it's not an anti-Americanism easily compound because your plaintiffs in doesn't change so the other product to get the 2 hydroxyl groups and from the opposite faces of where the methyl group was sodium double wanted to faces when you do dialog selection reactions in most cases you generate new strategic centers and you have to pay attention to that and in this particular case these are dire streamers into you couldn't write plus you can write plus we never do that in my class OK so pay attention when when there's a problem because double bonds have 2 different faces to but there are some who let me show you 2 different ways that the book shows you for doing this reaction an senator comment on why don't do it this way it's what the book is going show you they're going to show you to step sequence using Osman to drop site is step 1 and then a step to use a different kind of of reagent instead of an hour it's sodium by "quotation mark by sulfate that each desultory in water so this is what the book does the book says you take you out and yet 1 equivalent enlargement at trackside and then when your reaction is done you monitor monitoring with TLC until the Al-Qaeda gone and then when your reaction is gonna dumping sodium by sulfite an H 3 onions it's not as tho Fortis 0 3 the and this is the recipe the book uses over and over and over again no I don't actually that because no I know does it this way no Canada that that way because Parliament trucks super-duper expenses we only do these reactions were have catalytic amounts from of a Bosman to track said because it's so expensive and so that's why I'm not going to show you that way but when you do the sampling problems you have to worry about that the is that is and different well because the book I don't know why they show that nobody does this Parliament and here there's a 2nd edition you from making us hydroxyl groups and it's a 2nd reagent this is actually originally used for dips for TLC plates but it's totally inefficient so the book shows that you can use potassium manganese To do that same oxidation to put hydroxyl groups is to each other I don't know any canister does this the yields are never better than 60 per cent you get a lot of of by-products and that reaction so you may find some problems in the backs of the chapters that use these 2 different region combinations for making says October which I will never ask you a question on my exams uses those on no chemist uses those in laboratories not official reactions or else they're expensive wildly expensive with wasn't to trucks and so on soldiers but not on exam but you'll find in the problems in the back of chapter and I want you to work the problems every problem the backup OK so that's it for today OMB we still have just a few more things to talk about fact we haven't gotten to the best reactions these chromium oxidation in chapter but we'll get there late on Wednesday and finish the job
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Formal Metadata

Title Lecture 14. Reduction and Oxidation, Part 2
Title of Series Chemistry 51B: Organic Chemistry
Part Number 14
Number of Parts 26
Author Vranken, David Van
License CC Attribution 3.0 Unported:
You are free to use, adapt and copy, distribute and transmit the work or content in adapted or unchanged form for any legal purpose as long as the work is attributed to the author in the manner specified by the author or licensor.
DOI 10.5446/19483
Publisher University of California Irvine (UCI)
Release Date 2013
Language English

Content Metadata

Subject Area Chemistry
Abstract 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: 00:09- Vanillin Stain 03:16- Various Dip Stains 06:53- 12.5C: Partial Hydrogenation of Alkynes to Alkenes 08:23- 12.5C: Dissolving metal reduction 13:58- 12.6: the Reductive Opening of Epoxides 19:00- 12.8: Epoxidation of C=C with mCPBA 23:28- 12.8: Epoxidation of C=C with mCPBA-stereospecific 25:59- 12.8: Epoxidation of C=C with m-CPBA-draw all substituents 28:06- 12.9A: Two-Step Anti-Dihydroxylation 31:51- 12.9B: Syn-Dihydroxylation 37:33- 12.9B: Syn-Dihydroxylation, Slide 2

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