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Lecture 10. Alkynes, Part 2

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Lecture 10. Alkynes, Part 2
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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- Gatorade to remove controversial ingredient 02:36- Soybean oil vs. brominated vegetable oil 05:20- 11.2,11.3,11.4: Names, Properties, Examples 11:00- 11.5: Make Alkynes Through Dehydrohalogenation 16:48- 11.5: Super Basic Condns 22:29- 11.5: Make Alkynes Through Dehydrohalogenation 26:38- 11.6: Alkyne Reactivity 30:54- 11.6: Alkyne Reactivity, Slide 2 34:13- 11.7: Addition of HX to Alkynes 37:17- 11.7: Addition of HX to Alkynes, Slide 2 41:24- 11.7: Addition of HX to Vinyl Halides
coca cola power Drink type grade oil Arginine ether firm formulation cancer man Clenbuterol ingredients van Computer animation Gamma mixing Fettemulsion AdoMet stuff orange
Digital elevation model chain unsaturated Calcium hydroxide chemical molecule Dreifachbindungen Alkalinity polarity Eliminierungsreaktionen toxin Coordinating European Council for the Development of Performance Tests for Transportation Fuels, Lubricants and Other Fluids organizations surface oil properties chemische Reaktion complexes stocks firm end van samples coupling Gamma compounds heavy Brom oxygen Fettemulsion History form bottles stuff Pipette Kohlenstoff-14 bond biosynthesis density chromatographic sprays case man flow Magnetometer terminal control orange amino acids Propan storage level atom modules processes Drink power Alkyl Groups hydrogen bonding carbon Amrinone water Heck Reactions Natrium agricultural Drops conditions Computer animation function Biogasanlage Grease (lubricant) chemical structures mixing basic Mindestzündenergie Butane
Digital elevation model Bohr secret Stahl chloride set chemical Potassium Alkalinity race Meeting/Interview benzene rings Eliminierungsreaktionen toxin period Oxide basic organizations Double bond chemische Reaktion firm end OH- systems van Optische Untersuchungen Gamma compounds Alu element Brom form bottles Antimon sense Kohlenstoff-14 biosynthesis mechanism damage HCl factors man age Invar Magnetometer temperatures terminal Essenz <Lebensmittel> control report tool level mixture conjugate Halogene chemical formulae type Färben areas Bromide carbon proton Biodiesel charge water Natrium Wasserstoff conditions function substrates basic AdoMet den ammonia
Geochemistry mechanism chloride case Hydroxyethylcellulosen chlorine man Potassium Magnetometer sulfuric acid Eliminierungsreaktionen Halogene oxidation weight type oil Double bond Bromide steps carbon Katalase chemische Reaktion alkenes firm Cocaine Hydration water Natrium van Computer animation Can (band) Brom stuff
Halides vinyl des Hydroxyethylcellulosen chlorine chemical Dreifachbindungen Alkalinity Isomere Altbier Insulin core Halides Substituent organizations Double bond Maische alkyl steps Katalase chemische Reaktion cancer stocks end Germinal center van Säuren Optische Untersuchungen Gamma compounds By-product Pipette stuff ethyl bond Kohlenstoff-14 biosynthesis Candy Geochemistry activities mechanism HCl Substituted case methyl man Vinylgruppe reactive Magnesium age terminal Common sulfuric acid lithium mixture Halogene processes type metals Arginine Stickstofffixierung carbon proton chip alkenes Methylchlorid Hydration cap Natrium Computer animation function Dipole Moment Can (band) Pinot noir substrates basic Satellite DNA ammonia
sodium hydride mechanism HCl Bohr growth Substituted complications chlorine man molecule islands lone pairs electron Magnetometer Isomere cell nuclei atom period Halogene Halides areas Chlorethene nitrogen Double bond rates Sauerstoffgehalts carbon Katalase proton Organspende Electronegativity stability lone pairs Eisfläche van Computer animation materials Gamma compounds substrates oxygen Halogene form atom
I here we have an exam on Friday just reminded us of all of you know that is studying all weekend and are continuing to study of so there will be assigned seats for the exams all pose those on the grade book later today if you'd like to request the left-handed seek show up 10 minutes early and talk to the TA here who will have a seating assignments and they can do something for you on that means bring your idea because we assigned seats will check goes on and on forget that and there is no discussion section on Friday so fewer Friday discussion section and then try to make it 2 1 of the other discussion sections this week and again we have extra office hours this week check the website check those of extra office hours are 5 extra office hours today for example instead of just the stuff on OK so well but he liked to talk about stuff that I see in the news that relates to organic chemistry and on a series of restarted article on Gatorade the probably drink Gatorade sometimes they came up with this I'm not really an expert hearing this newer version that seems to be having natural ingredients as opposed to the total totally synthetic ingredients in their regular mix on the wall fascinating is the story is about them taking out some traditional ingredient that they've been using their formulation called brominated vegetable oil and hear the word of the words brominated turns me on that something interesting is going on there ,comma so apparently there's quite a few other types of beverages that contain brominated vegetable oil and I was totally unaware that and what they're pointing out is that the ingredient is being used as an emulsifier on dementia that's exactly correct but but you get the idea this would talk about what brominated vegetable oil is doing on In Gatorade or whatever drinks they're putting in there what was also fascinating to me is apparently this on the of Mississippi teenager was making all kinds of noise about this saying they alchemy putting brominated gradual and my drink that stuff out of so this seems to be catching on arms
was going on about what happens if you take a natural citrus fruit citrus oils and you mix them in with a drink but never taken orange peel and squeezed in sort of backwards you'll see seasonal spray cannot it's full of all kinds of organic compounds the taste and smell phenomenon and it would be great to make drinks where you can take advantage of those citrus oils and of course they do that on the problem with oils organic compounds as they mix with water if the you take any organic compound that exist in liquid form and you try to mix it with water the tiny little bubbles that form like an arm of the BBC delays Ontario these tiny little bubbles in the mix it really well all the tiny little bubbles are lighter than water organic compounds are less dense than water and they will all float to the surface and that's not very appetizing if you're drinking your Gatorade and all the organic flavoring Wales have risen to the top and forms of Watley she dreamed up in the 1st set so what they do is they put in ,comma a class of compounds called emulsifiers still make to spread out all the organic droplets but the problem is all these little organic crop would still have a tendency to rise because there less dense than water and so what can you do with your flavored droplets are less dense than water although citrus oils those organic compounds are rising to the surface some very clever person said well if we take so we been always sold his vegetable oil in the department in the grocery store and we were only that using only actually learned in the last chapter bromine is very heavy you've probably never picked up a bottle of becoming the 2nd graf realize how my gosh this is the star on when you brominated organic molecules they started to become more dense and heavy and brominated vegetable oil is heavily indebted got typical density from the stuff that they sell for these applications is around 1 . 3 grams per meal so when you mix this brominated vegetable oil in this during it goes into these little droplets in and you can adjust it so that the density of these little droplets is exactly the same as water so that all rise to the surface and so these delicious flavors of organic compounds the dispersed your mix on so they're going to take this out of Gatorade and put another dent organic molecules that are more oxygen is instead of a few bromine is on and interesting application I've never heard of 4 rumination reactions that you've been you've been drinking those compounds without knowing it looking so well we've moved on from Chapter chapter 10 which was the culmination reactions that just wouldn't cover Chapter 11 was 1 Chapter 11 so again the exam
on Friday will only covers chapters 1910 will cost the Wallabies S N 1 and to stuff from earlier chapters in of American history is always intrinsically cumulative but of course that the test will focus on Japan's 1910 no Chapter 11 Elkind stuff the farm there's no new stuff from Chapter 11 on the exam OK up so it's good enough wouldn't we talk about money on before we left on Monday what basically what said is without kinds CC triple bonds have on peptide bonds in them and they're going to act as nuclear files just like cc pipe bombs found in In this just regular outings that was good front end our conversation by by introducing a little nomenclature and not really I pack nomenclature on which is regularly "quotation mark just how I'm going to refer to these compounds will be stirred up by drawing 2 different outcome because there's an important distinction and want to make throughout this chapter also missed of the 4 carbon kind where the CEC triple bond is at the end of the al-Qaida and I'll compare that with another 4 Carbonell kind With the CEC triple bond is in the middle so for carvings that's butane but these are both you times right butane has no and saturation and this clearly has an all-consuming Red Butte tinier and the highest priority functional groups and Elkind armed and the name will end in I'm sort of an indicated this would be 1 of the tiny number of denying packing number so that the high priority functional group has the lowest number possible there would be 100 times so you wouldn't count the other direction and make 3 B Utah and over here it's it's arbitrary which side I start from no matter which side Leicester numbering from this particular time will be to beautify so that side-impact nomenclature and I think there's a couple of questions on the Sapling homework I don't have buy economically trying magazines but I might ask you a question why say synthesize the following internal kind or terminal how kind and those phrases I want you to know because I'll use them the kind of useful phrases so when it how would I distinguish this outcome and it has a CGT and personal kind has alkyl groups at the end to this week all the terminal time needed at the end of the molecule and there's all kinds of distinctive chemistry related to that so that's why I want you to know what the term while kindness and referred to them and this other 1 where there's alkyl groups to be ends in other words when now Our country belongs in the middle of a chain we call this an internal well I guess I want you to know that you you know that kind of nomenclature in case I a case of wrought riding on my overheads here and I refer to those terms OK so you know as far as physical properties there's not a whole lot office to say about all kinds of simply point out that that kind function group is this it's not like there's oxygen under some sort of elected negative ads on their Sukit expected that any alkaline function is not going to introduce polarity to a molecule so let me draw out a series of 6 carbon molecules there's hexane common solvent in organic synthesis organic chemistry but we use that on for chromatography specifically because it's not the soldiers right here hexane so we can compare that in it's imagine adding and how keen to that introduced someone saturation that would be kept seeing specifically 1 Maxine and not going to worry about that and I want a job for carbon chain bears 3 cartons for 5 and 6 carbons this would be 1 heck signs and if we compare but 1 .period to these molecules they all have about the same boiling point seems sort of arrange bowling points around 60 degrees for these Celsius OK so there their greasy molecules it had all kinds they don't they don't make that the molecule anymore polar on then than any other than any other current simple carbon-based functional group another way to resolve these sections in the book that talk about the naming about kinds are not going to ask you why you pack nomenclature the the property about kindness and there's not a whole lot to discuss as far as hydrogen bonding boiling points and then in Section 11 . 4 they talk about examples of all kinds can only encourage you to read through this section just understand why should I spend time learning about other kinds of arms and I'm not going to ask you to draw any of those structures on the exam on and I think they may talk about some of From the fraught toxin called histrionic attacks entering the birth control countdown final I but again I don't ask you to memorize organic structures complex organic structures just you can repeat them back to Munich focus of a lot of stuff in those 3 sections that is not really count the kind of stuff that I I want you to walk away from this class with I'd like you to walk away from this class understanding the chemistry of Adams and of organic molecules at the level of Adams and bonds sold stock about some chemical reactions to Hadley made all kinds of start off right out the here with a reaction that you haven't quite seen before we're going to do something to show you to different elimination reactions that you could use on it's Miguel kinds and so often this structure in just 1 moment and I'll show you a reactionary took a strong base and immensely powerful base so you can see about to isopropyl groups in between these 2 it's probable groups about 2 carbons and so it if I want to make an alkaline I can't just have a single bromine atom there because of a treat this with the base all that is an keen so here's 1 way to making all kinds you have to have to be ours so we can eliminate HBO are twice so we do to administer eliminations of HBO and we're going to want to use and powerfully basic conditions in order to make this happen and so in this particular case we have to eliminate HBO once and then twice a week and that all in the same part and so we're going to have to equivalent of a very powerful base sodium 89 and in each too and get ready to start using
that throughout this chapter why so we will talk about that it's superb 86 sodium he so that again when you can't see enough of drawing for you and moderates small because typically I wouldn't drawings hydrogen atoms for you but I'm just going to remind you that there's a hydrogen atom here and there's a hydrogen atom down here and so you're losing to HP archer Justin Toohey to eliminations will talk about this more and just a little bit OK so what's another type of substrate you can use to make an all kinds all draw another he lied here but and you could do the same to equivalents of sodium in my face and you know In terms of nomenclature you would call that damage sodium hammered but I try to emphasize with the word he might because there's another functional recalled and hammered and distinguish that so he irritates you just get over it and I'm calling it a nite this might see she you distorting the meaning like that and Simon writer potassium GB talks about the book writes the molecular formula the structural formula out but you'll find I'm going to start abbreviating the test the talks like this all expect you to know that there needs to to be toxic so true Beutel Cox II and well I might draw keep you owe potassium but this is destined to be talks that you've already seen a lot of now as we will see shortly attesting to the dark side is nowhere near as powerful as sodium and so whether the book doesn't not if you're trying to make it out kind with attesting to the talks said I want you to draw destined to be toxin is nowhere near as as basic as sodium a mind so I would like to draw heated typically the temperatures required over 80 to 100 degrees a little over 100 degrees so if we eliminate here there's too there's a 2 carbon chain dangling on benzene ring somewhere in the end the 2 carbon Alpine dangling off of that benzene ring and again you may not be able to see here where those 2 8 then eliminating HCl twice in this reaction here's 2 of the 3 ages on that on a carbon atom at the end so OK so to different reactions that you can use either 1 of these 2 to equivalents of sodium a mind for 2 problems destined to be talks don't forget to he that arm so you can see that these 2 types of substrates a southerly different so on the top substrate abducted the 2 bombings on different carbons on neighboring provinces and we a term for that when the 2 halogen join neighboring province this is what you get when you add bromine across a double bond so you already know how to make substrates like this we call this diver online that was and that means on neighboring province and down over here where the 2 had religions are the same car and we call that genitals a general diver online and I may use that terminology if I may say all of led to of HCl to animal communicator general died relied so I expect you to understand the distinction between a general I die he lied and this daylight you already know how to make this small died bromides just by adding year to across double bonds just like the brominated vegetable yes decor to whatever lies ahead but I said I don't bromide you're the gentle "quotation mark all periods have die chloride think you general chloride OK so let's talk about these 2 conditions we need powerfully basic conditions to diesel double elimination reactions mom 10 most powerful conditions are worth talking about 1899 basis or those are going to be super important found that sodium Maiga lifting me my basis when you get to Chapter 23 and 24 and in modern organic synthesis so I really want you to start getting used to sodium a minor look strange but this was going to take an example where were doing another 1 of these elimination reactions on and I wanted just focus in on this side so here would be yet 1 more example of doing a double-elimination Jamaican alkaline so there is my substrate and all eliminate HIV yacht from 1 side ancient br from the other side and let's talk about these fancy new conditions with the 2 equivalents of sodium in mind don't write accuse EQ don't write the cue for equivalents that means equation and that's the abbreviation for equation I didn't invent that system but have yet to write the Bequia all the way out the American Chemical Society decided on Monday that abbreviation system focuses on real wages synthesizing alkaline from this to carbon peace and this would give a terminal alkaline pretty sweet reaction I promise you that will be on this some form of this reaction will be on some examined in every single section of Kam 51 C so this these types of elimination actions totally money action and I'll explain why later it's so useful to make all kinds and specifically terminal kinds Gillis talk about the basis of these conditions and so what's the deal with tests until the topside and heat and what I want to do is I want to draw up a typical series of compounds /slash functional groups so you can talk about the basis city of those so let's compare ammonia that's pretty nucleophilic and pretty basic level chapter on means and ammonia coming up later in the book much later in the book the ground Chapter 27 on and I want to compare a series of of compounds that you may have seen used as basis and compare this with this might and I'm just come back over here and compare that with an 1899 there it is but it looks kind of like ammonia except for that
minors charged there so it's good and compare the relative basis cities here know all right this out relatives basis city you can get this by looking at the PKK is the conjugate essences of PK table in the back of the book just by knowing that the PKK of antimony mine if I stick approach and there's 10 and the peak water 16 and that I would know from that the relative basis cities of ammonia versus hydroxide in anger about 1 to a million so hydroxide is a million times more basic the pneumonia a million times more babies at a huge difference in basis city so so far in this in this book in became 51 you have been using the means is bases a lot that .period straight hydroxide canines have forgot to put this minus charge on TB talks over here and so how much more basic is TV Utah outside than hydroxide on it's actually a hundred times more basic so relative to ammonia TV Utah outside is 100 million times more basic ammonia the it's not just that it's scary relative to hydroxide it's also more powerful than a factor of 100 general at will if you ask a typical organic chemist about the relative basis city of hydroxide interviewed topside most organic chemists tell you all that's about the same basis as a factor of 100 richest that's nothing but talk about the relative basis city of sodium the people report said I think there's 20 doesn't matter how many zeroes I think there's 23 0 writing you can just wait attended 23 you won't get a sense for how much more basic areas so what I want to base a powerful based on having chemistry I don't go to the shelter and grab a bottle of TV oxide break a go by I go get some sort of a mining base so once you see that and now you can sort of see why I oftentimes it of hydroxide to be toxic those are pretty similar right compare that with United and so much respect the huge basis that even a minor is also more nucleophilic than these others but it's such a powerful based universities do nucleophilic reactions always grant protons 1st OK so yes you can use TV Utah outside too limited to make our clients if you want but I want you to heat it if you're doing it with sodium image obviously don't that you typically need to call those reactions town so they don't go exhaust Amoco you on while so powerful basis and will use it for 2 completely different reactions in this chapter sodium in mining OK so let's talk a little bit more about this Regio about this elimination reaction to Miguel kinds it's a to elimination reactions so they enjoyed a substrate for the general die chloride in there so here is the general like chloride functional group and you can see it all that carbon intensity to Hudgins on there there's an apple group on 1 side and a probable group on the other so far ,comma that means both sides are not equivalent so if I come along an employer might I'm so excited about my Super new sodium base and that's so a columns of sodium in mind when he in each to I'll get 2 different products out of this reaction when the jobless hydrogen atoms here just what can be clear about the fact that there's hydrogen atoms on both sides so ultimately the the reaction is a need to elimination reaction twice over ,comma so what's happening is that he might based on good drawl that in here I'm not going to draw the full mechanism His 1999 based Super basic house super-duper basic they can come in here and do any 2 elimination on either side and he doesn't care but here's 1 way it can you can go that would be the 1st elimination and I'm not going to draw intermediate but a mighty 9 doesn't know the difference since it seized 2 sets of hydrogen and it's not going to make any distinction between those so as a result let me redraw my 6 carbon chain here 1 2 3 4 5 6 what I find is people very often on you make a mistake in drawing out were how many carvings there are so I'm managers draw the triple bombing in all of this is distorted and I'm really ugly way I'm hurting me immediacy and how kind without 100 rebound angles but I'm just so adamant that you have some tool at your disposal that helps you to not forget to put in 1 of the carbons so they another 6 carbon chain so I don't forget to join in the currency union might have drawn the wrong number of carbon steel and yet and extra carbon so you have to the race that from your mind there other carbon atoms so you can't really stop this from eliminating the other way and that would be to put kind on the other side so you could have done another 2 eliminations of HCl if the 19 deeper than the other side in other words you would get a one-to-one mixture idiot I supra .period yet so far so that the question is why wouldn't you form this is a question that :colon Halloween on there's a secret to this reaction and that is that it's under equilibrating conditions and you'd actually get some of this initially on equilibrated to this and I'm just simply going to tell you don't worry about that just assumed in the form of whom never discussed and thank you for asking about that and so good question that does happen to some extent on capital and by sunrise over to the all kinds and you don't need to know anything about that OK so so there is this issue of regional control this is typically why I would never tried to use this reaction on To make an internal kinds it's this lack of regional control when you do elimination reactions from general died here lives so again if I ask you what's the product of this because they're basically in a 1 1 mixture is is no major product yet right both of them
that's all there is no major product OK so I just showed you how to make kinds you really got just 1 reaction that's W to elimination with either sodium in mind or
potassium to meet outside the OK so it's not about what you can do with our clients remember there were 5 reaction later that we learned of backing Chapter 10 wary added things to help teams we had HCL MHP teams weighted halogen like bromine like brominated vegetable oil and chlorine Cl to Keane's we need Brummel hydrants we did hydration reactions with sulfuric acid and water would entitle Mauritian oxidation were going to do for those reactions without all kinds were not going to do the Brummel Widener chloride formation but they're forcing reagents apply the same mediators to help clients on solid start doing the unjust walking through the same reagents hopefully some you may think this is boring it's the same stuff I did be OK but it's it's good practice to learn it again in the context of all kinds those guns office and it adds a little bit of a twist the fact that there's 2 pipelines on him in and out ,comma but this year the 4 cardinal kind the futile and if we come along to this and in this particular case under corner right to equivalents but HBO To begin at are across the pipelines of this outlined in the same way that you can manage your across the pie Bonderman and what you can be sure yet until we discuss it is where those 2 bromine stand so 1 of them will end up the more substituted carbon it's mark confrontation where does the 2nd bromine and so HP arm you can't quite tell my I added nature here all draw the that I so the 1st edition goes here where it is the 2nd HP Oregon and it turns out the 2nd stage you're going the same Regio geochemistry so you end up with the general died remind when you had to equivalents of hydro Haley across in our kind of about the Council to walk through the intermediates that forming this reaction on so initially what's happening with but England dropped them a mechanism for this to get started the London adding HBR across this double bond and I'll talk about the cat and the cargo so they're ready to be freaked out here Sunday just skip that mechanistic intermediate just momentarily after this 2nd edition of the AA-minus on initially were going to have this intermediate and the reaction that if you wanted to you could stop the reaction at this stage where added just 1 equivalent of 8 across this double that you had wanted :colon BHP or across the double 1 you could start displaying 1 if we want to become more common in the book they did you add the 2nd equivalent of HBO are To the general Dai bromide which you can then use to make it on constantly hydrology usually agents but it will come back to the car can find intermediate degenerate in just a moment and a freak you out like that immediately but it's going to be very freaky there OK so you
can add HDR across-the-board once you get into equivalent of HP across-the-board bonds and guess what HCl it's the same thing where I'm not going to redraw an example for you where you had HCl across a double what you triple bond you get that idea OK on and so that's 1 of the reactions were going to learn without kinds on the said another common reaction you might see over and over With all kinds it's related to the 3rd the debt-related that sodium and were just talked about 2 just general reactivity whenever I see now kindness to things I want to do that I want to add things across the Tiber once and I also want to convert it into a nucleophile so we can talk about 4 different reactions where adds the lecture falls across a double bond and then we're going to introduce 1 new reaction that's nothing like Al Qaeda chemistry and he that new reactions and it's a reaction that is specific to terminal all kinds of associated and you're going to use this and use this end users and overuse it ,comma for the next 9 chapters until we show you some really good nuclear files so if you take sodium mind you added to eternal time however I showed you could use sodium a mind to do with the 2 eliminations but of visible died reminded idealizes and general that he likes but if you have a terminal come it's already there and you treat it with sodium and this is such a powerful based this 1899 that it will ripped off this Proton from the end the draw that long yeah but minus here next 1999 plus annexed to the Soviet here's what happens remember how basic that sodium in 1990 has never seen anything like this before Wow that is powerful stuff right now and produce sure this is the only case so far were you have seen that we do impregnate any kind of a carbon atom in order to make a Carbon II nucleophile and that's the point of doing this is that is now card then I nuclear the sodium floating around and look at this the byproduct of that process is ammonia and you may be super attempted to want to pull the proton awful that ammonia and go back in the other direction but it doesn't work that way the equilibrium lies on the side Of this arm of this al-Qaida land I will talk about this it's called in a satellite and so this is what this is the point of this is your make on this super powerful currently about working to show you that you can use it to make carbon-carbon bonds will be issued 2 types of reactivity for our clients the triple bond itself here in Texas and nucleophile announced to things like R 2 HCl hydration reactions on and this other planetary activities would turn all kinds of candy proving them to make super-powerful carbon nuclear files so that you can construct on organic compounds you can use the way synthesizers very large organic compounds in Chapter 11 to 20 OK when we get to Chapter 20 and from then on you're going to stop using these guys will show you a much more powerful set but of carbon nuclear files were at carbon magnesium bonds and common lithium bonds on but until then this is all you've got and as I said the over uses that because once completed chapter 28 you're never going to talk about those again because that's what sort so much better the consulate's talk about this in detail let's talk about this edition of Ajax HP orange-yellow questionable once and I was I was afraid to talk about that cargo Caroline intermediate in but now I don't wanna be afraid to talk about that ,comma can intermediate so come back to that for carbon chain that I do before this is futile doesn't matter that said that it's a terminal all kind on remember we said these into Goma ,comma competition the motive of addition puts so puts the proton less substituted position and the nuclear under the more substituted position so if I brought a mechanism for this reaction by adding HCL so I think it's about drew the reaction I would draw each syllable the euro and the initial product of this rule of this reactionary Amir ,comma competition would put the house after college nuclear fallout at the more substituted position in hand and I'll draw the age there's 2 ages here from the drove 1 of them therefore you see conceded yet each year across the double senators of the claim doesn't end up on carbon 1 and ends up on carbon to focus 1st on Aero pushing mechanism here this reaction is just like our teens you use taken Aero India show that 1 of these 2 pipe bombs in the al-Qaida his 2 pipe bombs there the tax the proton acts as a base in deeper meets HCL and you can't tell where I'm going to stick that Proton yet well I guess you can look at the product until the draw that intermediate did the carbon atom that's left over there and there's the ethyl group sticking on you've never seen anything like this before right so that what's really freaky to good but 1 that look really freaky and the next you can guess what's going to happen on the next step here and there according and I'm floating around in it's going to come in and do a nucleophilic attack so all that you can get over this weird-looking Koble can intermediate this is just like we saw in the last chapter took out teams and added checks across the world so but let's talk about this intermediate we call this a final cat it's not called WTO reduced its talk about vinyl cat eyes because I hope you never drawn this before you do on this before now then it was a huge mistake on your part and it's the same idea if you had HBO are you also generate the same vinyl :colon intermediate come in but I don't want you get all excited about vinyl cat because they're very unusual let's talk about
Lionel Cann some this this vinyl cat I'm here talk about 2 potential approaches to make a final can I'm using a little docked there to represent the card thanks Madrona were people were told that only the feeling more comfortable OK so there is my vinyl Cannon intermediate and the way I just showed you to make those is to take some sort of an al-Qaida UK law groups on both sides of the aisle kind and you had H fax across the some sort of an acid and yes it could be sulfuric acid that program needs that this is not the same idea so this is OK and it has to do with the fact that and al-Qaida functional intrinsic instability and reactivity associated with that but here's what I don't want you to ever do I don't want you to everything that you can take some sort of vinyl here light into an S 1 reaction the majority -dash an undertrained and go home I just know that never saw vinyl he lies you never USN anyone and you never do anything to you not knowing mechanisms yet by which you can substitute a final here lies with the nuclear file so why is it that you can make vinyl from kind enough inviolability it's simply because our kinds are more reactive type of function but they want to react do things so I hope you already knew that and if not the leaders emphasized that how do you make vinyl cat fearsome substrates the on typical substrates that you're going to see in this chapter in incoming chapters where you're going to want to do chemistry "quotation mark allergens yeah put a tosser laid down their look at those great leading groups where but made such a big deal about what great leaving groups have are in chapters on 7 date that was the whole focus of the chapters and yet even although the great leaving groups when can you do this never others right no don't do that the can generate a lot of tournaments when can you do this now he never ever bogus what others benzene ring now died on the held by don't have to keep down so you have to resist this temptation here temptation will be probably haven't brain cancers than Monica Caroline's they form easily from many just when you provide al-Qaida you can't do it sent to reactions to Limoges super emphasize this that there is no mechanism of of substitution you yet know that allows you to substitute so in other words is not just as and when you can do you also can do as century on vinyl the alliance and it's nothing you can do chemistry finalized alive but not as someone innocent to business focus so far vinyl Caroline's no problem at the start of an alpine ,comma but don't try to do substitution reactions from and Duerson wondrous into on finally elect the special but this was stuck a little bit more about this Ajax's business edition of hydro hillock acids across all kinds and role may be more full mechanism here the cymbal taken internal alkaline and also at time but this time it's internal it's to too view time and so if we add I to equivalents of HCl as they just showed you before because my substrates symmetrical there's a methyl group on 1 side is methyl group on the other I don't have to worry about geochemistry issues I remember when you had a H X the 2 X is the 2 Haledon up on the same card and I'm not going to trawl whether to wages went to hope you can see that there over here and card to siege to you could also made the same product by taking the final here like if somebody gave you a line of the alliance said here you go here's vinyl you could also add HCL to that in relatively the same time despite having 1 equivalent of HCl so there's a of it that there's a halogen already have you already have a vinyl halide you can add HCl across that that I bought a case of stock about the intermediates and and I think it's going to go through the mechanism with the I was with the 1st edition of HCl across the doubled Monaco's 2 vinyl can find intermediate but the 1st edition will give me agency allowed across the double bond and you get a mixture of leniency isomers here when you add 1 equivalent of HCl you also get so this this has the priority group years chlorine and the high Priority group of this other governors methyl and those are opposite sides so this is the isomers right that this is the of the al-Qaeda and you also get In equivalent amount a busy isomer where the chlorine in the metal on opposite sides and that's because the chlorine attacks from both the sides of the vinyl caps on both ends of the people working on the Wildcats so you'll get a mixture of isomers that's not very useful and that's typically white people don't just add 1 equivalent of Ajax to an alkaline its internal because you end up with this mixture of isomers and who wants to get amateur licenses and that we can take either of these it doesn't matter which 1 they both reacted the same way and that a 2nd equivalent on the HCl me dropped the mechanism for additional that 2nd equivalent so now and we had that 2nd equivalent of HCl here's the mechanism I during the mechanism for the 1st edition and a it's the same narrow question if I use this year summer and the product you get out out of as a carbon can iron next to a halogen and we'll talk about that in just a moment here is that may look strange to was is happening is that a secondary cargo canon is more stable than secondary are less stable than secondary will talk about that in just a 2nd the next Friday attacks that cargo continents and that's why you get the general decor so again this 2nd edition of HCl occurs in what you would call mark on fashion again it will give them more substituted Koble and from an empirical point of view you can consider the coring just like an alkyl substituent and awards you generate them substitute cover can whether it substituted with methyl chloride OK so what's up with what would that cargo cat and as a halogen next door Stock about the
effect of allergens in general is a this Monday compared to different for carbon compounds at the time and if you take your time you react that With there is an addition of HCl across the double bond and I'm not going to draw the full mechanism there mom but if you compare the rates will what what would happen if I compared the rates of edition see get there as a product of this in this on this vinyl chloride here plus you also get the other isomer you get this the isomers well I'm only going to draw 1 of those isomers on lecture trip to see don't worry about that later good rate plus and this is the EIC mercy also get plus the ice is well the point is that if you got still have HCl floating around the next molecule of HCl comes along has to make a choice should I add to the Alpine starting materials which may stop adding to the product as it forms which is faster and it turns out that that chlorine has an electron withdrawing effect and so this 2nd edition the HCL is slower than the first one that's why you can stop adding 1 equivalent of H L across a double bond with the 2nd edition were faster every single out kind would immediately add a 2nd equivalent of HCL and you would be able to stop at 1 edition so on the 1st edition is faster the 2nd edition is slower so if you wanted to because that 1 opponent HCL and we'll just at once and you're out you can stop at a single edition again let's talk about that the Carbol can I to generate if you do you throw in a 2nd equivalent of HCl straw this cargo carrier and that the halogen attached there because I don't think it looks anything like anything you've seen before and want talk about 2 contrasting effects of that halogen atom on him to eliminate ,comma and 1 of the substitutes halogen the problem was with Adams like like Corina oxygen and nitrogen visitors to completely different in opposite effects and you don't know which of those effects is going to win in terms of cargo can stabilization I think the 1st and most obvious effect to me as the chlorine is lecturer negative you there's all these protons in the nucleus of chlorine that elected negativity is about as all these protons with a positive charge they all have positive charges in chlorine and they hate being next to this complicated Cat Island is a positive charge so that an effective elected negativity the fact that corners elected negative stabilizes sorry destabilizes the country cobbled can I if you don't have electromagnet Adams next to cobble can answer but there is a 2nd effect of allergens for nitrogen oxygen and that is that they have a lone pairs on them Major all those long periods and it only takes 1 but I'm going to draw Wallstreet emphasizes so there is a 2nd effect and 2nd effect is that the lone stabilize the cargo by donating NTP on the 1 hand chlorine destabilizes the growth area on the other hand the lone pairs calling stabilizer which 1 wins it's the lone pair stabilization and winds so over all this is more stable than a similar substrate no chlorine and so
that's why if you have this kind of vinyl chloride and you had a proton to them that's why I he had the Proton to the less substituted carbons what you do not do you don't get the protons To the cardinal "quotation mark To the carbon that already has the calling on him because this would be a less stable cargo Qatar OK so that's what you get mark on competition again out there when we come back on Friday the year earlier the hearing 10 until the candidacy because of its you're in for not in our seats with our exams on time then we're going to start later and we have to be out of here for the next class on about