Lecture 12. Alkynes, Part 4

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Lecture 12. Alkynes, Part 4
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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: 00:09- Beer molecule discovery bolsters Seattle biotech upstart 00:59- Hops 02:52- Chapter 11-Key Reactions 08:58- 11.9: Acid-Catalyzed Tautomerism 09:23- 11.9: Initial product=enol 10:34- 11.10: Hydroboration-Oxidation of Alkynes 11:33- 11.9: Acid-Catalyzed Tautomerism 21:23- 11.10: Hydroboration-Oxidation of Alkynes 24:26- 11.10: Hydroboration-Oxidation of Alkynes, Slide 2 30:19- 11.11: Acetylide Anions-Pkas 36:12- 11.11: Acetylide Anions-can be used for SN2 reactions 42:04- 11.12-Synthesis
Molecule Beer Vancomycin Versuchsperson Hydroxybuttersäure <gamma-> Chemical structure Biotechnology Set (abstract data type) Beer Wine tasting descriptors Man page
Semiotics Sulfate Chain (unit) Whitewater Bohrium Resonance (chemistry) Surface finishing Set (abstract data type) Atomic number Chemistry Alkaloid Atomic orbital Molecule Alkalinity Electron Isomer Film grain Beer Periodate Chemical element Killer-cell immunoglobulin-like receptor Quecksilberchlorid <Quecksilber(II)-chlorid> Doppelbindung Walking Sulfur Chemist Katalase Chemical reaction Solution Wine tasting descriptors Electronic cigarette Vancomycin Acid Tiermodell Match Chemical compound Isomer Bromine Cobaltoxide Thermoforming Stuffing Ionenbindung Species Reaction mechanism Geochemistry Brauwissenschaft Hydrogen peroxide Acid Man page Roasting (metallurgy) Mercury (element) Ageing Sodium hydroxide Tachyphylaxie Schweflige Säure Route of administration Process (computing) Setzen <Verfahrenstechnik> Area Amylin Stickstoffatom Rearrangement reaction Carbon (fiber) Carbonylverbindungen Adamantane Protonation Man page Water Hydrate Korken Sausage Combine harvester Sodium Hydrogen Drop (liquid) Gesundheitsstörung Iron Salt Base (chemistry) Separator (milk)
Bohrium Resonance (chemistry) Secretion Tautomer Hydro Tasmania Alkalinity Electron Redox Doppelbindung Walking Chemical reaction Solution Erdrutsch Electronic cigarette Lone pair Vancomycin Match Yield (engineering) Azo coupling Cobaltoxide Pipette Hope, Arkansas Biomolecular structure Ionenbindung Kohlenstoff-14 Reaction mechanism Ocean current Acid Man page Reactivity (chemistry) Mercury (element) Dairy product Enol Abbruchreaktion Schweflige Säure Sea level Conjugated system Monoamine oxidase Oxide Area Setzen <Verfahrenstechnik> Grading (tumors) Asset Carbon (fiber) Protonation Manganese Man page Water Chemical structure Blind experiment Base (chemistry)
Ionenbindung Diethylstilbestrol Hydrogen peroxide Hydro Tasmania Chemistry Man page Molecule Mercury (element) Sodium hydroxide Electron Ageing Isomer Abbruchreaktion Schweflige Säure Bororganische Verbindungen Oxide Process (computing) Setzen <Verfahrenstechnik> Redox Mineral hydration Peroxide Vinylverbindungen Carbon (fiber) Carbonylverbindungen Chemical reaction Alp (name) Electronic cigarette Wine tasting descriptors Combine harvester Vancomycin Functional group Boron Mixing (process engineering) Cobaltoxide
Ethylene Sulfate Species Bohrium Propionaldehyd Chemistry Man page Alkalinity Ageing Fire Lactitol Schweflige Säure Calcium ammonium nitrate River Hexane Setzen <Verfahrenstechnik> Carbon (fiber) Protonation Chemical reaction Water Vancomycin Initiation (chemistry) Hydroxybuttersäure <gamma-> Turbulence Butyraldehyde
Digital elevation model Bohrium Steric effects Molecule Dreifachbindung Alkalinity Fire Benzene Methylmalonyl-CoA mutase Elimination reaction Base (chemistry) Octane rating Walking Chemical reaction Anomalie <Medizin> Electronic cigarette Hydroxide Wine tasting descriptors Systemic therapy Acetylene Vancomycin Acid Orders of magnitude (radiation) Attitude (psychology) Cell (biology) Bottling line Ionenbindung Kohlenstoff-14 Biosynthesis Species Sunscreen Wursthülle Organische Verbindungen Ultraschallschweißen Methylgruppe Man page Ageing Abbruchreaktion Lactitol Oxide Setzen <Verfahrenstechnik> Area Alkane Solid phase extraction Stickstoffatom Carbon (fiber) Protonation Hybridisierung <Chemie> CHARGE syndrome Sodium Combine harvester Drop (liquid) Iron Breed standard Can (band) Substrat <Chemie> Base (chemistry) Satellite DNA Ammonia
Waterfall Ionenbindung Biosynthesis Biosynthesis Reaction mechanism Crystal twinning Methyl iodide Carbon (fiber) Set (abstract data type) Protonation Chemical reaction Electronic cigarette Methylgruppe Man page Sodium Vancomycin Satellite DNA Stuffing
Water purification Deformation (mechanics) Biosynthesis Biosynthesis Bromide Reaction mechanism Carbon (fiber) Set (abstract data type) Chemical reaction Electronic cigarette Noma (disease) Man page Water Sodium Vancomycin Iodide Epoxidharz Functional group Iron By-product Redox Cobaltoxide Satellite DNA Oxide
start news article talk about year and molecules and what's not to like .period not to be interested in that Our so apparently there's of biotech company that's interested in finding naturally occurring molecules that they can use to treat diabetes and for whatever reason they were looking at the molecules that you find in beer 5 in this but this particular news article talks about the the elucidation of the absolute structure of a set of molecules called him the loans and these are some of the key principles that lead to the bitterness that you find in beer and so I had no no idea what the new 1 is so I decided to look up the original article on and here's the the
work that they're talking about so if you've ever enjoyed a double up the year on India Pale Ale and shot bitter flavor these are the kinds of molecules that are present in there that lead to that stupid bitter flavor before I looked at this article would have been a 95 per cent sure that the molecule would contain nitrogen because usually you associate the bitter flavors infused with alkaloids with nitrogen containing so I was surprised to see so no nitrogen on so when you roast cops to help them and then steeped in the the year flavor there's a chemical reaction that occurs there's a set of molecules called human alone that I have a particular scarier chemistry here that are present in those hot and in the brewing process of those molecules undergo a rearrangement generated by members of cycling grainy need obviously this is beyond what will learn in this class this particular rearrangement nobody knew what the cereal chemistry S absolute during chemistry was of the sterigenics center on many people this biotech companies were able to get crystal structures of these products the super bitter compounds that you find in beer here is an example of a crystal structure and once they knew the steering committee of this since they knew that arrangement was stereo specific and preserve the stereo chemistry they were the back out the stereo chemistry of the original compounds that are present in parts is very cool to know next time you're walking down the or a bitter beer very cool to know what molecules are making their fear that there is 0 chance of this model will treat diabetes so actually they were just doing this because it the cool but it is cool to know about on the molecules that are making your year-to-year OK I I want to step back and hands and have an overview of what we're discussing in Chapter 11 now if you printed out these blank cost notes from online this is not 1 of the pages on there you just have to draw this out on a separate piece of paper and and I just 1 see the big picture here for what's going on in Chapter 11 would be in Chapter 10 we talk about 5 the reactions about the things had different electoral files Delcine CLP nexus in nuclear power was Chapter 10 hearing Chapter 11 were focusing on all kinds and focusing on our times on most of the reactions of the St. for 4 of the the reagents that were learning about a very similar or identical to the regions and learned about Chapter 10 minutes sense Chapter 11 is a review the other of Chapter 10 armed but there's a few spins in years so it is 1 of just wants to cover what are the 5 things you need to step out of Chapter 11 knowing things that I I can't imagine not asking asking you about these things on an exam on and it doesn't matter which section of 1051 the year the the kinds of questions that on your instructors will focus on on what you once you leave the university these kinds of things people expect you know such as reminders also of these 5 reactions we've already talked about the addition of of hydrogen he alights on 2 2 alkaline and so if you want to add maybe it's not obvious here but there's identity not just to be yard to this molecule you start off with an H on 1 side and then you can tell you that the product there's 2 wages so I've added in a chain of B are clearly on and so the region maybe is now obvious that the reagent you need for this is each year and so we already learned that and I spent a lot of time talking about the fact that goes to a final Cardinal cat iron is very weird looking marveled that on about where the NDP orbitals attached to NSP hybridized the 1 like there yet the aid to the less substituted side then we talked about hydration In Chapter 10 members the recipe we use for hydration with sulfuric acid and water and that is those are the key components of this hydration reaction that were using hearing Chapter 11 we still use sulfuric acid it's a catalyst we still use water that's the reagent that adds the agency OH on remember it makes a mean all that talk Tom arises to give this type of a key Tony on but there was 1 extra things that we had that looks deceptively similar to the sulfuric acid that's McCarrick sulfur probably you could use mercury chloride age seal 2 you wanted but on the book chooses to show the mercury sulfate salt OK see you need occurred sulfate salt in there when you hydrate and alkaline and again I'm not sure eat all intermediate because its present for such a vanishingly short period of time bomb Trinitron illuminating this this pages as best they can hear OK so the next reactions from being member were at the house the next reactions were going to see that's 2 of the reactions were going to see additional to allergens across a double I think you can guess the reagent that you need to do that but there's nothing special going on with this I will I will talk about this in the relationship between the 2 bromine atoms so and hopefully after last year after year you know with the reagent is that even if we haven't covered so there's another reaction that is adding water across a double bond the money .period had to wear these Adams argues in a chat in the substrate His in each item in the product but there's 2 more inches that weren't there before and there's an oxygen that wasn't there before we've added the elements of water to a Chissano across that all kind and so the region combination that we used to do that is the same region combination used in the last chapter what's different here is the we geochemistry and so it's a two-step process you have to enumerate these reagents step 1 we had boring sometimes in sapling there's some residual problems were they on where they show the diameter of boring B 2 H 6 I usually don't draw it that way but if you see people drop "quotation mark died Boraine speech which they think is dialog BHC because that was 1 of the ways you purchase boring so whenever you see some if you see anybody else refer to die boring into they mean boring and step 2 I hope you remember the cyber war Asian reactions is hydrogen peroxide and a base to the program at the hydrogen peroxide and the only basis we've shown you sodium hydroxide and that simply because you can't buy impregnated version of proximity to make yourself so that's a region combination you saw in the last chapter and I've already mentioned the next reagent here that's for deeper deep-rooted meeting and Bernelle kind it's sodium in mind and that's a reagent I showed you early on in In our lectures on Chapter 11 but the cities of 5
reagent combination recipes that I want you to keep focus on investor in a finish that up in this lecture will cover the last 3 reactions and instead of heart of time just talking about these 1st 2 reactions to set you up to understand how a all kinds different health teams and now we're starting to quickly blazed through these last 3 reactions from In the Chapter 11 so you need to know this stuff from Chapter 11 nature you know these reactions are they worth the mechanisms and things like that that was yes .period boring forms pop supportive to Borens as soon as you put it in solution the question is :colon refused diagram will get the same practice boring and you'll get the identical product that's the same region OK let's talk about this taught tolerance and business and I may have to step back here just remind you of what I'm talking about with talk tolerance and harmony the instead remind you what we said when we left on just very quickly put up a slider already already created in the last lecture remember last lecture I showed you that you could hire treating our kind if you included this mercury sulfate salt I don't require you to write catalytic next to the region I disputed to show you that those are catalysts on for the reaction if you just read mercury sulfate or sulfuric acid and or sulfuric acid without the catalyst that that's fine too on so when you hydrated Elkind you can't isolate even if you wanted to you could not isolate this all product that's just an unstable intermediate and in the reaction and it quickly forms a nice a special kind of recall the talk to on that has a carbonyl group in the carbonyl groups are a much stronger COW wants a much stronger than CC double-bond and that's why thermodynamic Lee on the equilibrium favors the carbon side and so let's talk about the mechanism for this this this tart harmonization reaction is unstoppable isomerization of any Denault into it he told parliament so so we talked about this tall Tamas Ajan a special type of isomerization but we didn't talk about the mechanisms and so I'm going to do is among the show you use the book mechanism and then I'm going to show you how to equivalent mechanisms that are indistinguishable where you might be saying Gee that's not what I do out how come I mechanism doesn't match and I'm going to point out to you that you just simply drawn the same thing that the book drew it just looks a little but a couldn't start off by of all drawn out and being all any malls are intrinsically unstable and because I'm going to draw the mechanism I no longer need better wage bond eventually sold them so here's indeed all species and way over here and leave room for an intermediate way over here on the other side of the page I'm going to draw carbon you yes I debauched happened you call this number can be so simple to but that of you think you .period wouldn't off I would have gone on for home that entire discussion focused little and dropping on this mechanism for this talk Tamas Ajan reaction I'm really drove the yen all over on this side then way over here on the other side of the state although the Quito this other isomer a special kind of a recalled the Tottenham and the only thing it's different here my tiny black and emphasized that there were 2 ages over this carbon at the end and there's still 2 wages over this common at the end and that 1 proton induced many oxygen is now Over here on the carbon so this type of isomer we only picked up a proton from oxygen department that kind of isomer it's not a resonant structure because we moved in Adam it's a Tottenham .period about the mechanism for this talk Tamas Ajan reaction under the conditions of alkaline hydration and when we when we hide the recipe for al-Qaida hydration is sulfuric acid these are acidic conditions so I'm going to show you an acid catalyzed mechanism for this taut harmonization in the book mechanism of this right book to remind you that this is the mechanism the bookshelves perfectly correct the draw that out some going to draw up a symbol for an acid it's useful for Aero personal draw a and H here and we're going to to use the out Al-Qaeda in this scene all as a base to pull off the Proton Federated could draw out town this double bonds picking off the Proton there we go and that's going to and you can't tell where I'm going to put the proton you have to wait for me to draw the next intermediate so I'm either going to attach the Proton to the carbon has to agents less ages and we already I think you should have an idea that when you probably in how keen he put the and the least substituted carbon and that's exactly what's going to happen here so when dropped this next intermediate I'm not going to draw those those 2 tiny ages and it's going to draw the HA just areas and I'm going to draw my OH I'm so I'm so crafty and drawing that OH bond in there because I know I'm going to that the next step in if they take electrons away from this double 1 to leave behind a cobbled Qatar and there it is and so so then the next part of this mechanism that I wish left a little bit more room here and the book shows taking this lone Perahia and drawing a resonant structure this is not a chemical steps there's no Adams the removing when I do this this is simply I'm going to show you a different way to depict this exact same species this exact same intermediate the straw different way to depict that intermediate what I'm going to do them manual resonance structure that instead of looking like on a carbon cap and I and my resonance structure will look like an ox Sonia Miami and oxygen With 3 bonds on it and I wish I'd like a little more room looks so crowded in there but you get the idea OK just 2 things in the middle of the leader of brackets around on just to remember that these are not too different there's no chemical reaction going on in the brackets sausages
to different ways to depict on that this intermediate so the next step of the reaction the book shows you taking your word you're conjugate base A-minus In Deep Throat made the proton picking it up off the oxygen you can tell you have to remove a proton from the oxygen because you just look at the product and you can tell it's gone and that's how you get the product this is the way the book depicts a mechanism that let me show you to the equivalent ways to depict this mechanism that meaning exactly the same thing they're equally correct that you you all the same points on on on an examiner for somewhere else because you'll frequently be confronted in a situation where you draw mechanism and you wonder why Hong Kong that's different from the answer to the You're the back of the book or a Europe you're solutions here your study manual I was going to order a different way to depict this it's equally correct so here's an alternative way that I could have depicted this mechanism totally equivalent called on my my starting material or draw exactly the same symbolic assets there Intel 1 nite I when I use the double bond to pick up this protons in the same reaction depiction in this same mechanistic step for a former New ch . I'm not going to leave a couple can I'm behind I'm going to use this lone pair to push downward and satisfied that new developing Koble Qatar and you could make a dairy here on the CEO bond or you could actually attack carbon with the area Bottom line is I'm not going to leave behind him In fact this is why it is so easy to probe making all heaters because that oxygen long pier on suiting up the reactivity of that Al-Qaeda this type of Al-Qaeda with an oxygen on it is more reactive than any al-Qaeda we've talked about Boston in Chapter 10 the intermediate that I'm going to get based on my hero pushing is the same 1 that I had already drawn over here this is no different from the intermediate that I just wrote but struck out that intermediate again the same marks only a minor 1 it's the 2nd of the 2 resident structures that I drew before so up above a two-step mechanisms step 1 new prove a carbon atom there's the proton and there's a proton stepped to the made oxygen so this this 2nd mechanism and showing you is also a two-step mechanism it's the same two-step mechanisms may look different but it's the same step 1 by Primakov there's the car at that each on the carbon and stepped to a deep-rooted made oxygen OK so that's an identical mechanism and there's no difference between the mechanism I put on top the mechanism I put on the bottom so the exactly equal a you a 3rd way that we can depict this this reaction equally it's it means exactly the same thing there's no distinction in what the and what this error correction mechanism means so there is a 3rd way to depict In Step 1 I'm going to do exactly the same thing I'm going to depict the proclamation of this carbon atoms fusing hero pushing this time I won't show the oxygen lone pairs engaging and so it's going to lead to this 1st type of residential structure shown before the draw that out and that's going to leave behind this cargo can resonant structure and I and destroying H there's he can see the H we just added this to Moriches on that and carbon but but I'm not going to draw that and so now I'm simply going to take that instead to I'm going to take my conjugate base A-minus and I'm going to lift the proton not using this 1st resonant structure and so when I draw that depiction of Take this C-minus and pluck off that protons and or simply use these electrons to come back down and create a pipe bomb and if you made that error and precisely on the continent as a couple can equally good so janitor two-step mechanism these are all the Seine To stepped mechanism and the only differences which resonant structure of this intermediate that I've drawn that's the only difference in these 3 mechanisms so you will frequently be in a position where you're wondering why your mechanism isn't the same it's because when they write the solutions manual they only draw possible mechanism and they leave it up to you to determine Collier my my mechanism is correct I've just joined residents structures and those are the simplest way to double check whether your mechanism is correct or were at least as evidence that it is it doesn't prove it is if you have the the same number of of steps up above it's a two-step mechanism residence is not a step down below here in the middle it's a two-step mechanism and then the 3rd depiction a two-step mechanism that has the same two-step mechanism so if you mechanism really is the same at a minimum it has had the same number of mechanistic error pushing steps OK so that's frequently going to be an issue that arises wise might Why does my mechanism look different ,comma maybe you simply draw on the same day and that would be a criteria when we grade on exams whether you've drawn the same mechanism is in key OK so that's not harmonization unjust or harmonization in the back of your mind because I promise you you going to see that over and over and over again and can 51 seats that will be a huge thing that collapsed he also and the nuclear felicity of the CC double-blind meaning all eyes OK so let's talk about another 1 of those reactions I drove oration oxidation so we're this is the wrong slide again know how much findings world home ideas for years now and that we're now in a little over feelings OK let me come
back to this and now realizing the USA lowered dramatically underwater sold keep correcting me and direct me as I go to these next words but it's also about war Asian oxidation which is scratch out it doesn't always mean also maybe I wasn't the I was totally off its and and try to rescue a considerable Hydro Mauritian oxidation arm and this is a reaction you already know without without teens and remember taken out kind substrate then being so crafty by picking a symmetrical all kind that internal because of I didn't would be and it would be very messy and will draw about what happens when we do the Highgrove oration oxidation sequence so I think you already have an idea about what would happen you know on aficionado would say Oh you know boring doesn't give greater yields the secret reagent you should use and are book doesn't talk about that so I'm not going to mention the secret version of Moraine gives you hire yields it's not an issue of concern for us because the book were using doesn't mention this you probably should guess that the end result of this will be the addition of H and OH across 1 of the pipe bombs in that way it's very similar To the Hydra abortion about teens and so I'm going to draw that intermediate here but as soon as I draw that I think you'll notice Gee this is didn't we just say that the laws are not stable and they very quickly and unstoppably I sometimes think don't yes we did say that so I'm not going to walk you through the two-step mechanism for talked harmonization and simply going to tell you that you have no hope of isolating this don't draw that as the product because you couldn't isolated the product that you get is going to be a key to and there's the key terms so in other words if you hydrate this alkaline using sulfuric acid in the current mercury mines in water on you'll get a key town if you had a war at this alpine you'll get a Quito tone and looks kind of like the same key term and and so why would you choose 1 of those regions over the other the start of the run scared to put this next level the order is correct and who knows what of OK it does that look like the order of the match what you have to OK so armed so you get a different regional selectively just as without doubt teams on where you had to worry about the degree of substitution on 1 hand versus the other and and such talk about that we geochemistry on as with has without you get into ,comma reduce selectively O H of the and the oxygen ends up on the more substituted into the outcome so it's good drawn on symmetrical the terminal alkaline where on 1 and I have and a chat and all draw that each year then on the other hand I have now killed group and so I treat this with my boring reagent some kind of award there's that pH font and the mechanism that we draw from this ,comma we
used Of course Quantock electrons it's only got 6 electron so it's it really is easy for anything to attack boring and as we attack that it starts to realize it's picking up a negative charge starts to ditch that Proton so there is a concerted on reaction where you add the H in the BCN on the same side of the Al-Qaeda so what's the implication of that CNN In another such an application for the end product but this intermediate at any time something and and it means that these 2 groups that were already there they are in the age that were already on the Elkind Haft and upon the same face and this intermediate that I generate this vinyl born this helped seal boring the boron the newly added a chapter B on the same side of the Alps and so it's an intermediate like this did you end up exposing to Hydro peroxide in and again you can buy Hydra peroxide 89 you have to mix hydrogen peroxide with sodium hydroxide and that's what converts the carbon boron bond window into an OH into a carbon oxygen but now not going to the Island had even going to bother to draw that you all we're done drawing yes the question year there were a lot of the time it was not the world body yet the question is is it these electrons in this beach ponder attacking this carbon that I've now put about on and yes is the electrons in a sigma bond the BHC about the coming back an attack 0 should precisely start from the middle of the DH OK so again enacted dropping isomers or the in Altheimer that you initially form I'm simply going to go right to the Quito here so you can see the type of product we generate so in other words when you do I drove oration oxidation on a terminal kind you will get an allied within an hour this is the opposite Regio chemistry that you would get it if you did this reaction on with sulfuric acid so let me just emphasize that so what's the Why should you memorize the stew different region combinations so let's take the example here so what I just showed you so now I flipped around the kinds the ages over on the other side if I treat this with my two-step region combination of hydro more Asian and
oxidation the carbonyl group ends up on the less substituted into the all kind gives you an album and just to help you see all draw the and there's you can see that this page was there from the very beginning that still there at the very end of the molecule I'd added 2 new wages in this overall process there they are and drawing the really small because normally I wouldn't draw those for you so Hydro orientation oxidation of an alkaline gives you an that I take that same substrate molecule that same starting material and I expose it to this mercury and catalyzed hydration and drop the whole the whole recipe there
metric sulfate I don't have any direct catalytic there but these are actually just catalysts sulfuric acid H 2 SO 4 and then the actual reagent is water which as a solvent that will also form a career that also generates need all the talk time arises and so when I draw out the product of that the turbulence of the Camorra substituted carbon of the alkaline and their egos 1 of those ages is the same 1 that was there in the beginning and the 2 new wages that are there for your help and pattern recognition those of drew them into tiny within 10 OK so you can see that you can control the Regio chemistry when you hydrated Elkind by choosing reagents this is the same game we played in Chapter 10 when he talked about how things but now there's this spin on it that you have to recognize that the the that the eat all of the initial products of talk tantalize rapidly OK so let's talk about the 5th type of reaction that we're on the river and the see in this in this chapter in its affiliate and on how it's super important from the standpoint of the pedagogy in the book ,comma because the book doesn't give you good ways to make carbon nuclear fires financial until can 51 C so in a way we're going to distort the importance of the species in a way that's that's not actually represented about what's going on in the field work and cans that's OK I'm so that the good news said of the I want you to know I want you to simply memorandums and I think I'll have to come up with a broader set of that I really expect you to
know so we start off with just a simple out L Kane this is at the wheel of his airplane and drawing 1 of the pages on anything I want you to know the PKK just a simple helping butane cycle hexane propane Hecht's doesn't matter at all of those have case that super high that means that there is no reagent will ever give you that allows you to pull them off there is simply nothing that is basic enough pull a proton often Al-Qaeda that's what it means that the PKK 50 means nothing can pull at Proton to give us a curve on and many contrast that with ethylene 2 carbons and the
only difference is this is known as P-2 hybridize carbon and finally contrasted with another 2 carbon species and alkaline and sort were simply changing the hybridization of this carbon atom in each case and so is remind you of what the hybridization is here were starting off with this 3 McGowan sp to and as and so what's the difference in city there so the PKK of of ch went on units 100 million times more acidic because it says the 2 100 million that's what attended the inadequate 8 on 8 PKK units means 8 means a factor of 10 8 In city so this Proton is now 100 million tend to be more said when I have endangered given kind there's a massive drop it's now tend to the 20 fear more acidic in our I tend to the 20 5th more acidic so these the PKK values so let me just rate that helped you should take the time to write out all the zeros going to do that so there's 25 PKK this difference between how came and and this so tender the 20 5th more acidic it's 50 minutes 25 equals 10 the 20 5th said in other words that the proton at the end of an non-Chinese solicited we can actually pull at Proton With if we use a base that is strong enough we can pull that protocol and we mentioned this before but I just want you to get how extraordinary area that is that you can pull the proton off on up of any sort of an out came out penal colony book ends 318 the area showed you this very powerful base is 1899 and iron nitrogen with a negative charge on an 1899 and sodium a mind is the 1 you can typically purchase if you buy a bottle of that so if you take sodium in 99 and you treat them with an alkaline at terminal kind is a C H on the end the age is now so acidic that you can just ripped that protons right now and now you have a really nice nucleophile for the reactions that you know basically Of the 4 reaction if you know which you would when users for 92 a base for he too because you can use the sodium and as a base for you to on but this is not for the next 8 chapters 9 chapters I think this is about the only current nuclear file that you've got around that you can use to attack things and will talk about it very completed type of CC bond forming reaction when we talk about and benzene rings on but the book is going to throw the statue in every single way as a nuclear interior actions on the matter that you'll never see it again because will show you better reactions but so do idiocy this for the next 8 chapters yeah yes this army is this sodium united strong enough know the PKI can remember what PKK the book gives you but that the PKK facility Munitis somewhere between 32 and 35 in other words this is 15 PKK units it's it's tender the 15th too weak to pull that Proton the differences 50 here still 15 basis orders of magnitude to two-week is a base so not even close can call a proton often here camp approach and there but it can pull a proton off of the deceased so that's the that's not the PKK this it's that it's the PKO on me write that down PKK of ammonia equals 35 again in so let's talk about these in mind this is called in a satellite online In a satellite in may some kind of strange hokum it's not called an al-Qaida-linked In so it whenever good answer for you had this is that's not happening but it's the name that was used for her on at least a century and so still sticks around so for welding these Oxy acetylene torches the other tangle acetylene gas if you're using you pack nomenclature you wouldn't call that acetylene collapse that's fine but everybody uses the old name steadily and so any triple bond molecule that is an online at the end on the end of the trouble 1 call in a satellite and I even know it even if it's not exactly derive from its focus was good and talk about now that you know how to make a satellite announced by throwing in sodium they might be what can you do with these will you already know what you can do with these
the book didn't make a huge deal about the satellite and irons but they were introduced you back in Chapter 7 so if you go back and look at the end of Chapter 7 gave you this table of nuclear files and some of those nuclear powers they were given you were set alight on items they were showing you that you could use those present to reactions in the problems in the back of Chapter 7 every once in a while they threw in a settlement and a satellite I'm doing innocent reaction to already seen disregard of the differences now you know how to make them so it's just practice using these threats to reactions will throw in a substrate that's that can do competitive elimination reactions all this can do this and to do so that's great so if I throw them there we go nothing special about that you guys are really good at this and reactions it is not used to doing this and why is it that the book loves this so much because it forms a carbon-carbon bond right until until you reach Chapter 21 this is going to be your key away making carbon-carbon bonds I accepted benzene rings with a special chapter of that sodium I forgot to put the charge is my sodium can't I'm still floating around so the leaders highlight that CCE bond here that's what the book clubs and that's why you're going to see problem after problem after problem and so on you know I'll be throwing problems that you that uses satellite and I and so on but that's the importance of this organic chemists all organic chemist myself included love to make carbon-carbon bond that's how you build organic molecules this was taken and another example of this in a more traditional depiction I would simply drop some sort of a substrate like this but there is my terminal alkaline new conceded 2 carbons with trip along there and that if I throw in as a region combination Step 1 sodium a mind what does that do it pulls off the proton that I didn't draw but I did enjoy that Proton for you at the end of the terminal kind but there's a proton there that can be pulled off with a 99 and then step 2 I can join another region that could now be attacked also agent that doesn't have any beta protons because I don't want to worry about the 2 elimination reactions from people so so what you make satellite and I knew use that present to reactions in the end result of this is that I will make a new C C bond new carbon-carbon bond and here's the new carbon-carbon right there feel beautiful areas and at the start of the you can 1 at a time called 1 side something cool approach on the other side and then add something and U.S. Acid reactions I want to caution you a satellite in irons on various bases it's kind of like hydroxide you have to be really careful about what you stroll a satellite on 19 with and so but let me caution you that if you tried to use in a satellite and iron to attack something that was secondary or tertiary elected carbons 1 anti-drug carbon atoms if you try to use a satellite online to attack the tertiary or even a secondary by me just remind you don't go totally Ohio with be the set lighting siesta nucleophilic and yes there so slim and trim it is like an we did you fire that's what makes satellite and I'm so good is not their super nucleophilic will show you some super nuclear files in 51 C but but they're very slender and so you have fewer problems of steric hindrance but they're still even know their slender you still are going to be stuck in this situation on that you have to worry about he 2 elimination Sofia the secondary or tertiary alkyl daylight instead of wiggling its way again and yes it's standard but instead of we're going its way in there you're still going to get this with this tertiary system you get all you need to elimination you would see any CC bond formation so I'm not going to draw the Elkin product shareholders right to so really you're restricted using satellite in irons on refinery alkyl he lives on terminal upon oxides In other words a pox I didn't know substitution on 1 end and and of course with methyl it's not really primary and OK so so you still have to worry about misusing it's satellite and irons and because of this limitation to but in the last section of this this chapter is basically just a reminder to start combining together reactions you know and I'll come I'm big on synthesis problems at home what about big on them but you know you see my exams the last pages synthesis problems the problems that's generally have synthesis problems on their insults this is the hardest thing about the camp 51 B that you never had to do in when you're in the morning retaliation can 51 a on you you may not necessarily do well and 51 B unless you start combining those reactions and were throwing so many reactions to the attitude that we expect you to know how to combine them together .period about multistep said this is not
just remind you of some of the reactions during of the vicious suppose that I ask you and this is not just a one-step Perot I ask you how to make this using an efficient set of reactions so it's going throw out some sort of a fictitious product here that but how would you do this you efficiently using whatever reagents so while there's a lot of stuff going on there that's very busy so how would we assemble using reactions that you already know so the 1st thing that I focusing on twin practice on account of a year ago to carbons so obviously I'm going to need to form carbon-carbon bonds that the other thing that I focusing his old there's no kind of my substrate there's an all kind in my final product although this alkaline and that all kind are the same so I need to focus on the fact that I need to make a carbon-carbon bond on 1 end some somehow when you do that and I need to make carbon-carbon bond on the other end and so how would you do that actually I can see short who worried that I could do this fall show you just a perfectly good synthesis the work so I'm sure you're not desperate to use your brand new shiny sodium a deprivation reaction so let's use it so if you throw in 1 equivalent of sodium in mind With this will end up getting the satellite online it there's no difference between the 2 ends of this it's equally probable and in distant distinguishable for your pull approach on the other hand so there you go you can make in a satellite online than you can use that an innocent you reaction to news that an innocent you reaction of throwing methyl iodide not only does had a methyl group there we go in a dozen ascent to I don't need to show the mechanism for the Szczecin to reactions the key is that it's going to make a carbon-carbon bond Tokyo made a carbon Colorado 1 and that's beautiful how well it works just throw in sodium a mind and then you're welcome relied and then you can do innocent you should do so now I've still got a C H on the other end so I can repeat that trick where sodium a mine and I ripped the proton at the other end there we go and now I'm
ready to do another resident reaction because all you know is to right now on and what I throw in a well I can see what I can see is Eckhard Estonian electrical and have a bromide hired tosses leading group there but it's actually when I 1st wrote this out that's not what I intended to do so all ultra-deep outright stretch out this synthesis to look longer than it needs to be and I just remind you that you can also open up oxides so I could open up uses to attack an epoxy 2 innocent you reaction on a Parkside and if I did that I would add 2 carbons and then oxygen and have been Allcock citing an I'm here they have that sodium floating around now usually work these up and isolate them and purify the eastern purify out some sort of byproduct but if I wanted to I could do without working this up with excess water without dumping in a town of water I could simply thrown electrifying do this this kind of love I'm just innocent you reaction with our with another al-Khalayleh and draw that out there is my 3 carbon fragment there when I get up iodide bromide Oracle Idaho bromide is the cheapest 1 common version of these regions I didn't show there are pushing mechanisms here that's not really required but that you can see there's a whole set of reactions that you now have at your disposal on the other was probably a shorter wait for me to get to the product but the important point is you can see a novel these reactions you don't want to listen to reactions and now that you know about a satellite in irons and how to make them you're not ready to make use satellite canines in CC by forming reactions that is a change for you to practice these a lot on the online 7 home practices a lot of work the problematic character and that's the end of Chapter 11 we come back on Friday were going to start on reduction and oxidation reaction


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