Lecture 03. Alcohols, Ethers, and Epoxides Part 2

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Lecture 03. Alcohols, Ethers, and Epoxides 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: 00:17- Student's Choice 01:41- 9.3: IUPAC Nomenclature 04:47- 9.4: Properties 9:51- 9.5: Cool Examples 14:18- 9.6: Alkoxides As Nucleophiles 22:00- 9.6: Make alkoxides with sodium hydride 29:32- 9.6: Strategic ether synthesis 37:16- 9.7: Don't displace HO- or RO- in Sn2 43:49- 9.8: E1 Dehydration of tertiary Alcohols via Carbocations
Molecule Vancomycin Storage tank Canadian National Railway Organische Verbindungen Chemistry Wasserwelle <Haarbehandlung>
Chain (unit) Mechanically separated meat Containment building Alcohol Chemistry Hardness Isomer Nana (manga) Chemical compound Hexane Elastizitätsmodul Mashing Chemical reaction Ether Zigarettenschachtel Acid Branntwein Glycerin ATR-Technik Auxin Tincture Lymphangioleiomyomatosis Common land Stuffing Sense District Substitutionsreaktion Highway Addressable Remote Transducer Protocol Hydroxyl Morphine Acid Hypobromite Lactitol Human body temperature Gemstone Mixture Inclusion (mineral) Naturstoff Dyeing Dimethylether Iodine Hydro Tasmania Functional group Solvent Breed standard Chemical structure Pharmaceutical drug Soap Flüchtigkeit Pentane River delta Kohlenhydratstoffwechsel Chemical property Battery (electricity) Hydro Tasmania Coal Ether Molecule Ethanol Lipide Protein Benzene Periodate Doppelbindung Gas Alcohol Electronic cigarette Wine tasting descriptors Lone pair Ampicillin Vancomycin By-product Chemical compound Pharmaceutics Aage Cobaltoxide Diethyl ether Nahtoderfahrung Biosynthesis Ionenbindung Species Recreational drug use Sunscreen Wursthülle Food Diet food Inflammation Ham Solvent Functional group Ageing PICT Heroin Gap junction Controller (control theory) Faserplatte International Nonproprietary Name Sea level Metal Setzen <Verfahrenstechnik> Area Meat Hydrogen bond Malerfarbe Carbon (fiber) Californium Water Hydroxyl Carboxylierung Screening (medicine)
Hydride Area Alkoxide Alpha-Linolenic acid Calcium hydroxide Steric effects Chemistry Chemical reaction Molecule Fire Öl Elimination reaction Halide Hydride Sodium hydride Octane rating Chemical reaction Alcohol Hydroxide Wine tasting descriptors Nucleophilic substitution Lone pair Vancomycin Shear strength Yield (engineering) Azo coupling By-product Cobaltoxide Medical history Chemical synthesis Fretting Stuffing Biomolecular structure Ionenbindung Sodium hydride Activity (UML) Sodium dodecyl sulfate Wursthülle Sodium Methylgruppe Ageing Common land Active site Calcium ammonium nitrate Storage tank Mixture Chemical formula Stop codon Alkane Biosynthesis Bromide Methyl iodide Carbon (fiber) Protonation Hybridisierung <Chemie> Adder stone CHARGE syndrome Californium Amrinone Methylchlorid Hydrogen Sodium Metabolic pathway Lake Iron Substrat <Chemie> Base (chemistry) Bromomethane Angiotensin-converting enzyme Pharmacy
Digital elevation model Rye bread Hydride Alkane Angular mil Operon Alcohol Alkoxide Titanium carbide Ethanol Fire Protein Benzene Library (computing) Elimination reaction Halide Sodium hydride Mashing Aluminium nitride Chemical reaction Alcohol Ether Hydroxide Lone pair Vancomycin Yield (engineering) Cardiac arrest Cobaltoxide Medical history Biomolecular structure Stuffing Biosynthesis Ionenbindung Sodium hydride Epidermal growth factor Spawn (biology) Hydroxyl Mill (grinding) Sodium Lead Ham Sodium hydroxide International Nonproprietary Name Process (computing) Golgi apparatus Biosynthesis Bromide Cross-flow filtration Carbon (fiber) Protonation Californium Sodium
Semiotics Cell growth Angular mil Gene Alcohol Steric effects Chemistry Colourant Elimination reaction Oxide Halide Sodium hydride Chemical reaction Ether Hydroxide Acid Seawater Bromine Medical history Stereoselectivity Stuffing Sense District Starvation response Kohlenstoff-14 Hydroxyl Hydrogen peroxide Organische Verbindungen Acid Man page Fluoride Ring strain Common land Schweflige Säure Active site Mixture Potenz <Homöopathie> Molecularity Biosynthesis Methyl iodide Iodine Ice front CHARGE syndrome Kalisalze Epoxidharz Gesundheitsstörung Functional group Iron Chemical structure Substrat <Chemie> Base (chemistry) Messenger RNA Übergangszustand Bulgarians Sulfate Skarn Alkane Dehydration reaction Chloride Institute of National Remembrance Alkoxide Chlorine Atomic orbital Ice Molecule Tidal race Gesundheitsstörung Match Benzene Cycloalkane Carbokation Teilentrahmte Milch Doppelbindung Elektrolytische Dissoziation Walking Alcohol Electronic cigarette Vancomycin By-product Cobaltoxide Thermoforming Ionenbindung Species Reaction mechanism Wursthülle Methylgruppe Inflammation Ham Functional group Sodium hydroxide Ageing Magnetometer Redox International Nonproprietary Name Process (computing) Setzen <Verfahrenstechnik> Ovalbumin Bromide Proline Carbon (fiber) Protonation Electronegativity Uric acid Water Drop (liquid) Iron ore Valence (chemistry) Aqueous solution Epoxide Can (band) Dehydration reaction Ring strain
Formaldehyde Chemical reaction Alcohol Ether
1 can normally in the event of a wave of invective of the contended that this is not a lot want in Albertson's yesterday and it's horrible is
automatic those checkout stands where you do your own
checking out of the groceries I noticed on the floor or there was this posters stickers handed an organic molecules on their asshole students cool I can walk and my grocery store nation indestructible organic molecules on the stickers a students choice by sort of rubbed off because those items selected by your classmates I wasn't aware you
have selecting hard narcotics because that's the structures that they haven't board on the molecule borders context for granted to working alkaloid related to heroin and morphine on when you go by constantly container methyl ether called dexterous Fernando method of the when you take the metal offers no accepted use of that molecule rather than to the views it as a drug like of morphine or heroin so long as they get the spirit of the advertising I think it's cool molecules on their you know maybe that is maybe I wasn't there but the actual molecule in Gaza selected OK select but get back some issues and business here ,comma we did not quite have a chance to finish up talking about are you pack nomenclature arm of alcohols and you you might recall that I said I'm not going to ask you why you can't nomenclature questions on my exams but I will ask you to question unsettling because you will get nomenclature questions on standardized exams like DAT and can get stuff like that and so that the point that I was making when we left was when you name when you name a molecule using the pact nomenclature you have to establish what's the highest priority functional group your molecule so the highest priority functional Group is a carboxyl aghast like this 1 right here in the name of that molecule is going to change in a weak acid if the highest functional grouping a molecules in alcohol the namely that end in all cycle Pantanal Putin all Texan all and there will be an O L ending all at the end of your molecules but if the highest functional group in a molecule is 1 of these other molecules like a weak acid you have a hydroxy group you're going to what in the name of the molecule and all you're use word hydroxy to show it is a substituent so it can be show you this molecule that has a higher priority function in the alcohol that this is going to be some sort of a carboxyl aghast it and so the way that you would name this is you start off as before counting the carbon connected to the carboxyl Aghazadeh as 1 arm and there's 1 2 June 3 4 or 5 6 and with the carboxyl gas it has with and I'll call you always numbers at the carboxyl gasses carbon as the lowest number of possible which will always be 1 because it's always at the end of the chain therefore this 6 carbon species is some kind of Texan Noah gasses the hexane tells me there's 6 Carbon-though tells me that it's a carboxyl gasses and now all I have to do is find out where those substitutes are attached or attach a name and number those so this case it would be 5 hydroxy X and O aghast at seeing notice you and you don't need the -dash their earnings the published destroyed omit the -dash and so you really catching up position so you can see the importance of knowing what the highest functional group priority function with the highest priority controversies and I'll call the name ends in all but if there isn't a different and even higher priority functional group users simply described as a hydroxy something that's OK so again what do I want you to do I'm going to .period overrun the screens at all then that carboxyl Ogasawara there or that alcohol over there I just want you to recognize those functional groups when I talk about them when I asked you questions on the exam about about compounds at a functional groups and I don't want there to be confusion about always talking about the alcohol molecule OK so it's good enough to skip a little bit pass this nomenclature business on the talk about some properties of alcohols find only think about the types of questions that I would ask on you but I just don't buy what would like you to know that I want to start by comparing 3 different molecules there's contains 5 carbons wrote and what I'm going to do amended take 1 of those Carbondale and substituted with an oxygen atom and I'm going to put their oxygen atom in 2 different places 1st opened in the middle and offered over here at the end still considers 3 molecule live very very similar molecular weights if you replace the ceased to be an oxygen solely defensive tenacity in the essentially the way about saying it's going look at the boiling point wedding .period for contain it's a very volatile liquid so in the lab painting is it boils almost at room temperature not that far off from you know close to human body
temperature but you know we use that in elaborate we want to solve and that's very volatile and very so if I come over here and look at diaper the leader that is also very volatile we used I affiliation will season reactions in Chapter 20 where you have to use any fears the solvent you have a choice and and if you want a solid Israel also DL good for that simply by moving on oxygen over to the end we double the boiling point that's no longer I would consider to be extremely volatile and maybe even compared to water which flows at 100 I might consider volatile so the point is alcohols are vastly more polar denied Adidas are out alcohols and it's that age at the end on attached to the oxygen that makes a huge difference here this is what accounts for the higher boiling point of the article but there's 1 more point that I want to make it's not just the fact that the word .period is higher let's look at the end of the piece of vaporization another words once you hit 1 of these liquids up to the boiling point you then have to add extra seats to lift those molecules in the gas phase so not just to get them to the blind .period but once the when you have to add even more so this would be called and it'll be vaporization 1 of the things that I think you probably learned about it in freshman chemistry if you look at the end the B of a position in the newsroom killer jewels from older dozens of units don't really matter so 26 controls from over pentane but compare that To Die ethyl ether at about the same once you raise the temperature of those 2 liquids up to the point where it takes about the same amount of energy you have to heed you have to raise the territory even harder to get to the boiling point of view to all about you and what you do you have to put even more energy into list those molecules out of the liquid phase and into the vapor phase a cost you in 2 different ways yet to heat things harder the alcohol have hit them harder and once you get the ball in anything more he could get the prize the impact of that is that if you take a mixture of Putin all Anita and put it on your skin and just sort of get to evaporate In the al-Qaeda leaders will evaporate faster than anything with a hydroxyl group whether it's water on alcohol will evaporate more slowly and so that's the big thing OK is that alcohols are harder on require more heat to get them into the vapor phase to get them to evaporate and that's all hydrogen bonding so any time you have an out call there's something they can do that out teams in the 1st cannot do and that's that they conform hydrogen bonds so typical Vermont looks something like this unless you have an OH there's no capacity to form the hydrogen bonds but to provide reminders about 2 that's not a good drawing typical item on about 2 engines were the typical always bond is about 1 Angstrom so that bond on the 2008 about 1 starting right that very clearly but that says to ancient it's between a sort of measurement the a 1 inch from OH phone so I didn't bother about twice the length of typical bonds to a proton and that awaits you sitting there vibrating back-and-forth between these 2 structures in its that stickiness that hold your proteins together but that's the unit that will leader Holger DNA strands together it's that stickiness of old water on the planet Earth if that's the case that keeps Kevlar vests from our from allowing bullets faster hydrogen bonds are immensely powerful also look for further bonds between and each because those have the capacity for but here before each lecture tried to tell you I'm showing the structures of some of those sorry for minor spelling years I apologize to you cost you are but I don't know these recalls structures to structures of the fears that I expect you to know you don't you don't have to memorize the book The section 9 . 5 and shows you some cool molecules of readers and alcohols you don't have to memorize the structures this structure I expect you to memorize this is checked for Hydro period it's a five-member ring theory and I expected to use that because it is 1 of the most common solvents and are when I say teacher on the Soviet probably much more important in the next quarter on I expect you to know that that's an ether solvents with lone pairs on the and I would expect you to contrast that with our diet assists them the single most commonly the solvent more commentator so to the point where we just call it and everybody knows you're talking about I only know canister not in that I know would confused when I see there I would think of what would you think that I'm talking about teacher even another both on officially the leaders focused when I say the ceremony and I believe the purchase the acceptance go because I expected other structures on you know nothing on memorization waters knuckleballs that I expected another name of get the nod that just because you drink it because a lot of medicines ,comma something called a tincture tincture of iodine iodine dissolved in ethanol Sofia here somebody a tincture on that means it's a medicine that's dissolved in at the low alcohol ethanol on the under-strength tinctures here sort of old school From pharmacology tied nomenclature pharmaceutical nomenclature should that because the example of another alcohol the Chelsea on a regular basis on this is to give you a sense that you get many hydroxy groups on it you can add compounds where every single carbon-have hydroxy group on their own a carbohydrate in an entire chapter on carbohydrates later on and can 51 seats on this is called glycerol it's important in lipid biosynthesis and lipid signaling when you make so by hydro lies in fact the communities all sorry that my writing is not so good they're all cultural pay attention to problem but would you hide relies factor makes 1 byproduct is actual soap the hard stuff to Jimmy bars out of the byproduct is glycerol swing by fancy boutiques of the leaders in there is a contaminant because it makes me feel really moist it's actually just less pure His all kinds of natural products that contain unit to draw this 1 out she his here expected to know this but this weekend when you to open up the dubious in order to celebrate his new relaxed laws that have been ingesting this compound on persistent Tetra Hydro Canavan all federal Hydro that's not the important part can be in all it's actually the delta 9 isomer we don't use but this nomenclature the Delta that means there's of double bond at the 9th position you can see the double bond but but it's got hydroxy group on there and I think in laboratory doing SMEs into reactions with hydroxy with benzene compounds recalls and also is in the area near anarchy .period notice even if I didn't know anything about the structure as soon as a cure-all some reason that that is all I know there's an alcohol somewhere in my kind of level I'd like for you guys to be operating at time so when you hear those kinds of endings you know something about what's going on in the action when that medicine although that package of food the
discovered some chemistry we had kind of a view a review on Wednesday for the kinds of molecules of some sort of spark your memory for stuff and Chapter 7 and 8 on so allotted Chapter 9 is basically just reworking stuff from Chapter 7 8 s into reactions as anyone reactions 2 reactions and so it's just a reminder of again doesn't hurt Seoul's bid to get this stuff down this would talk about what's happening use oxygen as a nucleophile lines and helping you make history molecules by using them nuclear forces would go through a couple of examples where we use well ,comma sides as nuclear files to attack things so here's a tertiary Alcock side on it's kind of hindered that depends on what any How to be a vase and age there would be an isopropyl alcohol and I'm call bicycle Parkside Forrester methyl groups said TV topside which you guys are to be familiar with very basic a little bit hindered because the hindrances not his it actually attached to the oxygen it's 1 Adam away all the steric hindrance is 1 out way over here so I would classify as kind injured on if I reacted with a completely unheeded I'll kill him was like methyl iodide the whole I'm going to get his to I am not going to talk about the methyl Qatar and will it could be worse than that you can make a muscle can time and I'm not going to do when elimination there's only 1 carbon in methyl iodide how can I make this easy double behind it there's only 1 copy the only thing this could do destined to this would be a good example of innocent you reaction where the Allcock never candidate is basically only has 1 choice and so when you mix those 2 together you'll get us into action going on and nothing else can happen really got to me looks like the kind of person action I would run out in the lab rather than lousy things they have with secondary substrates the book the data on To me and return to sound out just a after college instance view that you can get into reactions without Cox sites to work and I'm just make a note here so of course I'm careful to put my charge I'm only drawing 1 lone-parent oxygen of course there's 3 long years on oxygen not when I was an undergraduate in your position taking a class just like this I wrote every single loan it doesn't take that much extra time but it'll help you to reinforce your knowledge of bonding the idea of a question so it would be good record quickly because methyl iodide is amended so that the extra hindrance on the nuclear file slow that down from it's the methyl iodide part that may shed super-fast something else I'm OK so it was quite often I won't draw all the lone pairs on my nucleophile just draw 1 because all I need is 1 Ferrero pushing anchor duties or every lone pair on your molecules because you never know when you're going to need those Indiana so that I can have a more limited I could have a primary helpful like this is the a very it's a very common called Paolo bromide and in this case on the Alcock said could still attacked give me very good yields of listen you in that sort of assistance and so in this case is attached to different how little groups together find 1 of the biggest this is 1 of the most common in calculating agents from making fears the Alamo Group there's 3 cartons in here and I find that a lot of people seem to forget to draw this carbon right here so I you'll see this Elektra following World right common here Ferguson reactions it extremely good and unhindered and undergoes a much slower rate of the 2 elimination that's why I like to draw out as an example but again I find that a lot of people forget to draw that carbon right there soldiers rate don't forget going out of business they always 3 carbon serially maturing . 3 cartons there OK so what happens if we go from methyl or primary elderly alive those unhindered what happens if we had a little bit of hindrance on to the article he allowed will kind of wrecks your reaction where is the expectation of good results by switched to a secondary Oracle the daylight like this all I'm thinking when I draw this out is how many at this mixture made this horrible mixture because now it's morning injured but it'll introduce and I'm going to take the least candid Alcott I now hydroxide nothing is less ended and that as far as all mine is concerned but even with this unhindered thing all that hindrance in this secondary al-Khalayleh I'm going to be competing each into because all other I'm not going to draw the beta hybrids on the other side but is this hydroxide is trying to worm its way in here and attack that bromide like that it's going to find it's a lot easier to just stop short and pluck off that hydrogen that that Proton right ideas which Olcese elimination reactions occurring in competition with 2 2 different pathways on deleted 2 different products and you should fully expect Germany mixtures In this reaction and so the 2 products unit getting get the substitution products over here you get into and then you get on the 2 elimination and in this particular case the ratios are not all perfectly wonder 1 but pretty darn close you get 53 per cent of the alcohol to listen to and you get 47 per cent of the elimination from you wonder why and so this typifies the problem of trying to do nucleophilic substitution on secondary al-Khalayleh and that's why I would never go into the left and try to do because I don't like getting one-to-one ratio on the lease with primary at least in the cases above get very good yields of the U.S. into reaction I say no contest would ever do this reaction figures wise no chemist would ever do this reaction because when you get to Chapter 20 were not there yet we won't get to there until you take 50 on 1 side we were going to show you a top-secret met this is too secret me to show you were working 100 per cent yield with no need to hurry that you're going totally forget about all this he too innocent to business when you get to 50 by half way through this course we won't be talking about it anymore you'll never talk about that again when you get a can of 51 C because we're going to show you secret methods for doing things that vastly better and don't have problems with elimination associated with them yes this chapter 20 method you don't get a 53 you go 100 per cent yield and reactions done in 3 seconds OK so I guess what I'm saying is don't fret if you found has sent to the 2 business confusing because she had it's miss confusing especially when you talk about secondary elderly alights what book just has this and this has this fetish for secondary alkyl here was OK cool new reagent sodium hydride on his head enlightening anywhere that is the basis and it is very specifically a base not proceed to eliminations ever but for alcohol it gives you very fast and very efficient deeper nation about calls don't use it for S 2 and so much money show you how sodium hydride works so if I take any alcohol under the sun doesn't matter how hindered it is it it doesn't matter how much other stuff is sitting around if you take sodium hydride and I'm going to draw this time associated because that's what the book doesn't want to be consistent with the book so here's 1 representation of sodium hydride you can think of it you know it's not going to think of it as sodium lust and hydride minus and if that hydride minus looks kind of uncomfortable to good be as idiots and it's going to yank the hydrogen office of proton offered something and make hydrogen gas so when you expose things to sodium hydride we just draw at any
age and he and his acts aides for the purposes of Barrow pushing underlined sodium plus minus the school very rapidly full proton offered any alcohol so if you ever want to make an Allcock for nucleophile this is how you do it and I'm going to put a little descriptor era qualified here that is money reaction is very very call something on money reaction baby that is money and it is going to work every single time there will be some weird side reaction with this like the that this isn't a reaction will use over and over again even when we get into camp 51 sealed use and so remember that so what's the key to this it's fast and it's most importantly this year reversible that's the key I want to pull that Proton it doesn't go back and here's why doesn't go back because when you look at the byproduct of this reaction hydrogen gas but floats out of reaction mixture and hydrogen that hiding gas is never gonna pull back again and redelivery of proton Durocher outside scheme over but the fact this typical way you you use sodium hydride at least in this chapter is to make Alcock side so that you can use them as nuclear files cancel its good taken example in going to take as an example tertiary alcohol and I'm tired right TB also jazz this stuff is empowered to do more than just showing you hindrance has nothing to do with his reaction great reactions great than I have sodium hydride is my reagent and I'm not going to push heroes are not going to draw as H minus can destroy the formula for that as many so whenever I taken alcohol and ecstatic the sodium hydride I will now get an Allcock society and iron here's my sodium counter and now I can use that for whatever I want to use it for I'm not going to use it as a base free to elimination I can't bite to the topside base from the store I took the trouble to make some product and use it to make an oxygen carbon by so if I want to use this as a nucleophile into this go back to my friend here methyl iodide could I use methyl bromide for the active use methyl bromide that no chemist to methyl bromide is aghast so if you wonder why I never draw methyl bromide a methyl chloride at slow I like to work with liquid and like to hold huge gas tank out Of course when you're answering questions on exams doesn't matter to you you could draw methyl bromide if
you're wondering why I always choose iodized on this on nothing it's just because in the last we only use another life for convenience Nader look how easy of course notice how I was careful to choose from and alkali died can't undergo competitively to elimination of course this is a great synthesis of anything this is called the Williamson ETA synthesis this this two-step process we start off with alcohol he's throwing your money reagent sodium hydride and you make the so markets and then use that as a nucleophile into reaction and so the book will refer to Williamson eager synthesis the Sapling problems will be referred to Williams interest either sentences and it's this two-step process talking about look in the mirror urge you not to make a mistake and your tendency will be to say it all I need to make an Alcock side all that I can remember this new money reagents
I'm going use sodium hydroxide because that's the only basis can remember and you're in for a disappointment and the problem is that if you take some sort of an alcohol it doesn't ethanol t Budin any alcohol and you think you're going to deep-rooted made with sodium hydroxide unlike sodium hydroxide this is reversible did is fast but the problem is that it is reversible and tho I'd just like drawing a lone pairs on so yes the hydroxide will deep the alcohol but the problem is you will very quickly reaching equilibrium where you have a ratio of these that is 1 2 1 and nobody should be running reactions with a 1 1 extra nuclear bomb if you if you not going together was a good result there is no way you can get an efficient reaction of this nuclear power when there's hydroxide online floating around hydroxide online is less hindered it's just as nucleophilic you're never going to get a good result to by deep remaining now in the ladder going to take a very different alcohol from many say 51 LB lad you're going to use this method on alcohol it's a million times more acidic than a regular local here can work and the reason is this is a million times more acidic than regular alcohol now it can work now you don't get a one-to-one ratio I'm progressive link will tell you about that stuff when you take the lead when you take the 51 LB less commit for regular alcohols words not for the hydroxyl group is not attached to a benzene ring sodium hydroxide to want sodium hydride and allowed for a four-year alcohol on that has a tendency to create fires in the opportunity to catch on fire it's not good that reacted you wouldn't catch on fire and I don't know why they don't want look at that thought about some strategy here if they want if somebody gives you leaders of living highlights that the the problem is suppose I ask you guessed it on my exams and I can't think of any reason exam I didn't ask you show me how to make this thing that's the question that I also had I always ask those questions to make sure you're learning reactions so I ask you how to make arrests on Anita really reactions you know from making so far as in to take reactions and if I tell you to make this using Williamson ETA said this is you have to different carbon-oxygen bonds to choose from which of these 2 carbon-oxygen bonds would you make using a Williams the synthesis so so here's what here's 1 strategy for making maintenance let's try taking this left-handed portion here ethanol and what deep-frozen make that ethanol with sodium hydroxide To make sodium and boxer that would certainly work is 100 per cent chance that work and then I throw in their reaction mixture and how so you know sides very strong nuclear files not the strongest the strong so by throwing out bromide that that could make an oxygen carbon bonds may not know it could but you can see the problem immediately the problem is that there is is a high missions all over the place the problem is a tertiary output daylight hysterically and is extremely hard to get any nuclear file no nuclear power going to attack this particular tertiary al-Khalayleh here like at the Central Park and the only thing you're going to get out of this is the 2 elimination this would be a bad strategy for making history that I just showed you you can fully expected during the 100 per cent something alive so Beuerlein to muscle protein and in your OH backed off all that work you did a poll closing off the ethanol is not for nothing because announced that a proton :colon so this would be a bad approach to making this if you really wanted to get good yields out of this and this heater which you should do is you should start with this alcohol that that kind of looks like the right hand side of this molecule and treat that was sodium hydroxide and again reaction were great see get so you can see the topside access that do that because it's that's a cheap region you can buy that many more more complex alcohol you can buy the destined to be .period sides of the talks at the very cheap and somehow I could throw at this time the 2 carbon calculating agent promo as now there is still potential for elimination here but because that's a primary operator library I think is a primary like on get pretty good yields of S 2 substitution ,comma and probably less than 10 per cent on file in less than 20 per cent lead to elimination of this so this will give me good deals when this 0 minus comes in attacks
on without too much completed the 2 elimination so this would be of the 2 different approaches to make this particularly there this is the approach that will work well so in other words you always want to win U.S. into reactions shoes some strategy that allows you to attack the least handed out he lied on so that's important OK so I'll show you a type of products that are a type of reaction that I don't think you and million years could ever have guessed I just feel like this is extraordinary and based on the stuff that you know at this point H stands for benzene ring stands fennel how often use that because I'm too I feel too constrained can draw a benzene ring all organic chemist right pH to me fennel right that abbreviation here if you'd like to draw later go back and drawer full benzene ring on their Joe find that I often use abbreviations alright enemy from methyl the T 4 Ethel pH with fennel and I will expect you to kind of make sense out of those so In case you see me doing this it's out of habit and he is an abbreviation for a methyl group ETA is an abbreviation for and Ethel growth and then pH is an abbreviation for of benzene ring the final group so that's what I mean by that but gave you take this this particular alcohol the thing to notice is that she is not all that could be a nucleophile if I treated right and right next door there's a leading group and who would have thought this but if you treat this sodium hydride you'll make the Alcock citing 89 it will swing over and push out that bromide leaving group meanwhile what's amazing to me is I just happened to know the 26 kcal per mole of range-trading epoxy send these intimated that could swing over and create something that is so strange and you would never have known that that's possible until I just told you why I despite the book you would know so cost the sodium hydride driving intermediate is deep-rooted meeting this alcohol to Mekinock oxide and what you couldn't have known is that the all the outcome oxides floating around in this mixture hypothetically they could do we need to elimination is of proton here the beta position on the ground but this reaction is fast enough this is what you couldn't have known is that this intramolecular N 2 to create a strained rank is fast enough that it outpaces although 2 elimination reactions so that's an it's like Anderson to reactions actually s into requires 2 molecules declined 0 sorry about that thank you 1st OK so Jia who would have thought that this would be fast enough that strained reforming reaction would be fast enough to outpace all the possibility to eliminations this is a great way to make a peroxides will show you another way to make a park sites in I think Chapter 12 on oxidation reactions or or else in the next chapter character can I can remember where that it's covered but will show you a different way to take out genes make apart but told them this is your only way you got for making the parts the boxing functions and parts of the valuable because can use those too on his Elektra falls to do Morrison to reactions In the morning of a rule that you're going to have a tendency to abuse and I'm going to draw out some potential substrates ICE oxygen oxygen select negative and she elected negative Adams leading groups the chloride can act as a leading group at selected negative if you want of the strongest nuclear files that you really spending time working with chapter a hydroxide and iron and there's no hindrance with hydroxide on but no matter how good you think this hydroxide online as it is still not good enough in fact there is no nuclear nucleophile it's good enough to do an to even with this unhindered muscle group to draw dashed across the usual you know no not ever you will never do anything to reaction and this well asterisk to Bulgarian exception you'll never do this kind of messenger reaction and displays and I thought This is a leading so in other words the problem with this is I'm trying to use this as a leading what is really bad the group that's not to say it can't ever act as a leading but it has sent you that's a no-no In other words if I take another out Parkside here and it looks so seductive she likened I do this just displace hydroxide and about as hydroxide and I can buy hydroxide it can't be that bad you'll never do that kind of person to reactionary display and that's not to say that hydroxide can act as a leading group you see all kinds of that stuff in Chapter 21 taken 51 C but not its into reaction and its there's not a fundamental problem with hydroxide rockets leaving the fundamental problem is that s reactions are crappy crappy reactions you will forget all about who by the time we reach the end of the quarter while knowing when you get to Chapter 17 18 will never use those United users into reactions when you get to 251 without better reactions for you it's because they are sent to reaction is lousy but that's all you got right now so sorry about that I wish you had which we could show you better secret stuff you have to wait N there's a four-member bring so that good amounts of range-trading there and it is still much strange enough to allow innocent you reaction to open that OK so 1 of the exceptions what is the 1 example of innocent to reaction where you can pop out all courtside leaving Nevada mentioned to you before it's an epoxy the four-member rings don't have enough bring strain but three-member rains have enough range range-trading to allow you to open a lot of players who 2 reactions so if I take hydroxide 89 that now has enough Princeton just barely to allow you to do that you know lesson to reactions allows reactions the not very fast this has enough bring shame and it's only 3 Member brings not more memory is known now when you open up oxide it's just like any other with hydroxide in iron ore Alcock said and I this is just like any other race into reactions you attack at the least hindered center so the intermediate you initially get in this reaction it would be there and if you didn't have something you could probably get that could go on open up another Parkside side but if you're clever any reminiscent of a ton of water so this is roaming around in a sea water so you got aqueous sodium hydroxide the water could prove me that before the Alcock said something about OK so you can opener you can you can do as into reactions on the thirst if and only if the eateries an epoxy that's the only so again why did that work that works because of brings and there's more rain strain and 3 memorandums of 1 member of the three-member just barely works in the former Marine doesn't work and I just want to remind you why it's so fast to do a century reactions about the only lives while Why is it so good to do anything to displacement for example of methyl iodide and here's the reasons that's why it's so fast if you look over at the periodic table and I said laser pointer here that doesn't quite work but if you look over the periodic table at iodine which might lead .period quite reach here here's the allergens fluoride chloride
relied Ohio died and the bonds are along once you drop below the 2nd row below Flory those bonds get very long and it is much easier it is always easier to break long bonds undecided is practically all the way off in outer space here that's why it's fast and displays the alliance this is why we spent 2 entire chapters talking about calculi alliance and he liked leading groups the bonds the chlorine bromine especially iodine along and we wanted easier break the day graduate classes will explain that in terms of all modes and Molson frontier molecular orbitals that you just need to know the long bond's break more easily ,comma this was leaving school yes judges to contrasting Parkside bonds those on long at all the ring strain that's that's making network and regulating reader those ponder not long that's why it's so hard to pop out all is leading at we're going return back to a concept from Chapter 8 Nets dehydration and I'm going to show you a new reaction of kind of scary reagents sulfuric acid is very few reagents and let scare me that concentrated sulfuric acid is 1 of those scary regions he did just a paper towel and drip concentrated sulfuric acid on charge the tower his turns black and charge right in front year highs and he got them hands that the not good business so sulfuric acid is a super powerful acid super powerful books and so intended to grow and when you treat alcohol also sulfuric acid they will tend eliminated to make CC governor wants this is an important theme of this chapters that alcohols and ethers can also be induced to eliminate 2 gives you see double bonds this could drop the mechanism for this reaction whenever I see a reagent that's a super powerful acid like sulfuric acid and kind of expected it step 1 I'm going to approach something and for this alcohol the OH group is the only game in town so I see that super strong acids super-duper scary powerful acid there and I'm thinking Oh I want prove that now I am going to symbolize my ass I'm not going to draw sulfuric acid I expect you to know the Lewis structure also uric acid on them 1 to represent my ass and I urge you to do this whatever Joya pushing mechanisms and making appointed the bottom when you draw Kerberos mechanisms that encourage you symbolize acids and bases you Cordaro mechanisms by drawing a J for the acid and A-minus for the base for the kind if you doing a reaction under basic conditions the news assembled B-minus for the base and H B I don't want to it's not just that I'm too lazy to draw the structure when I need to I'm totally happy drawing big complex structures on us explained just a minute while why it's better to use these kinds of of symbols of if you want to control sulfuric acid in your certainly welcome news that step number 1 here is that superpower philosophies going to prove made by alcohol this way stronger than HCl as far as premier was significantly stronger In case and now I've converted my alcohol into a good leading Group this is an equilibrium process but the equilibrium very heavily favors sticking the proton Tom this will this will reach equilibrium in a fraction of a 2nd and an equilibrium I'm probably about only 1 out of every 100 million DVDs has no proton all the others the other 19 99 million 999 thousand 999 those all have protons on almost every single alcohol in their greater than 99 . 9 9 9 % opera made so that's why you sulfuric acid is it's powerful enough to put protons on almost all the article sales and not done this I now have I now have a good Leading Group and in this particular case I chose the substrate is very capable of forming a team you know cargo Carolina stabilized tertiary cobbled I don't have any good nuclear files anywhere in my reaction the byproduct of this would be a sulfate and which is not nucleophilic so we would draw out that that TV will cover can and I'm going to choose 1 of the beta protons to drop the course made of protons everywhere I'm just going to draw 1 of them and this is 1 of the biggest problems that you'll find when you transition from Chapter 7 the chapter 8 inch accurately stopped drawing all the season ages 14 we switched over to these line-drawing structures and I expect you instantaneously to know but this has 3 majors this says reaches this has regions even if I don't draw them forward because here we reached a steps and the book won't have drawn you have to know that there was an H-share and draw it yourself and you need at a trade now because what's going to happen is that the A-minus the counter from sulfuric acid can now come back in and pull that Proton after completing 1 elimination mechanism so that's the mechanism by which form that I still beautifully product now the reason I symbolizing the minus is there's another product that's floating around In your reaction intranets water so soon as you pass the water got water floating around you that sulfate and I this is called by sulfate because there's too what doesn't matter it's the why it's called by something to worry about the point is that you don't know which of these 2 species is pulling at the time you couldn't possibly know I could know and I have a lot of chemistry and that's the advantages drawing a minus instead of specifying that all of the sulfate in on this Poland and you don't know that Water is actually more basic than this so he so that's why it's better to symbolizes the HA an A-minus because initially know as soon as I put the Senate starts to be appropriated you don't know what's the acid that's transferring the proton there so I like those symbols it's not just because I'm out because I'm too lazy to draw the on bootlegs John itself 89 down here because I wanted a point when you see this this the 3rd new ball this 1 Of course year so that's any 1 of these 3 carbon atoms as aged 70 draw dots the Commons dot dot the city's 3 carbon atoms here when I popped respond of a cargo can at the central carbon there's the cargo can and this carbon is 1 of those who see here's 1 of these 3 of its 11 out there so this is a stage 3 this is same experience this is the 1st CH 2 plus 1 history this is the same age during this stage 3 Anderson as free agents and it's like I said this is 1 of the problems when you transition from Chapter 7 is you've got to practice to see all the hydrogen and OK so there is tumble down below him going to draw the fact that there's a sulfate counter Ryan associated with this can you might wonder why how come sulfate with its negative charge doesn't come back in an attack the TV will "quotation mark care see minus Scioscia was in fact that is happening I didn't ask you to show that this is happening I just ask you to draw the mechanism here but in fact this is coming in and doing it and we're going to try to use a different pattern color here so we don't get all confused but From once that attacks he will give you something that simply read Associates again and the book doesn't show you this and it leaves you wondering just how comes off 89 doesn't attacked well the sulfate Nanine is a tactic but once that's all fighting online attacks this is such a good leading Group it just pops right back out again and that's not really part of the elite you 1 elimination mechanism you don't need to show that even it's happening so In case you're wondering why it's not happening this but it is not important cares it doesn't need a product you have to show that so so not be worried by the fact that we didn't draw that we'll need all the things that needed OK
so when we come back forwards informal reactions with alcohols and ethers hands you can home in on what we can do with that


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