Lecture 02. Alcohols, Ethers, and Epoxides Part 1

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Lecture 02. Alcohols, Ethers, and Epoxides Part 1
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This is the second quarter of the organic chemistry series. Topics covered include: Fundamental concepts relating to carbon compounds with emphasis on structural theory and the nature of chemical bonding, stereochemistry, reaction mechanisms, and spectroscopic, physical, and chemical properties of the principal classes of carbon compounds. This video is part of a 26-lecture undergraduate-level course titled "Organic Chemistry" taught at UC Irvine by Professor David Van Vranken. Index of Topics: 00:17- First new drug in 40 years approved by FDA 01:17- Structure of bedaquiline 2:23- EEE website CHAPTER 7/8 4:37- Reactions of primary and secondary Alkyl Halides 6:54- Reactions of tertiary Alkyl Halides 12:14- Examples 20:58- Examples (slide 2) CHAPTER 9-Alcohols, Ethers, and Epoxides 28:14- 9.1: Introduction 36:46- 9.2: Structure 39:35- 9.3: IUPAC Nomenclature
Biosynthesis Recreational drug use Growth medium Operon Psychopharmakon Organische Verbindungen Columbia Records Chemistry Medicinal chemistry Man page Molecule Tuberculosis Tool steel Sea level Arzneimittelforschung Recreational drug use Tuberculosis Chemical reaction Alcohol Electronic cigarette Vancomycin Gesundheitsstörung Curing (food preservation) Tennessee Resistenz Pill (pharmacy)
Methyl iodide Skarn Diethylstilbestrol Alcohol Grading (tumors) Humus Chemistry Steric effects Chemical reaction Elf Molecule Tiermodell Electron Drop (liquid) Insulin Honduras Stratotyp Reduction potential Tamoxifen Elimination reaction Whitewater Cosmetics Mashing Resonance (chemistry) Topicity Katalase Chemical reaction Ether Lone pair Vancomycin Yield (engineering) Tool steel Locus (genetics) Bromine Chewing gum Stuffing Hope, Arkansas Biomolecular structure Calculus (medicine) Ethylene Ionenbindung Kohlenstoff-14 Species Multiple chemical sensitivity Columbia Records Methylgruppe Man page Reactivity (chemistry) Functional group International Nonproprietary Name Mixture Drug prohibition law Inclusion (mineral) Setzen <Verfahrenstechnik> Alkane Corpus mensurabilis musicae Carbon (fiber) Protonation Maid Man page Chemistry Water Electric current Nuclear magnetic resonance Gesundheitsstörung Metabolic pathway Iron Can (band) Substrat <Chemie> Base (chemistry) National Rifle Association Drug prohibition law Vitreous enamel
Creep (deformation) Collision Steric effects Chemistry Dimethylcarbonat Molecule Shear strength Amine Elimination reaction Oxide Cobble (geology) Octane rating Sodium cyanide Senf <Lebensmittel> Chemical reaction Alcohol Erdrutsch Wine tasting descriptors Lone pair Vancomycin Yield (engineering) Orders of magnitude (radiation) Azo coupling Zunderbeständigkeit Cobaltoxide Medical history Bottling line Stop codon Cyanide Ethylene Dietary supplement Ionenbindung Biosynthesis Species Recreational drug use Activity (UML) Bromoethane Gold Wursthülle Organische Verbindungen Reactivity (chemistry) Neutralization (chemistry) Lead Chemische Synthese Human body temperature Active site Sea level Process (computing) Setzen <Verfahrenstechnik> Area Alkane Stickstoffatom Bromide Seafloor spreading Carbon (fiber) Protonation Man page CHARGE syndrome Water Hydrogen Sodium Metabolic pathway Functional group Iron Carboxylierung Base (chemistry) Satellite DNA
Glucose Kohlenhydratstoffwechsel Chemical bond Alcohol Hydro Tasmania Titanium carbide Ether Chemistry Liquefied petroleum gas Ethanol Molecule Electron Chemical structure Cycloalkane Lambic Oxide Periodate Waterfall Alum Substituent Whitewater Doppelbindung Chemical reaction Alcohol Butyl Ether Systemic therapy Vancomycin Acid Gasoline Chemical compound Cobaltoxide Medical history Lymphangioleiomyomatosis Isotopenmarkierung Stuffing Biomolecular structure Ethylene Sense District Kohlenstoff-14 Ionenbindung Crystal twinning Fermium Organische Verbindungen Wursthülle Columbia Records Methylgruppe Reactivity (chemistry) Ring strain Tea Solvent Ageing Magnetometer PICT Lactitol Injection (medicine) Ausgangsgestein Cobaltoxide International Nonproprietary Name Oxide Naturstoff Setzen <Verfahrenstechnik> Hydrocarboxylierung Potenz <Homöopathie> Alkane Butanol Bromide Meat Hydrogen bond DNS-Synthese Carbon (fiber) Chemical clock Lightning Protonation Coal Water Epoxidharz Functional group Molecular geometry Epoxide Breed standard Base (chemistry) Carboxylierung Screening (medicine) Pharmacy Ring strain
Substituent Chain (unit) Meat Walking Surface finishing Carbon (fiber) Hydroxyl Chemistry Alcohol Anomalie <Medizin> Electronic cigarette Molecule Vancomycin Functional group Bromine Lymphangioleiomyomatosis Butyraldehyde Stuffing
OK so well and my intention is before every lecture I want to start operations something and I saw on a recent events this is January 1 article on spot the 1st new drugs for tuberculosis in 40 years what's happening now is people gave up on developing drugs for bacterial infections like tuberculosis because as kind of a solved problem bacterial infections we have a lot to be antibacterial so that you're going to prescribe become MDC brief locked Santa Rita mice and relatives of those so why do we need new antibacterial you go onto a plane and somebody with them ultimately resistant tuberculosis cops in the year you're dead you're just gonna die slowly of bacterial infection we can't cure and so it's only recently that it's on that medicinal chemists have gone back to try to develop new drugs for these for these kinds of bacterial infections on you you'll be beset by articles and news and all kinds of exposure to organic chemistry they don't get to see the organic structures underneath so I'd like for us throughout this quarter on to get a better picture of 1 of the structures that underlines these news articles and the things you see in the media so this is the structure of this new drug that was developed there's lots of new drugs are in development and I don't know that there's anything particular about this of course an alcohol and Anita over the top of the Chapter 9 that's what we're going to cover the beginning of this quarter but by the end of the camp 51 series you should be able to assemble molecules like this using organic synthesis level tools and technology to do that you getting out of this class and developing some new drugs to treat some human diseases solo again when I look at this I'm struck by by the fact that the tertiary alcohol will talk about some very particular chemistry as N 1 reaction chemistry tertiary alcohols are in Chapter 9 so again ,comma learned something from the class and get out there and make some develops a new drugs or if nothing else even prescribed but his Olympiad stopping go back to this thing that I mentioned about our about the website 0 no I have to
go all the way back to I'm going to try to
find our nation and our website
so I can just be mentioned again the this issue of of pay
attention to the updated scandal for exams and and the idea that there's this workshops OK so
this is our website of a people-oriented chance to visit that on so as I mentioned here on this link on the bottom on there's not going to be a Saturday Review section that's because the departmental peer tutors are running their own workshops and review sessions and so if you click on that link on a Web site will take you here to the peer tutors website and they give you a scandal for workshops and a hope to get you back on track on with topics like Elektra files a nuclear files totally the stuff stereo chemistry residents things that you need to know for chemistry 51 B you may not be totally up on that from the stuff that you learn can 51 a onto here's a chance to get back on track to kicked but in my class and that's what I want you to do on Sunday you can access this there's a link on our on the 1st web page of our website on that'll take you to this web page and that the link is down here on so as I mentioned before our syllabus is a little bit influxes I'm I'm still trying to create the notes for this class of you if you click on the schedule Tavildara alarming page it takes to do the scandal and I thought that I had moved the exam data maybe this is not the updated 1 I can't even tell whether and the exam they all have to look at my original files to see that this is where you should go to check and see what one-hour exams dates set for and roughly what in water and what kind of timing or am I trying to achieve when I cover material in the book he had some idea for how you would be studied but that's what's going on to the main business arm on tension was on the 1st lecture to cover the syllabus and then have a brief review of chemistry 51 and I didn't quite finish that and so let's get on to that that's going to finish our little micro review of the kinds of reactions that you know from chemistry 51 and so here's where we left off I just remind you that I immediately said look ,comma if you wanna feel like you're up on top of the material from Kennedy 51 a zoom right into Chapter 7 and 8 it's a bunch of SN 1 to be wanting to chemistry and that's what we're going to do in Chapter 9 rebounds take out alternators and a bunch of SN 1 s into the 182 chemistry and so the 1st thing that I did what we really only had time to don't talk about the Foley was the chemistry of primary and secondary alkyl here lies and we're going to be using those in Chapter 9 even the Losers Chapter 7 and 8 material from and the point is whenever you have unhindered alkyl their lives you can do as into reactions with those who take strong nuclear files they're not going to wait around for any Kanye information they're going to do something the growing either attack and substitute the carbon atom to reaction like this on tells it he takes something this Super Duper reacted so on and 1899 at something you're not really going to see much of until we cover all kinds I think in Chapter 11 and when they see a mining and I'm used as bases way way later in Chapter 23 in the book so there's 1 other Super reactive type of species word the basest city becomes more important than the nuclear Felicity in 1991 and Allcock side or the other you have to be really careful without side and I said yes very nucleophilic but they're so basic you often see to eliminations compete so I take that up hindered Alcott's I'd like TV talk side or hindered the mining iron those so basic and had so much negative charge they attacked the protons and undergo eliminations so approximately half to be kind of careful with and that's going to be the topic of Chapter 9 our mind you more of this partitioning between us into any 2 eliminations so primary and secondary out of their lives when you have strong nuclear files the bases get s and 1 I sent to hurry to chemistry but this was good and talk about them on tertiary al-Khalayleh it's just to review stuff from Chapter 7 and 8 so what happens when you have some steric hindrance there things turn out to be not quite so easy so I think that endured calculi lied when the prototype for this type of it he endured OpenDaylight on there it is always the beautiful but it doesn't have to be methyl groups and it's pretty interesting and I'm simply trying to make it easier for me to draw so if you have hindered tertiary Alcatel lies and you throw in some sort of a nucleophile usually nuclear powers are to hindered to attack that central carbon atoms and so things will collide nuclear files will collide even pathetic nuclear files like water can eventually react not because they're attacking on this carbon bromine bond but because with all the steric hindrance there preventing things are attacking this now has time to do an ionization reactions this man has time for this carbon roaming bond finalized and which you don't see it as you don't see attack even with a strong nucleophile you don't see a tactic that hindered center and so in the case of tertiary helping lights there's a chance on him and even a probability for this thing to form a stable Carville cat and you're use the term ionization unleashes popping part you to give alliance and that is not reactive enough it's not quite as hindered war over it is super-duper reacted it's not a positive charge that makes that carbon so aggressively reactive it's the fact that that central carbon does not have an opt-out of electrons that's why it's so we have the current desperately wants to have an architect and so now it can react with the nuclear file out and that's and the water which is really a pathetic nucleophile now not even water can attack this summer with its lone pairs so this is a two-step S 1 reaction this is what happens with tertiary out the alliance you don't see it s into reactions for you to reactions can you have to sit around and wait for cargo can information to occur and we'll talk more about this sequence because this is exactly the stuff they were covering the In Chapter 9 this is formation holes and we're going to see more this just showed the Chapter 9 material and then you're probably already covering that a in chapter on so there's another thing that can happen and this is it's usually very hard to get good yields of of of N 1 reaction so this would be an example of an S 1 pathway but that same Koble Carolina under the same conditions you'll typically get mixtures of 2 different products With tertiary al-Khalili it's not always but on it's quite common and draw out 1 of these hydrogen atoms that hydrogen atoms all over the place member already mentioned you how desperately that central carbon once had an octave electrons and probably the easiest way that can achieve not that is to have whatever is present that can act as a nucleophile can also act as a base assessing water molecule as it's as its colliding over and over with this with his cover canine intermediate will sometimes collide with the protons and then lead to formation of a double bond so that processes need to and so quite often you see mixtures of the 2 S 2 products so that's what you should have gotten out of Chapter 7 and 8 last quarter there was this is huge and blizzard of reactions since I S N 1 lesson to me one-on-one against people that straight the main thing to do is look in and see are you working with a primary or secondary al-Khalayleh are you working with the tertiary alkyl he lied to conform ,comma added that's the 1st thing you need a judgment when you look at substrates for reactions so let me urge you to do that OK so I'm really that's that's the key important stuff are the sort of take Western money just walked through a few examples before we finish the story you understand what you some examples of local daylight substrates and some differently about the bubble the back of the head to
explode he 0 yes thank you for asking that everybody should eliminate some of the slide of those kinds of mistakes that 1 In sorry about that and the other 1 elimination that they both involve Cobble care information there please correct that is the focus of its what examples aren't just some reactions about lied so that you can see house held ,comma of various nuclear files interact with local lights were going Chapter 9 were going to focus relentlessly on oxygen nuclear files on let's wishes walk-through and compare some of them most so I wanna do is I want look at some of so examples of reactions of our of alliance and what I want to do is I want to compare various nuclear violence and how they interact and on this rate compared Nikon's walk through every possible example but wishes walked through some examples you can see the way I think about this and what I'm going to do is that on what I'm going to compare the reactivity all college strength but that means is nuclear Felicity and bassist city they usually go hand in hand things that are more nucleophilic tend to be more basic I'm going to start up with something that is very low nuclear Felicity and no basis city and then we're going to have to compare the 2 things that I would I would say have higher and higher and higher nuclear Felicity and basis so we're going kind of in this direction as I drove various different quibbles I'm going to start with an alcohol the lone pairs the nucleophilic hotspot of a simple alcohol that's is still and it's not a very good nucleophile and it's not a very good on very basis so fighters take in hour and alkyl here like that I'm going to take it's going to be just ethyl bromide my expectation is that very little was going to happen I could take alcohol and ethyl bromide and mix them together and it would float around the same reaction mixture maybe if I waited long enough this is true for any chemical reactions in the universe if you wait long enough infinity of time eventually things can react but this is just not a good reaction because aren't very nucleophilic so on 100 years in theory that could happen but on a time scale that's of interest to you this is just too slow with the destroyers for the black it's too slow because alcoholic just not very nucleophilic if I start with the neutral species here and displays a negative bromide have to still a positive charge any time you see the bonds to oxygen remember to put the positive charge that'll hope you like things can pull up that the protest but that's not what I wanted it OK so alcohols are very good as nuclear files on let's call it make take an example of an oxygen nucleophile that's slightly more reacted so I'm walking down were now in reactivity and there's a carboxyl lately and I and I know something about the where I can go to a peak a table and there is 1 in the back of the book I can go to a PKK table use PTA's to help me to estimate how many times more basic is a carboxyl 89 than alcohol and just by looking at the case I know that that's about 7 orders of magnitude more basic carboxyl late in life so I take the carboxyl 89 that 7 orders of magnitude more reactive they just an alcohol and water and probably it maybe it won't surprise you To Know that those reactions are now fast enough to do pretty reasonable lesson to so whereas before I probably would have said no significant reaction up above by slow and really no significant reaction now the carboxyl that is 1 of the reactions that that you talked about last "quotation mark there has been a different lesson to action so as we increase in nuclear fostering the chance of the number of collisions between nuclear electric power lead to increasing formation of bonds misstated an example of another nuclear file that you were introduced to and this is going to look like the strangest and weirdest thing on the planet this is called a citing and my God look at all of those charges and what's that about and will I do with them pretty tame you can buy bottles of sodium a sodium plus the overall charge unease idea and I'm is minus 1 no 1 of the pluses in 1 of the minuses cancel each other out the point here is that this is an an ionic nitrogen nucleophile and is slim and trim like an area they can wiggle its way into U.S. into reactions were other things get befuddled by steric hindrance organic chemists love a I I and we love it because it's good for forming carbon nitrogen bonds and then we go to destroy the hero pushing so each ended on Ireland's nucleophilic U.S. and 2 reactions and so when I draw the product I'm still going to have this weird-looking a citing iron maybe it doesn't bother you but I sort of feel like maybe that's going to make you uncomfortable level these charges on here so there is my so the net charge of this net neutral molecule Afellay site and later on in the book will show you a chemistry that allows you to reduce a Zeitz 2 amino groups phase dance that useful in drugs other maybe an explosives on but the means are useful functional groups so I'm getting an increasing nuclear fostering a side has about the the same nuclear Felicity as a carboxyl late and OK so it's just about in nuclear Felicity to another class of nuclear file this society there's a negative charge on cotton this is your 1st best carbon nuclear file that you're going to have access to for another couple of chapters organic chemists love forming carbon-carbon bonds so although the nuclear positive just drawn here I love this 1 the most because it allows me to make a carbon-carbon bond Connecticut St. electrified and cyanide is about 10 thousand times more nucleophilic carboxyl so increasing nuclear Felicity like a side it's show a linear molecule no hydrogen sticking offer litigating to scare kindrence but it's really so little nucleophile here they can just slam right on informed carbon-carbon bonds that I mentioned I love carbon-carbon bonds enough all organic chemists love carbon-carbon bonds and there is my scion of group hanging off of there so there's kind of a sweet spot here when you look at nuclear files alcohols are kinder to pathetic halo a modest sum anything that's less nucleophilic and basic an alcohol is just going to be too slow to do this into type reactions but I as a increase in the strength of the nuclear power here these reactions get faster and faster and faster instead of having to keep the reaction you can run at room temperature so probably sodium cyanide you generally have to heed those reactions let's step up a nuclear Felicity so I mean long appears very basic and nucleophilic about 10 million times you know there's no negative charge Amin long pairs more nucleophilic by a factor of about 10 million in Sinai you can run a S N 2 reactions to the means at room temperature both the faster at elevated temperature but you can run in the room temperature that just feels so good to me great nucleophile economy all these things that you can do with nascent 2 reaction and then what's going to
happen sadly what's going to happen is I hate to tell you this but I of the time you read Chapter 14 you never going to be using the actions again because we initially you better stuff but for now this is what you've got to work with us and to include money to OK so so I mean the 10 million times more effective than cyanide Sinai it's which is trying to do some math and my head right now is about 10 thousand times more reactive than Zeidan carboxyl late and that was 7 orders attended the 7th more active now calls so I'm taking more and more and more reactive things here as I walked through this list of what walked through a few more reactions and why am I doing this because in Chapter 7 were going to relentlessly focused on oxygen nuclear files and I don't want you to forget that there's other types of nuclear files out focus let's take a look at all Cox sides so in these away more reactive than a means there's usually a account randomly draw that same electrified also just continuing to walk through this list and this is really totally chat and fact and I'm very quickly in our Chapter 9 Mitchell going to repeat this reaction s into reactions of Alcock sides on Monday he endured al-Khalayleh that's that's a good way to make carbon-carbon bonds it's a certainty that they use this reaction in the synthesis of that structural arm said that the anti-tuberculosis drug related show due to make a bond between oxygen and methyl carbon so that's a good lesson to reactions OK so that it's going to start there a problem that starts to arise here and if you look at the yield for this type of reaction of ethyl bromide and I'm just going to make up the yield will give you something that's typical typically in this kind of process you get about an 85 per cent yield it's in the eighties 82 90 per cent yield why is that why would reaction give you an 85 per cent yield the reactions don't just stop faith it's not like the rest of the molecules the other 15 Britons starting Chilmark assisted by United still feel like reacting right now I'm going to go do it there's a reason why the you is only 85 per cent of the mustard some side reaction there and decide reaction that's occurring this formation of this as we get more and more reactive with our nuclear files so we have to remember that nuclear files also bases and when we get more and more reactive with our nuclear files and get to the point of looking at all Cox side what happens is that about 15 per cent of the collisions there doing productive chemistry involves elimination some reminder of the fact that this ethyl bromide has a bit of history data protons on and that all courtside nucleophile was in there it is not only attacking the carbon but some of those collisions result In elimination heat to elimination and as I get more and more basic and nucleophilic I'm going to see more and more elimination occurring and that's what leads to the city to elimination product so yes Alcock sides or more nucleophilic comes from right too but there are also more basic so it's just at this point Allcock said start to see elimination creep in and if you really want to get a lot of elimination using handed out he learned that last quarter that term oxide with the steric hindrance tends to give you that you're agent of choice for the to Tunisian mansions OK yet in this case With a simple Cox said yes and other words of I ask you how to make that ETA indecent yield you could just write this Alcock Percival Roma so it would be 85 % about 85 per cent as sent to about 15 per cent each elimination the book doesn't give me those those kinds of distributions but let's step it up a bit in terms of nuclear Felicity and city but let me take a nucleophile that you're going to see a lot of in Chapter 11 and that an al-Qaida satellite and I is another problem nucleophile that's useful for making carbon-carbon bonds and it's probably the only carbon and I nucleophile other than cyanide that you'll see this quarter so if I take this same I the same nuclear following the same cool allowed electrified of I'm going to see even more to elimination with this you'll still get enough of a yield here the obvious into product for this to be a useful carbon-carbon bond formation but now you have more than 15 cent elimination with this so I'm just going to I'm not going to draw ethylene gas again I don't need to do that just rate plus the 2 GSN to reaction plus the Malik's stepped up even more in Harmony Gold something really basic is a 1899 only hands that basic yet more nucleophilic all I can think of this man is that basic that's more nucleophilic but I'm just thinking that has so basic that I mentioned that that's really basic by the time you get to a mighty and irons and again this is different from and I mean it has that is neutral with a mandate to listen and my next this is attended the 20th more nucleophilic and basic and and at a neutral on me when you get something that's this reactive you don't see any it's all 2 elimination so you see what happens as we get to more and more and more and higher and higher reactivity was on nuclear files the problem is that things that are good nuclear files are also good places and we get to the point where 2 reactions just aren't useful so startling scratch his because you don't get any of this right no to all you get is the 2 elimination so if you're interested in making Apple's synthesizing ethylene gas great way to do it but that's hard for Hugo from gas from from oil and gas drilling wells you don't need to synthesize and less so as we went to more and more reactive nuclear files this basis city starts to kick and there's a sweet spot where you can use things spreads into reactions if the 2 reacted you get to elimination if they're not reactive enough they don't attack at all like alcohol example so there's this sweet spot for into to nuclear files to try to remember the ones that are really good this is kind of the breakpoint right here where the word you can use Alcock signing an alliance to get decent enough yields but anything beyond the satellite you're going to have a hard time with any kind of steric hindrance whatsoever in any kind of scary on the nucleophile or mainly on the elderly alive or dead in virtually on the path to the 2 eliminations OK so this is your mind-set as we walked into Chapter 9 it's understanding of how how increasingly activity can lead to more and more elimination more elimination cited actions focus it's finally switched gears and switching to some new material from whichever so now I'm going to get ready to do a lot more into the 182 chemistry comes with oxygen nuclear files on what's different is oxygen leaving groups so the big thing Chapter 7 and 8 was you did everything without doing the alliance and in this chapter we're going to show you the circumstances under which oxygen can act as a leading group you've already seen oxygen nuclear powers now will will sort of supplement that with Thompson chemistry where you have but oxygen I am just noticing How
about life in the sense that OK so system really here something that you want to know that I can but I'll just give you my perspective on this this this chapter is about alcohol's there's in a special type of cycling recalled in a Parkside so here's an example of an alcohol so I I expect you already to know what alcohol is expected in hole about ethanol is probably bring plenty that maybe maybe not contrasted with Anita and it's going to take a simple and what's the 1 characteristic difference between alcohol and he said that the main difference is that in the In the 3rd does not have an OH does not have a proton on the oxygen what makes alcohol so distinctive and so unique is that H. Adams it's capable of hydrogen bonding capable of being removed to make Alcock sides on so this molecule ethanol I hope you know already expected of a structure of ethanol but just because it's an important molecules this is called methyl butyl ether I don't expect you to know the structure that on but it seems that what 30 years ago the start they stopped adding texture Ethel led to gasoline which makes it burned really smoothly in your car to the company's smidgen of something called Tech to Ethel led but as you might guess that's toxic putting led India gasoline organic LED compounds toxic that's not a good way to make it burns smoothly so they started adding methyl TB liter to gasoline and the 1 problem he believe there is a fear of gasoline and water the method to be deleted was out of the gasoline and into the water Qatar as alleged never did that and so what they've found is that water supply service started to be contaminated with this particular gasoline additive so they've become really concerned about that I think they stopped using them OK so again alcohol had their way through enemies the stuff from my digression is focused and that's what I see 1 of those is Anita 1 of those is now alcohol and that's what I'd like you to see when you see alcohols and ethers that await should be the focal point of your thinking and I don't have much more to say about that we're going to go into that in great detail OK so we're going to classify alcohols by degree of substitution in I look at ethanol and I don't just see it as a way to prove what I see is a primary alcohol that's not hindered so you learned this nomenclature last quarter when you use it without goal he alights primary secondary versus tertiary and we're going to use that same sort of a nomenclature to distinguish alcohols in order to understand something about the reactivity so if I go back and draw ethanol here this is a primary alcohol In that I look at this carbon atoms is is called the carbon all carbon we just put a little label here all right card all that I don't know that I'll ever use this terminology again it's it's sort of something that it's really organic industry lingo but on the cardinal carbon there's only 1 alkyl group that's what makes that a primary out of that I feel like this I'd be intuitive you because you already know where primary al-Khalayleh ideas so you can sort of see whether it's a primary alcohol a 2nd example of a secondary alcohol so here in this carbon all carbon and allied to Al-Qaeda groups attached that's a secondary alcohol so what if I point to the screen over here even if you can tell putting out I say that secondary alcohol I expect you instantly to know what I'm talking about this is super important us to distinguish primary and secondary from tertiary just like it was for Elko hillsides and finally when I jotted tertiary alcohols like this instead of Cheadle bromide which have seen over and over from individual T. butyl alcohol so that's a tertiary alcohol and the carbonyl carbonized 3 alkyl substituent so again this is familiar nomenclature to you on and you're going to get really used to this and then when we cover means in Chapter 27 in 51 are Morgan a fool you into and use it in a completely different way but for now alcohols and uncle here lies at the very similar terminology primary secondary and tertiary but his list of what's cycling eaters you can't really have a 2 bonds to the twin alcohol oxygen weapons of wavering where an oxygen atom is 1 of the members of the ring and I'm going to start up by drawing the simplest of those molecules and I'm not going to draw the curtains and we're going to use line drawings this is the simplest slightly Peter you can have and if that looks weird to you that's good on the name for this molecules called Boxer rain but I don't know any chemists who use artificial light happening on whenever you see this as a functional group in a bigger molecule that functional group is called an epoxy and so instead of me calling this boxer rain which I just go all out up oxide and every chemist knows what I'm talking about so I don't think you'll ever hear Muzorewa docks rain again I'm just going to say the punk side and of all the cycle Adidas that's really the 1 that's going to be the most important in this chapter because it has rings strain in that range training is going to make it react if I if I make the ring bigger by just 1 carbon atom this is this former rearing as clocks attain an ox attain rain and this molecules coal oxidation in every time you see those in this quarter there is nothing they don't have enough for industry to make them especially reactive rather not comment on natural products they get that I can think of 1 natural 1 drug or pharmaceutical it as of warmongering like that which is not very ,comma but now it's increased ring size by 1 more and this is an incredibly important ring size that right there is the solvent Tetra Hydro fearing a teacher but the parent molecule is called has double bonds and this is the parent molecule is called fury catcher Hydro fury and doesn't have any double bonds it's all hydrogenated so fury
and you're going to see lots of five-member rings with oxygen and and again this this this common solvent where you don't have double bonds in their used very heavily Nephi increases by 1 more ring size that's not called a pirate handling systems and I you pack decided that the parent compound was going to have double bonds in their political power and those the 5 and a six-member rings that's the basis for carbohydrate chemistry for DNA for glucose for diabetes and so on you're going to see a whole town of fury and Pyron chemistry but when you get to I think it's a chapter to chapter 25 or 27 which is the carbohydrates chapter but the also likely Peters so this is this is our chapter Chapter 9 were going do a bunch of N 1 innocent you Commissioner make heaters in alcohols and willing to do a bunch of chemistry releases in Apple's react and we get those 2 actors reading groups OK so there's another section in the chapter about structure and there's not a whole lot to say about the structure of the now calls but let me start with history by framing the bias by simply reminding me that when you have 4 substituent and carbon they want to have 109 . 5 degree find angles are very close to 109 degrees but there's this thing called valence shell electron a pair of Paulson theory this is the substituent want to avoid each other and that's what leads to these 190 bond angles and so it's the same for oxygen and there's this baby just take a simple the reunion alcohol they also want to have these 193 barnacles angles that's what's comfortable here of sort of draw these 2 substituent scientists say the bond angles there 109 degrees so that I hope that's not too new exciting but what I want you to do as I wanted imagine the frustration in this molecule right here in OCS arranges of Parkside molecules that is way off from 109 degrees if you look at the produce and simple geometry you'll be able to quickly calculate those bond angles and there deliveries 60 degrees so imagine how uncomfortable upon oxides are with them that trading there's 26 kcal per mole of In the Parkside functional and that may sound like a huge amount it is a huge amount of restraint so for Detroit hears from rain that is so strained they can do something it's almost inconceivable to me it is so strangers over an initially this later but 1 that should you now is so strange that an outcome oxide can come in energy this is just barely enough strain even with all that can push out Cox side leaving group in reaction that's so extraordinary no normally there and do this it's only a super-duper strained 1 so this is just that even with all that 26 killer telephone rings strain that's just barely enough restraint to allow you push Ivanovic oxide minus that's the only case you're going to see pushing out Alcock sides as leading groups innocent injections lets the value of strange looking so typical leaders are now calls 190 reviving going on that's the key .period you remember yes and With an epoxy but usually you have to go to more basic faces and Alcock said please you don't need to know that this court factory times OK so I you pack nomenclature on with pay attention to this key point of the year I don't put have nomenclature might seem like we have a limited amount of time we standards and I don't have time STI nomenclature but there are people who do put a technologically 2 questions if you take the graduate Geary examined chemistry take the and Catt DAT peak at on they have you pet nomenclature questions and therefore on a Saturday ,comma I've put some might technically ages because you know it's not my exams I want you to be ready for that stuff done you've already had I pack nomenclature and naming of compounds on whatever 1 remind you that which could start by talking about the meaning of compounds on hand Wednesday by talking about are molecules that Indians have in the fall so if you go back and you look at Appendix B In the Smith textbook appendix B is about how you pack nomenclature and there's a table in Appendix B that basically breaks down the functional group classes so you know what kinds of functional groups have the highest priority when you name a molecule so if I take it lets go and start up by drawing out a molecule so if I want to name this molecule the very 1st thing I have to do is I have to establish what is the highest priority function with now this is the way you do I have to go back to Appendix B and there's a much longer list than this in Appendix B and I say What's the highest functional group it's not bromide that's the lowest priority there's no carboxyl like acids is no the hides others an alcohol that's the highest priority functional group I immediately know that the name of this molecules going and the word all so how do we approach this meaning here so if OH is the highest priority grew soldiers right at the wage equals the highest priority group the molecule name is going to end in the in that the suffix all so what we do is we find the
longest chain that has the hydroxy group attached to find longest chain OH and we have alter that the ending a so in other words I count the currency the city 1 2 3 4 carbons for carbons butane that at the end of the day no matter what other stuff I added this molecule is called butane all its for carbons without hydroxy group on the next step 1 for carbons and then I had adultery and step to have to enumerate those to figure out Is that hydroxy group attached to carbon 1 2 3 or 4 there's 2 different directions in which I could enumerate the carvings in this change so 1 choice would be to numerator like this that's carbon 1 that's carbon to its carbon 3 carbon for now I did it the other way the hydroxy group would be on carbon 381 to enumerate in this direction where the left-hand carbon carbon 1 if I enumerated over here with the right-handed Corrigan was carbon 1 then I'd have the hydroxy group on and on and on carbon 381 to enumerate as hydroxy group has the lowest number so so in other words this is not just Budin all this molecule is too putin all the hydroxy group is not attached to carbon 1 it's not attached to carbon 3 it's not attached to carbon for hydroxy group is attached to carbon to and the last thing I do is I had all the substituent on air this is an alcohol that's the highest priority functional group calls attached to carbon too and now Sinama I have established the numbering of the system and so we we now name and number the substituent so this is not just to be acknowledged bromine group on Arab Bromo group and its attached to the 4 position this is not just to be in all this is for Roma 2 putin all and that's how that works OK so 1 and give you 1 more example before you go on I will rewrite the instructions and I'll show you what's different about this what happens if there is a higher priority functional groups the molecule will no longer and all it's going to end in the name of the Higher party to take off here and run out of time but there well when we
come back I'll finish on the meaning of that higher priority children ,comma animal talk more about some chemistry and Japanese


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