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Lecture 06. Alkenes, Part 1

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Lecture 06. Alkenes, 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: 00:22- Exterminators use rain-activated chemical to wash away bugs 01:54- Structure of bifenthrin 06:56- How to enumerate steps CHAPTER 10-Alkenes 09:37- 10.1:Introduction 10:51- 10.1: Introduction-Configurational stability of C=C vs. C-C 13:47- 10.1: Introduction-Contrast reactivity of C-C vs. C=C 16:59- 10.1: Degree of Unsaturation 20:40- 10.2: Calulate Degrees of Unsaturation from Molecular Formula 29:20- 10.3: Know cis/trans & E/Z 37:58- Physical Properties, Interesting Alkenes, Lipids 42:48- 10.7: Ways I Like to Make Alkenes (so far)
power type green drug Bohr mode media chemische Reaktion coal chemical Calcium hydroxide man water van Stream gauge Computer animation firing Wasseraktivität control report Carcinoma in situ processes
Maische container Nervengift man Alfred AMPs ingredients van Computer animation insecticides Wasseraktivität chemical structures derivatives toxin Granule (cell biology) Löslichkeit bottles selective
surface pilot mode chemische Reaktion chemical food man water AMPs van Computer animation control compounds nanoparticle stuff
phosphorus Bohr Hausmannit chloride set chemical optische Aktivität molecule Isomere transformations Toxins Holes Double bond alkyl steps chemische Reaktion alcohols stability end van model Gamma compounds Dielectric spectroscopy stuff bond Graukäse organic Bis (band) man reactive Chlorkohlenwasserstoffe Magnetometer Methane important processes areas Seltenerdmineralien Bromide chemical alkenes Natrium Computer animation initial function Peroxyacetylnitrat pore chemical structures substrates
Digital elevation model Atomic absorption spectroscopy unsaturated Bohr container chloride Hydroxyethylcellulosen chlorine solutions molecule Zellglas Klinisches Experiment Dreifachbindungen color Insulin modifications Methylmalonyl-CoA-Mutase Hexane Double bond Maische properties Katalase chemische Reaktion complexes alcohols Knot Alkane emission van spectroscopic samples match DOM coupling Gamma compounds Penning trap polymer Dielectric spectroscopy oxygen Lymphangiomyomatosis Pipette stuff bond severe Gum arabic case Propionaldehyd man reactive Zeitverschiebung age Magnetometer sulfuric acid tool packing atom modules Halogene Laxative processes chemical formulae molecular nitrogen Bromide Prolin Omega-3-Fettsäuren carbon proton man pressure Biodiesel alkenes Amrinone Wasserstoff conditions Computer animation Indicators function chemical structures substrates basic Butane
Digital elevation model Adipose tissue chain unsaturated Bohr LSD secret gene chemical Potassium Isomere Insulin Eliminierungsreaktionen derivatives Oxide Substituent oil Fatty Acid Maische properties alkyl chemische Reaktion Knot membranes Säuren packing Iodide glycerol Garden lipid Penning trap polymer stuff informatics sense Kohlenstoff-14 organic man lead Enolates important Common sulfuric acid aspirin active site Beta packing mineralischer FAS chemical formulae Alkyl Groups Gletscherzunge function standards chemical structures basic addresses Silicon Integrated Systems den Sulfate meat Calcium hydroxide molecule lipid Soybean oil benzene rings Morse biochemistry German Double bond Corn oil complexes alcohols firm fat end systems Paste van phosphate Ionenbeweglichkeit coupling Gamma compounds Isomere oxygen label Graukäse mechanism carboxyl group rates carbon De-ice food methyl Magnetometer cell storage level Monoaminoxidase Halogene Oceanic basin processes type mixture Arginine Bromide burning multiple carbon proton man alkenes Eisfläche Wasserstoff Computer animation Tau protein Dehydration Carboxylierung chemist AdoMet
chemische Reaktion
so I saw this little news report the From station in Baton Rouge Louisiana Texas green but then the news report was talking about was there interviewing some pest control person about how the deal worth of fire and problems with the problem you don't have your California yet it's coming on I spend a lot of time growing up in Texas Louisiana and I can tell you answer really nasty on what caught my attention is that this this pest control person was talking about and that and I'm sorry you'd see this very well have lost another laser pointers companies talking about some special powdery white substance and more importantly I'm he was talking about the media can use the mouse to come over here and try to 2 points here on the news talk about some granular product that is water activated and somehow or another that just turns me on because it sounds lot maybe there's some chemical reaction between rainwater yes well yes thank you for asking that but does not alter the turning up until we get to the next stage From but somehow the idea that there might be water availability the original the idea that water might somehow be chemically reacting with some pesticide and maybe who knows who hasn't 1 reaction user or some other type of substitution process such as sound intrinsically coal there's not a lot of pesticides drugs that are designed to react chemically on so I did some searching around to try to figure out what they were talking about what I had to Google few terms but what I came upon was this so this so all I'm missing the final years so there is some our pesticide by a green light on and let me see if I can go back I apologize for this I
should have gone with the PDF version of so there's some
pesticide here you can see that the cover that ,comma contains something that is cold water activity granules and if you look of course we always look down the active ingredients it contains . 1 percent by entering on immediately my hard sending is I know I know that this is going to be a croissant derivative and nothing new on you wouldn't know it from the name but there's a whole class of insecticides in the letters from each on the containers this three-member during an investor and the based on an unnatural and insecticide its founding chrysanthemum flowers I was pretty yellow flowers have a natural insecticide on that's a selective neuro toxin toward spots for parts so I maybe if you believe you ingested this entire bottle could affect you but it's super-duper potent against insects on encrustations and things like that so this is the structure of the active ingredient and there's a nested here which in theory could hide arising in the rain rain water but that's not the way works on actually the way this once this is kind of clever I think this is how it works so what's notable about this particular version of this chrysanthemums Esther that's that's a neurotoxin insects on his it's very greasy and has almost no water solubility on and if we go back and reread what this
pesticide control person was very excited about what he was excited about the fact that whenever it rains the into piles get soaked in all the it's come to the surface of the they don't drown drowned and so they're all hanging out on the surface of the Indian pilots and so what he does is he comes along he spreads his powder on top and he just sits there and sits there and sits there and the answer will be down deep under the ground in that stuff
but as soon as it rains the in Seoul climbed to the surface and here these particles and as it's raining local rainwater is Washington office outer coating that water soluble and it's leaving behind this waxy by entering the all these hands will just come to the surface find think food on the Main Justice Minister and so was not the chemical effect that I thought it was like I thought maybe there would be a chemical reaction with water this sort of a kind of cool idea so I'm not sure if this guy appreciates
how cool stuff is Jeannine second-row
toxins this happens to target sodium activated ion channel in neurons that's very cool as well armed but next time you're smelling of chrysanthemum flower on
your problem getting a whiff of some of those kinds of compounds OK so so let's let me make up a point about Monday Monday is national holiday in its university holiday Martin Luther King Day and I just want to remind you of this quote from Ben Franklin Drive By business or it will drive the you have an opportunity to choose what you do with your Monday university holiday on I hope you'll do something to honor Martin Luther King but I would hurt to just find some way to set aside some time to spend on organic chemistry it's very rare that you get the gift of extra time to get ahead in this class tried to use that time to get ahead OK me and also because we have discussions sections on Monday if you're in a Monday discussion section tried to attend 1 of the other discussion sections throughout the week and be 4 days worth of discussion sessions you'll be able to find 1 that you can squeeze into the Chris asked me to make a point about this the company issued it's going to become more pervasive throughout organic chemistry and some just going to draw that I want to remind you that we're going to start doing something in this class and his book on where you do lots and lots of reactions come from a single process so I want to give you an example this this is typical of the kinds of examples kinds of questions or be asking more and more throughout the quarter where I ask you to take some starting material and then somehow converted into a product and it will never be will almost never be 1 step it's going to be multiple steps and so how do you depict transformations that require more than 1 chemical steps thank you there we go so how do you depict transformations that involve more than 1 chemical and so here's an example of a question how do you convert this alcohol into this that and the fact that there is no 1 step way to do this now the key principle the key problem here is that you need to figure out how to convert that alcohol into a leading group and have all kinds of reagents that holes and leading groups final chloride and purity possible chloride infuriating to make possible the group's PBR 3 new appeared in his PDR 3 will make an alkyl bromide out that you can pick anyone you want I'm going to pick PBI 3 because it's easy but then the 2nd part of this is we have to do we have to add in some nuclear power like other like of methane violating an I'm like about dockside assistant a soulful and there on the streets sodium because so the sodium plus some about minds now this is immediately wrong it's wrong and it's wrong because if I don't enumerate the steps with numbers it implies I'm mixing everything together at the same time if you don't have numbers to these reagents and steps it means simply dumping everything together in the same class and if you don't have any kind of nuclear file in with Bosphorus Strait remind people react faster with the phosphorus tribe reminded the alcohol will and a way to make this correct is to enumerate the step where riding the number 1 and the book uses brackets I usually use parentheses and writing the number 2 then it's absolutely clear that what you mean is I'm going to take alcohol I'm going to treat it with phosphorus try bromide to make the alkyl bromide and then I'm going to purify the alkyl bromide and then I'm going to use my pure Cobra Lane and throw into a completely different reaction so more and more we're going to be doing reactions where I simply enumerate the steps because they don't want to draw every structure in every intermediate and if you don't enumerates steps if you simply write all the reactions in regions over 1 error with 1 reaction that's just not right so I'm pay careful attention to this idea of enumeration of steps because it means something completely different ,comma if you take the numbers out the numbers 1 and 2 OK so let's get on with on new chapter here we get a break China's new chapter on but we can spend our time on I had just feel like I am emerging from the woods into the bright sunshine finally getting away from this this hell of Chapter 7 89 in this S N 1 s and 2 in the 1 business that stuff is just awful he likened hearings and buzzing feedback effect and and all of state OK so we were going to start talking about how and I wanted today ,comma introduced this area by telling 2 specific things about our teams that differ from single bonds so the 1st sets to do with on the persisted with the reactivity of of single bonds and the American left off a piece of paper here but let me just go with this so wanted the we try to do this in the same order printed notes here that I can look at the missing 1 of my patients OK let me 1st talked about the configuration of stability arm of single bonds and because I lost my piece of theater right on simply going to show you what I have here and my on my on my written on OK so there is a key point in key distinction between double bonds and singled wants and that is you can rotate about single bonds like this and you hadn't really noticed doing this but every time we've drawn some sort of a structure like this I see every single 1 of those bonds rotate about and that simple out pain and that becomes very important when you have to think about reactions were 2 ends of a molecule have to bend around and get close to each other so they can react so we haven't talked about a lot of intramolecular reaction so far but we're going to is it as the quarter progressed and so when I see a substrate that looks like this somehow Alcock side at 1 end of a molecule and some alkyl chloride at the other end of molecule I recognize that this great nucleophile isn't going to do anything unless he can get close to the alkyl chloride nothing will happen if those 2 can get close to each other and so I would rely on the fact that unless but if I do rotate about the central bonds here that this is not a chemical reaction I don't really need to draw this is a chemical error the Datsun an initial requirement in order to get this close enough so that it can do some sort of innocent too and so behind rotation allows these groups to get close enough so that you can end up with an intramolecular displacement reactions some kind like innocent but it's intramolecular focus upon rotation you take it for granted and you've probably taken it for granted throughout this whole book so far and starting in chapters because we're talking about here you can no longer take that for granted the problem is let's take exactly the same model except that we're going to put a double bond right in the middle and the configuration of that double bond matters so I've drawn a particular isomer talk about this nomenclature on shortly this is called trans isomer and with this trans isomer you cannot with this double bond hearing you cannot freely rotate about that CCE pride bond about the double bond it's locked In that configuration with those 2 groups sticking far apart from each other and if you can bring his all mine is close to the corridor will never cyclists so double bonds matters there are locked in a particular configuration will talk about that with the groups on the same side of the opposite side of the Belmont and that's going to dictate some of our chemistry and so if you haven't been thinking about bond rotations previously you have to think about that now talking so that's 1 important distinction between simple out Kane single bonds
and double bonds the idea that the CCW once cannot configurations but couldn't talk about a difference in reactivity how does the cc single bonds differed in yet we're on I will the bottom 1 can't yes I got on there at a Jewish -dash terrorist indicated that some sort of fictional on treadmill and if it doesn't rotate the no votes with the intention of this these other things can't happen cannot start off trains and then suddenly be what will call Cecil introduced that terminology later chaos the bottoms of can't happen OK so what's what's the key difference in reactivity this kind of in a I'm going to some of this entire chapter for you so here's something that you haven't seen the Madrona hoping for you here and there's nothing special about the cellophane so far some of the most reactive reagents juiciness things like sulfuric acid maybe Hydro IOD Gass said new shown all kinds of things acting as bases in nuclear files to attack here's what you've never seen you never seen a single bond just come along the attack of protons or attack an electrified you haven't seen that in not going to see that so CCC Ingle bonds are not reacted they don't act as nuclear files they act spaces they don't and that sort of obvious state butane it doesn't do anything doesn't react with anything you could probably use that as a solvent but I want you to contrast that with Chapter 10 years we're going to learn in Chapter 10 and were going to do it over and over and over and over and tho I have emphasized that another reminder do this over and over and over again were going to take substrates that FCC double bonds in their and and analysts say until you're sick of it and hopefully will be happy about it we're going to use pot bonds between carbon C C double bonds has bases and his nuclear files and so we're going to do this kind of stuff over and over and over again so it won't always be attacking protons that woman use that double bond is a nucleophile to attack that's this chapter so get ready for that get ready to do that when I just didn't mean to be clear going into the Aero starts from the middle of the so we're going to that over and over again no it's not quite as reactive as an alcoholic cider and on and on In maybe depending on the type of electrical can be about as reactive as an alcohol along pair were going to see lots and lots of examples of this so that still exploded chapters about In looking at the little introductory idea here will want to characterize before we start talking about how I'm anxious to get started on those reactions but I have to resist the so-called missile much better than this destined to businesses that but they were going to talk about a way to characterize compounds based on their molecular formula and the structure and I'm going to give you a new sort of parameters that you can use to describe compounds and this will help you when we get to spectroscopy but when you're taking the 51 lb ladder would be doing all kinds of spectroscopy somebody's going to give you this super complex looking spectrum and molecular fun and say OK what's the structure of the molecules and you'll be going To be freaking out and so this is where this is going to help you so you have to hold on for a couple chapters to restart a mark but this is really going to help you when you get to that so we're going to introduce an idea called degrees of UN saturation it's a property associated with molecules and you can back it out knowing nothing more than than the chemical formula so that we don't you know how many degrees on saturation there are in some molecule just like somebody giving you the molecular formula you can very quickly ruled out structures that don't match and so to the degree man saturation on it's basically the number of regions plus a number of in the molecule that so a saturated came like hexane has no pipe bombs and has no rains so that 0 degrees and saturation such practice figuring out the degrees of and saturation in these 5 molecules here just by simply adding up the total number brings plus the total number of pipelines so how many rings are there in this on so beautiful in this to methyl propane 0 double bonds pylons there's 1 so this has a told degrees on saturation of 1 that is 1 degree of and saturation there you know you've mastered it McCain that switch over to this on my God there's an oxygen atom that make any difference OK so how many rings are in this there's 1 rain and retired last there 0 so another molecule that also has 1 degree of and saturation it's come over here Oh there's a triple bond there's no rains in there I can see there's no in this this is called a trial common went on but now I count the number of apply bonds that triple bond has to pipelines so I have to have the number to hear there's 2 pipelines natural wonders with each triple bond is composed of 1 single bonded Dupri bonds so this is 2 degrees of and saturation OK let's get to more complex structures how many rings here above I see 1 range How many pie there's Dupuy bonds that has 3 degrees of and saturation what you'll find is that typically the more degrees saturation in amount of the fewer hydrogen atoms in the molecular formula OK here's purity in its it's all talked about I 1 ring their quite plainly wondering and then how many private the street that has 4 degrees saturation so you have not mastered calculating the degrees among saturation of figuring it out I hope you were out there is an intuitive speed at which you can do this since any might make little mistakes missing some of these numbers but the generally it's pretty intuitive what would you can see yet is how you're going to use that and again you have to hold on with this degrees inland saturation thing to leave it to the spectroscopy chapters really going to help you focus so let's keep going and we're going to do the things the other way and now if I give you the molecular formula and this is more typical if I give you the molecular formula what's important is you can calculate the degrees on saturation just from a molecular formula future let's practice that additional all they have to give you and the steep falls it is going to be seeing super complex at 1st the cat can I apply all these complex rules when I'm under time pressure on exam practice that so you OK so here's our rules so if you have some sort of a C & H compound there's nothing this season ages with and cartons and you can figure out how many cartons just by looking in the regular formula so here's a example C 3 H 4 there's 3 carpets and upholstery 3 carbon compound jobs right here in mostly kind of obvious will get C 3 C 5 C whatever OK so hard we figure out the degrees when saturation what we figure out is what the maximum number of hydrogen you could have on a molecule that is 3 cartons and sketch it out here today I'll just use of different pen color somewhere so don't get in the way if I had a 3 Carbonell came like that how many hydrogen the most thank you guys are going that look and plus
2 that's the maximum number of hydrogen so if the if this compound had no 1 saturation at 0 degrees 1 saturation in order the HA but it's not H. hate it's actually H 4 the actual number of hydrogen is here for so you can tell it's missing some hydrogen C 3 H 4 missing hydrogen and what we do is we now divide this difference by 2 wish for hydrogen is missing somewhere and if there's for hydrogen we divide that number by 2 8 minus 4 divided by 2 so how I calculate this the calls the minus-4 divided by 2 divided by a medical student that's the degrees on saturation and the idea is that it takes 2 hydrogen is to add to a double bond a CC doubled while its waved bye-bye 2 OK so Oh I use this later when we do spectroscopy I'm going to say Here's a molecule with the formula C 3 H 4 on New year's spectrum what's the structure and the 1st thing you need to do is start drawing out some plausible structures that its C 3 H 4 so I can think of 2 things that have to to be rezoned saturation is a 3rd 1 I'm not going to drop the only only 3 out simple Keynes'-a simple molecules that had this formula so here's a molecule that is 2 degrees saturation fits the formula to double bonds or I could have won double bond and 1 rain so you need some simple way that allows you to quickly into out plausible structures and knowing how many rains in how many private there are a molecule is the fastest way to help you quickly sketch out some structures that's why you see how you're going to use degrees and saturation begin keep practicing here so I got some special several CIA for oxygen allergens and nitrogen so the oxygen rule Little add on rule is ignoring the oxygen they don't affect any of those things I just told you OK so it's come down to a molecule C 3 H 6 0 so here and cool serene and what's the maximum number either act hydrogen is number of hydrogen I can have event is equal to 3 boats still late the 3 carbon is the maximum number of items can be a and the number of oxygen you haven't doesn't matter OK coming hydrogen either on this alleges look at 6 the 6 and so how many degrees 1 saturation this molecule there's 1 8 minus 6 is too and I divide by 2 that tells me there's either 1 double bond or 1 in this molecule I can very quickly sketch out the possibilities once I know there's either 1 no longer 1 rain that makes a very quick for me to sketch out a bunch part possible structure OK halogen 0 little bit more complex are rule is so let's start off with this this rule against the C 3 H 5 CEO there's 3 cartons and so the maximum number of hydrogen C is still a that's always going to be a Mississippi 3 so that the maximum heightens the actual hydrogen is H 5 but we have a special little modifier will we have a halogen we have to add 1 to the actual number of guidance for each halogen whenever I have a chemical structure and I have a halogen on there I had to pull off an age in order to add that halogen chlorides go in the same place where hydrogen is due in order to come to back up the degrees when saturation what I need to do here is applied this rule where I had 1 to actual number of ages 5 plus 1 now I can take the difference now I can take the difference between the maximum number of hydrogen than the actual number of guidance so I say 8 -minus 6 this too and then to divide by 2 as 1 there's 1 degree on saturation indices 3 H 5 C so now that I know there's 1 degree even saturation I can very quickly sketch out some possibilities that have either 1 Ranger 1 double bond is 1 example I I could invent all kinds of structures that have either 1 ring 1 double what with an example of something has just 1 rain and a chloride somewhere and you know you can just remembered rings etc. so the way that see that's not seen 3 each story should be 3 cards has it's mostly a cycle propane so comparable chloride OK so I could very quickly sketch out plausible structures that fit that formula that have either 1 rain and 1 double bond OK so things can be crazy and complex looking here is a compound only has 2 carbons from the saying and is equal to to what's the maximum number of hydrogen should be 6 containers 6 hydrogen OK but now we look at the actual number of hydrogen it's H 4 and I had to use diesel modifier rules OK oxygen doesn't matter so it's ignore that for each chloride already lighter bromide right that I have had to add 1 Clerides dead 1 man but now there's another rule for nitrogen another rule for nitrogen free tonight should I have to subtract 1 from the actual number of hydrogen and so overall my mind number 4 hydrogen is going to be for because I had 1 for the chloride as subtract 1 for the nitrogen and so the difference between these 2 is now to again so now this has won even saturation that tells me that this molecular formula all compounds that at this molecular formula I've ever won rain or 1 double bonds and so I can quickly sketch out some plausible structures a case you're not going to use this this chapter will that the probably ease-of-use sapling problems to get your practice this year and end up waiting until we get to the spectroscopy chapters and this has come to be your favorite tool for allowing you to quickly sketch out structures when I ask you to tell me the structure some molecule that is the formula C 284 NO CL and matches this crazy complex spectrum that I'm going to show you what you need some way to narrow down the number of structural possibilities and that's where this is going to be useful OK so sorry I had to show this to you but but just along with this guy but it would belong Arabic sorry you're never has the scoring this quarter and I think that have flooring would fit with allergens is just not comment you can 15 so I should put it OK so let's talk about nomenclature can I really make it to the chemical reactions and I'm feeling really OK so I don't I don't ask Are you pregnant later on my exams on my exams they I do ask them and the sampling because on on the online but problems it's because the standardized exams ask you questions about our nomenclature so the main thing that I really want you to know is that help compounds the Al-Qaeda and set the Keane is the highest priority group in the molecule on Wall and as soon as you hear the suffix Union others announcing somewhere so here's a polymer and condition distort carbons here so this is not a very high resolution pen and this is a polymer with 4 carbon repeats over and over again on this is called neoprene so if you want surfing this morning in a wet suit was made out of this polymer and is from the name neoprene you know there now keen somewhere in the chemical structure of the Parliament there's also a chlorine atom herself you know that's that's kind
of a level at which I know nomenclature a year I listen for the word meaning it tells me all there's a double bond in there would have been let's talk about this idea of configuration that double bonds don't rotate easily I'm going to drop 2 types of molecules for you and we'll talk about this nomenclature system trams 2 years before carbon compounds it's not butane its beauties and 1 way that I would distinguish these these 2 molecules draw the hydrogen there could sometimes the best way for you just to keep track of Al teams and whether the sister transistor look at the hydrogen that drawn for for you that helps you to keep your focus on the fact that both sides of the aisle kinda different OK so here's to our genes to bewteen armpits to review team and they have different double bond configurations 1 of these is trains now means that the 2 alkyl groups on opposite sides the 2 highest priority groups we on opposite sides and the it's a description of the overall molecule if a molecule has only 1 double bond I could say all that trans bewteen over there and it's totally unambiguous what I'm talking about if there's only 1 double bond I say it's strands that means the 2 highest priority groups on opposite sides if I say but since molecule and there's only 1 double bond but I say that since double bond I'm talking about the double bond where the 2 highest priority groups on the same side look at the problem comes if I had more than 1 double bond in a molecule I can't say so if there's more than 1 cc double I can't say that trains out because you don't know which 1 I'm talking about and that's where are you pack nomenclature comes in so I impact nomenclature works uses these descriptors it doesn't use trains insists it uses the NC to distinguish these and it's useful even if there's multiple multiple double bonds in their molecules so according to IDD pack nomenclature so many writers above here that this is isomers the trans isomer and decison Maria's I would call this the SIS I might be the way I might also use these descriptors I might say at trains double bond and the other 1 is assist double bond I focusing on the functional group and described the double bonds that were OK but now it's switch over to the tie you pack and that means anything this makes perfect sense if if you're a native German speaker on but if you're not the use of the term of the letters leniency probably is not so obvious value patterning for this is that it's it's not butane it's a bewteen and specifically it's the 2 beauty what does that mean he tells you that that double bond a trans configuration that's what I mean and for these other over here it's also bewteen the double bonds and that the 2 carbon 2 and 3 efforts to butane and this 1 has that the 2 highest party groups insist to each other's we call that and I can't do it here with the pen but those are italics font so easy to beauty for the trans isomer z to team for the system and every time I have a double bond in there I have described that double bond is either years in all Olshan example the bomb so what is seen as 1 of these things mean on he stands for and begin German and gave it means opposite meaning on opposite sides Z's stands for its use on which means together and that means the together on the same side on you're going to need some sort of a simple while on here is a simple way fear not a native German speaker to notice some people say this Owens I you don't need to speak German to remember that OK so far typically the kind compounds you will be exposed to typically will not be name mobile by you using the rules we give you intend 51 is 1 of the most important of all molecules and lipid signaling on a biologist would call this fight each Pete but because they don't want to see the whole idea packed name which is 5 had a proxy 68 11 the 14 Cozart gasses the nobody wants to say that aren't that this would be an example of a super complex but important biological structure on it's important information on prostate .period signaling where you can go back and decipher what they're talking about so this is a carboxyl Aghazadeh conceded in a weak acid and I don't expect you to know the name of this sort out mean something is complex but I want you to see how this means the nomenclature works I can't simply say all that lipid molecule it's it's a trans isomer well there's more than 1 doubled on some of the double bond Eritreans and summer since I can't just say trained there since this is where we have to use it that and the thing so but you don't know what it calls attaches mean means you know it gas on you didn't know that there's a lot of carbons in there but this so if we number this standby using Value pack numbering the carboxyl aghast would get the highest priority number 1 and I'll keep counting down the chain 3 4 5 years carbon successor 1st double bond and look at this it's 60 and you know that that the the double bonds started carbon 6 is a trans isomer monarchy going over here I get the carbon 8 there's carbonate down there and so am I plan doesn't have high resolution and you can see that carbonate is agency on the same side it's assist double bond in the 2 substituent on there on the same side you could keep going so you can see how the ice pack nomenclature and this easy stuff works art and this is a typical molecule we have so many double bonds needed to keep track of which double bonds assists which double ones the configuration which doubled 170 configurations I won't ask you anything that complex of the crazy I don't ask you technically turned on Sunday if you're working some biochemistry lab and somebody flashes you this complex structure you might be able to sketch something out that I would tell you something about configuration OK so typically the way I never expected know nomenclature on my examine might ask a question and they would say something like drawl is the product of the following reaction and you would have to name the molecule but you need to know what is the isomers foreign de-icing and I expect you know system trends but is another there's all these other sections in this chapter that they'd stick in the front to slow down how quickly we can get to the chemistry the sections 10 . 4 5 and 6 is about physical properties like what's the boiling point of an Al-Qaeda on where some structures of interesting Elkins and where some help teams that you find in lipids Israel's very cool ideas that I'm not going to put these on my exam but the only thing I can really do exactly true false questions and I don't do that on my exams drop structures and stuff so let's talk about why should you care about how genes why should you care about degrees on saturation and I think the most important reason that you might care about things like degrees of and saturation how many double bonds on a molecule might relate to nutrition from if you look now on the back on the label of every single food items sold the site from fresh produce and meats and things like that they now sometimes for you the on saturation and the double bond content of the facts that are in the food the
cheerleading so mission just remind you of the structure of a that versus lipid so up above here I had a lipid molecule and it's got testers as functional groups 2 of them carboxyl Acosta's men has a phosphate as and these are attached to a 3 carbon unit called glycerol so that's a basic lipid and that's makes up the outside of membrane of all of cells and now you also have inside year dip the sites you fat molecule that looks very similar to a leopard and the difference is that with the fat molecule you've got 3 asters and there's no phosphate Europe on a molecule but what I'm drawn here with the squiggly lines are some very long chain carboxyl groups all little squiggly lines are drawn here on looks something like this that either look like this long chain with 2 double bond you can have as many as 4 double bonds in these long chains you can have as few as 0 double bonds in those long chains Oregon have 1 double bond those launchings chains and so on the main thing that you need to know is that the saturated fatty acids that Europe reason saturation tend to be waxy solid when you have that they have no double bonds in their those to the solids if you go to the grocery store and you want to buy some kind of a fact that the solid but shortening Crisco shortening those are all composed of saturated fatty acids if you want a liquid that vegetable oil Safwat vegetable oils is soybean oil that is going to tell you so sold soybean oil safflower oil corn oil all those all have double bonds in and lots of double bonds the more double bonds the more the in the liquid the more liquidity the liquid and so that's the distinguished this distinction that you that you need to know so you don't want waxy solids to deposit this is a sectional view of a clogged artery where you can see this reference little space in Europe the blood to flow you don't want the waxy fat deposits to start building up in your arteries there's this whole process it starts your immune system starts climbing onto that and it includes the arteries and what you could do arteries during your heart it's a bad situation so they now tell you when the food packaging just how many saturated fats there are in that proved the percentages of saturated fats they tell you that the telling you chemical information you know for years the group Trans Alp teams like this 1 here with the good fats the liquid he ones which is weird to me because when I look at the structure that trains keen I just happened to know what's going to adopt a configuration that looks like a saturated outfield and it seems like only about 10 years ago people started as I know what that needs to be grouped With saturated fatty acids you can't have any old Ltd In a fat molecule and have been liquidating it has to be assists Ltd so I think about 10 maybe 8 years ago they started to tell you not just how much saturated fat but also how much trans fats there are on because those are going to clog your arteries and you don't want to clog your arteries it's bad thing to OK so on saturation on every food packaging they tell you telling you about how many double bonds were in are on the molecules of the facts of the treaty the Switzer have a review let's review some of the stuff you've already seen in chapters that I just can't get away from stuff 7 8 and 9 and it's going to really tell you this stuff there that I just finished telling you on Monday because why not let's talk about the ways that you know for how to make out the jury know how to make out the words to synthesize them such as the reviewer I can review everything but all review a couple of my my favorite ways so some of my favorite ways to make Al-Qaeda's lead to elimination reactions and oftentimes so let's let's practice abbreviations often times I'm going to abbreviate CH 3 groups methyl with the letters and the Justice stylistic preferences it looks a lot cleaner on a page because subscripts and you'll find many synthetic chemists an organic chemist abbreviate CH 3 groups methyl groups as any and you have to get used to that so here is a man boxing group at the end of my Al-Qaeda and so there would be an example of how I might like to make From melting I have some sort of a leading group here here's to oxygen derivatives of Foxy group and possibly Group 1 of those is an outstanding leaving group and that's the tussling and I want you start getting used to using that because he spent so many chapters not talk about allergens get away from that and toss away too much easier to you can see them much more commonly so vital a strong-minded basin here in almost all there's not a huge difference between the most tainted in the standard of Cox the team he talks about is the 1 its most of most tended so you're here's another abbreviation that I'm going to start using their T Beutel so this is the same as what the book writes the book greater like this so that's the way we're used to seeing it from the book I missed radio TV and you just need to know that that's that's that's the same as that this potassium to review dockside so when I come along and say well I'm going to take this tussling here that was my I didn't call a heater I wanna focus your attention on the most reactive parts I said policy that tussling over there but still some key Utah oxide so might like this TB you 0 minus potassium plus for I might lead out the miners in the past and destroyed as a molecular formula kind of style and so this is going to do any to elimination is beta protons Baidoa on the beta carbon that will get pulled off and this would allow you to make a see reorienting like carbon chain that's OK so I started with 3 carbons I still have 3 gardens on tonight introducing a double bond so I expect you to know we to eliminations on and their great reactions the useful wouldn't talk about the alternative energy you typically have a halogen leaving grouper tosser leaving repeating good leaving groups free to elimination by the way he wanted to or not the most common elimination mechanism on organic chemistry here have to wait until Chapter 23 before we surely the most common elimination mechanism in organic chemistry it's not 1 and it's not and which they showed it you earlier but we will just have to leave that is a secret until you get through those chapters focus what's another way other than the 2 eliminations To make Elkins the stake a tertiary alcohols just as an example we showed you the 1 process as a way to do elimination reactions so if I take this tertiary :colon treat that with apocalypse reappeared Dean or strong acid into a dehydration and I can very easily dehydrated so the sulfuric acid approach so few sulfuric acid not HBR HI because I don't want nuclear files like bromide iodide and their sulfate is not of the nuclear file so that you don't get a 2nd 1 reactions the solar easily making out and again PHS and sort of trying to get you to practice my abbreviations the Pentagon not just mine the book will start using them on 1 more that stands for a benzene ring of fennel group ,comma there's 2 of them on here so you should be it's starting to get a lot of practice now with these regions that we the alkyl chapter Chapter 9 dehydration strong masses etc.
OK so those always that I like to make out things you should know how to make them so when we come back on Wednesday I'm going to show you of a bunch of reactions that you can do without him for the Al-Qaeda attacks on we will