Lecture 20: Conjugation, Resonance, and Dienes

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Lecture 20: Conjugation, Resonance, and Dienes
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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. Index of Topics: 02:39 - Conjugation 03:29 - Conformations of Conjugated Dienes 16:27 - Electrophilic Addition Reactions of Isolated Dienes 19:49 - Electrophilic Addition Reactions of Conjugated Dienes: 1,2 and 1,4 Additions 30:02 - Kinetic vs Thermodynamic Products 42:12 - The Diels-Alder Reactions
Conformational isomerism Ionenbindung Biosynthesis Bearing (mechanical) Chemical property Wursthülle River source Chemical reaction Food additive Optische Aktivität Diet food Systemic therapy Reducing agent Hydrate Hydrogen Sodium Computer animation Konstitutionsisomerie Cell (biology) Chemical compound Covalent bond Separator (milk) Periodate Ammonia
Conformational isomerism Metal Übergangszustand Ionenbindung Steric effects Electronic cigarette Optische Aktivität Heck-Reaktion Hydrogen Computer animation Human body temperature Covalent bond Active site
Conformational isomerism Metal Ionenbindung Tuberculosis Diamond Wursthülle Chemical reaction River source Chlorine Steric effects Chemistry Systemic therapy Hydrogen Gesundheitsstörung Computer animation Colourant Active site Stuffing
Chemical reactor Famotidine Left-wing politics Walking Chloride Carbon (fiber) Protonation Chemical reaction Chlorine Chemistry Electronic cigarette Hydrogen Drop (liquid) Computer animation Radical (chemistry) Resin Addition reaction Colourant Covalent bond Chemical structure Satellite DNA Biomolecular structure
Sense District Gesundheitsstörung Activation energy Computer animation Addition reaction Covalent bond Carbon (fiber) Katalase Diallyl disulfide Chemical reaction Wursthülle Chemistry
Chain (unit) Computer animation Addition reaction Covalent bond Walking Cryogenics Cancer Wursthülle Chemical reaction
Übergangszustand Activation energy Walking Growth medium Chemical reaction Molecule Computer animation Metabolic pathway Human body temperature Cryogenics Silicon Mixture Thermoforming Dipol <1,3->
Chemical formula Activation energy Bromide Genetic engineering Octane rating Chemical reaction Molecule Gesundheitsstörung Computer animation Halogenation Colourant Controller (control theory) Covalent bond Freies Elektron Cryogenics Thermoforming Stuffing
Knot Computer animation Addition reaction Diamond Chemical reaction
Alkoholfreies Getränk Setzen <Verfahrenstechnik> Ionenbindung Geochemistry Pilot experiment Diamond Chemical reaction Electronic cigarette Chemistry Systemic therapy Lead Gesundheitsstörung Machinability Computer animation Electron Fire Addition reaction Cell (biology) Covalent bond Chemical structure Medical history Isotopenmarkierung
Everybody relevant testimony Friday that didn't write about that brings up a little more about Chapter 16 as anybody who questions before we get started new 1 yes during protests no I think you ask him I analyze yeah I noticed that underwriting today I swear they say I want to cerebral little at all I would say that I only told you want to assure I will more than 1 so what I did tell you about mechanisms in hydrogen outlined guaranteed mechanism from Chapter 15 guaranteed and as I'm sure going to be another and that's good news for you because you guys usually do really well and mechanisms and don't do as well on synthesis of brought so the more mechanisms the lessons in predicting prices going to be a lot of synthesis in predicting products to the question say that a little louder than the hydration now ,comma you don't yeah alright requesters 1910 intended by where it is safe for now when we do it dissolving now that reduction we take a chunk of sodium and we put it into liquid ammonia I don't write NA NA story is not 1 compound is so young in liquid ammonia so if you have a marine right next to each other either leave a space or put it ,comma it's not any N H 3 has 1 ,comma OK that's a little heads up on that I was done except 60 day anybody what we all went up since sapling Chapter 16 over the week taking a low-grade I think that's enough part of the cell last time cares who we know going into this chapter read-only conjugated Deininger bear more stable than on diets that are not going to get and so on but how much stable much more stable so we do this it's very hydrogenation nonetheless we mentioned that he had not given often reaction and sensible .period at the same time that we can estimate that we can calculate the stability because this 1 releases only 54 releases 61 the world's going to the same thing so that means that this has to be lower energy to stop it we could do reactions like that to see that all when the conjugated and it's definitely going to be more stable when when they're not conjugated but also I talk about confirmations of conjugated dying territory possible stereo isomers for a conjugated dying these are a different case are employed and keep in mind is that set don't rotate single wants can rotate not double bonds so on these 3 compounds are actually stereo isomers of each other if you look here this double bond is trance OK and some people have trouble seeing them that's because of this group inaccurate opposite each other if you're having trouble seeing that would help since joining the hydrogen when you can see that those items are on opposite sides of that so that's a trans out clean and likewise this 1 right here is a trend and again I know I realize a lot of people have trouble seeing there and so it helpful it's helpful to draw the hydrogen in and you can see that and here there are clearly decided and on the top assumed on the bottom so they're on opposite sides Widstrand syllables are both trainers and for this 1 here this is assist system gives us here's our service here again if you have trouble seeing that drawn hydrogen and you can see that the hydrogen on the same side of the Stockholm and then we can draw the hydrogen zone on this side here and so this assistance and we have another stereo isomer where on 1 assist someone is France so this 1 here is since and this 1 hears trail you you can't can work on the trains assistance to the sister and without rotating from Hyde double bonds Arkansas so you they these are as separate Jerry Rice isomers with a different physical properties that different compounds there is also due possible conformations that result from free rotation about the carbon-carbon single on OK so and so the search stereo eyesores but there's also confirmations and you have a name for others to confirmations once France double Vontobel trends about the single bond and there's SCS where the double wonder says about the single 1 and this has to do with the rotation of the center bond here so this 1 right
here when we rotate out cause and so that's on the next page so a cost that is that there is a single
1 of them bonding between the 2 5 also
is you can rotate that far-right so I'm for as this 1 here is SS it's a little strange to look at but this is our single bond and can you see that and what store the hydrogen is here so this is it we're not talking about being double bonds you would talk about the single bond and that's where s in France and can you see that I'm not been that long it's in between the 2 dying that the 2 items are on the same side so that means that the Keane's here are also on the same side of the sport here so this is SS so this is the orientation of the 2 conjugated down double belongs here and they are on the same site here so that as soon mn and if army and ends and they can also so that students can also rotate 2 best this is what the the and let's see how we how the heck we did that and what we're talking about here so rights oriented so this is the bonds in between the 2 Keenan here's the bond it's in between the 2 OK so we will we will we can we can change this year we can't change the fact that this is trams and this one's friends so there's still Charenton product except which is rotated so we're looking at the orientation here of the tumult Keane's about that center Sigma von thanking you see that In once this is rotated this hydrogen is often the down so obvious to double bonds are actually trans to each other and you can see that if you change your perspective a little bit so this would be asked France so very strange but that's it if you terminology that we're here so this is as trance and and so on and definitely as transit is almost all the time not all the time but almost all the time or still more of a favor so the user going back and forth this double bond and a single 1 of the middle is retaining really fast there's Stewart orientations but if you look here we have a little bit hysterical with these 2 hydrogen is here in the SS confirmation so there's a steric hindrance here steer hindrance so the are strands is more stable more stable conformation it turns out that the barrier to rotation here it's 4 . 9 2 counts for more is 4 . 9 K accounts more I room-temperature talent energy we have of kinetic energy for rotation there are enough of to 20 22 20 k accounts for all at room temperature is what we have available at room temperature we have 20 key cows from all available for this rotation so it means that we have more than enough energy for levitation said to current kicked 23 counts from all available so therefore there is instrumentation rotation and temperature are 2nd example here and can you see that there's more of a problem with Derrickson hindrance this is the unprocessed confirmation and these 2 metals are actually there's that the were steric hindrance so I really have even longer and even shorter error the other direction if I can there but because it's less favored and so vast transmissible favor and
let's check that we haven't made a mistake so let's identify here this is our restaurants it's definitely favored and let's make sure that we done this right so let's go ahead and 0 and I were talking about right here that font right there and very helpful to put the hydrogen is and if you look at the orientation of the 2 outings are on opposite sides of that single bond that's in the middle of if you look over here on this side they are on the same side if you look at what we can't rotate but use a different color for the orientation of responded in this respond here that sits right not fast says that sets we're actually talking about the IOC this assess and likewise right here that so we don't want a change that the only thing we can changes that center bond and this is and when you want to be able to do for the final not for mid-term to his Theobald the rotate those without making a mistake without changing things that you're not allowed to change which is whether you have since trance you can change asses to ask France can change system trams most conjugated diners prefer the restaurant's confirmation so most of the time received as strands the more stable conformation of there are some exceptions here on this 1 here not obvious but we actually have a shorter arrow to the right and long era to the left and if we drop outs enjoying all the hydrogen is in there this would be the strands it turns out that there's a the steric hindrance with these guys these to the natural and the hydrogen it doesn't look like the Super close together but if we drew out these hydrogen so straw that out the consumer talking about those that Madeleine that hydrogen and getting a little bit too close together thank here the case of the steric hindrance more steric hindrance in the strands so in this particular case the Onassis's favored and that's because of the bad steric interaction In the astronauts confirmation good morning we NRC trance confirmation and then I had I wouldn't I wouldn't agree that it's difficult to see why these 2 metals are not in a bad streak interaction but this is actually worse yes I don't have that number off the top of my head I should benefit from that next time we so maybe make a model and if you want to I have a lot of models in my office you can to make a model and may be able to see the sole better but that this is better than theirs it seems like that might be worse but this is actually works and then of course and this 1 here can ask in this says that can this bond between the 2 but once cannot retain it can't when incinerating so this is a fixed in an SS confirmation aren't so that's just a little terminology pieces Trans SS as trans What's the difference I'm really need to be able to do this when we talk about the deals reaction which is coming out a little bit later today but 1st I would talk about a familiar
reaction to UN as Elektra fill conditions as of this part of this chapter should be really easy if you know Chapter 2 if you don't Chapter 10 likely you'll know before Friday and inserts on the test it's 1 of those options is the most reactive and this 1st example here laughter right but 1 won the right if we if we if we if we probably the 1 on the right the former tertiary ,comma cattle if we permit the 1 on the left the best we can do is a secondary so we're gonna probably the 1 on the right definitely and so that 1 is on more reactive because it forms the most stable ,comma so pretty straightforward question we can easily writing I was just going through the mechanism here just as a little recast Serena funded tertiary ,comma :colon and encourage comes in attacks so requires a little bit of thinking about what's going to be the most reactive that's going come occurring in in attack and so the product this 1 here with the with the with the chlorine on the right-hand side don't need to show very chemistry here because this car is currently and in the car which mysterious centers not so that would be a product with 1 of his HCl if we had 2 columns of HCl Morgan and Morgan from naval Shiites CBS questions I hear question was that it within a few several will descend from here OK so that is meant to enable sites I will go you that mechanism but this is what we look like so access for 2 equivalents you could like a great leader it's going to do it on both sides so that's what we have isolated darling a little bit different story when we have conjugated diamonds so really this is the last time in this chapter that we talk about isolated Dynes the rest of the chapter wouldn't talk about conjugated are excellent see what happens when we needed to do the same
thing with the conjugated died symmetrical died in years and doesn't matter which side we promote mate it wasn't symmetrical we would probably decide that would give them more stable ,comma we'll see 1 of those coming up I should do this down here that's kind of move that's that's just move this down here to pretend that I actually read through that moved down here or maybe I'll just a reason to do it the right way ,comma you can leave it there you have duration Barak Summers who do the same thing each Seattle world through which way and let's not go there when go local gonorrhea sent a 2nd OK so what we have here we're going to have be to only and so that's right here there's also to other protons so look like that right under that and how will it cannon whenever we have a little at anything that includes radicals that includes program that either which cover Catherine who wanted drop balls President structures because that's resident stabilized so we went on resident structure for that so there and this is going to go here and I am deliberately putting hydrogen is only and here because the most common mistake I see students do is to lose that last card in there so I'm going to be deliberately trying to drop hydrogen is on the ends of these and I encourage you to do the same thing on the test no definitely the secondary cover campaign is more stable than the primary cover Khaddam but they're both Al Lula contents of the bowl stable enough to form and so in 2nd step and I'll change colors here so we don't get confused with the errors version of my winning chloride on Canadian they can attack this curve Academy of Oregon have Florida 9 community attack this car can so that struck product here congress here and we also get 1 with characters on their hands and I'm taking all the time extra time to draw those 2 hydrogen think is the most common mistake is for students to lose that carbon adjusted the 2 items along with so let's look at what just happened here we have we had we added and here we added that there's the same hydrogen and the chlorides we have a different name for each of those This is the 1 to products and this 1 here is the 1 for product so the ones you product hydrogen that you just added on in the morning and adjacent province doesn't matter if they're in the middle of a molecule or at the end of its 1 2 1 here and 1 2 3 4 2 count carvings hydrogen is on carbon number 1 and then of the chlorine as a carpenter before so this is the 1 for product and this is the 1 to fight and we will get both of those points and that's all because the on how will the PLO Catherine is stabilized by residents questions so far anybody yes if we were going to talk about stereo Chemistry yes you will form management because you have a player ,comma can immediately get attack before either side came right now we're not gonna worry we're now right now and focusing on staircase if the conjugated dying is not
symmetrical the major products of the reaction results from addition to the most reactive double bond the 1 that forms the most stable ,comma repentance and don't forget about that don't forget about that on the final and don't forget about that when you do Chapter 16 satellite prices for possible products and you only get 2 of them if you're not worried about steering chemistry so we was most reacted the 1 on the left or the 1 on the right left will make a tertiary like if we do the 1 on the right make a secondary our tertiary onlookers more stable so this 1 here is the most reactive are excellent said HCL to the most reactor there comes from the pylon we grabbed the hydrogen we break the hydrogen falling bond so that gives us a tertiary Kerber thoughts we won whenever we make and how it anything we wanted our resident structures so this is and how little Aqaba Catherine so that struck the resin structures are not going to do that errors for because I don't want you to get confused with the chloride ion attacking also so CH 3 here the double bond moves over 1 to the left now we have ch and we have CH 2 class on me and here so those are the 2 resident structures for the helicopter Catherine and then the chloride 19 communion attack on either side some of the time it will attack on the let
inside and some of the time it attack over here on the curtains on the right side and if it attacks on the left-hand side you get product number 1 if the attacks on the right-hand side you get product number 2 you do not get any products from around program nation on the carbon on the rights so if you were to approach making this 1 of 1st you get 2 different products and you don't get those when to all those 2 products for you so when you run across this problem in sapling you'll see 0 1 and
probably the wrong 1 not these would be the other 2 products you would get if you probably don't need either side and you don't then again would not even considering stirred chemistry that increases the number of things you can get OK so you don't get the take extra that thank you and so these would be from addition to the other double bond 1st don't get also you certainly don't want to know what include those on the exam so why wants the wants that 1 of these so what's the 1 we get the major admitted the ones who as a major do we get the 1 4 is the major in and really it depends on the conditions of the reaction so that leads us right into and kinetic versus thermodynamic products In this tends to be 1 of the questions that people talk about and that's all DAT and then a course nobody knows the new and that very well the wild wild world of the new nonprofit competitors is the redirect politics is something that I've seen on cats before and DAT before right so went up a little bit about that where activities more than one-third pockets for more rapidly as the kinetic products that make sense that seems logical fastest Connecticut think fast speed that's the kinetic part of the project most stable as the thermodynamic product case aware that something new I keep in mind here the sportscasters Connecticut Providence product that dominate the called the thermodynamic and it's always going to be the most stable all right so for many of organic reactions the most democratic is the 1 that's far more rapidly
than is the kinetic and thermodynamic products are the same for electrical addition of Ajax to a conjugated dying however the most stable product is formed more slowly and that is the kinetic and thermodynamic product are different all right so and that there I've seen 1 example where that's not the case but will stick with this for now boxer turns out of if you but you added art to this conjugated dining in it's not symmetrical and he dismantles it doesn't really matter what we do with the dude at minus 80 degrees centigrade you get 1 2 0 1 4 edition but you get 80 per cent once you and you get 20 per cent of the 104 additional products it turns out that some of the ones you is the QinetiQ this is the kinetic which means it's fund were rapidly and if you are at very low temperature which minus 80 degrees centigrade is very low the kinetic product is going to predominate over here we have the thermodynamic products which means it's more stabilize that more stable why is the 1 for product were stable having only arbiter of onto to that that kind of thing to know when the kinetic fighters only once it's more stable locking some more stable because it's a more substituted double bond alright so let's look at the effects that cancer what happens if we
run their reaction at 40 degrees or we can actually run the reaction might now allowed to warm up to 40 doesn't matter how we do it we both ways and it turns out that when you allow that reaction to warm up for you run a reaction at 40 degrees you get 15 per cent of the kinetic product in only 85 per cent of the 1 in an 85 per cent of the 1 so the most stable product now predominates so what is the point series and chains around in order to answer that question we need to look at the entrance of dried out so let's look at the energy Icarus if we can figure out what's going on here the 1st step is the same for
both of these reactions if the the kinetic products of the 1st step is going to be the same for Poles and the 2nd the kinetic product is the 1 that has the lowest energy transition state right so this is the 1 to use the kinetic product here and at a temperature of the molecules have less energy right they have less energy at lower temperature and so they're going to take the lowest energy pathway here and so that's why that's going to be the major most of them are going to take the lowest energy path by fear which gives the 1 to prod when you when have action at a higher temperature and then the molecules are more energetic and sells more of them have enough energy to overcome this higher energy barrier which actually leads to the more stable right so this is the transition state 21 for products and the lower energy transition state is 41 products so this is the transition state Florida 0 1 2 product Our right now if we if we run this reaction at 40 we get our major product is going to be the most stable economy this 1 if we run into Morrisania and allowed to warm up to 40 missed we still get this 1 as a major product so is that means the reactions reversible right if we start off with 80 % kinetic anyone up to 40 and 85 per cent of anything it's a reversible reaction are excellent similar so that what happens so rattled temperature on most of the molecules go and undergo this slow this lower energy pathway of in order to do the reverse reaction and just a reversible reaction actually get back to this in media OK so that means that undergo reverse reaction left to come up with this much energy to go back to that of the direction and low temperatures from the molecules don't Silicon have very much energy to do that if we therefore at a higher temperature we can have both Connecticut and enter that you see that once the form this thermodynamic products were much less likely to go back again in writing why would that be much higher energy of activation so what we end up getting as as as soon as we formed the thermodynamic product it doesn't go back again because it's too high energy for it to go back stays so so we call this an authority and it well it's like the product is fall into the well and is too deep to ever go back again so even if we form so most of the time in form the kinetic products faster and because it's already pathways even at 48 the ones we formed a thermodynamic it's not going to go back again so eventually how we're going to get a thermodynamic mixture where most of it is going to be on this wonderful product so let's look at the bullet points underneath this and with you that it might say is not enough energy for the reverse
reaction to occur OK so that's even know where this is available it's still a high-energy activation for models to come up with that minus 80 to go up that energy Hill barrier arms at 40 degrees is enough energy for the rich correction to take place the products can refer back to the common intermediate products can now interfere bird to form a thermodynamic mixture and as we said once you form this product it tends to stay nobody knows product reverses less readily causes a larger energy buried in the kinetics so that's what we're talking about right here because the and this is energy barriers to higher when we do
that in a different color huge energy barrier this would be a for reverse reaction for the thermodynamic products it's just too high it's not going to go 2nd ago the reverse reaction so there's some journals unions over so that that's what the
reaction is irreversible and the conditions of the reaction it said to be candid kinetic controlling the relative amounts of the products will depend on the rates at which their form so at minus 18 we say that we are under kinetic control molecules are not energetic enough to go to do the reverse reaction but I'm back said 40 degrees centigrade on the other hand we're understanding and control and when we're under through genetic control we always have a reversible reactions wouldn't always end up with a more stable product for dominating OK so the question is who said that once the product is kinetic wiseacre wives that actually formed more rapidly let's let's look at the mechanism really quickly and see if we can figure this out so we have HBO here it immediately after we have that status to see the bromine the bromide I'm is right there it's very close to that is right where like other carriers form it's much easier for this bromine bromide I to come and attack the herb can because it's in close proximity to her returning to Formula One products this double bond is over we have to ,comma Kennedy ended in Berlin has to migrate over there to attack and has to migrate over it's going to be in the right orientation and all that stuff so on this form ,comma rapidly because of this we called the proximity effect there so close to each other and that reaction is going to be faster then the bromide I'm having to migrate so the bromine bromide ions is close by so we call them proximity effect and when you're at low temperature the molecules are not moving very quickly and not very energetic could have bromide identical over there and move over to the other side of it's going to require all on advantages something happen as quickly as it is if if it's just right there so therefore it attacks faster in this position all right
questions anybody still looks like
and we had a severe additions and dying to manage their addition to isolate and diamonds and we haven't heard conjugated guidance so that's 2 reactions so far in Chapter 16 right there's only 1 more reaction we have to talk to and talk about 260 knots deals we spend the rest of this chapter talking about deals or so deals a very famous reaction this is what
it looks like arcades and opined that country dying suppose six-member during its and you always make 6 members bring 6 members cycle had seen ranges of Boris cycling the dining rooms OK so this is 1 of like on my lights included dotted lines between the 2 ends of the pie system were going to be moving electrons around in a circle it doesn't matter whether we go clockwise or counterclockwise wouldn't moving electrons around in a circle and and always the way all you wanted use you wanna start from 1 of the double bonds I'm going to go counterclockwise here which you can also go clockwise so and if you look at what we're doing ,comma getting rid of this high bond hearing that get a double bond right here we're getting rid of the double bond here and using that to make a new bond between the 2 ends here this double bond here From there from their cell changes is going to move over here to make a new bond here and that's how we're making a six-member drink so this is what it would look like but stated that you narrow put 2 . 1 on the wrong side of the ledger that double bonds right here on yes fall there is a double what's right there if we haven't helped ,comma I'm seem the same idea and would have a double 1 would have dotted lines connecting the 2 hands but it of electrons around in a circle this time I did counterclockwise you're going to go clockwise does not matter the directions but result that all of these bonds are being made and broken simultaneously this is a concerted reactions so we don't want here we move we've broken 1 pylons and they'll kind but not the other 2 so we have a double 1 on the other side so the arterial kind is called a diet of final a lover of diamonds so romantic right this is a dying of fire it loves diamonds Bentley kind is also died in a fire it was conjugated diamonds concurred and then I this is the dining costs so there is a dire need and is dying of filed reactions a part to condition because the ring is formed by the interaction of 4 pilot tones on the dining with 2 pilot on the al-Qaeda all kind so there's 2 election lecterns for each of these 5 so this is for former high electron it's so let's label that this is for apply electrons and this is to to pilot this is for pilot projects the triple Wanda has actually for pilot turns were only reacting to move them so we would also call this the 2 pilot programs the other the other 2 electrons and the other primary not reacting so this is a forecast to cycle addition it's only 1 of the type there a broad category of cycle additions this is 1 example and really focusing just on this 1 example I really give you some examples some more examples here let's strong products here so super simple machinations ago counterclockwise six-member during so messed mechanistic lead very simple but we have a lot of issues that we have to deal with in this reaction stirred canister geochemistry would make which makes it more complicated all right so that so that looks like I'm not attempting to draw history chemistry at this point here because we talk about the coming up and then we have this 1 here this is more complicated to draw also I'm initially to different ways to do this under the first one is going to be a more complicated way the love that don't so double 1 here we have a double 1 here and we have a C O 2 CH 3 here I knew you'd like this OK so what makes this kind of like a little house you know there's the roof of the house with a little peaked roof right on it's it's a it's a bomb it's a bridge to by cyclic structure and that's why it's hard to draw bridged by cyclic structure now we call this right here at the juncture of the 2 Bridgeton this is a bridgehead position and this 1 over on the other side is also a bridgehead position and if you look at the if you examine the structure you can see that we have a six-member during right here but we come here 1 2 3 4 5 6 we also have a 1 2 3 4 5 Member ring here and 1 2 3 4 5 measuring on that side is actually 3 different things here alright if you don't like drawing it down later only give you an easy way to draw this you like better and this is going to be a bird's-eye view as if we were a little bird on top looking down from the roof if you're coming from the top and looking down on this then this this little bridge here sticking straight up toward the so this would be the bird's-eye view like that better you got to make sure that this is obvious that we have obtained here OK so coming straight out at 2 another way to draw OK so perfect stopping point we will continue to someone else the 1 fighting through