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Lecture 07. Alkenes, Part 2

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so far recently this summer news article on personal use this kind of stuff myself and my wife would on about some new products that I used is opposed to rejuvenate your skin army young and apparently it contains a multi patented gene activating they a are molecules and when I see the water molecule in news story of course I immediately turns me on the thinking of something called and I wanted to know what is hearing on your face and gene activating on and the mysterious letters before they are with the 3 a R and and so what is this about unsolved and wouldn't
looked up this for on articles this was developed by somebody in Utah and who was in Utah the padded actually it's of organic chemist just like me there that I made a very simple derivative ,comma got a huge amount of press has in the past decade and its resveratrol it's this this molecule the bottom of matches can see my laser pointers here at the bottom of the and it's it's a red wine ,comma have many people were touting its security died in these various periods of diabetes G unit every ailment known to man and it's very active in terms of this molecule is your on what state's super active potency but at some of the our things to target certain 1 so this is comically examine bonded to procreate specifically time settling and what is like this ,comma misappropriation acts it releases all kinds genes this function is the use lethal so they were correct this is gene activating molecules that trigger behind this war a R molecule is that it can continue to use their you know everybody knows that resveratrol is very useful for for me to another the because we have to take huge quantities the body clears resveratrol so fast that you have to sit immediately breakfast cereal and would keep an eye on your body to do anything on and so it so this can instead is went in and made a very simple Esther derivative that's the asteroid right here on top as cold acetate ester after the African will teach you how to do that but 51 See you may do that in the laboratory rats molesters that somebody's going to make it as simple as gave this molecule and hang time so that it should only need to eat huge quantities of this we have some sort of effect and I don't know if this is actually going to make your skin seemed seen younger and Indians to regenerate but it is a technical so trivial idea that you'll be able to accomplish just by taking a class like this on hoping your bio 98 unrelated classes remained cool stuff like this about biology on these are the kinds of things that the biologist care about these types of pathways in these types of activating molecules OK so let's go and get back to our financing there's a double bond right in between these 2 benzene rings and makes me want to add something to that double bond isolates go and talk about the chemistry of double bonds at the focus of Chapter 10 for this class and we spent the lecture on come on Friday which seems forever because there was a but we just had this holiday this university holiday we try to get this document came to mind you and so seems like forever ago since we just had a Monday holiday on but and this is what
undercover Chapter 10 week we spend our last lecture really covering some basic concepts that demands on the kinds of useful concept that
you'll use structure the cost but this is the spy reactions here are really Chapter 10 international if you can grasp these 10 reactions you guys and moreover he can grasp these 10 reactions your set up for the rest of organic chemistry especially chapter routine which is a big focus for this class that toward the end of the quarter on 151 seats and people are behind feel like they're totally lost I tell them go back to Chapter 10 and learn those reactions again these are absolutely fundamental to of understanding organic chemistry OK so user reactions were going to learn more and learn how the bromine atom bomb on an Al-Qaeda and there's a very simple reagent for doing this I can't imagine regions that are that much more simple it's HBO and if you want to add chlorine in the same way that HCl now this may look very mysterious to you because you can't see the H got added there but I had and not just the bromine I also added age and just in case it's not clear that there is a need all draw for you but I expect it to be very good by this point in time seen the ages and drawn there is the age that was drawn that was added with HBO OK so very easily he could do the same reaction with HCl I'm I've never seen anybody do a reaction like this with HIV hypothetically but that's possible he may depend on the structure of the Al-Qaeda on OK so if you also want to add up hydroxyl group to Unalakleet you can add the elements of water tonality but we need a trip here we have to have some sort of an acid in order to have the elements of water that is dead cat litter sulfuric acid and I'm very picky about which accident you want to choose an asset has a non nucleophilic counter so pay-TV are don't pick HCl use catalytic sulfuric acid and in order to make this work you have to add water and so I need and you have have a lot of water are what makes this reaction go with that water the solvent and its present in big access so whenever I draw reagent below the area if those regions are common solvents in organic chemistry like water or methanol or ethanol you can assume that that's present in a large excess focus again identity the elements of H and H here's the only from the water and use the Shh and if that's not clear to you that it is reminding there wasn't 1 each year before and now in the product there's images so I did add an extra general wage To make this product that you've seen both of these reactions before then enjoy dividing line you've already seen these reactions these are new and and you may think Why didn't see that reaction before what you've seen is you scene that reaction in reverse you've seen the elimination of patriotic outings we should be strong is like to be toxic to do that now and I'm showing music take that same out and go back again to the alkyl halide we show you how to dehydrate alcohols using cash using sulfuric acid as a catalyst which is left out the water was the trend now were driving the equilibrium backwards simply by running this reaction in water OK so you'll see the mechanisms for those 2 reactions I shall you better look very much like the reverse of mechanisms you already know I took a so so In a way these is a kind of knew these 1st 2 reactions but really that they're not that new OK book the reactions 3 4 and 5 year those on you and you haven't seen anything like this before and there's going to be a lot of stereo chemical issues that come along with the arm so if 1 had to bromine atoms here to announce I'm going to use bromine molecular bromine that's br 2 you don't have to drop bomb and showing the br has upon this is originally had used yet this class and you're going to use uses a lot and you can also do this with chlorine Cl 2 chlorine gas bromine is a liquid is just a dark brown liquid were scoring 2 gas that's when it will be very rare for people to do this with chlorine and academic glass of usually is bromine because it's convenient liquid OK we can take care of this same reagent bromine br to understand I'm going to draw a molecular formula because that's more convenient and I simply 1 of the reaction in water same bromine saying novel bromine together drop drop a few drops in there and if I run the reaction united in Alcoholics all entering water that water Oak Alexis a nucleophile and so I don't get to bromine they get 1 bromine and and hydroxyl group in this case now aren't you notice something particular about the scarier she to bromine on top here and indeed to each other and the bromine in the hydroxyl group also end up the ante to each other on opposite sides of of where the double bond was once that's 1 stereo chemical issue and wanted to hop on and make a big deal about and the other thing of course here is that we've got and symbolizing this with Plessey it to ways to mean plus an Indian see you also get the mirror image in the same gun on and arm I always front and my questions by saying on showing the stereo chemistry unless otherwise indicated this is 1 simple way for indicated there is also a mirror image that's produced just write Plessey and I will understand that to mean that you've generated a Rossini mixture of two-inning tumors OK so that's tuna reactions edition of bromine across a double bond or addition of bromine in water and you can't do both of those reactions but with tell with C O 2 with chlorine if we wanted you cannot do those reactions with iodine on maybe the 2nd 1 in special cases but that but I would never ask you to do that OK so the last 1 here is looks just like the sulfuric acid in water and what I'll show you is that it's complementary as I think it's the same product why would I use this complicated bottom reaction induced the regions than that for this complicated by reaction the 1st region as a region you've never seen before it's called boring yes that's a
boron atoms you can see anything at all on matters so we're talk a lot about that when we get to the discussion of these these reactions and there's a 2nd step here notice so I enumerated steps if a leave out the numbers it's totally wrong but I don't enumerated the steps is step 1 instead 2 then that means that simply mix everything together in Appendix everything together but I have a dangerously explosive mixture and I would get none of the product shown so you have to enumerate these things I've I I've enumerated these with Roman numeral II Roman numeral II it is Arabic numerals the book come just to show you the alternative you can enumerate things the way the book does the book uses brackets that's totally inconsequential in these Arabic numerals and generally in organic chemistry if used these little Roman numerals it means you didn't isolate and purify the intermediate after the 1st bursaries their numerals and use you isolated and purified intermediates and it it doesn't matter throughout this quarter you you may use Arabic numerals were values Roman numerals on and that's fine because you don't have to worry about what the details of workouts but they step number 2 on this day at Hydro peroxide and we make that in the lab by mixing hydrogen peroxide you can buy hydrogen peroxide and the book shows HO minus that a minus sign on but if you by I would prefer wrote sodium hydroxide that let me write sodium hydroxide it's bothering me there is no region the wage minus so that's sodium hydroxide unseen makes these 2 things together sodium hydroxide and peroxide and I know it looks kind of complexes look at all those steps in those weird regions you don't know anything about who get that this will launch and will will show you why you would want to do this other way for adding a wage on so again I'm just remind you that it added to the gains across this al-Qaeda was 1 each cheered the bottom in the beginning my hands who won 3 go there was 1 agent beginning in on this product is 2 inches you can see this 5th reaction here identity H and OH across that double bond so I urge you To to practice until you are expert seeing the ages there drawn for you I expect you to order the policies that there was any on it'll it'll hurt you if you can see that it will hope you're immensely if your fast focused most of my reactions of talk about them Bush's talk about them over and over and over again you'll see you in some ways the very similar to each other until we get to the last 1 and then things got kind of crazy focus .period scary chemistry it's a big issue in this chapter and stereo chemical relationships so minister of withdrawing the substrate in the middle of my page here I I'm going to try to pretend that I'm standing and looking at this this Albertini said John and I were standing in the and looking at this as a John kind of like looking at a piece of paper so that the people at the end I would see the city to substitutes going back into substitutes going forward said the sort of the age where trying to emphasize that I want I want total imagine looking out the so that I can see it as a top face an about face every out he has a tough race a bottom faces and I want you to imagine 2 of those library actions let's take a look at the stereo chemical consequences for 2 of those 5 reactions that we can see that sometimes things out on the top face where the face and their 2 modes in which the 2 Adams can socially to reactions from them list again the 1st reaction and I'm going to show you it is going to be the addition of bromine br too soon I had B R 2 across without being that's take a look at what happens to those 2 bromine atoms and we're going to have special meaning for this that allows us to discuss it in keeping straight so what happens is I'm going to get there will be no double bond in the product and I'm really trying hard to see unity relationships by drawing this in the source confirmation looks kind of like this this standard confirmation here OK so here's the the product and in the product 1 bromine managed from the top face and the other bromine ions from the bottom face and is always true bromine edition would be ordered to edition 1 always ads from 1 face and the other 1 against from the other face and also get a mirror-image product and will drawn over this period down the prominence of the size of the important point here is that we refer to this relationship in the product the relationship of these 2 groups as empty as Antenucci relationship and we call this mode of addition Monte so that's the description for the whole the relative orientations of those 2 bromine groups in this reaction coconuts go back and look at this boron region that was the 5th reaction because it's different from men and that this whole sort of nomenclature here it must be because I have something some alternative to tainted and so here is it doesn't matter where are as it can be ages alkyl groups and so far take Boraine molecule that is a pH bond the B and H add across the government but in this case you don't get anything on the relationship between the way the B and H that those advocacy in orientation including job as being this age so here's and here's this weird born out of hope you're going to see what's with that boron thing we've never seen that before it's this whole group with the 2 are groups attached the way but those are groups doesn't really matter OK
so notice clearly in our history that the born in nature now on the same face if the ball on ads from the top place age will also led from the top place and if the boron and from the bottom face the arm the Natal also led from the bottle there usually a one-to-one mixture of edition from top place about things we call this relationship
between these 2 groups since and we call this mode of since so some of the reagents that I showed you on the last page I should reaction to talk about over and over and over again some regions when bromine and glorious some ratings on CNN but this Boraine with the beach bond the hydrogen bomb and son-in-law give you mixtures of sand Auntie and you're going to have to keep that straight for everyone of those by reactions I want you to know I expect you to know whether the motivation is seen unity and I expect you to understand the mechanistic origin on of that but that's scarier selectively OK so generally would find is that reactions involve cargo Carradine's give you mixtures of seeing indeed and things like hydration it's your additions OK and we'll talk about that OK so note those synergy relationships but that's about our 1st mechanism for their 1st reaction that I should you the addition of HBO or across the belongs some members struck by drawing a substrate will be a simple tries substituted and I've chosen itself keen because I want to make make it clear that it is particular case the 2 carbon atoms at 3 1 carbon atom has to say to sustain joints to metals were that's the 1 on the bottom where the carbon atom on top of in the AL team has only 1 muscle group the then because of the the reaction will exhibit some regional selectively sold going from my reaction with HBO and dropping the HBO on bonds because I'm drawing the mechanism for you so I can have H & B R cross that double bond a chance to 1 common enemy Ltd the yards to the other carbon handing out and the mechanism looks something like this I regret this a double bond here and this is what you haven't seen before and this is really that this error 1 about to draw is really this chapter in a nutshell this chapter in shows Al-Qaeda tackling stuff Elkins Acting as bases into nuclear files and there you go that way I've seen 3 chapters already were alone pairs attack days and now you're telling me that pipe bonds can attack the things from yeah In fact that's we're spends both this chapter on hand Chapter 11 and Chapter 18 talking about Over and over and over again and that's the heart of modern organics synthesis OK so you have to bring the bonds to the 8th stage br bond if we attack so really we're just doing an acid-base reaction and say Who would have thought that now he can act as a base will figure super strong acids to connect to the base but nowadays is intermediate what you can tell and this is what's frustrating about area pushing news of kings destroyed a narrow here where the double bond attacks each but you can't tell from my taking care which carbon picks up the you won't know until I draw the intermediate which of those 2 carbon atoms helping picks of the year some people get really frustrated by that they want to they try to make their arrows stock from 1 carbon atom not only made the Aero stock from the pipe bomb that's what acting as the base that's the pair of electrons that engaging this HBO are going to go and although the interviewed for you it's this tertiary Kerrville cat cannot draw the dangers that here there's there's 2 inches on it on the Kinas 1 major news the other so I started off with 1 each sticking out of here and I have to reaches so I didn't have to draw those in 4 years just to help you see where they each but leaves of a part of the broad 99 means that the broom and I'm still floating around right here there's 4 pairs of valence electrons I'm just going to draw 1 of those long pairs on and that's sets me to see what's going to happen
next the next that is going to attack the cattle the poor lonely cargo and it doesn't have an architect and beyond minus will satisfy them and that's what gives you this final product With 98 HP or across the double bond typically drop like this I typically Waldrop each the latest you have to get over this stock were not going to draw ages for you anymore you have to in invasion where those ages are focus we just showed you that's that's additional HBR Cristobal bonds you do the same mechanism with Seattle hydrochloric acid it's very cheap creating common laboratory on you could do it with a child very uncommon and typically alkali Badger so unstable and you just don't see people doing that very often so sold HCL HP are the most commonly focus we're going to see that kind of reactivity were double bonds attack things over and over and over and over again yes the question is how do you know the cover can and will be on the bottom carbon at another club again will not be in the top I will talk about that I will in just a couple here is surely something called Marconnet collateral which tells you that you looking but that
reaction generated cobbled Cat Island and we've been trying to teach you in this course whenever you have a reaction generate public that intermediates you have to watch out for rearrangements so here is an example of a reaction the generator a couple can and you have to watch out for rearrangements so when go ahead and draw what you get years of there's a substrate and what I see when I see this reaction allocated 98 yards across a double bond that I immediately and drawn to that streamed for 100 well it's straining at former like a school where they bonds don't wanna be square in organic chemistry In 1 of 109 degrees so maybe it shouldn't be that surprising to me that somewhere in this reaction pathway this molecule found the capacity to rearrange and get rid of the 26 K cows from all of strain the four-member Grant and sister to follow this through so if I asked you to explain and generate is this final product from it's like all kinds of crazy stuff is happening there on 1 trip that I I usually emphasize that I want you guys to try to home in on this if you have the mechanisms if I ask you a mechanism and you're sitting there which you can see what happens tried enumerating the cardinal try to track which carbon atoms and where as just a basic tool so here's some of the things that I see yeah the I see the starting job that Al-Qaeda there is no out here in the product so far arbitrarily starting number might carbon atoms I might call this carbon atoms ones To that's a C H 2 notice I'm not just looking at the Adams and looking whether they stare ch siege chooses CH 3 so carbon atoms H 2 our 3 is a siege to grow they're all in recovery for the siege to group and the symbols user arbitrary action is smiling faces flowers and the doesn't matter understand these numbers because they're easy and what I'm trying to do here is just come alive officers OK let me try numbering some other atoms maybe carbon wine is 1 of these 2 carbons between the rains I don't know which 1 but 1 of the things that I really seized 3 CH 2 groups in a row I'll bet it's reseachers on this side or on the other side of 2 3 and 4 right in the mechanism I'll break every single ponders just a few bonds the break and so I don't really know which of these is carbon atoms to three-year for I might overturn do this 1 4 3 2 1 2 3 4 4 9 don't really know what's attached to what you start off by by making the hypothesis and if anywhere along a mechanism the numbers start matching then you back up and start over and number of different ways so encourage you to number carbon atoms and your oftentimes picked the wrong numbering at 1st but at least it helps keep you focused on is my mechanism heading in the right direction OK so it's going dropped what happens if I probably is out the 2 different places you could probably make this but you could prove that the proton on you on the right-hand side on the left-hand side on I'm going to try to prove meeting over here on the right-hand side which will lead the positive charge right next to the strained drink and you wouldn't necessarily know that this is going to work out might have to try from meeting the other place 1st and then if you can get to the right place so it if I draw that Proton adding the Drolet Proton just in case it bothers you that you can't see where 2 there's the proton that I just added that leaves me with a secondary cargo carrier doesn't matter to those carbons April made I'm going to get a secondary public at 1 1 ahead of Proton the double bond and now this particular intermediate I have to be very worried well I don't know what worries that too the correct emotion here just what I can see is that it this has the capacity to undergo 1 to help she to make a more stable ,comma Caroline those reactions tend to be fast 1 to Alcatel shifts in generate more stable harbor parents particularly tertiary ,comma conference on tenderly very fast and if they relieve range-trading when they do that in a 3 4 during the unstoppable so in other words let me draw this other other counter-violence floating around you may wonder will Gee how could I have guessed but the bromide doesn't simply attacked Qatar and it's because rearrangements that really brings train always faster under conditions that you see in this class for always faster than that this kind of attack bromide the counter on the complicated OK so McGowan draw that rearrangement of the from claiming it so fast zoo the officer was OK now here's a place where you might get mixed up really easily no time I make sure I do all of these carbon atoms faithfully and this is where number can often help you if you're worried that you're not going to have to redraw this intermediate correctly on a number of carbon atoms can help you so in this case you might want you might consider finishing enumerating all of Adams 5 business each to number 5 years of siege to number 6 there's a scene With the help he number 7 years of siege number 8 and writer on I had to match these are looking for a C H 2 number 588 still attached to cotton once all draw that a siege to members of the siege to member states In that matches or his associates Jr the 6 is still attached to 7 I have to explain my mechanism somehow carbon 7 picked up an extra protons and if this is right now and that is very clear G currently now has all these carbon atoms attached so again you your number and could be wrong at 1st be just Be ready to back up with your mechanism and start over so I let me keep number in the numbers still calling here and this rearrangement this is where I really have to keep track to make sure I don't mess up drawing intermediate try to make this five-member during this 1 over here where carbon 1 5 7 and mandate and you don't have to number York if you're good enough to figure things out without number of great not just as a tool to help you and things start to get really confusing so I moved break this carbon 1 to bond so carbon for not breaking so ,comma has to still be attached and covering 3 still attached to carbon for carbon 3 I'm not breaking that bond so they go in and enumerate those you can see no 1 at my character she didn't break the bond between carbon 1 for bio pushing didn't break the bond between 3 and 4 and I hope shouldn't break the bond between 2 and 3 but according to my error question I broke the bond between 1 and 2 and I made that bond move over the carbonates in the draw that there it is In I take electrons away from carbon 1 I have to leave the cargo can I is that current can the German car and
just to be clear there was a major architectural carbonate will see those ages and it's still attached their carbonate in this intermediate and it is still attached to the product so that's a relief for the summer veering off in some weird direction and I'm bromide account Tri-Nations floating around on and it's ready to attack the tertiary cargo Qatar it's not drawn in a particularly beautiful way of what ended up with this the right ring system with 2 five-member brings and and a tertiary complicated and snow might remind can try incoming attacked the tertiary cover OK so what's the important thing is that this is not new the idea 1 2 rearrangements this is just a different reaction that leads to cobble can intermediates the addition of HBO are and HCl across double bonds leads to cobble Caroline's just like and 1 reactions with a couple can answer watch out for rearrangements of cargo especially if they lead to a more stable ,comma kinds and in the unstoppable if they really bring strain industry and murdering ministry of remembered with yeah so this is the 1st to you yet said yeah you have to assume in this class that's true it's concentration dependent solely for the reactions that we show you in this class you have to to assume that at the concentrations were showing you that the rearrangements of 3 and and four-member brings to make tertiary couple can faster than hence I'm kind of doing a bait-and-switch because it's also reversal there's a potential reverse ability to market you need to worry about that just assume it's faster but 3 OK so how do you know which carbon you're going to have a proton to and that's answer by she had know how all this will exceed this award from the British 1800 or on maybe that's wrong maybe maybe it's early 1900 does about the time frame such take a look at sums on symmetrical out scenes and I'll show you a simple on really impure Walter Smith's was developed without an understanding of the matter is the basis for long but how do you predict you got an Al-Qaeda as 2 different types of and you had HCl arrange ATA idea know which end of the Al-Qaeda gets the Proton which interview helped him get alive and that's what work on Castle was good for Wal-Mart ,comma said will look at the al-Qaeda and then you have to decide even if the 2 two-engine non-identical if 1 is more substituted in 1 is less substitute for right less substitute the top end result he is less
substituted and the bottom end of the Al-Qaeda is more substituted and he's going to abbreviate substituted there so that 2 different standards and the contrast was very simple you proton To the less substituted card we just need to remember that so I'll refer back to remark on council later in the class it's an empirical and you just have to remember all that means that a chance to the less substituted carbon so strong the product for this here is the product of the reaction but what I hold on what where is that change bulletin and dropped the is there here is the strangers on stock methyl group that I didn't draw for you but there were 2 in the beginning and I say substituted I don't mean age is not considered substituent remark on a cultural I mean substituted by alkyl groups opposed to wages are still there and use that 38 and I emphasize over and over that
you have to be very good by this point in time it's seeing ages and drawn he conceded agency or across a double bond H goes on the less substituted carbon In the nuclear file chloride bromide goes on the more so because it illustrated in this if we really mastered this month ,comma cops with OK a differentially some Montana HCl use HBO on and I had across that the belong so you should be able to figure out which of the 2 cartons in the outfield and 1 of them gets the H 1 of them gets this year so we apply Marconnet castle inconsistent pure observation that Jeter less substituting currently at stage it's this 1 down here at the bottom so now the 1 on the bottom is less substituted another 1 on the town is more substituted and by the end of this chapter you're going to be very fast and recognizing OK that carbon is more substituted becomes less substituted into my mind all this product out bromide is going to be up here and that age could use the don't drop we use non-drug age all draw for you is down there the United draw the other regions such as seemed weird to me than drop that 1 In no case of age goes on the left substituted carbon so well you using this over and over I expected is good with that that's a common kind of question for and cats and stuff like that look at what is at work why is it that this house house at the market confidence this out and he didn't know anything about the mechanism you could have invented this rule if you knew the mechanisms actually don't need the recall if you
understand the mechanism for the reaction so take a look at what's going on on mechanistic link that makes the h adds to the less substituted card and then to come back to that initial example and I'm going to try to to draw kind appears vertically in the middle of my page because I wanna show this substrate has to possible pathways and chooses 1 all figures in the top carbon in mountainous is less substituted in the bottom of his more substituted and this has 2 possibilities would against HBO are draw my HP are molecule seductively hovering over that waiting to do so it's got to pathways it likes the bottom pathway that I'll show you in a moment and then we'll try to rationalize why doesn't take this is a top pathway and so damages which is known for ourselves that this discarded Adam over here on the bottom of this is more substitute because this is what we're paying attention to the ,comma cultural and the top of carbon is less substituted here we go in a case when this double bond Jackson Miss pipeline this CC pipeline attacks on that age proton although like hero starting from the middle of the that's the way we do it and we want a pop out the bromide Leading Group and so the question is does the proton go To the bottom ,comma with the top and what I showed you when I do that mechanism was that protons likes to go To the less substituted carbon the top carbon give tertiary complicated a just in my tiny Kenya sketch out at each other and understand it it's not our fault .period the point is that this is a tertiary cargo carrier obviously tertiary class that's tertiary if I probably make the bottom ,comma if I did stick the proton on the more substituted carbons it starts to look very painful there is that range and now I'm I'm left to over with left with the revered as a secondary cargo cash more stable level Cameron's form faster this is a rule you already know organic chemistry and I'm not telling you the more stable products always form faster in organic chemistry that's only true at the time but for cargo plans more stable ,comma parents formed fast and so given a choice to put made on the top carbon and formalist stables a source from the top ,comma from a more stable tertiary cover cat and that's the choice and the Al-Qaeda's not pick up the proton on the bottom ,comma because that would lead to an unstable secondary cargo cat that's why Mark ,comma cultural works ,comma works because it had basically when you stick a proton unless substituted carbon you leave a cargo can iron and more substituted Co and so that's why I McConnell conservation correctly predicts that the nuclear file will be attached where there was a more stable so there's the bromide after attacks there's a Chatham typically don't draw little droid in there so you don't get lost there OK ,comma cultural works you don't generate less substituted couple cannons when it's a race it's more so more substituted more stable ,comma canines that form faster OK so that's why so that you don't have to remember Mark cultural if you can work if you know the mechanism for the reaction there you can just fall back on G more stable cover cannons form faster in organic chemistry I'm not going to draw that this other possible pathway
consists of artificially the top pathways not favorable OK so Tuttle a bit more about issues of stereo chemistry because this whole idea that we can add top faces about faces of double bonds on some very real implications for how you should draw your answers I for my exams for your understanding of organic chemistry so good and plot out how you get these 2 possible products in this reaction so if you edit the art across the South and generally online discussion section problem sets and my exams they say clearly indicate scarier chemistry in the presence of stereo isomers Finney so you you'll try asking draw the products needed or something like this will drop plus the username tumors each other and so I don't get to Indian tumors to tell preceded him when they try to draw the substrate edge on again because I want to try to envision this idea that there's a top facing the bottom face to this molecule so that the bottom end of the Qaeda has an absolute I'll destroy half group like this and then out of if I if I'm trying to envision this so I can see those 2 phases and some of the suggestions will be sort of angle back and some of them will be angled forwards and is trying to draw this edge on-site concealed carry out he has a top face about it's a reality has top facing a bottom face this electron density on those faces about how keen on and so when this HBR it's equally possible you will get a sentiment that ads from the top face the bottom-placed something important .period people talk about that in just a moment so when I take my age HBO molecule and I use that calculator as a baby which is weird to think about the outcome of the base to grab Proton from the HBO I want to look at them at the cargo can the generator just to remind ourselves that we look at it ,comma can language and also when you try to draw edge on him denied that SCH if I pick up the proton follow ,comma cultural or contrast empirical rules says I want to put the proton on the carbon but that is the substituted so that's now going to be a CH 3 groups it's kind of weird all the cement drawing is a C H 3 words here just symbolize its normal you have to travel to the street and I discovered that I intermediate that fat NTP were there and is equally possible the bromide count trying to attack from either the top face the bottom phase so if I make the bromide ever from the top the face of the cargo carried that will give me more this inane tumor here and if you assign conning more prolonged exterior chemistry finance the SME him on but it's just as possible that the bromide could add from the bottom face it's all right for the bromide ads from the bottom face you know there's no way steering the difference between these 2 faces I could spin this the civil absolute around anywhere I want if I had made the year-ago little closer here's to do a good job of drawing so I made my bromide attacked the carbon from the bottom face that's going to give me the other anti-American and I'll get a one-to-one make those in intimacy because it's equally possible for the bromide to attack the top and the bottom it's not something you should already know from and 1 reactions this is just like the products you get when you take tertiary alcohols anew at HBO are mom which is generating the couple can intermediate in a different way OK so that last year chemical 1 of what I'm doing here is I'm spending a lot of time to hard .period security chemical issues and all these things that I'm seeing for HBO are you HCL that the true for HCl and also true for the additional water which will talk about that when we come back on Friday to really them innocent of those 5 reactions that I spent that I said were so important we basically spent his whole election just talk about reaction Number One OK let's talk about different issues and again on Monday to different pathways 1 going toward the tightening going toward the bottom and I'm going to take an allocation and this case I'm not worried about my ,comma cost will I just wanna come back to this idea that there's 2 faces to every hour and so when I had for now the minister different faces the proton command from the top of the body face and so they could draw of the system and it will happen if I programming this out for most the Toffees surviving face and that's not what I'm not going to worry about the fact that there's 2 different comments on top and
bottom because those those are the people reactivity so vibrant made up the bomb currently there's 2 different places where did the Proton from and so on the top half pathway year old Drolet happens if I made that helps feed from the top thing so the Proton is on the top facing that methyl group is now pointing downward effect provided the time place and now in the bottom half radio show what happens if I prefer meat that Qaeda on that same card except for meat from the bottom there is my Proton on the bottom and there's my cargo is the only likely but some that Signori geochemistry on 1 worry about approving the tough carbon I just worry about faces of the al-Qaeda now so it's equally likely to cremate made from top and bottom face all have a one-to-one make sure these intermediates floating around now when I do that this is just to show you how various things can get and why you have to know understand the mechanism to appreciate the product distribution so now I have to remind counter floating around along with that of the couple can I remember what I just told you in the last over here I just told you that was cobbled had since the bromide can attack from both the top face in the bottom face of the Carbol so this complicated I'm in the top pathway can give to different products if bromide that from the time the bromide ends up on the same faces the age that would be seen edition so and from the town at I'm tempted not to draw this Proton here but I'm not going to waste just we usually don't drop protons the Irish structures so if the bromide heads from the top that ends up on the same face as the as they age and again that's in addition to not label everyone but it's equally cannot it's also likely that the bromantan attack from the bottom face and so in that case the bromide would be down With the dash and that will still be a and now the agency B are on opposite faces that would be the enterprise so I'll get both of those products in this reaction both CNN and the addition come and that's because you can probably 8 the generator couple can iron and Nikkei like an attack couple can face it's follows through with its bottom pathway and and we'll see how the product distribution relates to the debt from the pathway above so I am going to avoid attacking positive charge use my hero to attack the carving OK so once again the bottom half way the differences that I was drawing out From the initial proclamation accruing from the bottom so both of the products they generated here will have that Proton going down look at all these products here so the bromide ads from the typeface should run this others line going down to the bromide ads from the top face now it's going up and that methyl group is going down and so now that gives me the energy product so I started from you know I didn't mean to do defuse and it's going become very difficult for me to I'm scratch that out and the bromide 1 the most let's consider what happens if the bromide attacks from the bottom and just want this to try to match the bromide attacks the couple cannon from the bottom of the list will be the same product agent about compromise on the bottom and if I take that same cobbled paradigm and I had the bromide from the top face that would give me the NT product so there's more products that will arise from this really simple reaction I take any al-Qaeda irate br across across this now there's a simple relationship here these 2 products foreign maintenance In other words as long as you drew 1 of the Plessey and these 2 Indian products those are also in tumors as long as you don't want them to be just right plus the it if you were asked to draw drop serving CDs and anti-America relationships you wouldn't have to draw for these for products injury actually just right 2 of them men right policy is on the right to
focus so that since the 1st reaction 5 reaction on that and go through all this stuff those other reactions because the concepts of steering chemistry and work on a comfortable
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Metadaten

Formale Metadaten

Titel Lecture 07. Alkenes, Part 2
Serientitel Chemistry 51B: Organic Chemistry
Teil 7
Anzahl der Teile 26
Autor Vranken, David Van
Lizenz CC-Namensnennung 3.0 Unported:
Sie dürfen das Werk bzw. den Inhalt zu jedem legalen Zweck nutzen, verändern und in unveränderter oder veränderter Form vervielfältigen, verbreiten und öffentlich zugänglich machen, sofern Sie den Namen des Autors/Rechteinhabers in der von ihm festgelegten Weise nennen.
DOI 10.5446/19476
Herausgeber University of California Irvine (UCI)
Erscheinungsjahr 2013
Sprache Englisch

Inhaltliche Metadaten

Fachgebiet Chemie
Abstract 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: 00:16- Resvology Debuts Anti-Aging Skin Care Line with Gene-Activating Molecule 00:54- 4-AR molecule 04:18- 10.8: Addition of Electrophiles to Alkenes 14:03- 10.8: Syn and Anti Relationships 19:09- 10.9: Addition of H-X: Hydrohalogenation 23:56- 10.9: Watch for Rearrangements of Carbocations 33:39- 10.10: Markovnikov's Rule: Add H to less-substituted carbon 38:18- 10.10: Markovnikov's Rule is Based on Carbocation Stability 42:57- 10.11: No control in formation of stereogenic centers 46:53- 10.11: No control in formation of stereogenic centers, slide 2

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