Lecture 8: Methods for Converting Alcohols to Alkyl Halides

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Video in TIB AV-Portal: Lecture 8: Methods for Converting Alcohols to Alkyl Halides

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Lecture 8: Methods for Converting Alcohols to Alkyl Halides
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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: 00:49 - Secondary and Tertiary Alkyl Halides 03:33 - Other Methods for Converting Alcohols into Alkyl Halides 31:28 - Converting Alcohols into Sulfonate Esters
Bromide Reaction mechanism Walking Hydroxyl Chemical reaction Alcohol Chemistry Wine tasting descriptors Molecule Water Hydrogen Computer animation Freies Elektron Periodate Isotopenmarkierung
Vinyl chloride Ionenbindung Stickstoffatom Reaction mechanism Bromide Phosphorus Walking Rearrangement reaction Hydroxyl Carbon (fiber) Chemical reaction Alcohol Ethanol Hydrogen Solvent Computer animation Yield (engineering) Functional group Aage Cobaltoxide Base (chemistry) Thermoforming Periodate
Setzen <Verfahrenstechnik> Alkoholfreies Getränk Ionenbindung Reaction mechanism Walking Carbon (fiber) Sulfur Chemical reaction Chlorine Alpha particle Hydrogen Computer animation Electron Functional group Covalent bond Freies Elektron Ausgangsgestein Elimination reaction River Cobaltoxide Base (chemistry) Periodate Process (computing) Methanol
Precipitation (chemistry) Halide Species Reaction mechanism Chloride Wursthülle Chlorine Electron Essenz <Lebensmittel> Benzene Elimination reaction Salt (chemistry) Periodate Process (computing) Walking Vinylverbindungen Sulfur Carbon (fiber) Hybridisierung <Chemie> Chemical reaction Electronic cigarette Computer animation Functional group Salt Cobaltoxide
Ionenbindung Reaction mechanism Hydrogen chloride Chloride Wursthülle Deterrence (legal) Ausgangsgestein Periodate Conche River mouth Vinyl chloride Atom probe Stickstoffatom Walking Rearrangement reaction Protonation Chemical reaction Cigarette River source Solution Alcohol Electronic cigarette Hydrogen Acid Drop (liquid) Computer animation Yield (engineering) Wave propagation Medroxyprogesterone Substrat <Chemie> Base (chemistry) Bromomethane
Computer animation Walking Chemical reaction
Printer Command Language Computer animation Reaction mechanism Data conversion Chemical reaction
Biosynthesis Species Reaction mechanism Atomic orbital Chloride Hydroxyl Wursthülle Artifact (archaeology) Pharmacist Meat analogue Organochloride Electron Methanisierung Colourant Elimination reaction Periodate Process (computing) Area Walking Rearrangement reaction Sulfur Addition reaction Hybridisierung <Chemie> Protonation Chemical reaction Alcohol Computer animation Functional group Azo coupling By-product Cardiac arrest Substrat <Chemie> Cobaltoxide
Fluoride Vinyl chloride Computer animation Functional group Chloride Cobaltoxide Chemical reaction Grade retention Chemistry
Chemical reactor Computer animation Essenz <Lebensmittel> Walking Chemical reaction Alcohol Chemistry Grade retention
I think it's got a lot right alright today and talk a lot about different ways to turn alcohols and good leaving the hydroxyl into the living room so number never waste preview of how delivery mechanisms here so I'm really any and that you have seen in the last foreign discussion is a potential mechanism for some of the major coming up OK alright OK so we left off last time talking about on secondary and tertiary article in the light of the ATP are and why it's not necessarily good reaction for instance Houston we were talking about steering chemistry here and as you can see in the 1st steps need for make the alcohol right here Water Lilies has soon water leads with make ,comma carrier will lose all our stereo chemistry this now becomes a kind of clear molecule here so this column this comment hydrogen is currently are on the same plane and perpendicular to the plane we have our Laura Laura the orbital plane so perpendicular that plane so what happens in the next step is the bromide scientific community attack this is a player adheres to the bromide can in attacked here Kenyan attack the bottom 5th comes in attacks from the top you get 1 Indian Summer Africans in attacks from the bottom you get the other than it's equally likely to do either side facing a renegade maximization just like we got with us and 1 far-right so yes it really and sometimes when I open it doesn't show up will take care of that this is a list of early-afternoon OK thank you for letting me know I write some bromide comes in the king came in from the top here indeed taken from the bottom so the move will go here or it'll go here attack on outside of that size the Anselmo that leads to wrestle positions so you guys you can see when you have on certain chemical issues here you do not want to me making a cop Academy if your stereo center on because you're gonna lose stereo comes from the immediate rationalization label seller of planar intermediate lose optical curious planar intermediates lose optical period all right so might
not be the best thing to do for secondary we get rearrangements and we also have our rationalization if we have serious involved so we really want to avoid using are secondary alcohols quantities in other ways that will work better so we we do need alternatives far-right so there's cheering actions pediatric carrying and vinyl chloride .period wanted to go over and above both of these and they work they work better and you get better yields and you don't get any car pavilions of rearrangements so I know cargo-carrying rearrangements here and and and that's so that means and that means we're not making car Academy intermediates if we make ,comma kind intermediates will get recover plan remained so it needs both of these reactions we don't form ,comma carrying intermediates so I offer
.period carrying that's the most common when you can also use on PCL 3 period he got the idea 3 period but the most common 1 that was seized on TV hearing and so what this looks like innocent Stewart will use ethanol here and we have the artistry so no other possible mechanism for mid-term 1 so think about that I'm for wishing it were aware of washing is going to involve the oxygen and 1 of these bromides and so on I need to make sure that this bromide that I'm going to be involving in this era pushing it has all of its sold here RX so what's going to happen is we're going to have this oxygen error comes from old terror attacks the phosphorus but we kick off a worldwide leaving now you booked under Steve 3 without hearing I'm going to include security whenever I used you're free and with the terrine does is it it's arm of solvents and it also can act as a base and so when it's going to do is in this step right here it's been a Canadian indie program 8 that oxygen so here comes from the locker nitrogen and then we break we good grabbed the the hydrogen we break the hydrogen oxygen bond all right and then under bromide ion that we kicked off in the 1st step it's going to community backside attack so we're going to move in grab here attack this carbon were going to break the carbon oxygen bar so that is essential 1 and and so on that it will what it's done is we've taken the badly finger pier hydroxyl bad Leading group and we turned it into a good living so great anger bromides agreed so we we have felt the the same overall process but we're just doing it a different little bit different way OK so assignment foreign
carriers is very similar to our enemy doing a mechanism that's different than the book on don't use the book mechanism on the test I still will see people do that we're using a different mechanism because the book mechanism is incorrect and the reason that am the book is using this mechanism is there on the offers made a determination that this is an easy mechanism for you to learn at this point it is a little bit easier but it isn't the correct mechanism so I'm teaching you the correct mechanism I I I know I've talked a long time and I know you guys are ready to see the correct mechanism and by learning this mechanism now it makes it much easier 51 see when we do many more mechanisms like this so the mechanism that I want you to see what they want when I want you use on the test is going to be this 1 so this on a possible mechanisms for return to fix 1 of the ones where I often put this mechanism what terms so I'm not promising it will be on the midterm but I do often put it on the chin are right so I let's let's slip let's go through it we're going to use methanol here so here so I knew for a week and I don't want to oxygen we have a chlorine chlorine and sulfur and has a so we have a of lawmakers on oxygen here and what's going to happen is in the book of babies of the oxygen attacked the sulfur and kick off a leaving River that's not the correct mechanism what happens is of it's a two-step process to give reached that same point were going to attack the Salford and never been kick electrons up onto oxygen that has a bad that mechanism is called an addition that step is called and addition alright and then after that this is what we have this is where everything looks like so certainly different than the PBR 3 mechanism we get topside here in an hour we have to chlorine 1 of those .period is going to get kicked off Sunday to put appears on the chlorine and kicking off adjusting to kick off this 1 and we do have a lot of parents sulfur and so in the 2nd step electrons are going to come down from oxygen written former double bond with a reform that double bond between the sulfur in the oxygen averted kick off the leading group and that is called an elimination it's a different type of elimination and we've done so far what we've done so far is bigger elimination this is an alpha elimination but it still is elimination and then after you do that we get the same thing that you get in a new book except we just don't have a two-step process rather than a one-step process so then everything after that point I was gonna look the same the peering out is going to the parenting acts as a solvent as a base in this reaction and appearance in a canyon it's inoperable differently oxygen is going to do the same thing here that it did with the that's because that makes it easier to remember Serena remove this hydrogen here this is an acid-base reaction so what so what we have is that it is a I'm a multistep mechanism but this that the steps and you're seeing are on the move certainly already seen massive a step many times "quotation mark and the effects need to draw them for identity drinking this here so I'm gonna drop region redraw that once when I was in my mechanisms I want any bonds that are breaking into the drawn-out so I would be breaking this carbon and oxygen volunteers a draw that bond out as a was going to happen is the online insist that we we took off in the 2nd step is going to come in and do backside attacked kicked off the leaving so this whole group right here is leading work
an arena continue on the top of the next page will finish the mechanism on the top of the next
page so we get CO CH 3 we also get around this oxygen sulfur species and I'm so the sofa has long pairs the chlorine has little hairs and so then an hour in the last step we're going to have this is going to break apart is electrons Oregon income going to come here make new bought a double-wide itching the sulfur the oxygen the air in a kick off 4 eyes so soviet sulphur-dioxide which is a component of smog that's a gas and so it's going to blow off the reaction nature so that's 1 of the composer stronger turns at Brown OK and then we get this is going to be important later here this insoluble salts so those the appearing and works as a solvent it also deeper needs oxygen and the other thing it does is it informs the precipitate with without any excess chloride around so this week this precipitate so we have to be from gas reaction and refer precipitate most put both of those things that to drive of this reaction so in soluble salts precipitates all right so are molds for the little Ancira an arrow going down which means the to fall to the bottom of the flask questions on the mechanism anybody yes on a talk about that was so why we wanted the mechanism the other way so this is the way the book doesn't so don't do it this way and so on in this matter this is the way the book shows that just have this common and kick the chloride right off so we they just accomplished in in 1 step we took 2 steps to accomplish I'm so unlimited-use benefited against this some people when they go back and look build copy that injured on the chest OK case that's not from the correct mechanism why not the advertised to the leading of is not as P-3 hybridized SNG reactions only occur on as 3 S P 3 hybridize Adams OK so we
mentioned ,comma at the end of the chapter 7 which was at the end of last quarter that we don't get any time attack on vinyl halides for example Prince so we don't get this happening within you could focus and kicks off a leaving group on as Yukon so as the 2 the answer leaving Group therefore no essential and we also mentioned there you can't have found you can do this with the benzene ring also we don't get substitution they don't get as anti-war as anyone on Univision's here so we don't want we don't want to have that either and so what are these 2 things happen :colon so this can happen and that can't happen so let's go ahead and put an X through there and this 1 here is also an S 2 carbon are down to a leading group therefore I know too so and that's what they're doing in the book is showing us says in essence you and so we don't get that and we don't get that in both of these cases this carbon is isn't as Chukotka and this is also known as P 2 cars are excellent .period number 1 we want to show that is 2 steps when we have things there going to hybridize rather than doing direct substitution we do Addition followed by elimination with the overall effect being the same but it is a two-step process the other thing you
don't want to do is the probe make the alcohol 1st so if I ask you this mechanism on the test and and it's probably a good likelihood that I'll do that homicide guarantee but it is there's a good likelihood I don't want to propagation should National certainly would have shown you I don't want you to on the different the alcohol 1st and I often get this question why why can't appeared in the program at the alcohol 1st so let's go through that show why that is not favored so the nitrogen comes here grabs the hydrogen Will this is an acid-base reaction so let's drop the equilibrium and then see if that reaction is actually favor "quotation mark replacement and then we would have made it Carradine watches appeared Indian ion parts of Freddie acid-base reaction was to the direction equilibrium look for the acid on each side of the equation so let's do that OK so here's our asses here we look at the conch these parents 1 his picked up proton here's our efforts here on this side look at the case arm for alcohol the aid it is a approximately 15 and this this is a this acid here from PKA is about 5 so can you see that the is favored in the other direction so since direction here and on every cigarettes difference in the case we of actors an equilibrium how much we have of each and the difference in K is 10 so that people around we have turn to the turn 2 1 attended the 10th protonated alcohol to deeper alcohol so that's why we don't want to dethrone the 1st it's not favored attended the 10th to 1 so I'm so the answer is why is this not favored and the answer is the equilibrium the office locked so we don't want it out that way axle period music carrying of the solid from these Jackson because it prevents the build-up evades a poor nucleophile so Carradine non-nuclear it's a non nucleophilic so that means it's only going to act as a basis not act as an equal for all so that's good because of we don't want we don't want acting as a new default on so we were not going to get any of this happening where this accident if the file amenities you might have been thinking about cable nitrogen to come attack of the methyl bromide once reform it can go in and do that and then the answer is that that's not going to happen because it's a non-nuclear Philippines we know it's non-nuclear those days because I just told you and we've done a lot of reactions and interactions in the file so we need now characterize it as a non-nuclear Philip base so we don't get any of that thing happening so we'll put an extra so absolute base instead so if we happen to form any states the obvious reaction it would not allow that to happen because it's going to depress soon as reforms so I could spend a common ground that on and we're going to get again appeared in union I on and that's kind of a nice reaction because it would actually Our removes the head of the army HBR from the solutions so we get the period any of ion and appeared in a mine on tends to precipitate with the he lied so in this way on all of the HBO are and HCL is real HCL and of course if we used a giant we could use that also Israel alright so unwary worrying about if taking up enough because I only know that an HBO are HCL were child to but must now home a it yes you are c all party or the of other reaction we just talked about the Union class in the last half of Minocqua with it the previous reaction and we know that there some problems with this OK problems with HCl this each HBO are to each other but it it OK so we're wary problems Maciel experience either we just talked about the beginning of class Westernization right yes it's no Oh turned on end but I am rationalization there that's much better thank you In cover Qaida cover can those are 2 things that we're trying to avoid him by using his other markets so these methods by these methods and the PBR the purity and vinyl chloride work well for mouthfuls of and primary and secondary alcohols no tertiary alcohols why no tertiary alcohols the therapist who were there isn't this is innocent reaction in our key steps of repent and so the mechanism is essential which means that we can have tertiary alcohols and therefore there's no with them tertiary substrates right and the other thing is is that any it there's also know as anyone a little boy instead ,comma go but know someone either because why when we need aggressive 1 L the following are like guidance .period because there is no the color-coded solid right so we deliberately chosen solvent that's not been molded products so that we can get arson 1 Bond yields
ahead for these reactions rearrangement Segarra are rare the enough because we have no catalysts no cargo carriers equals no rearrangements both reactions are scarier specific still please pediatric care name or title chloride 13 we get and lower to stickler we did the reaction school that let's track if is common was
a serious and it's not but because it was a small step this 1st step doesn't all that current so it stays the same on this step here were making up it also doesn't involve Ackerman so it stays the same step here were reading from a dozen of all the credit would happens here the backside attack and so therefore versions so you what you need to know for this reaction is that the Guinean version of configuration there are so my the question where I want
to draw the products Winstar and this is why you would the time quiet appearing in get chloride for pediatric carrying to get the worldwide you can of course also use a PCL three-year P I 3 the Buffaloes 100 per cent conversion need to know that In the good news is if you know the mechanism you'll note on what historical archivist for the reaction
advantages over Ajax reaction why we even talk about this reaction at all and that's because we have found no Marino rearrangements was secondary substrates and we also get no rationalization With secondary substrates questions aimed at Mark we're in we have 1 more amendment to talk about career novels into soulfully as 1st announced today government also Tulsa later sultanate Esther the foreign newsmen and process we take a region-wide Pennsylvania chloride argument invariably there's a couple once on the news on Monday that he is 1 of them but this is the reaction here and I'm so users are battling group hydroxyl we have also in this reaction and this is what we isolate so soon really similar to undefinable Florida reaction but would only isolate the final quiet reaction we isolate the alkyl chloride in here we don't we just so we isolate this whole species so this whole thing is I could leading group this whole entire thinking this is a fat leaving groups it's a great so in this reaction and we don't convert are around welcome our alcohol into helpful here might be converted into a tosser late for a sultanate Esther let's show you the mechanism business and then on nominal needed to you to think about what we don't get the chloride here OK so it's going through this mechanism of this mechanism is also different than the 1 in your book so I want you to use it the way we're showing here so here's our alcohol and you can see a lot of similarities between this mechanism the final card mechanism the arrests over an attack sulfur we're going to kick electrons and fond of oxygen in the air that of course is an addition reaction the 2 were very similar which is that it without extra oxygen going on here and in our group attached to the sulfur so that's the difference In early in the 2nd stab the same thing we did was sign of it's gonna happen but times and oxygen are going to come down there really take off course just like that so so far as to exactly the same that's a elimination of course you book did that in all on 1 step and adjusted innocent we know it's not innocent OK and and this is so similar what's going to happen next yeah that information was period security has going to communal and approach In the whole entire thing is a good friend of it's not
letting change colors and also most of this whole entire thing here evidently because you're greatly because there there but it's still worth the contagion degree were submitted what's our side products which we don't normally worry about but we're going to think about it here so I want to try to do on your own you really think about this and I can tell you the reason why but of why is it in this reaction the chloride or it doesn't community backside attacking kick that Leading group why don't we isolate the chloride light the isolated this group and said Why don't we isolate itself from the start that Italian while you think about so I recommend is dropped 9 acquired mechanisms druggists right underneath is seeking can figure out why we need a different product industry Our so again hero just like with the final quiet reactions don't do it this way if you do it that way you can actually misses some of the women mechanisms usually workers there 2 or 3 points each and each step and if you combine 2 steps in the 1 you miss the point both the steps soared .period or recommend that you do that so I don't want to do it this way and that's for the big extra there that would go to the same thing but it is not a one-step process so I'm not gonna show you the one-step process why is it not a monster process like this because we can't do innocent children and there's not a speed to hybrids is that is not that sulfur is not 53 hybridized so we only get such as in Turin as 3 hybridized OK so the question is so why not sold for there is not as the 3 artifacts so there are sent you can only occur on S P 3 books on S P 3 hybridized are questions on that reaction in about In this case think so yeah I'm glad I was hoping somebody would actually me how that is not these 3 hybridized because it used to be a city right and you would see a has 4 groups around so should be as the 3 hybrids but as the 3 hybridization can only accommodate was like 2 electrons per orbital right so that is more than electoral and so on so I think if you go back to the camera when did this with larger Adams it would be it would be like deed DST to as we examine letters the 2 4 6 8 10 the PDS D 2 Western feared to have something like that we even deal with the orbital satisfy last OK so that's why far-right so there's many of these and the good news for you as I'm only using 1 of on this 1 here this is the only 1 I will use so there's many different ones there's 1 with victims try for analog that's actually even better living groups of this different meanings of abilities or not to worry about that I think there's a sapling problem where they use methane sulfur no Claude this is the 1 that I'm going to be using the proton soulful Florida is the most common in hasn't abbreviation T O S C Allen for you will also see it as a TSE so feel free to use that abbreviation of using this as a region in the synthesis but you do need to know what it looks like as I may actually have a drawdown test make sure you know what looks like a in so let's look at some examples noticed area
chemistry here so this year's Stossel glory we have cheerleading prime Minister of the product to In a total roster if I had to draw out the tussle group this is what you want your promise to look like so react with tossing fluoride in our product is called a Tulsa late what is the stereo chemistry but that reaction fates retention of configuration here this car retention configuration that is completely opposite to what you get with Wikipedia 3 3 purity and vinyl chloride appeared right when we get figure 3 Final Four appearance a version that's why we needed and on we need this reaction because it gives us the opposite stirred sometimes we might need to have attention are actually give you 1 more example just use it to a token easily fit but again on the testimony of using tussle Florida's lethal chloride and then some this ring is drawing a little bit strange it's just drawn perpendicular to your page so this White House would be coming out of your page and you can see that this side here we're going to have a mouthful and a hydrogen and on this side here this oxygen is still going to be sony's or chloride is what we would start with and this would be an easily any retention of configuration at this Scott the attention of configuration the sultanate asterisk in the record of writing
advanced undergo as interior action is not known hysterical outcome of this step if we take this reactors with the nuclear file backside attack right all the grandfather we talk about in Chapter 7 as the ones we could use for this this of course is an essence reactions so now we're going to get version Manginelli driver weaving through the tussling with England so notices during chemical an outcome and sent to attack that stirring center which means inversion this alright so if we used the if we have an alcohol use the year 3 purity to convert it into a good Tinker that was the university right if we had a nucleophile University did so get overall retention if use a Tulsa Salinas did we get tips we had a good policy is instead convergence cities you have the opposite outcome and that's why this is a very useful reaction and so I'm really great that complementary to the other 2 will stop right there will continue this on Monday
of President Reagan tests