Lecture 6: Alcohols, Ethers, and Epoxides

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Lecture 6: Alcohols, Ethers, and Epoxides
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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: 00:47 - Introduction 04:15 - Nomenclature of Alcohols 10:47 - Nomenclature of Ethers 14:59 - Preparation of Alcohols, Ethers, Epoxides 34:06 - Elimination Reactions of Alcohols: Dehydration
Alcohol Alkane Octane rating Vinylalkohol Containment building Hydroxyl Carbon (fiber) Soil conservation Death Ether Computer animation Functional group Azo coupling Data conversion Active site Medical history Biomolecular structure Stuffing
Substituent Kohlenstoff-14 Alcohol Tumor Substitutionsreaktion Diamond Hydroxyl Carbon (fiber) Ice front Ethanol Computer animation Functional group Chemical compound Ausgangsgestein Hexane River mouth
Alcohol Computer animation Library (computing) Chemical structure
Substituent Setzen <Verfahrenstechnik> Alcohol Chain (unit) Substitutionsreaktion Organische Verbindungen Chemistry Combine harvester Epoxidharz Computer animation Functional group Smoking (cooking) Ausgangsgestein Cobaltoxide Butyraldehyde
Biosynthesis Alcohol Chemical property Haloalkane Chemical reaction Hydroxide Ether Nucleophilic substitution Computer animation Functional group Essenz <Lebensmittel> Common land Active site Elimination reaction Body weight Stuffing
Biosynthesis Ionenbindung Bromide Carbon (fiber) Fluoride Iodide Computer animation Metabolic pathway Active site Sea level Cobaltoxide Oxide Thermoforming
Semiotics Alcohol Biosynthesis Forkhead-Gen Chloride Memory-Effekt Wursthülle Molecule Tidal race Ageing Colourant Active site Elimination reaction Mixture Oxide Area Sodium hydride Bromide Methyl iodide Asset Carbon (fiber) Chemical reaction Wine tasting descriptors Hydroxide Water Hydrogen Sodium Acid Computer animation Functional group Azo coupling Proteinkinase A Base (chemistry) Medical history Bromomethane Isotopenmarkierung
Psychological trauma Setzen <Verfahrenstechnik> Molecule Biosynthesis Computer animation Functional group Active site Chemical reaction Wursthülle Electronic cigarette
Biosynthesis Alcohol Hydroxyl Chemical reaction Organische Verbindungen Solvent Acid Computer animation Chemical compound Schweflige Säure Dessert Dehydration reaction Cobaltoxide Solubility Hydrocarbon
Alcohol Ionenbindung Reaction mechanism Walking Hydrogen Computer animation Electron By-product Schweflige Säure Chemical structure River Cobaltoxide Conjugated system Biomolecular structure
Alcohol Ionenbindung Reaction mechanism Octane rating Walking Chemical reaction Water Hydrogen Acid Computer animation Functional group Generic drug Schweflige Säure Beta sheet Elimination reaction Dehydration reaction Cobaltoxide Base (chemistry) Conjugated system Halogen
Cadmium Hydrogen Acid Computer animation Electron Functional group Azo coupling Walking Acetone Schweflige Säure Hydroxyl Copper
Systemic therapy Water Ionenbindung Computer animation Concentrate Walking Schweflige Säure Chemical reaction Thermoforming Process (computing)
where is the accepted an IOC date palm I'm going to to have death come on many going fast in the 1st couple of pages it's just introductory stuff it's not very exciting and not super important so I am going to do a tiny bit of nomenclature but we're not going to worry too much about nomenclature has by probably will have a token nomenclature .period question on the test His a Converse a little bit and I but it was been allotted time on far-right we need in this chapter we talked about how alcohol eaters in park and this is really a continuation of Chapter 7 8 knowing it would just be such a huge chapters so we'll put them all together into 1 chapter so outlaws container hydroxy group always which is always group wanted to the 2 were as the 3 carbon In and so overwhelmed with we look here we've got pointed to as the 2 examples we have found here's our hydroxyl that's our hydroxyl group this would be methyl located in the common responded to the always has as 1 of our group that would be primary so 1 of our group carbon monitored the hydroxyl is bonded to to work groups it's secondary bombing and benefits bonded to 3 it's tertiary and so you really actually already familiar with the surgery because we've been using Turkey topside the conservation this alcohol found throughout Chapter 8 so that would be 3 art groups are we also have some examples of always wanted to as the 2 carbon and so this would be vinyl alcohol that's a vinyl alcohol also known as mean all I will come back to that term coming up in a hotel but that's also an evil units for the out all is for the alcohol that's why it's called it in all of this would be and this would just be fennel and then I skipped these 2 1 what would we call this alcohol rate here L alcohol I heard somebody say so you can you can cut tires of on the back for them that sell alcohol and this is Denzel alcohol so that has a pencil group on part of bonded to the let's histories of that and C Y L with his friends all alcohol as is a pencil group bonded to the hydroxyl eaters have to alkyl groups wanted to an oxygenated alkyl groups can be the same where they can be different if they're the same week although this is a symmetrical ether and on if they're not the same This is a novel and symmetrical ether so nothing so terribly exciting if the EPA is part of a three-member during its Singapore Parkside so this is the Parkside you will also see it as some textbooks :colon answering I learned as a part sites so I favor that turn you will see me calling answering that's it that's a common long-term also for a park sites for created like isn't very briefly going to do some nomenclature ,comma
names we need we need ,comma names or talking also like that he'll alcohol the kind that you drink without knowing the ethyl alcohol would be the company's we can also call that ethanol that would be on that would not be the common so if you do so some some of them we need and all of you OK so are you pack let's talk about I names following release to name a compliment as a function groups suffix select the the longest continuous carbon chain to which a hydroxyl is attached the parentshave name by dropping III of the Keenan adding 0 and then on the new number that continuous change give the carbon-varying the hydroxyl the lowest number of this number is included in the name so this would be this is about the difficulty I would give you test so let's let's do that we are right so is the longest change some 5 carbons and so it would that would be pentane but we drop the median at L so the parents parents that's our parents in an hour Morgan a number in the direction that gives the alcohol that the and lowest number so we're number this direction here 1 2 3 4 5 so our substituent here we have to manifolds so we have come and Eric Kobren we have 4 4 and so they're actually now that we have all those the students that we can call this you will see balls for 4 diamond sold so far ,comma -dash Diamond fold 2 pensioner "quotation mark the 2 is there to tell you that the alcohol on carbon number 2 that's very important that you do that on the other where you can in this year's for 4 Diana can P E N T a -dash too OK more common to see the 1st wearing unsold Allwood doing here the only difference here is we're taking it were putting that you right in front of them all well rather than at the beginning of the Pantanal and both of those waiter absolutely acceptable for us question yet no there is no easy after the Pentagon we dropped the United allowed so that's this right here in the 2nd 1 note we dropped the and add 0 well so we do not add that backed now we don't OK if you have an outside if you have an alcohol a in numbers not
needed to designate the position of the functional of Suffolk Stanisic compound because it's assumed to be the number 1 position so and this is automatically going to get number 1 so that hydroxyl what we say is that hydroxyl has priority over all of the outlawed group's against the number 1 position yes that's a little bit different and more career of Frank so there would be a dialog it would put the numbers in dealing with another substantial yet and we want to dial and redial forward or something like that OK so we want a number of in the direction to give this the next substituent the lowest number so will look like that so a number and then in the direction to give the next substitute the lowest if I right so parents and this is a six-member brings so it's as cyclone text saying we dropped the EU had a well so the parent is a cycle and all the substituent or let me see what we have a tumor manifold we have a floor asshole nullified after we have a 5 that to level of financial and so this would be 5 Ethyl Ethel comes 1st because he comes before and the alphabet 5 fold 2 mouthful cycle maximum notice I did not have to be put a 1 in front of the cycle hacks and all I didn't have to say cycle hexane won all because the 1 is understood OK thank you could do that when something like that nomenclature meters
OK in Auberry briefly going to cover nomenclature of the there's I'm not going to test 1 nomenclature visitors only exam about that the regular alcohol you know when I was
a student and it was really important to cover nomenclature because I had to go to the library to look these things out in a book and if I did not name the correctly I would never find them in a million years now all the search engines you can actually draw the structure and the it's not so critical that you know the exact name so I can't take it like that and I say we're running a little bit and nomenclature so we can converse on but I don't want to be too hardcore about it are right so I mean you'll see some
some odd high-school chemistry classes and they say Oh we taught smoke him in our classes and basically what that means is they did a little nomenclature and as like this so not even in the and all types in organic chemistry as you probably are appreciate right OK so common a needed to our constituents in alphabetical order followed by the word either we're going to be hard for about half of the alphabetical order uncommonly and snow OK I'm all you packed name as now came with an oral substituent an substitute is named by replacing the deal ending with epoxy
show you what we're talking about that way so that's 1 for example its name a common 1st to utilize properly utilize a purple Easter would be the combination of IT pack In what we would do is we would all we would take the the longest of the chains are the 1 that's the simplest of the changes and that will be our parents so this would be right here that's our parents so this would be butane and then there were in a name number and were named as this other group from this is a nice appropriate rights so including that oxygen so inseparable groups so that so I supra Part C so I supra local and we're going to drop the y el because it has arc oxygen and shapes set so this is ISO pro proxy so that's our substituent bicycle proxy so far I am I name would be while I suffer proxy future into did like really hardcore on this if we wanted to were not I'm not even going to ask you to name a suspect by name and these are what you recognize what it looks like and I would probably call at fixed by the fights coming from consulates on 104 millimeters but questions so far anybody yes the tough the 1 is necessary so that the only time no 1 would not be necessary is if they could only be a 1 so in other words of this I supra poxy group right here that can be heated air it here but a zone that would be at number 2 was so we do have to distinguish those 2 possibilities part so if it wasn't Ethel then you we evolving differently but there's only 1 place it could are right preparation of alcohols
heaters in a park sites and this is going to be basically a review reactions from Chapter 7 so that no news no terribly new stuff so far alcohols and ethers are common products of nucleophilic substitution if we want to make an alcohol we take animal alkyl halide and hydroxide OK I would be in essence to reaction backside attacked kickoff worldwide and we get an alcohol so that's synthesis of alcohols we already know how to synthesize and alcohol skates synthesize all alcohol that way we can certainly synthesized a large amount of alcohols that way Anita's prepared by treating all Cox said with an uncle here like this is known as a Williamson ETA synthesis so we were meaning that reaction we had needed before but we've already done this reaction over and over and over again in Chapter 7 so when you take out Cox cyclists and Qalqilya light on you have Williamson ETA synthesis so let's write that down so if you need assistance emphasis Alcock science plus purely To make the ether Williams Iverson's alright so under the same ideas as a hydroxide we're going to have the great nucleophile this is going to be innocent she reaction coming due backside kickoff worldwide as a leading group here instead of using alcohol wheezing and Allcock sites so that is going to give us great weight making 1st are right we have to be really careful here but when we're synthesizing 1st and the reason is is this Alcock Sybase produced strong and we know we haven't had a great people felt as strongly as we have to watch out for elimination so literally take our alkyl halide really carefully get elimination as the major property when you're trying to synthesize something you
don't want the minor projects product to be major I
write so for example here this is a synthesis
problem so this is a rather than giving me giving you the 2 regions and asking you to predict the product you're asked to synthesize this so this is probably 1 of the 1st time you've ever had to do that we'll start doing a lot of this quarter parts so the following 3rd choosing regions that would give the best field so you can as you can see and we want user Williamson eat synthesis we want me that 2 possibilities we could argue that the 1 possibility here we can form this bond here we got to oxygen carbon bonds and we can for either 1 of those let's call that pathway 88 and the other thing that we can do it as we can form this bond will call that pathway I so Williamson the synthesis of Kylila Cox if we're going to form respond right here which Alcock said would we this will die right here is going to be our Cox said some with oxide on so if we want a form this bond we use on the thought site on right here and then this would be a kill here alive so nice alive if order form this over the course of this bond on the other hand right here there's Cox II Cipro Parkside is our Parkside and we use Nestle and therefore have halogen some level here bromide iodide fluoride something like that so let's let's write out those 2 possible pathways and see which 1 is going to be best are
excellent do some rather a 1st several made we would use I supra Parkside In a solider was a season begins I die chloride bromide I feel Allied either UK in 1 year and we're in the driver's seat and pick whatever you want to to take a stand very powerful things are right let's some show rout beat now I'm feeling on pro-life history a case are upbeat but we have eyes focal oxide are it's so the question is which route as the best round around the it is the best of wise throughout the bad fantastic you guys are doing great the reality is that because we have a secondary and a strong base and this is a strong race if you do this rout you're going to have the 2 as your major product alright so this guy's going to be the best a local here light not he injured really get any elimination with methyl iodide no why we get any elimination there's no America of carbons means nowhere hydrogen so no elimination or we have no competition for this reaction we will get 100 per cent of the fact that we OK so Upperville is not hindered and has no hydrogen therefore and there will be no easy to OK so that's the thereafter you want so race were starting to have to be a little analytical here were figuring things out which will which we wanted to questions on an example anybody I don't think he's due for a pause in outcome cities to make any the Alcock site can be formed by treating in alcohol with sodium hydride rights so worries so you might drive to turn alcohols into all cops acid-base reaction was strong make sure it's favored in the direction we want to go so on Our are conjugate asset is each to the hydrogen gas so I went the Lagasse symbol in the area means that it's to bubble away that's going to drive our equilibrium to the ride isn't it fair and if we look up GKI Sicily this 0 just means this is gonna bubble off reaction mixture well we will look at the the out we will look at the of acid on each side of the equation on this is our acid on this site so that's going to be PKA about 6 about 15 using a peak is rounded to the nearest 5 found this this is our PKA and this is acid over here PKA areas 36 that's not 1 of the ones you need to have memories I would have to provide that for you alright so we have definitely very powerfully driven to the right they had done but maybe there's a little bit of adverse reaction if we catch the age to 4 couples often reaction mixture as possible but at equilibrium we have about but we have 21 once you tend to the 21 so if he did not the last quarter basically what I did it's up to the difference in the case and that means that any equilibrium that's ignoring the fact that the hydrogen is bubbling often driving even further to the right and we will have 1 molecule of each of alcohol for every 10 the 21 molecules about our so this is a fantastic this is that Springer was shaking like that OK it's stopping them OK so that is this is a really good way to confer alcohols to oxides right it's essentially to completion are so now let's go and look at you know the question comes on like it we just use
hydroxide a former Alcock said from alcohol let's look at that equilibrium and that's going to be doable I really do the same thing already use a much more familiar base let's try this again far-right wirelessly with regard to I'm staying away from the purple color and services have mostly throws up OK so we've got this year OK so we're all wondering you just like really it's really killing and the anticipation is where is really killing you know so many God's Army there is a relic lopsided OK are conjugate base is water let's look at the PKK for each of these navigate on these got is is that for both of those also we know those weak case rounded to the nearest 5 as part of the case round to the nearest that's 1 of the bills are 2 of these while 1 of the 8 OK so this is about 15 and this is about 15 so what that means is that added so we have a 50 50 mixture here so I'm at equilibrium we have about 50 50 50 50 so what that means is that we're not really going to be making enough of that of that ad hoc to use it in a Williams synthesis let's say we wanted to make up and we wanted to make a fox side and we mixed it with hydroxide and we added methyl bromide only getting making 50 per cent tax on again mixture because we're not making enough of that Fox's said so the base that we want to use definitely is but is sodium hydride the base to use this is the only place that I will use the base to use to make an our from an alcohol OK intramolecular version of the Winstone synthesis provides around to epochs science let's look and see what that looks like H minus that socket base the base we wanna use let's do Arab pushing here now many keep soccer this summer can't sit in the same orientation as soon as I want .period something out to you OK so on what's going to happen is is this Alcock side is perfectly situated to do intramolecular backside attack and to kick off this spur line Iraq Estrada product we get from that notice this is a three-member during Easter also known as an approximate so our nuclear file interleaving group are in the same molecule so let's label those here's only the
file and here's are leaving so we call this type of reaction within the family leaving group are in the same molecules that intramolecular reaction so this is an intramolecular Williamson Anita synthesis a molecule that contains
both of these can actually undergo in trauma in turn had we decide case really the question here is not only know that of this Alcock site has been attacked in the same molecule why can't that Alcock said come back and kick off a little bit but another molecule that would be inch turmoil it that would be intramolecular in molecular when it attacks in the same molecule it's intramolecular like alright so let's say here an example here but simply can't decide so this is siege to end so we're talking about very ring sizes so listed the intramolecular down here this is without flag a little bit larger ring isn't it but it's still the same thing In end of the do that we form a ring if we don't do in trouble and we do Internet straw that In terms of molecular what would that look like we would have found this out said Canadian do backside attack and kick off this leaving groups in another molecule so can look like fast so we we get is something that looks like this that's what it would look like if it did in turmoil like so we want to be able to know what we're
going to get 1 of the older predict what we're going to get so how we know what happens is depends on the size of the range so there's a there's a magic number 3 5 and 6 Member brings the rain is favored the ring is stable so if we can make it three-member bringing in only 7 members of the ring were counting the oxygen so this 1 appeared the apart said that's a three-member bring on and confirmatory 3 of 5 or 6 ring is going to be favored if it's of 4 and or greater than 7 so that's a greater than 7 doesn't look like that are are greater than 6 that make that easier to read him for greater than sex ring is stable In therefore you're going to get under the reaction on the top-tier intramolecular instead questions on Williamson the synthesis anybody really
talk about any reaction called dehydration it's gonna look a little bit familiar to you but it's still a very familiar to you hopefully I'm very worried and so basically what we do is we taken alcohol concentrated sulfuric acid Tosic acid or H 3 PO 4 will tell you that the only ones that I will use will be these 2 so fast for a desert I don't use so I won't use their own tests for you guys so what is to others .period toss against relax this diary here 2 years wage toss sagacity and so on he concedes in the same family of sulfuric acid basically all we've done here is we've taken 1 of these hydroxyl is off and replaced it with an but they're both really really strong acids so we don't we don't change the you'd the changes starts today be a little will change a lot the reason why we sometimes like to use this acid instead of sulfuric acid is that this acid has better solubility with organic compounds because it's not that you know this this hydrocarbon Park here on better soluble selected but those pretty much we're going to be using interchangeably cancel this 1 here is a more soluble in organic solvents are right where you going to on to the
mechanism now and the mechanism depends on the structure of the alcohol as you can see the 1st step will be the same for every alcohol so 1st step for all alcohols I write so I'm I'm I'm very particular about mechanisms every professor has certain things the particular about and suffer mechanisms I always wanted the IRA to come from a pair of electrons you there'll pair of electrons in a bond in all of the Adams at all bonds that are breaking are drawn out and dumb everything that's involved in the air pushing its lone hair so I wanted to pushing involving this oxygen only so that means I don't have to prolong present all these guys but I do need to put puts it won't Harris here and I do need to put little appears here alright so what I'm doing is I'm gravesite here In a minute break this hydrogen oxygen just like that so now donors and for me to the alcohol so it's like this From our side product would just be the conjugate basis sulfuric acid so that's going to be the 1st step where the river primary alcohols secondary alcohol tertiary alcohol for the 2nd step of of secondary
and tertiary alcohols go through in the morning mechanism OK so let's I want to draw secondary alcohol here so Oregon and doing is really going through the same step here but that's good because it's good practice we've got sulfuric acid if you wanted to ride out all those bonds you just have to drop the bonds that are being made and broken so we can do this little business here we 1 save ourselves some time OK so Marina coming grab this hydrogen we're going to break the hydrogen oxygen bond and I'm actually going to draw reversible Arizona comeback and a reversible errors here the steps are all reversible we know that all the acid-base reactions are reversible this 1 also is reversible so secondary and tertiary alcohols vitamin B 1 mechanism and that means that for secondary alcohol 1 mechanism is faster but it needs to so what happens in any 1 mechanism this leaving group is going to leave where the maker of herbal announcing to be a rate determining steps so R D S 4 rate determined steps all right and we just learned EU wants its 1st on our minds of what we do in the 2nd step of the 1st half of anyone are leaving the police so only difference here are living there was water rather than a halogen a silly difference in the 2nd step of anyone but we eliminate a and B hydrogen so what are we getting useful for that let's see what we have here probably we we have a little bit of somewhat stitch the conjugate base of sulfuric acid we have a little bit of water here and sulfuric acid but not very much it's usually like concentrated sulfuric about that 96 per cent we do have so on alcohol also lets just going musicology evasive sulfuric acid here to do this elimination so the 1 thing I don't want you to do is just use a rather generic P R A 4 acid on is real things that are actually in there so the sooner ,comma removed beta hydrogen then there's a the text that then you know and answer
all those guys out I think you guys like it better when I do that anyway so it will be easier to see there's a ranking product debts are dehydration product so on and I wanna go back here and do another reversible error here OK so that's our product questions on combat readiness of anybody that's a mechanism for dehydration the secondary or tertiary alcohol but the 2 of
primaries go through need to why can't a primary good for anyone the he make a primary copper cattle so so why can't make a primary cover perpetrators are so strong we're still have the same 1st step which is proclamation of the hydroxyl why do we permit the hydroxyl 1st any of that exactly exactly 1 indicated that a review of hydroxyl is appalling group he came conjugate acid is about 15 cents a terrible year were not inhabit leaves so that's why we are prone needing it so that it can leave more easily I write so since refinery were not going to make a primary copper cadmium there's opera meted out already to go home I accept instead of having it leaves 1st it's going to leave as we remove the beta hydrogen so while some old you are can't basis sulfuric acid if you wanna do it abbreviated it would look like this this is going to grab the hydrogen remove electrons here leaving groups going to leave still reversible there's our product so that's the simple way of drawing and I keep I keep doing I keep telling myself began tried out this is better for everybody if this is the way you more easy way to see it will drop this way alright questions so you want me to see how this is kind of a continuation of the previous
chapter Chapter we saw a couple minutes guys and
because of all the steps a reversible this is an equilibrium process the 2 signal bonds broken in this reaction or stronger than applied bond for since equilibrium price the reactions to ever more stable price equilibria Sierra to the left in order to obtain a knocking product the reaction has to be driven to completion perhaps it's uphill reaction we have to drive to completion use English Austria's principles system at equilibrium will react to counteract any disturbance in the cooler rooms and here's our complete reaction drawn Alex to drive people were reimbursed different ways to do this but 1 way and you'll do this in the lab is to remove the Alpena as its forms so you're going to be running if you if you have my loudly we've already done this if you don't have my lab later in the quarter you'll be doing this reaction and you're out here is that the gas in it's going to be removed as its force that drives you equilibrium so like distillate then the other way is to keep the concentration of water alone and to do that we use concentrated sulfuric acid that's why we use concentrated sulfuric acid here if we use dilute sulphuric acid would go back the other direction alright we will stop right there and we will continue this on me once they organized long weekend