Preparation of Amines

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Preparation of Amines
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This is the third (and final) 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: 00:20 - Acidity & Basicity of Aromatic Heterocycles 01:27 - Alkylation of Amines 09:20 - Reduction of Azides - Another Route to Primary Amines 16:10 - Hydrolysis of an Imide: The Gabriel Synthesis 19:39 - Reduction of Amides & Nitriles 24:03 - Reductive Amination - Reduction of Imines and Iminium Ions 30:57 - Reduction of Nitro Compounds 41:44 - Amines are Good Nucleophiles 43:02 - Reaction of Primary Amines with Nitrous Acid
Separation process Left-wing politics Haloalkane Heterocyclic compound Aromaticity Methylgruppe Reactivity (chemistry) Molecule Shear strength Electron Amine Acid dissociation constant Hydrophobic effect Stickstoffatom Methyl iodide Concentrate Alkylation Methylamin Protonation CHARGE syndrome Lone pair Combine harvester Acid Computer animation Functional group Chemical compound Salt Chemical structure Base (chemistry) Ammonia Methanol Hope, Arkansas
Dicarboxylic acid Haloalkane Aluminium Amine Collision Alpha particle Dreifachbindung Electron Cyanohydrine Amine Colourant Elimination reaction Aluminium hydride Alkylation Benzyl Walking Solution Hydroxide Electronic cigarette Ethylamin Acid Cyanidion Chemical compound Stickstoffwasserstoffsäure Cobaltoxide Isotopenmarkierung Ethylgruppe Reaction mechanism Azide Carboxylate Hydrogen chloride Hydroxyl Hydrazine Methylgruppe Ammonium Acid dissociation constant Hydrolysat Redox Active site Beta sheet Lithium Conjugated system Palladium Setzen <Verfahrenstechnik> Hydrocarboxylierung Stickstoffatom Bromide Methyl iodide BET theory Carbon (fiber) Methylamin Aldehyde Protonation Water Sodium Hydrogen Computer animation Acid anhydride Functional group Nitrile Substrat <Chemie> Base (chemistry) Ammonia
Ethylgruppe Reaction mechanism Hydroxyl Platin Wursthülle Amalgam (chemistry) Ammonium Alkene Nitroverbindungen Mercury (element) Amine Colourant Redox Nickel Beta sheet Lithium Sodium borohydride Aluminium hydride Palladium Setzen <Verfahrenstechnik> Hydrocarboxylierung Methamphetamine Stickstoffatom Aldol Walking Carbon (fiber) Chemical reaction Man page Iminiumsalze Henry-Reaktion Ethylamin Sodium Hydrogen Acid Computer animation Cyanidion Functional group Zinc Nitrile Covalent bond Cobaltoxide Isotopenmarkierung Condensation
Decomposition Oxygenierung Haloalkane Resonance (chemistry) Meat Amine Hydrochloric acid Chloride Chlorine Alpha particle Molecule Machinability Electron Amine Addition reaction Benzene Elimination reaction Sodium nitrite Nitrosamine Hydride Alkylation Aldol Salpetrige Säure Walking Veresterung Electronic cigarette Lone pair Carcinogen Acid Nitrocellulose Enol Chemical compound Solvolysis Cobaltoxide Diazonium compound Thermoforming Condensation Isotopenmarkierung Ionenbindung Reaction mechanism Action potential Hydroxyl Organische Verbindungen Reactivity (chemistry) Nitroverbindungen Acid dissociation constant Redox Beta sheet Palladium Aldehyde Hydrocarboxylierung Setzen <Verfahrenstechnik> Grading (tumors) Stickstoffatom Ketone Asset Formaldehyde DNS-Synthese Carbon (fiber) Aldehyde Water Hydrogen Computer animation Functional group Covalent bond
Computer animation Lecture/Conference
all right so we left off last time you are predicting of the Bey's acidity and this aim bait and basicity of an it is ol all right so do we have any acidic
protons on in minutes all anybody yeah we have this at this design acidic proton if we remove that proton it does not affect acidity or base it doesn't affect aromaticity so yeah we can remove a proton we can't remove but we can't pollinate this nitrogen here on the bottom but we can deprotonate it does not affect aromaticity still aromatic so pKa of that here's some pKa of several nitrogen heterocycles you do not need to memorize these numbers but this is nice it's a nice place to have all these PK's because they're sometimes hard to find and so here we have here we have all the pka's just for comparison alright questions on acidity and basicity anybody let's talk about preparation of amines and then we're going to do reactions of amines so preparations of amines you might have you might remember that when you were doing chapter 7 problems and you had ammonia attacking an alkyl halide that you got a protonated product as your as your product and that might have thrown you off a little bit and it turns out that it's a little more complicated than we led you to believe in chapter 7 so let's get the real story here all right so that would be a straight chapter 7 problem and this would have been the answer you would find in your answer key for a chapter 7 substitution maybe showing the counter ion okay so you would get a salt but this is actually going to further react so if you look here if you have ammonia and we have methylamine our product we could get an acid-base reaction we're going to we're going to predict the direction of equilibrium here so I'm just going to draw a box here all right so we want to predict which way is the equilibrium favored just by not looking at pk's but just by knowing what we know about structure so let's compare the two bases and see which one's more basic so here is our hope this would be protonated here here's our base on this side and here's our base so we can compare acids on both sides we can also compare bases if we're just using structure then we can compare those two things directly you compare the bases which one of those bases is stronger ammonia or methylamine so we have this lone pair here is a meth electron donating or electron withdrawing group electron donating so it's going to be feeding some a little bit of electron density more electron density into the nitrogen and ammonia so this is a stronger base so the equilibrium is actually favored to the left but you can get a little bit of that happening so remember the equilibrium always goes from stronger acid stronger base to weaker acid weaker base here's the problem that we didn't tell you about and in back in chapter 7 and that's over alkylation so as soon as we form some of this compound here and we can form this compound by this deprotonation that can happen here even though its fate is not favored it is still going back and forth and when we form this compound here it can actually also attack another molecule of methyl iodide so that's what that would look like and in fact if you're comparing the nucleophile strength compare methylamine versus ammonia which ones which ones more on nucleophilic anybody have an idea which one is more nucleophilic we're looking at the concentration of charge on nitrogen methyl is slightly electron donating and so this one has some electron donating methyl making that more and more electron rich so this is actually a stronger nucleophile than ammonia and that's why we get over alkylation because this is more reactive than that so as soon as we form some of this and how we form it is we do a substitution and then we deprotonate now we have this it's going to be more likely to attack methyl iodide than ammonia and every single time we put another methyl on there it gets more reactive still so what you actually get in this reaction and why I really never asked you this on a test is you get this you're going to also get and doesn't really matter how much you use you're going to get a combination of all these things if you completely methylate nitrogen that's called exhaustive methylation all right so even if you limit if you limit the methyl iodide to end and then mean to one equivalent of each you're going to get a combination of all all of these products so you're going to get one methyl two methyl three methyl for methyl combination okay and so that's a core course all all according to accounting for the different nuclear plus dy over alkylation that's because you get once your your product is more reactive than your starting material so now we'll draw this out what I was talking about methyl is an electron
donating group so it's donating electron density to nitrogen that's making it more more electron wrench so more electron density on nitrogen therefore it's more nucleophilic and every time you methylate this you add one more methyl group which is going to add more electron density to nitrogen so every single time you add a methyl group you make it more nucleophilic all right so if we want just one methyl we want if we want to take a me ammonia we want to just form methylamine one way around this is to use a very large excess of ammonia these are very large excess of ammonia so that ammonia is the most likely thing to collide with methyl iodide rather than once you methylate ammonia and you get methylamine there's less collisions by using a very large excess of ammonia and so that's one solution and that's why if you're just using ammonia if you're using something that is not expendable like ammonia that maybe you've made an amine and you want to use a large excess you don't want to do that if you synthesized something you don't want to use a large excess and throw it out so I'm going to show you some alternative methods below that will work a lot better for you then using ssme alright so let's look at some of two alternatives alternative number one reduction of azide is another route to primary amines and so what you do is you do a substitution you guys probably remember sodium azide from 51a that was in Chapter seven and so what you do you have a zine ion negatively charged nitrogen and you just do an sn2 reaction works really well attack the carbon bearing the leaving group that leaves you with benzyl a side and then you can reduce the a side to an amine so two ways to do that lithium aluminum hydride step one followed by water so we're familiar with that reagent or you can use h2 and palladium hydrogen and palladium so you could do a hydrolysis you can do a hydrogenation and that will take you to the amine alright so what do you remember about azide from Chapter seven what was it was ooh I used that one a lot as a nucleophile why did I use that as a nucleophile a lot do you remember I preferred azide over ammonia and now you can see why I prefer azide over ammonia what was the bull was the big reason now what do we have to worry about with substitution elimination and a site is a much weaker base than ammonia so means you get less elimination so this has a bunch of things going for it you don't get any over alkylation and you don't get you get much less elimination so azide is a great nucleophile and a weak base how do we know it's a weak base we look at the pKa of the conjugate acid pKa of hydrogen azide is four point three compared with ammonia conjugate acid is ammonium ion where the pKa of about 10 so this is a much weaker acid it's not just it's about six times it's not just six times weaker it's 10 to the 6 times weaker base so that means we're going to get a whole lot less elimination when we use it so there's two advantages here those are two advantages that we don't get them as much elimination and we don't get over alkylation so but the big deal here in this part right here is that we competing eetu eliminations are lesson so it means that this is great for primary and secondary substrates all right so advanced is using azide / ammonia well as we already mentioned know over alkylation and of course let's just say it one more time is this a side ion is a strong nucleophile and a weak base so lessee 2 plus C 2 then with ammonia all right so let's give an example here and and and all of those beta phonetic Allah means the two types we're going to go we're going to make those synthesize those various different ways throughout this chapter you can use this method to synthesize the beta fern ethyl amine that has a hydroxyl in the Alpha position so we would just have a Z come in here this is a good example attack on the least substituted side after protonation we get this compound and then h2 Palladium gives us the type of beta Fenella mean that has a hydroxyl in the Alpha position so let's label that
and let's just remind ourselves attack at the least substituted side that goes all the way back to chapter 9 alright questions anybody on using azide instead of ammonia for substitution alright let's see another alternative here to using azide I mean to using ammonia for substitution this alternative is called the Gabriel synthesis and it uses a compound that's like an anhydride except it has a nitrogen instead so that's what we see here so if this was an oxygen this would be an anhydride instead it's a nitrogen and so let's go through the Gabriel synthesis this is also a really good alternative hydroxide ion to what the hydroxide ion is going to deprotonate nitrogen then we add in our alkyl halide and we do a substitution and so that nitrogen is got not going to be nearly as basic as ammonia for also because it has electrons that can be delocalized onto two carbonyls right okay so that's going to be less basic than ammonia so then we do substitution so now the nitrogen is bonded to the r group whatever that our group may be and then and now we're ready to take this all this other part of the ring off that was only there sort of as a temporary measure and so there's actually two ways to do this you can use HCl h2o and heat what's that going to do so we have sort of and does something that looks like a diameter it's going to hydrolyze that so we're actually going to get a carboxylic acid so you may want to try doing the mechanism for that dicarboxylic acid and our nh3 plus so if we're forming an amine and acid it's going to be protonated and then we would use hydroxide in a second step to deprotonate so notice this is a great alternative to using ammonia the other way that you can do this I'll do this in a different color the other way that you can do this is to use hydrazine that will give you this compound and after I draw you can kind of think about how we would make this comp n plus RN h2 so can you see what's happening there so so what's going to happen is the hydrazine is going to the nitrogen on the hydrogen is going to attack the carbonyl kick electrons up onto oxygen all right here kick electrons up on oxygen electrons on oxygen come down and kick this nitrogen off and now this is going to attack the other side also okay so it's just it's almost like transesterification but with an amen' okay alright so that those are two alternatives I feel I believe there's a sapling problem that has this and but you can also do it this way on the test alright so it only gives one product and therefore is a great way to synthesize primary amines so that's alternative number two we have some more alternatives questions so far though stop me now if you have any questions so far the other way is to make a means is reducing carbon nitrogen double and triple bonds this doesn't necessarily give you primary means but it can give you primary means so that if you if you treat a nitrile with lithium aluminum hydride in water we already talked about this reaction right so even though I'm talking about this today this is fair game for the test right didn't we mention that one and what was that chapter 23 22 chapter 22 end of chapter 22 okay so we can reduce a nitrile that will give us a primary amine that primary amine happens to be one carbon longer than the previous one that we did but and maybe that's what you want the other thing is to reduce them and a mid with lithium aluminum hydride so another reaction where I'm talking about it today but it is not a new reaction so this is chapter 21 right so you know that reaction those are two more ways to make a means reducing Amin's and nitriles reducing nitriles provides the route to two different types of beta phonetical amines so let's look at this one here so we have Sinai we're just going to do an sn2 reaction backside attack kick off bromide as a leaving group sn2 right that gives us a cyano group and then we can reduce that with lithium aluminum hydride followed by water to give us the other type of beta Fenella me where we don't have a hydroxyl in the alpha position so this would be yours your simplest beta Fenella mean that you can make but you can also with the nitrile you can make the other type also the beta Fenella mean that has the hydroxyl in the beta position so so the cyano group is going to attack the aldehyde remember what that does I'm going to just just trying to draw right on top of this after acid that gives you a cyanohydrin remember that that is and also a review reaction what chapter was that in that's chapter 21 let's we'll label this after I finish this so now we can let the aluminum hydride right so here's a good bet there's a good bet that on the final you'll be asked to synthesize both types of beta beta for ethyl means and I'm going to show you several ways to do that so you'll have choices okay so that's lithium aluminum hydride reduces the nitrile to a ch2 NH 2 and that gives you the second type of data Fenella mean all right so we got lots of choices here so let's just remind you how let's label this this is a cyano hydrant and that is
chapter 21 and the lithium aluminum hydride plus a nitrile that is chapter 23 or chapter 22 now chucker 23 chapter 22 okay right so that none of that's actually new except the fact that now we're recognizing what we made as a penny at betaf in ethylamine all right so that's more ways to make a means we got a lot of fun ways to make amines and then another way to make a means is it called a reductive amination this is a brand new reaction and it's a really really widely used in organic synthesis guaranteed I will put a reductive amination product on the problem on the final if one if not two it's very important reaction so here's what it looks like and you guys love amines in aminium ions okay so that's what we're going to do here we're going to take an amine and it could be primary or secondary and we want catalytic acid or we want you could just write pH by so you're familiar with that reaction that's a chapter 21 reaction I'll show a reaction with a primary amine so we make an amine you can actually isolate the amine or you can throw everything together which I'll show you both ways to do it so it mean is often not isolated so let's label that so that's why I have it in brackets you can isolate it often not isolated if you want to break this into two steps you certainly can but you don't have to break it into two steps then we do a reduction and what I usually use h2 palladium or another way to do this is a region that's very similar to sodium borohydride only it has one of the hydrogen's replaced by sini group sodium cyano borohydride and that's another way to do this and and that's the most common way to do it here I would say let's label this most common and so what you're doing here let me show you what we're doing before we draw the product where it's easier to see from the hydrogenation so we're just going to add a hydrogen to nitrogen we're gonna it's just like we're hydrogenating a double bond we're going to have a hydrogen the nitrogen we're going to have a hydrogen to carbon and so we're hydrogenating that double bond even though it's an alkene we certainly can do that so let me let me I'm going to draw this out well let me draw it in red and then I'm going to draw the hydrogen's that just came on in a different color so you can see what's happening here a little hard to visualize so just going to draw here and now let's add hydrogen here hydrogen to nitrogen hydrogen to carbon okay so what that means is that we are get within this double bond goes away of course so what we're going to make is this all right so the nitrogen goes where the carbonyl oxygen was and then you hydrogenate everything great way to make amines so that's one example we can also throw everything together all in the same pot and that includes whether you use hydrogen and palladium or platinum this one's using platinum I almost always use palladium just to have less for you to worry about but you can you can combine everything here can combine everything we still want to have some catalytic acid here though catalytic h3o plus or you can write on pH 5 so then so that now notice that's a secondary amine so we're not going to make it Amin we're going to make an iminium ion so what's going to happen as your intermediate and I'll draw the intermediate in brackets you're going to make an iminium ion because you can't make an amine here so that's formed in the reaction mixture and as soon as that's formed it's going to be hydrogenated so that what you isolate is this amine here all right so that works also really well here's reductive amination to make us well speed em feta mean this would be is this nymphetamine or methamphetamine methamphetamine so what you do is you make the let's add let's add our pH 5 here or you can add H three o plus catalytic in this case we're not throwing everything together we're doing it stepwise we're making an amine and then h2 palladium so again the type of a diplomat will mean where you have no hydroxyl in the beta position questions on a reductive amination yes excuse me you mean formation even if you do form the enemy the 'man that you Naveen can be reduced by the hydrogen and palladium okay yeah all right let's talk about reduction of nitro compounds another way to make a mean so we got a bunch of different ways are you sensing the amount of synthesis in this chapter there's a lot already and we're not even you know it's just one lecture okay reduction of nitro compounds so this is what it looks like we have a nitro compound we can use h2 palladium or h2 nickel or h2 Platinum and we can reduce a nitro group to an amine the one I usually use is the Palladium this is primarily well not only but it's
primarily used to synthesize aromatic amines that is also not a new reaction didn't we learn that in chapter 18 so you can take benzene wherever you nitrate of this so we're just saying a lot of these the reductive amination is new but a lot of these are not new reactions this is chapter 18 was there another way to do this reduce a nitro group do you remember the other way to do it Clemmensen yeah or zinc mercury amalgam and HCL that also works too okay all right a great way to make the babyphone ethyl means is the henry reaction we got another named reaction similar to the aldol we've seen examples like this this is an aldol like condensation all right so here we go here we're going to go through the mechanism here of course the mechanism here for everything we're not going to show the hydrogenation mechanism but the mechanism here this is not a new mechanism this is review right so I click put this mechanism on the test right this is just aldol right you agree with that sure it's aldol okay so let's write that down not a new mechanism this is chapter 24 and chapter 24 is on the test so who knows I don't even know why we're in the test yet I did start it
though so I'm thinking about it it's so tough because I have so many mechanism so many mechanisms so little time right you to make you to have you guys take the test if we can have like a machine grade the mechanisms I would do have way more mechanisms than I do alright so everybody see what's going on we deep protect this what is this what is this functional group right here so now for asset l so we can do protect that do not not deprotonate D protect if we D protect that we're going to get a dial and formaldehyde and that's dopamine so that's a way to make dopamine how about that but just to remind us that this is a review mechanism let's go through the mechanism of the Henri I'm not going to show the hydrogenation but I do want to go through the mechanism for the Henri alright so we have CH 2 CH 3 we know that hydrogen's alpha to a nitro group are acidic in fact what does this have a pKa of 9 it's really high I mean it's really a low number pretty acidic we can go ahead and push the electrons on carbon or we could push them on to the nitro and that's why the skies so acidic and we actually have good resonance stabilization for this molecule so we can go here we can push electrons on to this oxygen here we got delocalized electrons definitely and so I think a good idea for the final well if you're thinking about the final at all I think a good idea for the final is knowing how to draw a nitro group because I think I feel like if you guys have had ochem for the whole year you should know how to draw a nitro group without having five bonds to nitrogen and I see that a lot in 51c so I may be testing you on I may be asking you that on the final alright so you get the idea here highly resonance stabilized but it's an enolate like compounds so so I'm going to redraw it so we don't get confused here let's draw our aldehyde now what I usually do is I say you guys already know how to do this I'm not going to draw this mechanism but I'm showing it now I'm showing you because we're in good shape here timewise let's redraw I'm just going to redraw the this first read this this second resonance structure here I'm going to go I'm going to leave the electrons on carbon and use that alright so we we tack the carbon you kick electrons up on to oxygen we get an alkoxide since we're attacking a type 1 carbonyl we don't have a leaving group so our choices are we can we have a two choices we can make a beta hydroxy carbonyl or we can we could do an elimination and get an alpha beta unsaturated carbonyl what's going to happen here because of this benzene ring here we're not going to be able to stop at the beta hydroxy carbonyl but I'm still going to draw that because we do need to form that first and then we're going to eliminate so just remember if I do ask you aldol condensation and that you when you do the elimination that you do a 2-step elimination you make the enol a first and then you eliminate don't do it in one step you lose four points so if you if you've decided you're not going to do nomenclature you're just going to miss the four point nomenclature question and then you do a one-step elimination there's eight already points gone so you want to make sure you make the enolate first so now I'm going to draw the Nitro group again because I need to UM remove this I and I can leave it on the Nitro group or I can I can leave it on carbon or I can put it onto the Nitro group let's just leave it on carbon then I don't have to draw the Nitro group so we make the enolate first and then after we make the enolate we kick off the leaving group so just a condensation but but helpful helpful leaving leading up to the test to see this mechanism again so make the enolate and then we kick electrons down and kick off hydroxyl in a second step so when we do reduce with the hydrogen and the palladium it's going to reduce the double bond so there will it will be alpha beta unsaturated any longer reduce the double bond and it will do reduce the Nitro group so the reduction is going to with h2 and palladium which we're not going to show the mechanism for is going to lead to protected opening questions anybody anybody have questions on that one yes uh yeah you know what that should be resonance huh this should be reversible
arrows huh thank you for pointing that out really didn't realize I did though yeah thank you for questions all right so that's aldol condensation we know that really well so now we talked about a bunch of ways to make a means now what can we do when we have a mean so what this is reactions of amines once we already have one what are the things we can do with it we already know some of this we could do one for addition two carbonyls we could do with acid chlorides we can make amaz we know a lot about amines with ketones we can make amines if it's a primary if it's a secondary amine we can make enemies with esters we can do ammonolysis to make a Mammoth's within hydrides we can also make amaz and then of course there's all of the sn2 reactions that we did way back in 51 a the end of 51 a such as a 1 substitution with alkyl halides is problematic due to over alkylation we already talked about that so we have some alternatives and means they're also strong graces so e2 competes with sn2 so I want to want to always keep that in mind there's a new reaction that we're going to talk about a reaction of primary amines with nitrous acid and so nitrous acid HNO 2 is a weak unstable acid generated Institute by treating nano2 with sodium nitrite that's the same noti'm sodium nitrite that you find in hot dogs and with a hydrochloric acid which is in your stomach right so this is some potential reactivity that's happening in your stomach when you when you eat cured meats that have nitrite in them right in the presence of acids nitrous acid decomposes to a nitrous Soniya my on which is a nasty carcinogenic nasty compound a powerful electrophile which reacts with primary amines to form diazonium salts and so this is what it looks like how we form it in the first place we're going to be protonate oxygen just like that and actually we're going to protonate that oxygen twice this is not a mechanism I usually ask on exams by the way so just showing you what's happening here hydrochloric acid super strong acids going to protonate that oxygen twice and then once it does that as you can kind of guess that that's going to we're going to lose that hydroxyl as water now that we've protonated twice it's going to it's going to come off as water and so as you can imagine once that leaves once this leaves to make water we form a compound that's super super unstable notice we do not have an octet on nitrogen so if this is a very reactive intermediate so we pretty much avoided ever having nitrogen without an octet so this is a reactive reactive intermediate it has a very very short lifetime so if you've formed this intermediate in the presence of a primary amine what's going to happen is it's going to anything with lone pairs including DNA okay it's going to attack that so it would look like this after that happens again don't worry about mechanism here I'm just trying to show you what's happening here you form this and then deprotonate with chloride ion and then we're going to skip a bunch of steps and when we have whenever we skip a bunch of steps it means I'm not going to ask you this but what you get is something after you deprotonate with the chlorine oops do that wrong this tablet's going quickly here get something that looks like that and this is n nitrosamine which is a potent carcinogen this gets converted in many steps which I'm not going to show you to something that you probably haven't seen before but what it looks like is this is called a diazonium salt and it turns out that this group here if this leaves as a leaving group it is the world's best leaving group right here nitrogen so this is and this is an electro file with a fantastic leaving group so it does all sorts of things all the things that we talked about in 51 a 51 the sn1 e1 sn2 e2 not very synthetically useful so why did I show you this in the first place because there actually is some very good synthetic utility if you use aromatic amines to do this reaction so but let's just label this because I'm going to show you a good good thing that we can do with this reaction but for this it's not synthetically useful all right we will stop right there and we will
continue this on Monday I'll see you on Friday for the exam