Logo TIB AV-Portal Logo TIB AV-Portal

Addition of Water, Alcohol & Cyanide

Video in TIB AV-Portal: Addition of Water, Alcohol & Cyanide

Formal Metadata

Addition of Water, Alcohol & Cyanide
Title of Series
Part Number
Number of Parts
CC Attribution - ShareAlike 3.0 USA:
You are free to use, adapt and copy, distribute and transmit the work or content in adapted or unchanged form for any legal purpose as long as the work is attributed to the author in the manner specified by the author or licensor and the work or content is shared also in adapted form only under the conditions of this license.
Release Date

Content Metadata

Subject Area
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: 00:25 - Addition of Alcohols 04:35 - Important Points about Acetal and Hemiacetal Formation 17:26 - Cyclic Acetals are formed more readily than Acyclic Acetals 21:30 - Addition of HCN 27:10 - Addition of Primary Amines (R-NH2) to give Imines 45:17 - Addition of Secondary Amines (R2NH) to give Enamines
Arginine mechanism Colamin Stickstofffixierung operation hydroxyl groups chloride Bock chemische Reaktion man originators water Säuren Computer animation electron Magnetometer Brown adipose tissue compounds remove chemical structures oxygen basic basic
Glucose chain mechanism Bohr hydroxyl groups case man firm Zeitverschiebung Magnetometer Brown adipose tissue Library board Inneren areas asset carbon Waldhonig Bock Ethylen-Vinylacetat-Copolymere chemische Reaktion alcohols firm Paste Säuren Computer animation Peroxyacetylnitrat remove migration chemical structures form den Ideal methanol label
aldehydes Bohr formal operation chemische Reaktion gold stocks alcohols man water Hydration Computer animation electron Tau protein function Gamma Altbier shot Common standards remove form atom standards
power bond sodium hydride Toluol mechanism density Bohr chloride gold case Humifizierung man Orlistat hydrolytic plant sulfuric acid benzene rings active site Acetaldehyd period standards chemical formulae aldehydes type progress Gases domain chemische Reaktion alcohols stocks variety water Säuren conditions Computer animation function Beta chemical structures Zigarre mixing benzene rings form den condensation
Digital elevation model transition states Bohr los interface gene Humifizierung Sterics Alfred Klinisches Experiment enzymes Orlistat color shot Insulin Cycloalkane duration Maische steps Deep sea chemische Reaktion alcohols firm reduction systems van Säuren Cyanide Anion coupling Gamma amines By-product compounds remove Arsen Alu element Hab oxygen form Cyanide antigenic bond precipitation species mechanism Lochfraß sickle diamond hydroxyl groups hydrazine deformation striking man formal analogue Zeitverschiebung age Magnetometer Inneren chemical formulae reactor type probe mixture nitrogen carbon hybrid Hydrogen Cyanide Hydration water conditions Computer animation function Iron basic AdoMet
breakdown Humifizierung electron fiber protein Insulin Spring Double bond rates steps chemische Reaktion OH- AMPs Säuren yield Gamma remove Hab oxygen form stuff mechanism plant hydroxyl groups case Diazepam man age Magnetometer Applikation <Medizin> report level Einschlüssen areas Carbonyl type metals Flow injection analysis phase nitrogen Arginine Gravel mode hydrogen bonding carbon proton water Wasserstoff Drops conditions Computer animation function coordination Peroxyacetylnitrat chemical structures Dehydration basic
Computer animation
the Act did Regan started wearing continuance after a 21 any questions before we get started anyone riots is certainly already have test next week he that I just as much as you do by the way something lobbying floors and they haven't seen what company put it brain here it will just you know give your Graybill knows the origin of the brain and that I would have to be willing to do tests right he'll thought to study the matter is my dream chloride fucking through talking about and I think have tell mechanism last time it was interesting very high likelihood there with the as Intel mechanism on the test OK so we went through the base catalyzed reaction and with the base catalyzed reaction began against the Taliban it started in any attack so something to keep in mind that we stop right here the acid house announcer callous reaction I generally can't stop it right here so if you want to make a handy as tell you should use based on generally not school will go away acid house so we did went through the base Callas mechanism to formally as town and we went to the acid catalyzed mechanism to form the the acetone here we are we stopped at the enemy has the talent and on the next page we were continuing with the tacit operation alright so the 2 ways to do this ,comma Bolton methods the you the hydroxyl here because that's going away and white turns out with these acid catalyzed mechanisms that were going to be doing over the next several weeks not enacted mechanism you always from believing the 1st OK so I here would approve a 1st and then the way I do is I had electrons and oxygen come down a off water when you can certainly show at this way the makes you draw 1 more thing here this week and then we can draw the resident structures of these are 2 of President structures for the same compound just 4 brackets around there now is also fine OK and I keep going down those were not done yet so then I
mammals intercommunion attack so we basically were replacing I'm not familiar with the talks agreed with a high job-seeker but we're not doing it by a nose into reaction so as you can see we are 1 step away from him the acetone but we have to deal with the last act but as it is to divert made so homages to with methanol Sony Classical oddsmakers were of a different meaning anorexic and regenerated catalyst so it's like that questions on the acetone mechanism anybody yes I don't crave reversible errors so why don't you need to worry about these guys on exam migrate Kerberos so don't tell me you don't get worried about this part here greater more questions anybody far-right warm woods about any assets soulful recently as does cannot be converted into Aceh tells with days we mention that already so there were making a point again you Jessica tells us to go all acetone incentives difficult to isolate the listing areas tells part of a 5 or a 6 member during alright so if you have something like this and you
didn't intramolecular reaction you can actually isolated Aaron Henry tells David so in this case on the economy as tells favorite and don't have to drive the were really wants to be in a six-member so most of the time they all of the key to his favorite but in this case the Henry talents a favor and the best example here this is glucose as as a young hydroxy elder heights and and only a very small percentage of glucose is in the old women ,comma opened chain for sows the open Shane form it likes to be in entering and so long era to the right sure arrow to the left and and this is going to be ready talk about this more in depth in the very last chapter in 51 C and you get really good at drawing so you thought you were dealt with during shares now so not is obvious Drexel's area in Equatorial position so that certainly makes it easier to you remember the structure because harder is to actually pick out the honey as a tell carbon so remember when we look for him he has tell you what carbon it's bonded to a hydroxyl animal foxy so I'm right here this carbons only bonded to a hydroxy so that's alcohol all likewise that's an alcohol that's an alcohol that's an alcohol on this 1 right here in a country that a little weird looks like there's no I think that on this carbon right here responded to hydroxyl and alarm and so it's a very acid house so that serving the acid tell current so they go back and fix that Karadzic averaged upon a look at that and we 7 out of things are really Is that better yeah and Alex label that in the absence of carbon so there's a question exactly might have already run across from they ask you to say would certainly hasn't helped us to tell you know right away and there is a small there's a there's a small issue here with the words can be as detailed and an acid tell on some of our OK and textbooks used only as a town after Telfer everything other textbooks that we've used in the past use key talent if it if it's from Iquitos and acid tell from an elder rights OK so there is a distinction there and I use I learned in Kennedy Town Hall and the she Tal acid tell but then you know the books that we've had over the years don't do the key talent more but if you see that that's what they're talking about so we just use and acid telling this book for anything that has a carbon bonded to a hydroxyl and awarded whether it came from a teetotaler outside OK so there this a little bit you Myron across many key talents is the same thing is that is just comes from Quito are as a child comment and done so this is glucose in the 90 s tell form and I think that at equilibrium and this is this is definitely greatly feared an equilibrium I think there's like less than 1 per cent in the open chain formed so this is a great favored equilibrium so with these guys where you have the tacit tell on units 6 surviving members bring you can stop at the Intel's fastest because that's what the questions on that point there anybody say that as the governor also governing board
remaining asked operations so you can go back and review that the more stable the Carbondale the less favorable the addition and edition favored for formaldehyde in aldehydes with electron would join groups just exactly like with With hydrates so we can if we can call the same principles reaction must generally be Germany completion English shots with his principles and sold and to drive equilibrium he Siviglia user logic says about already or remove water as it's being formed or a ball he do both things so there will be a logic says here let's struggled Friday but all are prime OR finally got to of them here Our sigh product is water which we wanted to pay attention to for trying figure out how to drive equilibrium so large water or remove water as it enlarge excessive alcohol or remove water as it's being formed so those are the 2 most common waste from standard way to remove the water as its form is to on easier trope which benzene or toluene Our isolation with the setup looks like for that and then this is using a Indian stock dropped kind of a really cool reaction I did this reaction from all this is cool synthesizing water in this reaction so that on the next page and I'm sure you what that looks like so this is from
on the ground and phone book that
we used to use the really great drawing investors I would love to do this in the undergraduate labs with the Dean stock chapter really expensive Parise here's the idea here here's your reaction you have on let's just say allied with over the and the using and using alcohol you gonna have to to alcohols because you incorporate into our calls in new product and a mix that with the benzene toluene why benzene or toluene in this case the using because dancing forms it is you drop with so what's an easier trumpets it forms a in the Gastein informs the structure of the boiling point is different and benzene in different than water it's at some intermediate intermediate value so they actually goal gold they called distilled so you're you're doing this reaction Europe Wyoming benzene density has a lot of this formula is it opens here comes up here comes up here and there goes into this condenser right here right I'm so that this commensurate once once it condenses the benzene and the water don't mix anymore do they they form a separate layers so on what happens is the only comes down here and our internet's down in here but once more dense than benzene water Water goes to the bottom OK so on these once was so this is condensers they're no longer together and so the water goes to the bottom of the benzene goes to the top and it and so you you want to get too much benzene here if this overflows adjusted spending right back into the reaction OK so that allows you to Due to you can and you can actually measure the amount of water you have here the 1 that I used gradations here so you could measure how much water might actually forming in this reaction and they'll know when you're done here and that it's gets too full of water you want the water to go all the appearance of back in here you could just ring with the stock so this is how you very ,comma waited drive water off and hazards for and that's what I Dean start apparatus so you can call it a dual stock contract so really really nice drawing that bonds sold by the same token of Vanessa tells a place in excess water with a trace of acid the teach or recover from their reaction mixture this is known as a hydrolysis so this is a
reversible reaction we have the reversible errors right here I'm an equal every other key challenge is the thing that's favored so without driving it it's gonna wanna go back to the key to replace the once you put that acid talent on the comes off very easy so this is what it looks like so here is a acetaldehyde just made above reversible errors here it's 3 0 plus each too well annually only need catalytic exterior plus all you need and it wants to go back to Quito same mechanism by reversed direction you need another do you need another mechanism in both directions by next week in the session we will do the reverse reaction OK so noble to bolstering during a both mechanisms and so the Soviet and discussion week for his will do that so you may want to try it on your own Long before it before next week and see if you have it matches what you would talk about and discussion all right so similar .period makes ourselves we idolize rise under very mild conditions to regenerate original Carbonell they often uses projecting groups railed I think he tells where they make great protecting groups rather hides in Quito allies in key towns only so you can make an ass itself from Ronaldo and you can make it from the Tony you cannot make tell from Ernesta and ended an acid chloride is a carboxyl against and this is only aldehydes and he tells and more commonly rather than making this type of acid chose to make a cyclic acid telling your using this as a protecting the so this was the most common and as would be the conditions of tossing you can also use catalytic sulfuric acid but more commonly Tosic acid so very similar to sulfuric acid so that's what toxic gasses toluene Dean stock apparatus toluene more times more common in benzene understandings of pretty bad person and some try to avoid it and if we can and this would look like this and will look at the mechanism for this reaction in discussion also next week so that's a cyclic accident site product is water so we would drive this the exact same way using that Dean stopped track questions anybody
on acid tell formation are so we were not as tells the reason why sickle tells me is more commonly known as the protecting group is bomb virtue reasons number 1 recall that we have recall this formula from Delta genes Eagles Delta age minus the Delta has and mostly we have been ignoring them we've been assuming if Dr. Julius it favorable the Delta ages favorable were wearing been mostly ignoring his entropy components but the enter key component can play a role in some reactions we've just been pretty much ignoring it spun off our radar so on this reaction is that when you make a sickle tells more favored because if you think about it we have 3 reagents here and if you look at the products the 2 products sewage decreasing entropy here so decrease entropy is not good His creasing enter the the disparage reaction and if we make a cyclic tell we haven't you reagents here and we get to reagents Protestant so not as not as bad change so similar interface so that's reason number 1 by reason of virtue is that intramolecular reactions are more probable so if you go through the mechanism of 2 to make the cyclic acetone which we will do in discussion in the forward and reverse directions nearly getting intermediate that looks like that and then you're going to have the alcohol attack here OK so that would be intramolecular In remember making a 5 or 6 members during his very favorite this is going to make a five-member and if you compare that to making a non-cyclical itself this is what it would look like if you go through the mechanism you're going to get around the alcohol attacking like this this would be an intermolecular so in the intramolecular reaction you have to wait for those 2 species to collide you have to wait till they collide with enough energy and you have to wait till they collide in the right orientation if it's intramolecular you don't have to wait for the 2 species to collide so much faster reaction of much more probable reaction and remember this is a natural reaction but we're we're forming a part that's less stable than the reacted so this is more probable all right so for all those reasons that's the typical protecting group that will use for an how the heights in the world any questions on acid tells so that the 2nd reaction we did hydrates 1st we did ask tells 2nd and I wouldn't have edition of cyanide so cyanide arsenic Carter given al-Qaida fetal deformity detector intermediate colors cyan migrants so yet another new functional groups for you so here's what it would look like cyanide ion in step 1 this is a big nuclear violent attacks Carbonell directly they are the ones that attacks the carbon whether we get we get a Deep Throat native science writers we haven't had negative charge on oxygen we just formed a new carbon-carbon bond so this reaction needs to go on carbon-carbon bond forming and then I found in the 2nd step we had passes to prove it Sosanna hydrant is a carbon that is attached to hydroxyl and sigh and a group of cyanide group and so and again at this two-year carbon-carbon bond following cage this is a new carbon-carbon bond forming reaction all right so we make a couple points about this reduction on the next page aside from the new carbon-carbon bond forming strategy for allies in most aliphatic remember what aliphatic means not aromatic aliphatic means no aromatic trail than most of the details of this Goering favor Suyono Hyder information so siren heightens or more more favored than acid tells or hydrates from any error he Quito's so that so that we're all means were remaining right here that we have aromatic he tells for many Arab Quito's hysterically handed aliphatic he tells the position of Eagle Rivera starting material so strictly hindered aliphatic tone so let's show an example here maybe but she tell would deter turbulent group on 1 side and then enough on the other editor who view group on long balls side so we start getting steric hindrance there you saw their reaction down quite a lot alright so here's an example bands elder iron hybrid also known as Mandela 90 trial this is a synthesized by needs this is a reversible reaction it's in a reversible reaction chapter synthesized by millipedes it's also found in bitter almonds and peach pits so if you if
you have diamonds and 1 of the always is better you probably want a spit it out because you're going to get a little bit of a Sinai you don't impeach pits OK they also don't want you want peach pits from so I had to do entirely turned white as a ghost and said I would sure piece fits a loss is that occasionally you're here a lot relied define proficiency and I think so you're fine but anyway so when threatened it's released OK of millipedes releases 1 friend said inside the animal that investigates the this will that that this gets shot on line undergoes the enzyme catalyzed reverse Ionel hydrant information the undergoes enzyme catalyzed Versailles and heightened formation so it goes I'm back to Ben Zelda hiding in and out of the side product is hydrogen cyanide not enough hydrogen cyanide to kill an adult but enough to kill a small mouse so little interesting fact about the same writers questions on sirens anybody look at we have another function referring to talk about their on Indians and there talk about unity sold Anthony functional groups in this subchapter so additional primary armies to give me a means Siamese also known as Schiff base since fighting on the restive basis so I don't call them Schiff bases but I know where I went to grad school and so it is what I was talking about those Schiff bases or what is he talking about I have no idea how it develops a system interchangeable word for what it means and so here's what the product looks like something completely different do what we've been talking about but we ran into these last in the last chapter did away this so it would be a it's it's like nitrogen analog of a carbon so instead of the oxygen and you have a nitrogen so that the nitrogen of course has 3 bonds because obviously it's not oxygen and other debts inning side frontier is water army and there's a couple different ways to do this reaction you can you remove water like we talked about with acid tell uninspired but sometimes you cannot precipitate the Amin so the reaction it is true 5 precipitation if applicable you to do that precipitation of the inane or removal of water as its form so this is another popular reaction the product is actually less stable than the reactor OK so you will have to drive it if you want to get at any decent amount of Indian industry action followed cargoes related to money also react from similar compounds so you can if you use a hydroxyl Indian if on something called an scene you don't need to know these names but you may run across these if you use hydrazine it forms a hydra zone if you settle hydrazine it forms a fellow wider zone it used to for dying Nitro fennel hydrazine but it forms did something with a shorter name assured abbreviation it forms 4 d pH is the abbreviation and so these are very very similar so I'm very similar to an innings so if you had that used hydroxyl OK instead of this in a place on the map you never away right here in the 50's hydrazine in the place of the map will you just have another nitrogen jets submarines just like that the mechanism is going to be exactly the same still mechanism I'm yearly having acid catalyzed mechanism for this we're not going to do a base-catalyzed mechanism and I'll show you why in just a minute after catalyzed the th 5 5 is the best the H 5 is the best so what happens is so what that means is you're going to have a pH fighter going out some of any improper maybe but not all of the Amin probe now's nitrogen a nuclear bomb yes it is actually so it's Sigourney provides going to attack directly we're not going to promote may 1st even know we had signed on acid in here we have a mildly acidic conditions would not be a problem 1st because the is a really good nucleophile only a small amount of the nite the Indians from and were not appropriate the oxygen 1st so did nuclear file so this is really are exception here good nuclear file attacks Carbondale directly rights again reversible errors but Suu happens when we do that we have to things that we need to do here we need to on nitrogen scan of a positive charge he did probate nitrogen and we need to prove oxygen could we do that intramolecular early what you think let's count Adams Yatsenyuk a 5 or 6 of the transition state 1 2 3 4 Noah carriage so we have to turn this into 2 steps all right so at th 5 we have some pro needed demeanor find do
this step 1st that it's it's OK if you don't do this stuff 1st definitely I'm reading this step for somebody from nitrogen and then I'm going to use the output needed nitrogen to probe oxygen in the next step so when at last that I just used up I just made prorated will onion and that's what I'm usefulness alright so scanner can grab a hydrogen were going to break the nitrogen hydrogen bond this is what we call a carbonyl meaning another functional group that Cardinal mean analogous to an area hospital so carbonyl Maine that's the 1st phase of the reaction in the 2nd phase of the reaction from Marina do dehydration so on we're going and where you know we we need a loser hydroxyl group and our rule of thumb for all these reactions as in an acid catalyzed reaction we always brought the leading group for least so we're going to translate that leaving before late so I'm going to redraw the carbonyl winning here ended Friday oxygen and this is the whole reason why we have acid industry actions slightly acidic conditions it is because we really want to present this leaving before it leaves right and they want to happen is overloaded home person nitrogen are going to come down and we're going to kick off early evening so we've got a lot of mechanisms in this chapter but they're very very similar each 1 of them is very slow and as you can see once we do that we're 1 step away so this is in any of my honor now we just needed a program to make the inane so understated approach with a mean were .period about EPA's assurances and mistakes that all right so that you can do that and says yes accidents in information such a point through reaction the reaction was that's well as slightly acidic I was going to draw graphs for you are having already drawing here but I didn't so we're going to draw graph right now I just ran at a time during that non breakdowns and that no on spring break that they'd like to call a break OK so let's the room rate of the reaction as a function of opiates so pH down here whenever 1 2 3 4 5 6 7 that's good 89 OK and see what happens this reaction as a function of the age Paraiso starts off here really was small rate of reaction right here starts down right here invented Peach said so where is the only way to reporters say 5 it's probably closer to 4 . 5 and it drops down to nothing at 8 To Giselle extended 5 sort of hoteliers looks better than mine so this is about the age of 4 . 5 you'll see on some looks more like finds some looks like finding writers safe I just around it alright so let's look at so want the reaction the 0 at a pH of 1 essentially 0 so was so let's look let's go back and look at the 1st step here what has to happen in the 1st step the attack the the Carbondale if that and if that Amin is completely protonated Kandic attacked the carbon now so that's why we have 0 rate reaction said 0 greater reaction arm and so that's in Seoul last week as we raise the pH we have more and more mean that's not permitted the reaction can go quickly I'm white a drop down what what happens in a while we have 0 reaction at 8 if we ever-changing we're not we're not terminating the hydroxyl at Leeds OK Namibia's that doesn't mean a bigger a lot to you because we seen hydroxyl leave before in certain instances but in any way we can have a hydroxyl leave I would we have we're making a Carbondale it indeed is not as stable as a also would you really the reaction goes way down so on that's why we're doing acid catalyzed mechanism because that maximizes the rate of the reaction so what you really need to write if you're making an Indian on exam is you right here and in the years right th 5 and all those accolades from in the plant so slightly acidic so that leaving group can leave so I will grant on laborers say all the things I just said so you have to go back and look at the podcast to get that down but at a lower pH then fight that's all Maryland it is significantly protonated
right so awareness it's been like is this and that's no longer any of the following just slowly from a gallery change that Armenians electrified so no longer nucleophilic no longer to attack with then on our 2nd thing is some high teenagers higher pH than 5 the leading group is not is not currently the leading group but is not terminated it drops pretty rapidly here and hydroxide is not gonna the hydroxide can lead to form of carbon yield will see that will see that in Chapter 21 but took the arms in Chapter 22 but the hydroxide is not believed to foreign all right so that's point number 1 questions about that aspect of the reaction anybody the 2nd point I want to make about as in most of these acid catalyzed reactions we cremated oxygen 1st and we don't hear so why is that so in 3 years the fastest catalyze reactions referring to curb 1st and annually Covell attack OK and so in this reaction that doesn't happen we said because the Union is strong enough to to on different make the Carbondale and this means strong enough to attack the carbon all without coordination with the other reason is that this is not warranted because the initial decrease the department at 1st and the will be approximated 1st sorry about that so metal means a stronger base then Keaton that's not the reason very well it's the level means a stronger basement In this case acetone all right and if we were to make desperate needed carbon and in maintaining nearby what would the 1st we needed to Africa where we deepening that oxygen it would permit the office so we so in this this is the 1 reaction in mean formation in we don't have make the cardinal 1st questions on any information anyway yes not not usually so it's like any yet just as secondary means to give a in so on yet 1 more I think we're done with functional groups here after this I think so we'll see but there's something I'm forgetting so the breeze to make a a you primary means misuses a secondary the secondary Maine gear even mean instead prices start struck the structure of any double bond between 2 carbons sigh product is water so you can drive us the same way we did you means you can drive this the same way we did acid tells so very common to see how this summer removed as its form to drive equilibrium more so mechanism the 1st post step of the mechanism each of the carbonyl means exactly the same so same step 1 for any information the 2nd step is dehydration in every step except for the very last 1 is also gonna look like any information so let's go through that in the last minute will see how far we can go so let's draw carbonyl mean that we get and you'll see why this is different we're going to probably are carbon only a from oxygen so it can leave you don't see any oxygen in means we know the across a gravel proton from impregnated does is also pH fiber catalytic acid so far the same this next step is the same but turns a nitrogen come down kick off water only the very last step is different now in the last half of any information we did protonated nitrogen can we did protein nitrogen here no there's no Proton to program so that's why this is different so what we do instead is we eliminate what we call a bit hydrogen so this is going to come in and we're going to grab this Proton we're going to move electrons over here and onto nitrogen and that's our meaning so that's the difference here if we had a Proton to remove on nitrogen we would have done it but we didn't so we're stuck with the
alright that's story will stop right there we will continue this on Friday