Lecture 15: Tautomerization, Oxidation, and Reduction

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Lecture 15: Tautomerization, Oxidation, and Reduction
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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: 00:54 - Mechanism of Hydration 07:13 - Important points about Hydration 12:03 - Addition of Bromine and Chlorine to Alkynes 15:08 - Hydroboration/Oxidation of Alkynes 28:59 - Designing Synthesis: Part 1 37:10 - Introduction: Oxidation & Reduction 38:19 - Recognizing Oxidation and Reduction of Organic Compounds 47:20 - Reduction Reactions 48:55 - Addition of Hydrogen to Alkenes
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you after really get started alright we are going to ditch Chapter 11 today and start Chapter 12 so lovely everybody has started cataloging there's their reactions there is a lot of new reactions in Chapter 12 there's a lot reactions in Chapter 12 that you will use a lot the rest of the year a broken think so I I also and I just looked on our website and there's an addition summary sheets that summarizes everything we covered in Chapter 10 10 I looked and it's not there so I'm going to put that out and you can take a look highly recommend you take a look at that hand out alright so we left out last I'm talking about the mechanism that this was guaranteed to be on the the mid-term correct yes it should be 22 UTC Our somebody else accessing as he has said China should be OK for Resendiz mechanism isn't guaranteed to be on the midterm so let some things here sorry when we 1st mayor ,comma catering area but the positive charge on the most substituted side requires that 1 doesn't have a most substituted side but it was a terminal Alpine would pointed out the most substituted side this is a mark on accommodation and end up as a couple dozen will look the terminology they were going to be adding here on this is this type of structure where you have a I'm the vinyl alcohol it has a special name it's called an mean all so when you name alcohols you you use it all ending and when you named Al Qaeda's use it in ending so that's where we get that name from it's an e-mail and generally speaking 99 per cent of the time but what did these these structures are not favored at equilibrium so you know all the words generally unstable there new form in reactions but then there converted into the more stable form so the more stable form would be this form right here which is we call the Quito for so while we call this morning in all or we can call it that all forms and this is the Quito form and we haven't been all forms ratings sonorous equilibrium arrows here but we haven't had any and all and a Quito form equilibrating love we call that a touch harmonization so these 2 structures the in all and the Quito but I made the error the wrong direction with sticks that they enter converse so long arrow to the Quito form very short arrow to the vinyl form and the vinyl so this is called a top harmonization and the ii in all men the Quito former charterers so basically as soon as we formed as Eagle Forum then it's going to automatically talk time rise in equilibrium and to aikido also not favored at equilibrium so therefore and it will talk ,comma To a Quito so this whole process circle everything that's at the touch harmonization going this small part right here is how you talked on so going between the species that's the relations so you want make sure on the exam that you actually show that this did exactly how I've shown it here so they go from because some students will just draw the vinyl alcohol and animal distraught heroes and all draw the Quito formed opinion :colon miss all the points here so let's add up how many points this problem is really beyond mid-term to it's the way that I do my
mechanisms of this usually 2 points 1st step so we have lots counted at 2 4 6 8 I wanna see both of these and other residents structures 2 4 6 8 10 and 12 and then I want you to label that you know form and I want you to label the Quito forms that's 14 points on mid-term too so that's the lowest score and it's going to be on mid-term to Rikers that's all you have to stay the 114 points that's all you have to study so that's what I was talking about that will be my lowest score and I say I wish that was meanwhile a score OK so the way we do mechanisms is it if you're missing arrows like say you just do this 1st arrow and you don't secondary you get points for that step you have to have all the arrows if you're that if you're missing long Pearson charges you missed points and that and I believe me the points add up and so make sure you take a look at your test and see what you did wrong and you test with the mechanisms on the test all right so you get partial credit if you don't have charges if you're missing arrows you all of you will get some points for you you'll miss partial credit and if you combined steps and more than 1 step then you miss the point 3 steps of the combined 2 steps in the 1 thing you miss 4 points so that is coming gives you an idea on how that's created questions on this mechanism anybody yes all the very thing to point out so when I graded mechanism I don't care if you do these reversible errors I'm only focused on the Kerviel's that it so don't don't don't worry yourself about all of I don't universal whereas I don't care about that I just care about the Kerviel's barring important points about this reaction and
this is gonna come back in 51 season this terminology toddlers in form Quito form that's coming back and 51 see big-time so carbonyl compounds without a hydrogen is well we unaware of the hydrogen but the hydrogen that are adjacent To the carbon yield so this Carbondale right here as 6 sulfur hydrogen current problems without fighting on equilibrium with minor league alcohol isomers called deals the 2 isomers it Inter converter are called torturers so this 1 would be the Quito form and this is the Eagle form and most of the time organizing 99 per cent of the time the Quito form is more stable so that which event actually on isolated from the equilibrium for this particular once we have the the key equals 7 times 10 to the the minus 6 so that certainly tells you that the Quito form more favored and that's that that's the case of winning get 51 seals show you a couple of exceptions to this rule that the Quito farmers were favored there's a few of them fume for once but nothing we have to worry about now so the Quito form usually favored and equilibrium so when you're doing predicting products on me in terms too if you dwell on it in all it's going to be the wrong answer still were not welcome the isolating needles because they're not stable at such a time position might be said conversion of an e-mail to a key town by proclamation the carbon the double-blind of the oxygen atom bomb this torch harmonization can happen in an acid or base you do me a little bit of a catalyst here so that the 1 we see the mechanism we saw on the previous page was acid catalyzed factorization on the next page will receive base-catalyzed talked harmonization so there's 2 of them and you're going to need to know both of them and 51 C certainly Paraiso winning Allston reaction was making to deform the presence of trees evasive don't draw any England as a product this is not don't draw an e-mail as a product Paris edition of water to all kinds falls more ,comma cops rules so the on hydrogen adds to the carbon With the most number of hydrogen and that's certainly to get the more stable cover Catherine terminal kinds are less reacted and require use of an additional catalysts H S O 4 OK so this is an additional catalyst and fraternal all kinds you will want include that if you're doing this assess synthesis problem like this additional catalysts now there's a mechanism that goes along with that additional catalysts I'm not going to show you that you're not you're not required to know that so when I put this question on the to it will not be eternal O'Connell the internal OK I don't need to know that other mechanisms products always except when acetylene is hydrated so the only way that you can get Aldo hired With hydration is if you use a settling of Sept magical internal cranes will give a mixture of products there's nothing you can do about it so this will give 2 products so if you were if you want to make 1 of these 2 products he would probably do it a different way because these 2 products would be really difficult to separate from each other so that's something you have to keep in mind questions on hydration of an Alpine anybody let's talk about additional bromine and chlorine as you can see Americans spend too long on this Michael what equivalent of balancing you trans team if you did you had allergen you can get a drawn from a well came rather than and draw the products this just go through the mechanism here I'm a start with my alkaline here if you know the mechanism for Brohman Asian in Chapter tenders will be a very easy mechanism for you he Cervera comes from the I bond we attack Romine we break the bromine bromine born and 1 of the lone pairs on Brohm comes and attacks the other side so we make a bemoan this would be this was not abroad monuments of bromine on so likable anti-mine except we have a double bond tuna molecule same idea about this we have relied on command fact cited this is symmetrical so it can attack on either side I just attacked great here so there's a transcriber allow Keane which 1 equivalent and then have we not another equivalent of rolling and you could do that mechanism that's a Chapter 10 mechanism overlook just exactly like the mechanisms for Chapter 10 Morgan Micawber ammonia lie on the media backside attack and I'm not attempt to show an Easter chemistry here because there is no story chemistry here we don't have any stereo centers because writing bro means to each Carbonera no stereo centers so the product after 1 equivalent is that answer the product after 2 equivalences this really straightforward students tend to do really well on Elkins anytime I tested students tended to relate what are not stupid difficult all right where a man was tied operation and observations about clients like out Keane's kinds undergo right of racial tree with boring regions it's going to be the same idea yes yeah yes was change that Tony thank you will fix that right now thank you for calling an outfit to roam wild came yes OK I rights so the same concepts that we learned for hired operation in Chapter 10 Oregon also apply here there's 3 different but boring reagents that you will see in this chapter the THA war 9 B which I introduced to you in Chapter 10 9 BBN or there's another reagent tends to work really well without L clients and that's called dice ii more boys which is similar to 90 that it's more boldly than a typical it's more boldly than the 3 certainly so you tend to get better results so this 1 here is called dice I am more worried Soon addition right
just like in Chapter 10 so there's ah are a region Veron so that you notice is that the boron and the hydrogen both came in on the same side so this is a sin edition I'm symmetrical out the Alpine skier mixtures and better to use 90 and here definitely 9 BBN is much better 1st someone subtle differences in the groups on either side of the alkaline so here we have the hydrogen you get both of these if you use the H 3 if you use 90 the or dice I am more boring you also get your major 1 is the 2nd 1 so major on 90 Indiana or die same boring turn all kinds also undergo originally a strategic does not work very well for terminal crimes are not I'm choosing not to make an issue about it but you really fraternal all kinds you need to use die same no-brainer 92 billion so it's cross set out 9 BBN you still see answers that you still see problems on Smith and you will still see problems in settling over the use 90 years H Street and the problem with the H 3 is that it tends to add twice and that amended then that causes all sorts of problems in the product that you actually isolate right well I saw I'm drawn product that you get from moderation is really not super interested in those products In this class anyway so what we normally do as we oxidize he's right basic hydrogen peroxide so let's see what happens when we oxidized news on the next page now when we oxidize Our Heidemarie Cintron we've put on oxygen right under drops when the warrant was right the the same thing here the try that I know we that we look at that product what type of product is there it's an e-mail do we wanted tribunals and any answers and on a test now so yes we do for me you know and I want you to be able to recognize reality no I shouldn't so what this is going to do is as good a tall Tom rise so long nearer to the right short arrow to the left and when you talk to ,comma this where the hydroxyl is is going to become a curvilinear so this is good so that's what you get for the 1st example and 1 in official the mechanism works it's different than the acid catalyzed so that's also when you and again exactly where the hydroxyl is a double bomb goes away and they're hydroxyl student ,comma carbon you so for both of these this is base-catalyzed hot harmonization so where you want on the box is the key is the Conrail priority but see with that mechanism looks like so we knew I already showed the acid catalyzed that someone is guaranteed to be on the mid-term let's look at what the base catalyze look looks like I will just start with on a scene all right here and we're many do 1st is deep-rooted oxygen so I am doing something very different in base that I didn't ask In the acid catalyzed hot harmonization rehydrated the double want we added We appropriated the double 1 here were Deep Throat needing oxygen there's something reversible errors here because this is a reversible reaction and I drew resin structures in the year acid catalysts taught opposition and they do the same thing here in the base-catalyzed hurt harmonization so I know that this has is residents stabilize I can move these electrons here this goes all the way back to Chapter 1 so now incentive of errors ago both erections and the user residence 0 so that's how you get that double 1 there so now now in negative charge on Carbon II concede to get to that product we have here all we need to do is probably that carbon so base-catalyzed where Bernadette carbon with water that regenerates the base that we started West severe this really is only catalytic so let's put brackets around these 2 resident structure so exact same outcome just a little bit different mechanism because it's acid catalyzed verses base-catalyzed and I know some of you had trouble with that we get a pox I'd say about acid catalyzing base-catalyzed mechanisms are as extremely important 51 C so that's why I'm emphasizing now make it much easier for you next quarter so stepwise mechanism you don't wanna combined steps we talked about that I'm so don't do this me show you where were you when you what you don't want to do for this mechanism salt dried and then you gonna tell me what's wrong with that and just in case you don't read the don't do this when years studying will put a big exodus mechanism after we draw so there's Arenal we would touch on rice so I'm basically imminent which is gonna come to the same thing only I'm going to do it all in 1 step combined steps here so I grabbed this year following of these elections come over here and I wouldn't have the double the the pipeline coming Clavel hydrogen from water that would do my staying in step that back 1 I doing wrong what why would that be a very unlikely process here there's 3 species all coming together simultaneously With the right
orientation exact orientation and all of them colliding with enough energy to Rio to react the very very it's it's a rare events that we don't want we don't want presume that that's happening so I know we call this term molecular reactions no turn molecular reactions and so when you combine stepson a mechanism you generally speaking are doing term molecular reactions are having to make things happen at the same time so that means 3 molecules coming together simultaneously part so don't want us don't do that 1 suggests that president Menem resulting which along kind of disaster college hydrogen versus abrasive what was intended ,comma other once work on so remember where the oxygen knows that's where the Cardinals so moderation Nugent recorded calls and then hydration gives you mark on pop so it's really nice that we have these complementary procedures so sometimes we want 1 of these and sometimes you on the other we have to have have 2 ways to do this at our fingertips we can use for synthesis alright questions bodies so far we're going start at this point getting into more complicated since the since only give you 1 example here and then by the time we get to the end and Chapter 12 you're going to have much more ,comma complicated synthesis of this is the time to buy getting here and start practicing a lot of sense so you this is the time when you'll see at the end of the chapter once you do all the predicting the products there's a synthesis part where we have never reactions from multiple chapters that you wanna spend your time on and you want to try to solve those without looking at the others so implying a synthesis depending on what we're trying to plan but we might need to construct a carbon skeleton that's more than enough to do in this example while functional group in conversion were doing at this example or taking Elkind converted into a key Tong so that some functional group in the conversion we are going to have to control Regio ,comma straight so here's a really good example years previous example here that we we were controlling regional chemistry by choosing the correct reagent and on and on some examples were going to have to control stereo those are going to be coming up at the end of Chapter 12 so we gotta think about all of these things this particularly when we don't have any steering committee so don't really have to control this consistory consistory repair following compound from a satellite so looks enormously on complicating using Erector synthetic arrows going to really help us for this is a acetylene and I'm not a bother going in the forward direction I can see in the forward direction but and maybe you can too so in certainly do it that way but I'm just gonna work backwards from the park so I'm going to use my reticence sincerity a synthetic arrow that can be made from and I'm a work backwards so again let's label that retro synthetic arrow means can be made from and this is where the recognizing those functional groups we've really only talked about 2 ways to make a carbon deals so far so that makes this a little easier by the time you get to 51 sealed the 10 ways to make a copy and then as little more complicated because it's in our own little limited and this is the time to jump in and get lots of good practices so this 1 can be made from well if I had I only know 1 way to make a carbon you right now and that's from an alkaline so that I would have to do it from if I had this a or kindness would be H 2 of this I I want the carbon you on the most substituted side here so I would have to use hydration H 2 O H 2 SO 4 and because its terminal I need to add G S O 4 as a catalyst all right so I need to carbon pieces so I would have to take this down further so I know I can make theirs gosh if I had this right here from wide I could have chloride wide-eyed or tossed straight and if if I had been I could do a substitution reaction that's Chapter 7 just into reaction and then now I'm going to have always going back and looking at what I started with and I certainly can make this from acetylene try different meaning it right what base when I use for that and image or any NH 2 or you can write I don't care for an age to minus so I don't on on not particular about you including the counter if you write that in the synthesis that's totally fine with me OK so we've got a plan now it's right persistent the system the proper directions so when I agreed to ask this of this would be the kind that's the open ended kind and I don't crave Rachal synthetic and it's too hard to I can't see the way people are thinking it's so I only grade the read the synthesis and the 4 direction so there was an open-ended what I call open synthesis for I asked for products from each step it would look something like this definitely won a number of those 2 steps and appropriating and then adding propofol and then and in my last step here it would be an H 2 O H 2 SO 4 H G S O 4 so this is 3 steps the 3 substance synthesis for a on a test they might look like this if it's not an open-ended this 1 where you just feel and reagents I do have more of that type on the test just because he's of the kind much harder the great we gotta worry about these things when you have a lot of students alright so that I might have on like this and and so that would be then you would have to do the regions and you would number the individual steps step 1 in each other's choose any age step 2 troubled step 3 h tomorrow H 2 us of course SHE S O 4 there has to be age to arise not age 2 what would happen if I didn't number that what would happen if I mixed sodium hydride untroubled bromide H 2 to US authorities yes of course a very a potentially explosive reaction we've between the sodium hydride and their sulfuric acid or Sony my bread and water it's an extremely strong base and we knew what happens when you mix extremely strong faced with an extremely strong acid you cooling you just throw them together it it explodes I think it might not blow out a wall but it will blows compound all over you know that you you don't want all over you so that's why it's really critical that we number the step as we're doing them when they need to be numbers correct that is Chapter 11 start Chapter 12 now any questions while I'm calling a chapter
12 takes a little while to say this so what can I do anybody have questions far-right Chapter
12 pretty excited about this now here's the thing I like about Chapter 12 there's no mechanisms in
Chapter 12 I like mechanisms right they also have to learn what the reaction is actually doing so this is as close as you can accommodate organic chemistry to a chapter which is all memorization I know a lot of people think Coke was all memorization there really it's a summarization and this is all memorization I will show you up proximately what's happening in a couple different things but I will not ask you any mechanisms in Chapter 12 and the reason is the mechanisms are a lot more complicated more complicated than were ready for OK so that's where were coming from Syria summit oxidation reduction so 1st of all recognizing oxidation reduction organic compounds that I think this was in like Chapter 4 viruses 6 or something like that it was covered on my Minnesota you don't remember somebody covered again but you will see the exact notes found in 1 of those chapters if you look back and 51 alright so it's a little bit different in organic chemistry then general chemistry to recognize oxidation reduction here's the good news is everybody remember balancing a redox reactions we don't do that here at all the case so that was that brutal I know so let me give you energy can example we also are going to be excised signing oxidation Umarov assigning oxidation numbers at all we don't do that you can't I we had sex 1 time did that and believe none of the other ones have submitted we just you don't need it so we're not gonna cover so that copper shiny red metal reacting with silver plus copper loses 2 electrons right so as loses 2 electrons and transfers those electrons over the Silver of electrons are transferred completely from 1 species to the other so that we get it to the blue copper plus also could print cool color changes I like these things but this is getting gaining Christine's electrons OK so arm we know also that if 1 molecules oxidize and others reduce that from Cameroon a carry that forward and the electrons are transferring completely from 1 molecule to another that's what happens not like that in organic chemistry
so inorganic chemistry were not actually transferring electrons completely in war-wracked were changing the direction of the flow of electrons so oxidation is loss of electron density carbon loses electrons reforming bonds with elements that are more elected negative and it is so what we're going to see for oxidation is loss of a carbon hydrogen In gain of a carbon oxygen these both practice happen at the same time Bulls captain for oxidation and that's what we're going to look for was carbon hydrogen gated carbon-oxygen so what are we talking about electron density will follow Elektra negativity carbon is 2 . 5 hydrogen 2 . 2 carbon is 2 . 5 and rather than use oxygen their overdue generic here was just 2 X that's a little better Urban tax so on 2 . 5 4 carbon an X greater than 2 . 5 so what we're doing here is we're shifting electron density with a carbon hydrogen bond electron density is falling Towards the carbon because it's more like against what we replace hydrogen with an X it's flowing towards acts so we change the direction of the flow of electrons sofa here acts equals oxygen and nitrogen and halogen typically these are the ones that will be safe that means you have an oxidation and it's important we
will recognize if you're not seasonal reduction because if you if you have an oxidation then you'll know you have to use an oxidizing agent if you have a reduction in the latter only to use a reducing agent not that helps you figure out what they want the 4 use production is
the opposite the loss of they had Ch so as you can see here we have electrons flowing to act now Iowa changes of electrons are flowing to carbon and again here exit equals oxygen nitrogen halogen also say etc. because it could be anything for election so the police's stepwise oxidation of nothing most reduced form of carbon always up to Carbonado dioxide which is the most fun oxidised form of cottonseed can see what's happening here as we go from methane to methyl alcohol methanol we've lost a carbon hydrogen and we've gained a carbon oxygen so bold things have to take place so therefore it's an oxidation moving to the rights and oxidation and then we have we do that 1 more time we we break another carbon hydrogen -minus carbon hydrogen plus carbon-oxygen regain its 2nd carbon-oxygen by the because now we have double bond the carbon so that's also a oxidation an insane thing here we lose another carbon non-hydrogen engage in carbon carbon-oxygen because now we have 3 bonds corresponded to 3 oxygen so minus carbon hydrogen and plus carbon oxygen and then were also the Woodward were losing another carbon hydrogen gaining a carbon hydrogen carbon oxygen so that oxidation stepwise oxidation so for steps to go to from the most reduce for apartment to the most oxidized or if we went back the other way I'm not going to draw that here but it's the exact opposite if we go from here backwards over here we're losing a carbon oxygen and a carbon hydrogen and so that's reduction was just do 1 of those allotted to all of them everywhere at weakens making go the opposite direction step back going from here to here we come minus carbon oxygen plus carbon hydrogen therefore reduction all right so very helpful to be able to recognize so characterized I recognize oxygen reduction in the following examples here so what's tapping here we have 2 hydrogen there were replacing those with 2 carbon-oxygen trying so loss of 2 carbon hydrogen a gain of 2 carbon oxygen therefore oxidation definitely oxidation there let's look at the 2nd example here were losing her we're losing 2 walks aginst to carbon-oxygen there were gaining 2 carbon hydrogen therefore it's reduction so if you wanna do this reaction is any need to use a reducing agent In the 1st one of the game oxidizing agent to do that reaction so let's look at 1 here that's what we've already looked at this is an oxidation reduction reaction that's something that's not in this chapter so it's not it's something that we've already talked about it's an addition reaction right so we know that by looking at them that's sedition it's an addition reaction we know that from Chapter 10 and so let's look at what's happened here we game they are the ones carbon oxygen and we Jane 1 carbon hydrogen you have to gain model is the other so it's not it's needed oxidation nor reduction it's an addition questions on recognizing oxidation reduction and inviting so wanted no matter do that for a mid-term to
put energy reduction 1st and ran into oxidation and investigators school reactions and you're going to go home and make index cards for the there's 3 types of reducing agents there is not the 1st time for every ad H 2 plus a catalog that's called a catalytic hydrogenation Annual generally Cecil H 2 palladium platinum on nickel those would be the common catalysts that you would use for catalytic hydrogenation the 2nd type a reducing agent add to H falls into electrons we call these are dissolving metal reduction Britain talk about all of these and then the 3rd types were you had 1 H minus followed by 1 h plus and that is a metal hydride reduction so I can't emphasize enough the importance of the regions in this chapter you will use them over and over and over again when you're doing synthesis are right so that 2 minutes so let's talk preferring to talk about all
3 of these in the same order that the fearing right here so will 1st talk about catalytic hydrogenation I reject that hiding a cat
addition widens into all Keynes and we'll talk about edition of hydrogen to our clients so what you do doing a catalytic hydrogenation is you add the elements of hydrogen each on each side across the desert a double bond and I'm deliberately showing stereo chemistry here what type of edition is that when the 2 hydrogen is coming on the same side yes so this is a stereo selected see in addition so that means the hydrogen come in from the same side of the aisle came I need to know that piling extra Thurrock reaction but requires a catalyst because of the huge energy of activation the catalyst changes the nature the transition state thereby lowering energy of activation will talk more about that next time