Lecture 14: Electrophilic Addition Reactions of Alkynes

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Lecture 14: Electrophilic Addition Reactions of Alkynes
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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: 01:15 - Sample Flashcards 05:33 - Acidity and s Character 14:59 - Relative Acidities 16:32 - Some Reactions after Deprotonation 21:50 - Preparation of Alkynes 30:54 - Addition of Hydrogen Halides to Alkynes 41:59 - Addition of Water to Alkynes: Hydration
Substitutionsreaktion Complication (medicine) Hydroxyl Operon Alcohol Wursthülle Chemistry Sample (material) Halogenation Abbruchreaktion Library (computing) Chemical compound Area Flash evaporation Walking Rearrangement reaction Carbon (fiber) Chemical reaction Chemistry Alcohol Wine tasting descriptors Ice Transformation <Genetik> Pyridine Screening (medicine)
Chain (unit) Nitrogen fixation Asset Electronegativity Kohlenstoff-14 Chemistry Acid Food additive Electronic cigarette Chemical reaction Lone pair Acid Electron Atomic orbital Abbruchreaktion Kernproteine Marl Kernproteine Polymer Electron Base (chemistry) Conjugated system Base (chemistry) Nucleolus
Biosynthesis Surface finishing Electronegativity Wursthülle Acid Chemical reaction Atomic orbital Lone pair Ageing Electron Cupcake Kernproteine Conjugated system Base (chemistry) Alkyne Carbon (fiber) Kohlenstoff-14 Chemical reaction Chemistry Acid Gesundheitsstörung Atomic orbital Proton-pump inhibitor Kernproteine Electron Barrel (unit) Base (chemistry) Satellite DNA Ammonia
Species Alkyne Asset Angular mil Chemical reaction Acid Chemistry Electronic cigarette Hydroxide Acid Ageing Abbruchreaktion Proton-pump inhibitor Explosion Base (chemistry) Conjugated system Base (chemistry) Ammonia
Epichlorohydrin Chain (unit) Alcohol Radioactive decay Chemical reaction Molecule Alkalinity Halogenation Data conversion Elimination reaction Waterfall Base (chemistry) Waterfall Halide Chemical element Vimentin Ene reaction Walking Chemical reaction Alcohol Hydroxide Electronic cigarette Lone pair Germinal center Acid Gasoline Hydroxybuttersäure <gamma-> Molecule Cobaltoxide Methanol Ionenbindung Bromine Reaction mechanism Substitutionsreaktion Mill (grinding) Wursthülle Columbia Records Ammonium Reactive oxygen species Sodium hydroxide Ageing Abbruchreaktion Human body temperature International Nonproprietary Name Conjugated system Mineral Process (computing) Bromide Alkyne Carbon (fiber) Chemistry Alkene Hydrogen Sodium Imperial Chemical Industries PLC Deferoxamine Functional group Iron Can (band) Data conversion Methane Base (chemistry) Satellite DNA Basenpaarung Ammonia
Epichlorohydrin Asymmetric induction Lebensmittelfarbstoff Resonance (chemistry) Transport Chemistry Chemical reaction Alkene Molecule Wine tasting descriptors Electron Halogenation Addition reaction Vitalism Halide Reaction mechanism Filler (materials) Öl Doppelbindung Induktiver Effekt Crystal twinning Walking Vinylverbindungen Chemical reaction Food additive Acid Addition reaction Ionenbindung Bromine Reaction mechanism Elixir Columbia Records Hydrogen Abbruchreaktion Controller (control theory) Aage Mortality rate Iron Argininosuccinate lyase Alkyne Deposition (phase transition) Carbon (fiber) Chemistry CHARGE syndrome Alkene Hydrogen Gesundheitsstörung Amine Covalent bond Hashish Data conversion Electron Halogen Atom RWE Dea AG
Ionenbindung Species Reaction mechanism Vinylverbindungen Complication (medicine) Wursthülle Chemical reaction Sample (material) Water Halogenation Addition reaction Colourant Mortality rate Process (computing) Area Reaction mechanism Octane rating Mineral hydration Alkyne Vinylverbindungen Carbon (fiber) Katalase Chemical reaction Chemistry Electronic cigarette Carboniumion Hydrate Hydrogen Addition reaction Functional group Halogen
Nitrogen fixation Reaction mechanism Ketone Sunscreen Resonance (chemistry) Hydroxyl Hydro Tasmania Acid Columbia Records Ageing Electron Water Schweflige Säure Periodate Grading (tumors) Reaction mechanism Induktiver Effekt Mineral hydration Alkyne Walking Hydrogen bond Carbon (fiber) Adamantane Chemistry Hydrogen Addition reaction Resin Chemical structure Cobaltoxide
reactant area .period I I'm a share of the a sample flashcards that I put on mines you really want to start doing flash cards because we're going to be having a lot of new all embody started his appointed new reactions there is going to be some there's a point in Chapter 10 appointed Chapter 11 very similar results and then I'm about to new reactions in Chapter 12 there were reasons that this is a lot and then it just keeps going it's and it's a major reaction of course here so it helps to keep them all straight ahead of anybody have questions before we get started was so let's say you want talking about here for flash cards so this is under the practice link I was not screen there we go OK so I depending on how many ways there is to do something you might wanna use a small class size harder a big flash cards some people like to to put up with this on the talk here on 1 side of the flash card and ways to do it on the bottom sometimes there's only 1 way to do it in this case there's more than 1 way to do it so we knew we get used to thinking about and a half hour ago from alcohol to use something that has the same carbon skeleton but now the alcohol the good leaving to talked about a bunch of ways to do that Chapter 6 so I've listed all the ways here and there over here and notes about it OK no tertiary no tertiary careful with secondary alcohols rearrangements reservations so that you just have that right at your fingertips and you're ready to go on because these reactions are going to be using all year where accent that way .period now halfway through OK and so for the rest of the year broken I'm using example here where we're at you have a terminal Al keen and you're converting it into you you doing and Timor ,comma edition of HBO are so but we don't now that we have to do in 2 steps right now In Chapter 15 regular one-step way to do that so right now here in year of ice have this on you have to do hide operation a case in which the sea and democratic of edition of an Watan 19 years preparing or you could do it here it's a it's completely up to you this is a reaction were not aware until Chapter 15 so these are just some ideas for you and and that's looking pretty complicated on this 1 OK so what we're doing is if you if you take undertake this apart now we start off with the sulking and work for me in April hydrant right so you want to be able to recognize OK this is a worldwide bromine 1 carbon adjacent to it I have a hydroxyl and they are in to each other and so then your brain goes and says OK I know how to do that I can do that with them I could do that and there's 2 ways actually do this to give different radio ,comma this will actually help you when you're doing a sapling which is due tonight right this will help you news flash card will help you just a little too there OK let's let them but let's look at this the Ethel Is this is a is some transforming not the Azul is transformed the knuckle here so that we maintain the same stereo chemistry for the sulky and now we just have a brawl will heighten here if you want to this radio chemistry with the bromine here the borrowing would be if you did is you brought me water would be this chemistry it's the wrong 1 that doesn't match that of if you want this exact radio chemistry here where the bombings on the most substituted side you have to do it this way he would have never thought of as right you make you do that you make a promo Hyder and unity program you make an epoxy side and then you had HP argued that the opposite really geochemistry every may see that hydroxyl Onley substitute inside hydroxyl on the most substituted side so that would be a more complicated ones but that's it's helpful to be able to have that your fingertips this is something really talking about in this chapter al-qaeda you the tell this is the Marconnet half product and this is the way to do also that talk about a way to do that in time ,comma got so you're gonna start accumulating needs and you'll be really happy you did when you get into 51 seekers you'll have already for you and right before the test you just get a rifle through these parts that made so good investment of the time it's really going to help you questions on flashcards anybody Mikhail
disclosed that far-right someone really lost last time we're talking about which we talked about the fact that if you have a terminal outlined where the outline is at the end of a long chains or short chain but then that Proton is acidic and we're reminding ourselves wide that is acidic they were talking about the long care here the lone pairs in and ask P orbital therefore electrons are closer to the nucleus when the electrons are closer to the nucleus that nuclear is that stabilizes the conjugate base it's a more stable base it's as if commented that is sp highrises more elected negative we know of event ever the negative charges on a more electromagnet added pulls living closer and stabilizers and that's exactly what's happening here therefore conjugate assets is more stable Is that right conjugate is more stable while fix that conjugate base is more stable Marty wrote that means that could of have let's fix that goodness that's not what I want say at all therefore if they give you a more stable conjugate base was that say the acid conjugate acid is more acidic much of it as saying it is
said alright so and and this is just a little down here this is just comparing as to 3
as as the orbital looks like when we hybridize the orbitals they take on the character of what we're using the hybridized so if we combine 1 s and 3 peas it's gonna look more like a P then but as we have less pleased we have less and is looking less like a P and more like a possible only here we just a high rising innocently I remember an ass or evolve electrons are very close to the nucleus In a P orbital electrons are further from a nucleus and so that's all we're doing here is hybridizing means so this is Remember when and ArcelorMittal looks like that's an ass and this is a P appear electrons are further from the nucleus so when you combine only cake on the flavor of what you used to combine them and so as you can see L & St Aubyn also the the barrels are closer to the nucleus the stairs shorter Earth's water wider and looks just takes on the character of more and as character here compared to S P 3 and so that's what we're talking about so because of the fact that this Proton is the same not super but we can actually use reasonable basis to nature and all kinds and done so we want to make sure we take our base is very very carefully here I'll thirsty bases that we're going to use only 2 To do this and that's an age to minus 4 H minus all laying basis to use on and let you pick which 1 you like to use and synthesis but both of those cases at bases will work what some look at any any to this anyway to is usually done in we'll see in liquid ammonia this would be the solvent so ammonia is normally a gas if you call it down to minus 30 it's a liquid so we have any any age 2 and liquid ammonia if you're using this as a reactant I don't you don't need to write the liquid ammonia just showing you the common conditions for doing this and so basically what we have is on an age 2 -minus very strong base it's going to grab that citic Proton we're gonna push electrons onto carbon let's draw finish this ah acid-base equilibrium here we had the conjugate base the satellite ion and we get ammonia and we're trying to find out that the army which way and acid-base reaction is favored we look for conjugate acid
base there's a conjugate acid-base base the 1 that has the extra Proton is the acid we have another conjugate acid based here Harris here at any age to minus in each story this is the acid and if you do this correctly you should have 1 acid
on each side of the equation you look at the
PKS 3rd terminal all kind thinking is about 25 that's 1 of the 8 PKK is you need to know rounded to the nearest 5 so that's about 25 and ammonia is also should be on their own and has a PGA of about 35 every remember equilibrium is favorite in a way that we go from I'm stronger acid to weaker asset equilibrium always favors more stable species this species right here is more stable because it's a weaker Rossi announcer means this is more stable than best so Sowerby both of these products are more stable so reaction favored to the right I and just a little check to see if you are using this as a base we want to make sure we pretty much essentially complete with the approach made it and so we we do is we take a difference in Sears there's a difference in the of its hands so add equilibrium we have no 1 to turn to the 10 reactants to products so although in equilibrium were always going back and forth between report we say this is essentially to completion end are excellent music that's and we're going to be a really good basis for us to use the news definitely don't want a user hydroxide on Ireland to do this the probation was seen by that'll work where did the same
thing we don't respect now reduce hydroxide as a base so there's a satellite ions conjugate acid for hydroxide is water we're going to look at our conjugate acid base pairs here psychedelic previous page there's a conjugate acid-base pair this 1 has the extra Proton that's the acid were going to look at this conjugate acid base pair this 1 has the extra Proton that's the acid we should have won acid on each side of the equation and we look at the PGA's this is approximately you 25 and this is PKA approximately 15 so these are ball that makes this job really easy because we deserve some of the ones we needed know rounded to the nearest town 5 and so what we can see here is that the reaction is actually favored to the left strongly favor to the left so add equilibrium the the difference in the game is about 10 we have attended the 10 to 1 reactants for every product sold hydroxide Ireland is only going to be promptly 1 molecule Adam attended the 10th it's not a strong enough case to use that's why you don't want hydroxide for this are relatives cities and this is where we the relatives the city is cities kicking in in this chapter so I had my students last year a last quarter memorize these decays rounded to the nearest 5 and will need to do that also so I will be testy on this so we have 0 for and where these all have in common we have oxygen with 3 bombs alone .period positive charge there and 1 of those bonds as a hydrogen that's very sick very acidic very acidic very acidic and these Rangers ranged from minus 1 . 7 2 a high drawing line and somebody's alike minus 6 miners 5 minus 7 something like that so I I just want you to know their lesson 0 which is going to have all those in the same category that we have a CD gasoline about 5 we have frozen Aidid that means so ammonium ions OK those are all 10 their we have alcohol and water 15 we have 25 for a terminal Alpine and we have 35 for enemy that's not appropriate don't get these 2 mixed up these appropriated means with a positive charge these or not and that we have 45 in and then the last of course is the other just straight out canes with no functional so need to know that question so far anybody the OK the airline drive from diverse nation is a good new good value saw this nuclear fallback in Chapter 7 you might not remember but you saw back in Chapter 7 and so again solvent is optional here this is the solvent and I don't want you to get thrown off by that liquid ammonia and then we just appropriate that we make the a satellite and then the satellite or ion here leave out the sodium is a spectator and so we have this carbon here indeed backside attack kick believing that this is a Chapter 7 reactions just another example of the things you learning learned 51 a coming back to you so that's pretty much how we're going to make a terminal alkaline into an internal alkaline by doing a substitution reaction the other thing we can do with this that you saw at the end of Chapter 9 but maybe didn't notice too much you can also these also can attack apart science it's a strong nuclear fallout strongly nucleophile therefore attack at least substituted we only get 1 we only get substitution the most substituted side when it's acid catalyzed of please don't be thrown off by this high drawing on their think don't think all ICI drawing a line on this is an acid catalyze reactions it's not that the separate step entirely we start off with this that's gonna react and 2nd 2nd step we program 8 so this is going to open up the visa detective parts and substituted side we break the carbon-oxygen bond the acid is not present in that 1st step and so we don't 1 included in the 1st step I didn't write you that it was stopped that you wish you could get your paycheck and so a change now I really shouldn't then the spot but I don't have room here and I'm not know I'm not going to worry about that because I can but it should look like this all minus but we have the young are going back there's a hydrogen it's coming forward so it looks like that and then we in and we add acid in a 2nd step see nothing did that with the overhead would have blue all over my hands and I'm younger like this and I don't realize enduring blew all over my face and all that so this is better from that perspective anyway I write so 1 thing we want to be careful about we were using a satellite Ohio on the satellite iron is the conjugate base of eternal kinds it's a great good fall but it's also a very strong base very very strong so this will work with primary or methyl alcohol he lied or toss a will not work with secondary reaction was secondary uncle hillsides will give each year rather than innocent too OK so let's see what this looks like a specified hydrogen honest cop in there it's also executive happened as I hear rather than doing substitution it's such a strong base wants to act as a base expanded were eliminated made hydrogen off rally so major product you he 2 . a careful it's a really really strong base the case 25 of its kind in Aceh so that means it's a really strong base so substitution doesn't really stand a chance there Our
was talk about preparation and all kinds this is a review reaction when did you learn this that's put the outlines like just now right to Chapter 8 billion this quarter traffic is so what we do is we have a bizonal died lied To equivalence any to how we get our time I wouldn't tell you a little bit more about this reaction now that I didn't tell you the and Chapter 8 almost let's just go through this so let's go through the mechanism even our show this to you already forgone eliminate hydrogen that is on-site of bromine 1 of the following it's here an earlier 1 were roaming to eliminate so that 1st elimination games those relatively easily the 2nd elimination is harder to do because were breaking a N S P 2 carbon hydrogen bomb that's going to require more energy that is a stronger so this is really where we need the very strong base here so don't try to do this with hydroxide I can tell you right I can tell you 1st that it doesn't work out we used to in my class when I when I inherited the honors in the majors of and land there was an experiment where we had this all bromide and we we use solid elements of sodium hydroxide we added that this will die here like me he needed up to 250 degrees so not very favorable and that's why it to heated up so high In honestly it turned to talk did not work at all so you want use a stronger basis so that we had the reaction can happen at reasonable temperatures and just didn't we we got maybe 1 per cent of the product so it's just not a very good reaction OK so there's are out there is a outline careful you're making a turn kind unique 3 equivalent so this is the new thing that I didn't tell you before why as soon as the terminal outline is formed it will be deeper needed by the strongly basic and its to minus acid-base reactions are faster than the 2 reactions so on let me show you what I mean here this is super fast iii if you don't use 3 problems you will run out a base will get incomplete conversion Serena came out to minors molecules readers mechanism 1 more time sewage funding the last and renewed his wartime and their accounts any age too so we're already done these 2 steps was due again the only difference here is that this 1 we have on 2 hydrogen is on the carbon on the right so we are going to be making a terminal crime where the Klein is at the end of the year ,comma chain cancel student will time 2nd elimination notice some throwing lone pairs on not leaving group wanted to that let's see what we get now terminal alkaline in the presence of any age to minors that's an acidic Proton right so you can stop this next step from happening as soon as that term alkaline is formed it's going to be departmental by an age to we just prove that that reaction is very very very highly favorable and acid-base reactions are very fast so that's what you get when you're done with the reaction and so in a 2nd stab you need to do 2nd step you need to add water or acid and we will sometimes call this when we do this as city worker that's common terminology so that means we have to new acid in the 2nd step in order to get our terminal so encounter an each choose theirs and there's number 1 there's number 2 there's number 3 so I get a lot of students to say and I know your customer you're thinking as well like and I just stop right here than I would have to have a 2nd step of acid the reason you can't stop right there is because this is so fast this reaction is so fast that the only way that you could do this reaction enviable the start here and some of you I know some of you think this is the way it happens because it happens so sometimes reactions happen so fast we think that every molecule was reacting simultaneously remember when we do reactions the molecules after colliding have declined orientation and after colliding with enough energy to react so not all of them are molecules interact simultaneously so the only way that we could stop right here is if we line up all these molecules and said OK I market said do step 1 then they start wait for you and then you say OK now do step 2 then and then there would be none of this laughter and then so this happened this step would happen if you just used to acknowledge that we know that molecules don't react that so some of this is going to be formed before another molecule this even gets steeper the eliminated and until we do an elimination so we have to do excess acid so there is a sapling problem that there's a separate problem in the opening up this the sapling on assignment today is a separate problem it deals with that so make sure you keep track of the number of candidates to minus molecules that you have questions anybody on this it's too bad we can't tell the molecules what to do like that that would make on my undergrad students and it would be a lot happier every Molik every reaction would work like it was supposed to alright so if you add if you're making internal kind you must add a final
nations that this small dying elixir made from Elkins and brought Nickerson of NLP into an Alpine therefore involves 2 steps or if it's terminal 3 steps so this is what it looks like step 1 2 that's Chapter 10 step 2 when a and H 2 To equivalents that's Chapter 9 which after 8 as chapter 8 if it's a terminal outlining 3 steps step 1 will mean step 2 3 equivalents of a any N H 2 step 3 um acid H 3 plus or water I would take water also OK so that's how we make a alkaline from milking questions the British From right so let's talk about collector filler condition reactions about clients and use the part of this chapter where it's going to be really easy for you if you know Chapter 10 because of the same reactions it's doing the same exact thing there's a little bit different but not very much OK so what's to HBR 1st if we have an kind we had 1 equivalent of HP or that means we may we had 1 bromine HBR molecules crossed the Elcano we get 1 only if we had a 2nd equivalent of HP are we get to means so we get edition of 2 molecules of HBR across the double 1 OK here's the mechanism again you know it's the artist's assistance has a slight difference to it but if you know it's beyond mechanism this is going to be easy for you so possible mechanism for until more chronicle of additional hydrogen knows only substituted sidecar ,comma counting those on the most substituted side work on accommodation this is a vinyl cattle I will talk about stability of wildcat I'm in just a minute here From comes in attacks occur because a vinyl can iron or you can call it vital cargo category so the positive charges on the carbon it's part of an it's an S P 2 carbon is part of a carbon-carbon double bonds and Oregon and Indiana this is our 2nd quarter so this reaction were in charge we can dictate how much HBO want want to add unlike the previous 1 where we really didn't couldn't control all right and it turns out that the 2nd
edition is also work on accommodation the son of a deposit charge under more substituted carbon hydrogen going on the lease substituted carbon right and might not be obvious why that's a more stable cover recounting his we have read basically we have a bromine its electoral withdrawing think about this we have 2 things going on here we have an inductive effect from electron withdrawing that's gonna pull electron density away making their carbon and more or less positive more positive and more positive means less stable but we we have so we have an electron drying effect inductive effect but we also want pairs of bromine leaking in and make a double bond there 2 former residents stabilized cargo carrier and that's actually the more important thing here so we can prove we can push electrons in here and we can draw resonance structure where carbon bromine bonds bromine has a positive charge snobbery the fuck that but we knew the more important thing is that in this 2nd resonance structure all items have an architect and we have an extra covalent bond so that's really important here that's more important than where the positive charges so so the choose the 2 key things here are our own we have an inductive effect bromine it is an oil is electron withdrawing this destabilizes destabilizes the Carbol Colorado but can stabilize by residents and when we have opposing things happening with an inductive affected residents suspects the residents effects 99 per cent of the tire 1 portent OK so that it can stabilize by residents and so let's write that down what I just said is when that when these 2 things conflict so when inducted and residents effects conflict residents usually rents right and in the last step withdraw the last step here I'm going to draw I'm going to redraw this cargo Catherine because otherwise if I don't regret at the errors are going to get confusing so I'm going to redraw this what happens in the last step is exactly what we would expect that the bromine comes in and Texaco so this is the last step so there's Jerry chemistry to worry about here we don't have any stereo centers sonar control on worry about it problem left as it is bonded to 2 bromine ,comma the right boarded 3 hydrogen so we definitely don't have anything that we have to worry about with respect to Sterry chemistry here questions on that mechanism anybody some of you might have noticed well With so much money about stability of a vinyl copy if you looked at the Comic-Con instability on hand out here a little bit worried about this you know it we said we can make a primary and a vinyl Catalan is less stable than primary so there is some at some doubt about whether by accounting is actually Foreign Ministry action and there's 3 reasons why number 1 vital cannons are very unstable number 2 trams products usually predominates we were really get the transport product there's no trans product in the final product
that if we did 1 equivalents we tend to get so if this was an odd group here we would get this strands so that's something that's kind suggesting that it's not really a cargo Carrington's ,comma can gets this and entranced products and at the end if you measure the rate while the rate of gives its ideas about how reactions actually taking place more than 1 halogen appears in the right OK so this is a mechanism where the it's true mechanism on 19 I'm not giving you the true mechanism in case so I and this is the true mechanism is a lot more complicated than this this is the mechanism going learn but the reality is is that the true mechanism is more complex To mechanism it is more complex so you can imagine if I if I ask you to come up with a mechanism where it had more than 1 halogen and the rate while you might have trouble doing so that that tells you it's something that's Super Comp complicated and so this is just to remind you about cobbled Kanye instability here we have tertiary here we have secondary this is a secondary alike and secondary minor-leaguers approximately the same as primary these guys are about the same but here here is a primary vying elect where dictate where the car kinds only bond to 1 other carbon and that's about the same as mouthful so these guys are about the same so we really do we really have no business trying vinyl cat lines and mechanism doing what is been kind of overlooked that words and it we would like that so much related to again on the next page so we're just going to kind of thing 1 really areas in some sort of a bridging species bridging hydrogen speed I'm not going to go into it but it's there is and there is an explanation for it it's just too complicated for this plaque alright let's talk about additional water and all kinds hydration I don't do this very
often I do this twice the whole entire year where I tell you something will absolutely beyond the test and I will tell you this mechanism will be on the test OK don't do that very often it's an important mechanism why do I have this guarantee on the test because I really like this mechanism no it's because it's been a very much help to prepare you for 51 and my job is to release you in 251 have you do well because you have a good strong foundations so that's my that's my job so I'm going to do here is we're going to form a this was not 1 of the ones that was on the sample flashcards assure you but we definitely want a seven-hour and I wanted to break colors was I'm sure mechanism will be on test what's what and when the dangers to when there we
go a mechanism will be on tests so let's go through the mechanism was getting a mechanism and analysts that Adam how many points this will be on the 1st test and then sends everybody knows it will be honored there there will be nobody with the score less than this right I wish OK I wish 1 of these days so yet you know certain things don't happen like I've been teaching for 20 years and no 1 ever has gotten 0 on my exam except for 1 time last year something that unique and so it is never have so so these things can happen they're just not there very uncommon so debt relief it's a multiple-choice don't ever leave it empty right because you can probably certainly gets an answer are right does the 1st step look familiar to you this is like an outfielder permitting an OK alright so we're going to make a vital Catalan again and I have something at some symmetrical so it doesn't really matter which sided with the Catalonian ornament the hydrogen on 1 side it would put the kettle and on the other so so far it's looking just exactly like the mechanism we just did by the way my daughter and of becoming an English major and I can I can assure OK so waters been attacked a car began I know that you couldn't even predicted that right so far it's looking and I wanted to hear is omitted due to go back and do reversible errors here now I get a lot of questions on all do I have to remember to be reversible error was a on a test and I say no the only thing I grade when I'm creating a mechanism is the curvy heroes not the reversible errors but on destroying them here to show you that each of these steps is reversible alright so what we did was we aren't we put the positive charge on the wall doesn't matter here this is we have it it doesn't really matter which side they pose on a plane and so then we have what we have so so far this is looking just like what happens with the Al-Qaeda so what we need to do next you probably do we need to procreate that oxygen right this was oxygen OK we're going to do it now we're going out with an appropriate 1 more time OK so just like we do with HBO are inappropriate 1 more time so that had drawn a line over here by the way and everybody CY amusing Hydro New Line on it makes it a little easier number 1 and number 2 if we take ages to also for catalytic and we put it in the water it's going to completely dissociate anyway so it's a little easier to draw high drawing line events to draw sulfuric acid but if you are to be if you like to draw sulfuric acid you certainly can you would get on full credit here so really do this 1 more time From probably 1 more time and just like with the HBO are we're going to put the hydrogen on the same carbon we put the 1st hydrogen serving of Aqaba Caroline I think that in the wrong spot protect fix that given away cheers and I would have had to cover carrying on that same carpet so just like we did with HBO assists some parties are really similar and we have the same situation here where we have inductive effect this hydroxyl pulls electrons away from the car destabilizing abide by resonance we can kick electrons and I'm stabilizing and that's going to be the more important factor and so I'm going to draw the resin structure here and then you can see how very close we are to join the product once we draw this resonant structure so on the test when I ask you this question I I I also want you draw the resin structure I'm just going to do CH 2 CH 3 because that's what this is right here think that a little easier residents stabilize Carver Catherine's we have on oxygen we have a long period and we have a positive charge you can and then some everybody's 0 1 step away i've we just approach made the 2nd residence structures structure that we draw we will have our product so this is good at dancing a you break the oxygen hydrogen bond hearing uniform for of product so it looks like the 1 that is final going to stop right there we will finish this next time is not done yet