Lecture 9: Reactions of Epoxides

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Lecture 9: Reactions of Epoxides
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This is the second quarter of the organic chemistry series. Topics covered include: Fundamental concepts relating to carbon compounds with emphasis on structural theory and the nature of chemical bonding, stereochemistry, reaction mechanisms, and spectroscopic, physical, and chemical properties of the principal classes of carbon compounds. Index of Topics: 00:50 - Converting Alcohols into Sulfonate Esters 07:27 - Substitution Reactions of Ethers 19:07 - Reactions of Epoxides: Acid-Catalyzed Ring Opening 47:58 - Nucleophilic Ring Opening
Cyanide Alcohol Whitewater Bromide Digoxigenin Cell growth Gas Structural steel Surface finishing Hydroxyl Chemical reaction Man page Grade retention Electronic cigarette Sodium Acid Computer animation Halogenation Functional group Common land Chemical structure Conjugated system Calculus (medicine) Process (computing)
Alcohol Weakness Reaction mechanism Substitutionsreaktion Wursthülle Solvent Ageing Lactitol Addition reaction Elimination reaction Conjugated system Bromide Gas Hybridisierung <Chemie> Chemical reaction Water Iodide Acid Drop (liquid) Computer animation Functional group Chemical compound Base (chemistry) Stuffing Hydrocarbon
Alcohol Iodide Acid Computer animation Dimethylether Gas Thermoforming Ether Methylgruppe
Lone pair Alcohol Hydrogen Iodide Computer animation Halogenation Reaction mechanism Iodwasserstoff Walking Cobaltoxide Organische Verbindungen
Alcohol Ionenbindung Reaction mechanism Copper Hydrochloric acid Wursthülle Methylgruppe Ethanol Singer Corporation Process (computing) Bromwasserstoffsäure Gas Vinylverbindungen Rearrangement reaction Carbon (fiber) Katalase Chemical reaction Food additive Water Mill (grinding) Acid Iodide Gesundheitsstörung Computer animation Functional group Substrat <Chemie> Cobaltoxide Biomolecular structure
Setzen <Verfahrenstechnik> Epoxidharz Computer animation Reaction mechanism Bromwasserstoffsäure Rearrangement reaction Active site Hydrochloric acid Chemical reaction Chemistry
Metal Setzen <Verfahrenstechnik> Alcohol Reaction mechanism Bromide Weakness Walking Gezeitenküste Carbon (fiber) Chemical reaction Wursthülle Methylgruppe Water Hydrogen Acid Drop (liquid) Computer animation Functional group Cobaltoxide Base (chemistry) Sea level Conjugated system
Water Alcohol Acid Computer animation Tidal race Initiation (chemistry) Reaction mechanism Elektrolytische Dissoziation Schweflige Säure Chemical reaction Thermoforming
Übergangszustand Ethylgruppe Sense District Ionenbindung Left-wing politics Bearing (mechanical) Reaction mechanism Resonance (chemistry) Substitutionsreaktion Economic sector Containment building Copper Wursthülle Methylgruppe Diet food Romanian language Electron Film grain Active site Bromide Death by burning Walking Carbon (fiber) Katalase Ice front Hybridisierung <Chemie> Chemical reaction Kupplungsreaktion Water Connective tissue Computer animation Radical (chemistry) Functional group Resin Chemical structure Mixing (process engineering) Cobaltoxide Stereoselectivity Biomolecular structure
Metal Ionenbindung Phase (waves) Bromide Reaction mechanism Octane rating Growth medium Walking Carbon (fiber) Hybridisierung <Chemie> Methylgruppe Chemistry Hydrogen Computer animation Isomer Chemical structure Active site Cobaltoxide
Metal Reaction mechanism Octane rating Walking Hybridisierung <Chemie> Spawn (biology) Chemical reaction CHARGE syndrome Propionaldehyd Sample (material) Lone pair Hydrogen Acid Gesundheitsstörung Computer animation Ageing Resin Schweflige Säure Chemical structure Cobaltoxide Base (chemistry) Conjugated system Methanol
I believe will never do that to that I did finish Chapter 9 today's yes are examined in the on chapter 8 and 9 finish Chapter 9 lobby asking for less questions today so if you have questions you can come and ask me after class I really need to finish after 9 otherwise we're digging a really deep hole ourselves when it comes to the end of the the 1st in the class so and so that's I wanted you to know they were going to get started and everybody knows have of midterm on Friday yes are so we elect our last time talking about making tosser lakes in order to turn an alcohol into the living room once you make a tosser late and you can reacted with any of them the also talked about in Chapter 7 so examples of common files would be and 3 minor cyanide I need a reminder they just might direct so wise is often a young man I such a good leaving group of them I believe this army bases right good reading groups on the basis of the PGA of the conjugate arson was the conjugate acid tossing gasses TSO we talked about that at the beginning of this chapter but is minus 2 . 8 not so we it's a good leading group and 1 of the reasons why it's a good living group it is it is highly residents stabilized so I have all the residents structures are drawn here and I'm so its residents stabilized and we also have a negative charge the localized over 3 Adams so and we can make its hot-selling can trading with any of the new growth also we talked about in Chapter 7 of the other thing we can do is we use it treated treated with 1 of halogen and other energy and we can make a calculator like that way in a two-step process so this is what it would look like I'm going just drive some five-member drain on its side and that's looking really ugly there but you get the idea OK and so and wherever we make a tosser late we have retention of configuration so we have our hydroxyl that means are tussling is up so we went right of tussle 0 tasks to abbreviate that and then what we do and the sodium bromide that's going to be and has sent you therefore in Virginia and when we do that we get overall inversion of configuration so we can make outfield here realize this Swabia tossing plates just another another reaction to put in our arsenal here reactions were going to actually start cataloging reactions in Chapter 10 were not going to do it yet but we will need to do it started in Chapter 10 will talk about that when the time comes are excellent summarize alcohols can be converted
eligibility age furiously CLA died of heart purity .period 3 carried in addition alcohol can be converted into a tosser late treated with pro-life writer iodide to converted into an out here have a lot of different methods here and of these methods are complementary so it's important that we have more than 1 once you have toss lightly to do all of the substitution elimination actions seen in Chapter 7 and 8 so we really are minutes the alliance we can actually have postulates we can do eliminations from chapter in Hindu on substitutions from on Chapter 7 here's what you can do a lot of people trying do on tests which will not work on
a lot of people say Well what don't I have to memorize all these ways of converting enough alcohol into a here lighter toss 1 and I just treated with acid from alcohol make a good living room I'm so this is what some people try to do come on down and number and a drop what you're thinking and they were gonna say why that doesn't work so if you're feeling very clever about this idea and I don't have to memorize all the stuff I could just use this and so when drove up the product it seems reasonable this would be the idea here and other that actually doesn't work so we're going to put the X 3 during this year case this is what's going to happen instead here's our and 3 minors it's going to the so what you end up getting instead is your alcohol back again groups didn't want that and then agent 3 hybrids or gasses that Switzerland again so why doesn't that work wonders does that work with BHP are the reason that that works with HBO artist because I when you probably the alcohol at HP are you left with bromide ion which is an extremely weak base and so and it's also a really good nucleophile so the brawl comes in and does backside attacking kicks off water and 3 minus is not an extremely weak base PKB conjugate asses 4 . 3 so it's just too strong base to do what we wanted to do which is substitution when the fastest of all reactions after action and so that's why that doesn't work so make sure you don't try this strategy is also sapling problem that asked the same question on and so take take notice that I put them on test before because it's a really ,comma misstated students make are sold the last thing we talk about in this chapter is heaters wouldn't talk about regular readers and wouldn't talk about Parkside so the still mechanisms for part signficant potentially beyond the testing might typically ask to hold them there is an acid catalyzed reaction in basic catalyzing a typically asked both of them because those reactions that prepare you well for reactions are coming up so that's why I do that right so 8 was like hydrocarbons remarkably in the 2 most chemical reactions this is why they make such good solvents here's some common solvents you've probably used diaper weaker lab already haven't you yes on tend to hide Ferran another 1 will see a lot of Chapter 10 talented writer program not as frequently and once for dialog saying you might have heard of that we're not going to use that too much we most serious diaper leader of the things that we like like about solvent is we don't want the solvent to react with our compound so these are really very very stable compounds
eaters are however lead when he with hot
concentrated HIV or aged he already these are the only ones that I'm going to use and I'm so let me give you an example here and if we take this Easter champion along 1 side interviewed on methyl ether and we treated with at a time when equivalent of gasses so what I say 1 of the morning a one-to-one ratio between a child and the ether and if we do that we get to products weekly the ether we break it into 2 pieces we get if we use of HIV get out an iodide and alcohol if we continue to reacted if we had a 70 second equivalent of patriotic acid from this alcohol that we just made is converted into a methyl iodide the original the 1st form part of the state exactly the same so we'll still get this
but the alcohol will be converted into an iodide so when they get into things that was that was the mechanism and then will talk about how we figure out if we just use 1 equivalent handling figure out which 1 is the iodine which 1 is the alcohol surrendered mortgages stepwise methods for figuring out 1st let me give you the
mechanism the 1st step is a program nation I mean already you're starting to see that probation what we learned the mechanism will buy back in Chapter 2 is it is also used so frequently we use it over and over again and we will continue to do that throughout the whole year of organic chemistry so arrow comes from the lone pair oxygen regret the hydrogen we break the hydrogen iodide Bonn are excellent but this is looking very similar to his arm when the programming made in alcohol right soul of this natural on the right-hand side here was a hydrogen that looks exactly like we provide in alcohol so the only difference is that now we have a map of the instead of the 2nd step is going to be
and we've seen this over and over again in this chapter S water as into depending on the substrate so that's the decision we're going to have to make so on these are the 2 of considerations here How we decide the it's departure of leading group gives a secondary or tertiary car Catalan or residence stabilize carbon cargo-carrying then a secondary tertiary cover kind or residency stabilize ,comma Cannon Mills world 1st that's what you have to remember OK so if we can make a secondary and tertiary or 1 of those residents stabilize ,comma cat eyes that's the 1st thing that's going to happen and therefore if fruitful recover kind 1st and that means with the S 1 s and 1 will be the fastest 2nd consideration it is so if we don't have that we don't have it can form a secondary or tertiary stabilize ,comma kind of every foreign unstable Michael a methyl vinyl error and stabilize primary than cover can and will not force the headline I will attack the least hinders side so and therefore S 2 will be the fastest are right so let's look on the next page and see if we can do this write so many go through this process with the substrate here I suppose people on the left-hand side of F along the right must go through the process 1st HP recruitment you will only see this with hydrobromic acid and hydrochloric acid because these are extraordinary makes it extremely strong acids what was that like this I would say child care won't but states that finalizes the virus is a giant OK the singers our decision-making person .period first-ever diseases we reprogramming the oxygen and that's what we're doing is we're actually making it better are right so it looks like the left-hand side we have and I groups and so if we break that carbon oxygen bonding conformist secondary cover kind that's been the fastest we can form a secondary copper so there was going to happen is that this group is going to leave boom just like that that leaves us with no bicycle ,comma Catalan secondary ,comma Catherine we always have to be alerted when we make a copycat ironed for rearrangements can that rearranged to anything now so we don't have to worry about in this case we get that class and the other side is ethanol soldiers drawdown and then what's going to happen next iodide that we just made this is pretty much an extension of the HI reaction we talked about was the beginning of this chapter of the highlight is a committed a tactical Cat and then we get some although here H 3 I symmetrical iodide plus ethanol see how we figured out which 1 is the alcohol which ones that iodine my reasoning way through the mechanism following the 2 guidelines with the 2nd equivalent of shy from the ethanol can now be converted in it in just like we did at the beginning of the chapter what's going through that 1 more time that's a good review for us a this is primarily so we know it's going to be in S 2 so you should know this mechanism like the back of the hand right because that's a possible mechanism for this upcoming midterm OK just like that and kind being such a weak faces not gonna wanna deeper wrote again what's gonna wanna do instead is undue backside attacked and kick off water so that's how we get converted into the iodide so if you use access or to equivalents you're going to get everything converted to an identity can be converted to arrive here's a 2nd example here
example to we have metal and as the 1 on each side let's go through the process again can former secondary tertiary arisen stabilize cover can now that means we're going to do in a century OK so what strong proof needed in our approach needed of the 3rd OK so no need ,comma Carolina no good cargo Katerine therefore renegade getting us into what's side is not iodide going to attack on least last sentence I in century fight it's an attack on size and that's the backside 3 carbon-oxygen bonds so we get those are the 2 products we get if we use on equivalent of wide gasses if we use a 2nd equivalent then that means we're going to convert the ethanol to I'd I'd just like we did right here so make sure that that's and that's the thought processes requires a lot of thought process here we have a attack the substituted side I want to say that and I also want to go back up here and make
a little known about them what's Aqaba
Kettering rearrangements and that's what we're going to do it any time you make a copycat especially Secondary 1 by so in order to Cleveland ETA
which is so stable we can use it as a solid most of the time we have to use hydrochloric acid hydrobromic acid with defeated up provided to do this if we have entered Anita that's three-member ring of course which we call a pox side this reaction hats happens readily at room temperature why would that be so sorely strained reading writing wants to open back up again so there might it's much more reactive this is 0 degrees centigrade the kid and the majority of the 2 products we get in the ring to talk a little bit more about this mechanism so Parkside mechanisms are going to help you with Chapter 10 an epoxy mechanisms are going to help you with a large amount of content and 51 C and that's why I emphasize that and that's why you're likely to see only 1 of each of the 2 types were doing here on this upcoming midterm right so we have this go into that went wrong and fix that so were also been seasons Derek chemistry when we're opening up these apart you will see stereo chemistry in these types of problems and that's going to be really important that you show showed up on the exterior chemistry when you're doing reactions with the pop sites so it is still give you a little warning had time for that we will be working on on problems like this in discussion this week so really good idea to go this discussion this week and to prepare for the mid-term because everything that's in the discussion worksheet is potential material for the senator alright so let some of these guys these
these guys by by the way a nationalist are
excellent steering mechanism works like this is going to be on acting catalyze mechanism which is mechanism of a tide of this certain type that would be on the mid-term in acid catalyzed reopening of an apart side the 1st step it is the same for stuff that we've been doing every time we have page size reprogramming the oxygen are right so far and and we do that we we we we probably 1st that's the fastest reaction that occurs 1st acid-base reactions are extremely fast and that also has a bonus in that it coordinates to of make the the oxygen better so just like that and then what happens is that the bromide that we just liberated this is our conjugate base comes in and does backside attack OK it can attack on either side apples sides eagerly substituted as on the sea was unlikely substituted a dozen attack on both sides but in this case and it does attack on either side legally so let's have attack on the left-hand side just like them and it's a backside attack therefore inversion of configuration so what's going to happen is just like we did in version in Chapter 7 in the movies groups up a little but they still stay in the same orientation and the inversion happens when the new good thought comes in on the opposite side of the leading group that's where we get our version so let's drop product there and I usually draw incoming nuclear file in the oxygen in the plane it was a little easier to see here on the right-hand side we're not attacking the right hand side and so those groups are going to be in the same spot here on the left-hand side we attack bromides opposite the leaving unsold just moving this hydrogen up a little bit by moving the metal up a little bit but they still have the same orientation so just like that all this is I believe enough room for a CH 3 just right any is a good abbreviation for level that you can use the use that on the test alright so that's 1 possibility and the other possibility is for the bromide to attack on the right-hand side so let's try that so Soviet attack on the right-hand side kick electrons up 1 2 oxygen the hydrogen moves up version that the methyl moves up but they still keep the same orientation so now I'm here's what it looks like here this is the other intentional so we moved the hydrogen up a little bit we move the metal up but they're still in the same orientation on the left-hand side we keep the group's exactly the same way that they are so that we have an attack that carbon there's no inversion on the left-hand side so it looks like that and these guys are inches I think it shows that the notes that from what he wants you program and Parkside its sole reactants that you can attack it even with weak nuclear files bromides to conclude that the public attack with water and alcohol and you will open up easily so let's look at some examples of that so
strong acid catalysis I'm lost water so I usually write it's real class because if I take 1 is strong acid catalysts like sulfuric acid and I put it in the water What is it too was a strong effort to zip it it is essentially completed associates so our main thing here is states here plus I often use exterior plus in my mechanisms when we have a strong acid catalyst in water and this is what it looks like I'm a drawing the product and then we will show you the mechanism coming up I'm a reckless endangerment so basically the way that I handle that we have a permanent U.S. form but when they 1st start testing on it and what you'd actually dropping Angela and then after that you graduate you can write policies but for this 1st test if there's a permanent formed I want to show both of them because I want to make sure that everybody knows how to drop urban interest because not everybody in this room knows how to do that so I want to be able to make sure that you can do that 1st OK so this reaction here and go through the mechanisms here say mechanism as about except that water is water attacks instead of pro-life and you can also do strong acid could catalyst with an alcohol and this is what it would look like we're going to drop and again we're going up eventually won away at 1 where another the mechanism to both of these for both of these reactions in the way we do this as we do it either here or we do it in discussions so any mechanism that you see here in class or in discussion is possible test material start where all here on that sort of thing so we have this person In an unsafe mechanism as about soldiers to do marks and accept national tax instead of water are excellent as the acid Eliasson is a
catalyst direction because it appropriates the pop science which makes it a better living room which makes it very easy for nuclear vows to attack opened up the race and this is especially important initiative also weakened the such as alcohol or
water right so we said that this was a symmetrical side we can have attack on either side let's see what happens in you might be surprised about this if we haven't done symmetrical topside so I didn't bring my my laser pointers still in my car so let's talk about this do you see on the left-hand side we have an excellent that bullets were substituted on the left-hand side on the right side we have just enough so let's see what happens here OK so minister offered optically pure single in insurer I write what we get here's our product a renegade through how we get that only 1 product single products we do not get a pair of insurer's we do not get the and so on and drive and never again and that's not even Union shores and what it would be called this product bromide attacks on the opposite side Romanian insurers we have actually different connectivity here so these are not even in inches we call them actually read your eyesores Barak so and that means that I'm in 1 side and in with the 1st part of the attack on the left-hand side the 2nd on product we tackle on the right-hand side we don't get any of the 2nd quarter so let's put the extra that we don't get any of that there are called to possible Regio worse but only 1 is formed so we call that a Regio selective reaction they earned under terms of the wouldn't lose sight is the new good while attacking on here most substituted the substitute the 2nd most substituted siding with the only attacks 2nd most substitute site that doesn't sound like innocent reaction does it it you if it wasn't us into a pure into a wooded we did get inversion of configuration and then it was back side attack but we certainly if it wasn't as interaction we wouldn't get attack on the most substituted side so so something's amiss here this is not exactly what where we would expect same goes for other radicalism savoring ring reactions again every start with a single an insurer as long as it is on symmetrical we only get 1 read your license so we have methanol come in here and you can see the knuckles just taking the exact place that the on the roaming text everything else that we draw is going to match the top red drawing exactly accepted now instead of the bromide we have methanol so we have only 1 I read your license so the question is on and why that happening but there is an explanation in
your book where they talk about the transition states for the 2 possible Regio Weiss and so what I did a couple years ago was I I went through the explanation to the way the book explains it and then I went to this explanation is which is an alternative explanation that I'm going to show you and how much of a show of hands to see who like to which explanation better and be most students like this explanation I think it was overwhelming so I'm doing a different explanation from the book for this this is not something I will ask you to explain on the tests too complicated but if you if this doesn't make sense to you look at the explanation in the book that makes more sense to you then the Inglewood that doesn't matter which way you choose grain so here's here's of an explanation that most students find a little bit easier than looking at the structure the transition states and so the explanation is bonding appropriated outsiders and symmetrical with the more highly substituted carbon bearing considerable partial positively charged the nuke without taxes carbon even know what is more highly substituted but that doesn't sound like it's easy to understand also lets go through this so what I do is I would take this program needed a pop side permeated here will skip that step and and Robinson structures so now remember the rules for residents structures were going to be doing something a little unusual here but the rules for residents structures are added to stay where they are to move around electrons we don't commonly break a single bond in a resonance structure but that's allowed as long as we're just moving electrons and not at so I many be drawn 3 is so here's the 1st resonant structure right here OK after probationers are 1st resin structure and in what we can do is we can't go here and we can break the signal born again as long it's weird looking but as long as we're not moving items we're moving electrons that's OK if we do that we get tertiary ,comma Caroline as a resonance structure I think we're moving the other way so I use a different color for that if we break the bond this way the net gives us a seance secondary copper can't I'm much better at tertiary sector to tertiary cover pattern is better and so this 1 of course is the best resonance structure but this is the 2nd best they're both very minor with the 2nd best and if we look at the hybrid and want it was only a draw hybrid and just the the 1st year resident structural and only about the 2nd 1 ability just a hybrid of the 1st to and then you can come see where this is coming from so here's my hybrid here so I'm dieting respond here so that long-term and it turns out that bond is going to start twinkling in the transition state anyway because we have a very high degree of range-trading and so that bond lengthens a little that 1 that I have died and that's going to release strain over on the right hand side and so that's going to be happening here's my here it going to do a hybrid of the 1st 2 so that means I have a personal positive here because I a positive on oxygen in the 1st 1 9 on oxygen in the 2nd and the carbon on the left has powerful positive and so it turns out that the nuclear file is gonna want Kenyon an attack side that's the most electron deficient so the nuclear file attacks inside that is most electronic efficient and that's going to be the left-hand side because that makes a more stable ,comma Katarina as a as a resonant structure that's the most Elektra Philip Cochran so that means that has paralyzed in a comedian still go here and there to break that bond here and so that's why we get the only product where the bromide attacks on the most substituted side so this is kind of a strange mechanism because it's it's part was sent to you in that we get back side attack inversion of configuration and is part 1 because we are performing some partial positive charge on the carbon that would make the best can even know really not forming a complete Carver cat so as it's kind of a mix of S 1 s and 2 is the best way I have to explain it so mix of but as 1 and S 2 so if you're saying to yourself why we have to go this big long explanation it's complicated and understand why can't we just have a regular ,comma kind reaction why do we have to have a personal thing happening why can't we do this so here's the Why can't I wondered why can't we just as a much more simple explanation of what it so inclined ,comma Academy forums then it would look this is what the mechanism would look like and let's see why this can't happen a stake ,comma can make a full-blown Kirkland White of something weird bridging something weird thing why do we have to do that why can't we just make the cargo Cameron so let's see what that would look like and then you're going to be able to tell me why we can't do this CH 3 so we know what cargo-carrying looks like if we make it ,comma Kanye and that means that the bromide containment from either side right so the bromide can come here on the talk and that's the key here the bromide can command from the talk here and the bromide can command from the bottom since was so what that amounts to his own backside and front side attack here so on the strategy products that you would get if this is the case notice that the bromide is coming in on the same side as the leading group the hydroxyl and if it comes in at the bottom then we will get this product g going back and forth with methyl ethyl and methyl and and CH 3 incidents solid findings to to do that by the way OK if that happens we would get to products do we get to products we don't get to products so that means that can't happen we don't get any of this we
only get this and that means the brawling cannot command an attack on the opposite
side there and white candidates In the reason it Canterbury look here at this time structure
right here the reason I can't comment on that out of a society that site is blocked by the oxygen because that bond is still intact I think that bond rate here is still intact so the bromide kick in from the side that has taken from the opposite side so there's or explanation so if the enemy was a propaganda department at the
top and the bottom of the inning amateurs stereo isomers stereotype chemistry the prime clearly shows the Japanese that not only on the bottom phase of the pop the was there be more like appropriated part a plane or car account alright so this is what I wanted to look like you're show the proclamation steps if I have this mechanism on the tests you do not need to draw all all those residents structures you do not need to draw the hybrid they all you do is you Prometheus the Parkside and you go like this so it's as simple as a two-step mechanism here we the FOR we move the methyl out we still keep the same orientation and on the right hand side hydrogen stays metal states so so all newly backside attackers observer all the backside attack and so therefore can't be a carbon content in the media are so doing so here's
the ears and the thing I just got through saying I don't expect you to draw all the resin structures I don't expect to draw the hybrid but this is a sample test question you might see this exact test question or maybe something so similar that you think it's it's exact spot very high likelihood of that accessing the free points on the tax rate OK so let's look at that so the 2nd question predicted Friday of the following action provide a mechanism for explanations shoulders charges incurred the ire of do not combine 2 steps into 1 so let's do this now I can write each to us so Oregon right of age three-hour-plus catalytic doesn't matter let's do it with what we have right here were in a primary oxygen 1st Eric comes from the lone pair oxygen grabs the hydrogen we break the hydrogen oxygen the so far so good so that means no
one's going to miss this problem on the test right fishing you know exactly should look just like I'm doing here methanol attacks do we do propane methanol know that we do we don't approve make enough all the Sox sideline is not going appear in acid catalyzed mechanism what we are going to do is attack with oxygen on the most substituted side it's from needed sorry yes did not appropriate that need to do that deceived the entire show you what you not the OK were good I was just going to catch that when I'm drawing product here OK so that looks like that we need a positive charge here also don't positive charge so grown there should be wake here and we have appropriated methanol what's the last step here what would be the last step here I'm showing Sturges removing example up on moving the metal but they still are in the same orientation last act is too deep wrote nature of the enough and all that just attacked and I can use other methanol that's in the reaction mixture of this is used as a solvent or if you prefer you can use the conjugate base of sulfuric acid so both of those will be OK to use as bases to the program and then usually only show 1 product some which 3 were going far-right in condition that 3 ministerial so we can do instruments Dorian this is just for it's easy OK acid catalyzed mechanism we got downright this base-catalyzed or strongly believe I strongly believe I'll write so easy this is pure and sincere that doesn't look like it in here as in to what happens in the side comes in and Woodside as an attack on the substituted side appearance into ball can you do that this is something that only happens with the park said you cannot do the equivalent reaction with the 1st not a million years they so this is something that only happens with pop science this is curious and choose those should be very straightforward for you and here's our medical here and we only get 1 product so you could file a tax on the least substituted side nuclear file attacks on the substituted side if you try to do the same thing with the regular reader you would get no reaction Barak so on and so what we have started the files or base-catalyzed the nuclear file is attacks 1st we do not prove Nagy pop 1st and so this is what it looks like here let's go through the whole mechanism in the last minute his word that OK with that this should be the easiest problem on the test would attack animals substituted the substituted side we get all minus the 1 happens when we need to do to finish the reaction we need a pro-gay oxygen Delaware when we drove oxygen when there's no acid present so don't throw acid in there what we're going to do is work is not at all and as you did at the Apollo use not policy we actually regenerating are catalysts we only need a catalytic inanimate Parts and there is he answers coming up on Friday I hope so that would be amazing opposite radio selecting the word don't worry we're not going to worry about the talks until Wednesday and our continent is actually being verbal explained that I was invented do what you know noble that these mechanisms .period regarding continue this next time