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Lecture 3: Stereochemistry of Elimination Reactions

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In some elimination reactions were talking about most of the time in the most stable product predominates In some elimination actions unless they've allowed Keane is the major product and when that happens is when we have a very candid based in a very handed out of here alive know your book will tell you that I the Obdulia line has to be tertiary fans of the Alcock side at the base has to be right-hander also but I think in in the laggard me during elimination experiment my students to the last week and I think what students found is that you know the secondary out kill him life and as any hinted base the major part of Sicily substituted you you looked at it already so yeah so it's pretty much secondary and tertiary out till he lights in a very injured basic Turkmen topside qualifies you get not the most substituted but the least substituted just has to do with the fact that so the base has a hard time coming in with who show you output which I'm prepared with everything except boys but the base this very limited basis to community it's going to make the most substituted out here it has to remove 1 of these 2 made a hydrogen and that's hard for it to do because it's so hindered so it's much easier for to grab 1 these are hydrogen a on the outside it turns out that that's the major product and get for this very major base removing 1 of these beds instead of that move that 1 in the middle it's a harder to reach I think Her inmates so let's try
the product here to in typically do get to products that the major ones should used well I don't want that alright so that is try substituting product and we also get dies substituted products so that I would look like this show some of you are still at the phase in this chapter where you're here even having trouble seeing what the product is going to be your being able to predict in seawater moved past that point rather quickly because said stuff is much more complicated so CH 3 this would be an awful lot so this is the most substituted its try substituted and this is dice substituted so we're looking for are groups here I'm so you have a lot of trouble seeing this don't feel bad if you do cost a lot of people not those same wake up I think it's easiest if you draw the hydrogen since it's easier to see how are groups when you have a hydrogen is actually so this would be a germinal die substituted product this would be a try substitute products it turns out that we get the 28 per cent and
72 per cent because the base removes the most accessible hydrogen when the Bass family I'll kill him are very 100 so like we said as think you'll see when you get into louder than this Bob Smith will tell you that it's only of tertiary but we've always secondary the major product is that we substituted hold Price and compare that with this 1 here to retake the same substrate so we still have our tertiary I'll kill him lie which is very dangerous
but now we're use an unhindered face-off oxide is a good unhindered base that does really good in each year reaction and now we're in have remained at the scene to products but this time the most substitute is going to be the major so that's the same 1st part we got about try substituted and then the 2nd product is the same we got about but we do get both the major 1 going to be the least substituted this would be done I substituted so let's see the actual numbers we get here
69 per cent In 31 per cent so they don't the the terminology in the book a look at it was all I and even have to draw those experiment next to it is under the amended fixed the next chapter so that it doesn't scroll weird like this so you guys did just that in yourself there is major book doesn't use the name but there is a name for
both of these they use sidestep so this is design
itself it the be the least substituted is called the Hoffman primer so there's I'd step is the most substituted from their Hoffman is the least so most substituted and often is the we substituted far-right question me that's what we did was change the base yes are we don't 1 our
confrontation with the need to finance the
stereo chemistry elimination to occur in
hydrogen in the leading group must be in the same plane Ken are hydrogen leaving groups must be in the same plane In the best is yet period cleaner and this is the only 1 you will see in this class all 1
you will see in this class so there's 2 possibilities there Dante carry player which is the most common in very rare circumstances you can get seen period cleaner and that's with written rules and things like that they cannot do in type carry plan we will never see in this class if you are a chemistry major you will see examples of this but if you're on a chemistry major his so I want you to show since Gary Player Kaesong and applauded the accidents won't see in this class alright so in type carry plainer there hydrogen and leaving the ball just abbreviate algae we are in the same plane and on tied to each other and as well as center Gary Player is on higher only under special circumstances not in this class all right so let's good let's do an example here so what we see is here and what's
going to be really helpful in this chapter and move remember how to do this is to take three-dimensional structures and put them into Newman projection that will help you
grade in this class this was something that I wanted to know how to do so we thought you were done with that you know and do need to know how to do that and and so on on what we have here is this is the bane of hydrogen here's the
leading group so we're always going to basically put this into Newman projection here's the leading group the debate on hydrogen to be removed as on the adjacent carbon it's not on the same carbon on adjacent carbon so here's the beta hydrogen to be removed when it's strong nicely like this with the beta hydrogen and the leading group in the same plane and tied to each other you don't have to put it into a new projections so you can see here this is our beta a hydrogen and here's are leaving group so easy to take out the believing group not necessarily easy to pick out the beta Huygens the the carbon bonded to the leading group itself up and right next door is the beta we also have another beta don't worry yet this 1 here but what we haven't uninjured based on nodding and worry about that 1 because I'm not going to draw you the major product here right so what's going to happen and so ominous show both ways the oxide comes in Thompson is going to ground the debate hydrogen
gonna break the carbon hydrogen fault and then the leading group please since the leading group is leaving leaving I wanna see low appears on it some Yeltsin so that's gonna look like this since the strike this way is a little strange dropped that it works nicely and achieved a mouthful going back I'm going to keep the federal coming forward the metal on the right-hand side is going back and this hydrogen is coming forward now we usually don't dry out Keane's that way we usually call the draw them flat on the page but in this case I'm just drawing it tilted so the perpendicular to your
page that's OK to do that so again rather than flat on the page it's just tilted like this so that it would look like so that's from the -dash but if we do it the other way here we're going to lose
that this is after loss of HBO rights aren't going to remove the HBO are I'm many keep the Newman projection here it's just wanna make a point here so this metal here's still here the panel was here farther back there's a raffle here I haven't moved anything on the back this is the hydrogen wallets a little strange to see it that way but remember the carbon-carbon bond here's the from carbon right here in this round thing is the back Robinson that still stays this is the final arbiter in this round thing is the back of it and so as you can see our Al-Qaeda's like this so in order to figure out what that looks like we just gonna connected to alliance
you a little hard to picture but you just see that it's going like that I'm very dry without the cervical cancer looks a little strange with the circle the band so noticeably job double bond in here right here there .period on the same side of the double bonds the same here I just kind of rotated it this way
Of these 2 structures are equivalent it's just that no 1 is in Europe in the planning your pager was perpendicular both of you can draw that either way on any exam questions on how I did that anybody yes you this will you want to see the circles a little strange OK I just left it their CVC where things are come from you don't want to have a circle so I would write it like College Circle in Canton so you can write it like this or you can write it like this I just officer because that's all strange that it is not like what is it with this at rate OK Soon elimination of the same Malkiel he
lied does not her requirements drawn on the next page cost you guys have less of a parliament
that same page we're going to fix the solid Chapter 9 knowing what this programs about Simon said but so all groups are eclipsed here so we're not telling going from here to there can I get them on the same page at the same
time no to that but see what heard cheated I
kept the front office saying and rotated
back so methylphenidate writer Jennifer Aniston at
the same and the back rotated that would give you see an elimination some factors rotated so the number 1 reason we don't it's an elimination is because if in order to get in the nation all groups have to be eclipsed announced this favorable that's going to raise the energy transition
state and near the thing is is that if we have the
base year coming in on the same side if we
trawler all this is 1 of several relational quiet so not only are all the groups but we got this nucleophile coming in and this nucleophile surrounded by woods that 3 sets of lawn care is coming in close this vicinity to the leading group which has 4 pairs it's not going to favor the reaction so that's why we don't get sand and so that we draw the product that we don't get it but again depending on how you doing using draw like this metal still going back still coming forward hydrogen goes back metal coming forward but that's equivalent to flat contrived flat also it turns out that you don't get any of that song and put a big extra that
spent on cancel this is going to do you gets so
you're reasons why this doesn't work transition state has eclipsed confirmation those are the things you want to look out for and I'm right here is you can see that the based the leading group on the same side so it's also staring into space we think about the lone pairs on the basis of personal providers at their accounts of the incident is that gets close to that so that's the 2nd 1 it's just our rights so that some
on the next page talks about when you get there
Everything we just mentioned the entire period later
staggered confirmation this 1 has a class of favorite in winning the bronze inside the molecule was hysterically to slavery in the entire elimination on opposite sides in what those guys as far apart from each other as possible sorry questions so yes will I'm not going to ask and awaiting trial so you're only going to get into a period Britain's class so I know I have students who I guess it's possible that have been and are a reaction from 1 of my predicting products that historically I don't use you many of them I don't usually have reactions there's no reaction usually have an answer so I have students before that we're not doing well the class in R & R & R for every reaction for 2 predicting products that's not a good idea and my class they don't often have reactions and the analyzes will give you 1 and that has to happen that's confirmation right OK so let's see what happens when on a six-member bring out with more
complicated here this is mental chloride on 1st we want to see a couple of different things that person wants to find the hydrogen 1st things 1st let's find the hydrogen so weakly 0 in on
leaving room so this is our right next door is greater OK so now and so here this is the
most stable conformation where the halogen in the eyes of vocal groups are at Equatorial like all groups rate which was the scene most stable conformation but the hydrogen and leaving are In time period .period In a cyclonic singling debate on
regional leaving the consumer-oriented pre-clinical permitted only when they are both axial so the claims on axial and debate Williamson severe Huygens are actually the clearly also has to be axial so in a six-member during the entire period planar equals translate when a six-member the entire period when equals transatlantic so both to leave England Benarbia hydrogen have to be axial and they have to be on trains to each other if there are not trans-regional will never get a reaction in years and so on but that's OK because this when is flipping rapidly back
and forth right so we can we can actually flip this spring including in cooperation with the chlorine is in the backs of position you have to do that right and chapter said he thought you were done with the islands after finding fighter redundant that knocked out that we still have to know how to do do that and so on and so does so I remember we're looking for the headrests here's the this
is all going up here headrests that's the rest so when we thought that this carbon right here is going to be down in discovery here's going up so need in order to do that but it so that means that the size global group which is down is not going to be axial it's looking a little weird stuff there is a problem was stand
hydrogen itself the region with him we travel around the ring would enable clockwise to the next hurdle here is chlorine chlorine is going to be up finally we want to break the back of entering the mechanics of starter John there but the quality is going to be if you draw the line text says he wanted to break into that but break the back of the ring clearly around the scoring next next carbon to hydrogen service giving now and we have this 1 here this Netherlands up Our alas not the most stable compilation but it still is flipping back and forth and that's the confirmation we need to be able to come eliminated .period hydrogen stall
plan joint inside the Sphere so can you see that there's
really only 1 hydrogen that we can we know they have to be chance I axial so this hydrogen right here this is not to its sister the quarry so we cannot find a million years eliminate that hydrogen we can however eliminate this hydrogen if we we eliminated Inspector General give us the most stable while keen public can eliminate that hydrogen because that would be seen without this season so we're going to eliminate this hydrogen so in order to get Sinn elimination on Tiananmen Asian can't be possible OK so this is not that's not going to happen so this is the only hydrogen and we can eliminate and we know 1 thing is that these
antechamber freely among temperatures so the
fact that we can eliminate from the confirmation is not a problem so no problem cheerful this rapid even at room temperature far-right so so here is our our frontiers are made here's can't eliminate this hydrogen because it's not trans fatty says then you can eliminate the societal jails this is the only hydrogen and you can eliminate Our excellent eliminate that hydrogen leaks use :colon see just this explain
what's going on who please put the case of toxic
contends Bloomberg said hydrogen ensconced here leaving the players I'm drawing the wrong way and not the right way so let's try the product the wrong way In the morning putting nice time drawing in an experiment OK ,comma Georgia the Maoists guys final rates on its territory I'm so embarrassed and thinking next year it was worse taking a long time to make this point are OK what's wrong with that can't save this items like terrible what is the point is valid veteran can you inhabit transdermal body in a six-member ruling you kids and it's geometrically impossible trying to do it at home you can call it able to deal with it with that was those models together in a green box my models are a little bit more flexible operating next time so you can see it you can come to my office next week to see if it is absolutely geometrically impossible to have a transdermal born its six-member ring so they're really the best way to draw this is actually flat and I will let you drive flat because as soon as we play double bottom at 6 six-member grant it's not a chair anymore anyway is it it's not a charity OK so so we want to make it can change colors that cemented when an X through this and what we wanted to do was willing draft the right way looks like some registrars Plaxico mixing Bloomberg mortgage so we wanted to I like this on the exams are improving OK so there's there's always a problem here that's Saddam's everybody's see that this is so funny that's down what about this trip over here that's inevitably even on and that's not isn't it that's the best way to do all this "quotation mark that's the right way to do it so this is correct so on page right here have transdermal born in the six-member going I'm not going to draw here because it's kind of like a kindergarten landed this is the correct way to interact clause and in questions anybody so
we keep going like this this is a lot of drawing in the
story here so we cannot confirmation is less stable elimination occurs through the confirmation because the Bayer hydrogen and think you are transsexual yes descendants have and how alright with mental
glory Garrett Street relicensing can be eliminated this is Neil mental clarity that's looking at 1st of all it's final all right
so Alfie is the carbon bonds in the leading group we have to make hydrogen in view of things happening here both of those heightens inside and in the same place the Transkei axial which is in which is which is the same exact thing a six-member drink could Gary Player is transitory axial so we got to possible approach thinking eliminated so let's do 1 of them moment you 1 of the main rant like there eliminate this hydrogen here but judging from general kick to leaving operates that's 1
possible product look strong on the recall that
welcome to the attention Indian for his Bloomberg losers will change colors that's Inc but strong Department job flattened as there are still some brief here and all these things flats so this never wears off here's our double bond trades here don't strong decisive will group down why don't I wanted to have a sizable group down it's down here to see how it's downright here why don't I want to drive with a wedge 10 it's trading environment remains landings this Carbon Factory in back of the neck inaccurate all the same way as so there's a 2nd problem like that ass you take all the problems ,comma all of items that are in the same place and so we have double 1 here so that in this province in same that was the 1st Avenue attached select those cognizant I'm going to put an X on foot permissible in this problem right here this paragraph that carbon that In this hydrogen so did you Adams of the double bonds and the 1st Adam attacks we are all in the same place so you don't want to drive that image so that's 1 on you what's keeping Switzerland I'm risking things here but still call
this clean His oxide navigation route removed the other day and hydrogen I'll just put this
area on the other side here but struck product
be the move back to the analysis we are going have to give them a little called noticed template here that is a double bond on the ball that's another small islets This is a nice approval struck wave but right now which 1 is going to be the major problem you got to possible products which 1 is going to be the major Taliban Top honors more substituted so who will we actually gets
78 per cent here 78 per cent and 20 per cent here so this is not necessary because it's the most substituted only right that knocked me right now is because most of Sumy still have 2 more minutes of this kind of merchandise often turn on again we just have to keep going old far-right OK OK so
definitely let's writers for posterity most stable favorite because more substances got
1 1 minute when mixtures terrorized this is possible from the 2 reactions students and wanted the same way I made a ,comma goal season trans isomers will be informed because there 2 was always the begins to the odds be eliminated or inside the outing with the ball history on the opposite sides of the doubled while reforming Gradyville because the more stable outlook all right so that's the last part of this and we've got to possible products here I still is still hasn't the club has not the yet so we have this he and trance well it's it's a series of Transamerica say because we have more than 2 groups attached which 1 of these was the Bocuse groups on opposite sides 1st where the the 2nd 1 the first one and major 41 per cent In this is 14 per cent In a very minor is the least substituted all drawdown quicken the war ends here this 1 is mine participants stopping weapons operate there were continuous and next time we get a great weekend
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Differentielle elektrochemische Massenspektrometrie
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Magnetometer
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Computeranimation
Prolin
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Metadaten

Formale Metadaten

Titel Lecture 3: Stereochemistry of Elimination Reactions
Serientitel Chemistry 51B: Organic Chemistry (Winter 2015)
Teil 03
Anzahl der Teile 26
Autor King, Susan
Lizenz CC-Namensnennung - Weitergabe unter gleichen Bedingungen 3.0 USA:
Sie dürfen das Werk bzw. den Inhalt zu jedem legalen Zweck nutzen, verändern und in unveränderter oder veränderter Form vervielfältigen, verbreiten und öffentlich zugänglich machen, sofern Sie den Namen des Autors/Rechteinhabers in der von ihm festgelegten Weise nennen und das Werk bzw. diesen Inhalt auch in veränderter Form nur unter den Bedingungen dieser Lizenz weitergeben.
DOI 10.5446/21622
Herausgeber University of California Irvine (UCI)
Erscheinungsjahr 2015
Sprache Englisch

Inhaltliche Metadaten

Fachgebiet Chemie
Abstract UCI Chem 51B: Organic Chemistry (Winter 2015) Instructor: Susan King, Ph.D. Description: 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: 00:08 - Regioselectivity of the E2 Reaction: The Zaitsev Rule 07:51 - The Stereochemistry of the E2 Reaction

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