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Lecture 09. Alkynes, Part 1


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Title Lecture 09. Alkynes, Part 1
Title of Series Chemistry 51B: Organic Chemistry
Part Number 9
Number of Parts 26
Author Vranken, David Van
License CC Attribution 3.0 Unported:
You are free to use, adapt and copy, distribute and transmit the work or content in adapted or unchanged form for any legal purpose as long as the work is attributed to the author in the manner specified by the author or licensor.
DOI 10.5446/19478
Publisher University of California Irvine (UCI)
Release Date 2013
Language English

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Subject Area Chemistry
Abstract 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. This video is part of a 26-lecture undergraduate-level course titled "Organic Chemistry" taught at UC Irvine by Professor David Van Vranken. Index of Topics: 00:11- Why Europe's Healthiest Economy Has Its Worst Drug Problem 01:36- Morphine and Fentanyl 02:56- 10.8: Recall Addition of Electrophiles to Alkenes 06:46- 10.16: Hydroboration-Oxidation 10:47- 10.16: Hydroboration Step 16:58- 10.16B: Oxidation of the C-B Bond 21:16- 10.17, 10.18: Keeping Track, Alkenes in Synthesis 29:25- Multi-step synthesis CHAPTER 11-Alkynes 33:49- 11.1: Introduction 38:09- 11.1: Reactivity
so this is news article caught my eye total why Europe's healthiest economy has its worst drug problem and I thought I was going to talk about Germany because I always thought that they had healthiest economy of all of the countries in Europe and I was surprised to see that they were afraid of 2 very different countries here but since Estonia and I don't know if you can see with my laser pointer but appear on the map in red that's the country of Estonia so apparently they're doing pretty pretty well you know Europe is in an economic downturn at the moment and up for what the drug problem that they started talking about here is a drug that they referred to his China Light which is sort the unofficial name the actual chemical name for this drug is spent in the relates to a class of molecules that we've already talked about and that's obedience on what's amazing about this stuff is that it's anywhere between 100 and a thousand times stronger than stagger which is harrowing 120 thousand times stronger so imagine taking a hit of heroin but something 101 thousand times stronger than that and I think we can get a sense for why that might be super addictive and a superbly about mystical look at the molecules behind the story on what is gag
US Gaga's heroin I'm of course from heroin gets in the body disasters on bond here to ascertain testers here that allowed across that allow heroin cross the blood-brain barrier but importantly win when it gets inside the body gets converted into morphine and that's the drug that binds to mu opioid receptors in the central nervous system and gives the pleasurable feeling so this is what ultimately binds to receptors in the brain and what's amazing is this very simple maybe not to yet but by the time you get 51 seats will look like a very simple molecules fentanyl we'll know how to make molecules like this just by taking him 51 C and the fact that the chemists can make something like this and it's 101 thousand times more potent than this molecule that's optimized by nature but I think it is pretty extraordinary ,comma so I'm in the good part of sentinels not free as an addictive narcotic but of course it's a killer oddities clinically OK and until wanted to be chapter before we talk more about them about how to construct a molecule that type and that's coming up I think in Chapter 24 7 I think in the book and can 51 see Hutchison's bring ourselves back to Chapter 10 the largest remind you where we're at right now in the class chapter 10 is about 5 reactions over and over and over again you were talking about these 5 reactions and we have not talked about for these 5 reactions were going to stand today I of finishing up those last reaction and not talk a little bit about how to approach this is problems multistep synthesis problems and I can just show you a little bit about all kinds of things obviously we think of reform because probably didn't download physical lecture pages to write stuff in media can just say some general stuff about all kinds of cases Chapter 10 of 5 reactions so let me enumerate these because they keep referring to these 5 things reaction number 1 1 of the 1st thing you covered with the addition of H B R M HCl across Al-Qaeda double bonds and it generates cargo can I answer to the initial protonation of double bonds on by the to Fiorentina ceiling walls of carbon content to worry about rearrangements reaction number 2 that we talked about was hydration of double bonds the addition of h OH although 11 for you so and water across the line endangered the initial event prone nation of the double bond and generates a couple can just like edition of Fiore CLC have to watch out for Karval can rearrangements 2 reactions of double bonds 18 something else across a double the 3rd reaction we talked about was additional bromine and chlorine across double bonds B R 2 in sealed 2 there's no cobbled plans in this reaction remember you go through this site collects three-member during the ammonium ion or its if you adding sealed to chlorine then you go to a site clicks remember recall only mine but there's no cargo can answer that this is very weird all jobless well into withdrawing in this example is running but they go through the site cycling three-member brings some can and in a century action opens at the 4th reaction this is where we left off I showed you that you could run in these B R 2 reactions in water we had a sealed water there it's water that opens that cycling Catalonia Miami and so that the class of molecules that Uganda called Halo Huygens this model year would be called Bromo hydrant and and throughout this last lecture I kept emphasizing the issues of stereo chemistry and suggesting to you that you need to pay attention whether species ad from the same face the opposite face in these last 2 cases reactions 3 and 4 the relative disposition of those 2 groups situated in the to each other to notice how was so careful throughout the 2 bromine atoms in the and pushing it into that and you when you had R OH across a double bond also leads to intervene and that's where we are now so we're going to spend just 1 wouldn't have that much left to cover in Chapter 10 here on we're going to finish up talking about this last reaction it's actually a 2 step sequence and you always at least for you in this class you always use these 2 steps together and you always have to enumerate these 1 and 2 or a and B if you want for our Arabic numerals 1 and 2 but if you don't enumerate the city's simply list all the regions thrown together that's wrong will come that along OK so credible oration Jeannette looks that looks deceptively light majority there looks deceptively like the sulfuric acid in water reactions and so why would I be asking you to learn this set 2nd reaction was looks good and talk about what this 2 states 2 step sequences about OK so as to step sequences called Hydro operation oxidation step 1
inside war Asian stepped to his oxidation and here's what happens if you take this molecule Boraine over time and again this is a born on adamant there I'm going to try to direct your attention to a close living in sketching out we all draw you a little miniature periodic table here that's walk across the 2nd row of the Periodic Table of lithium and beryllium you'll never see anything with
beryllium on the way over here on the left hand side appeared table and then in the 2nd row here is the meat boron carbon nitrogen we thinks so lithium beryllium over here on the left-hand side of the periodic table this is the 2nd row boron carbon nitrogen oxygen and flooring is a little too wacky for us in this court will see a lot of flooring chemistry so those are the 2nd row elements so that a little bit about war on chemistry so you haven't seen anything at all about that yet so far I don't think of boron but its electoral positive is more electoral positive and carbon and that's going to make it very strange but this secured a 2 step sequence when you take analogies and and you add Boraine that's this molecule here it is right abode here that's boring so here may refer to that Beechtree what you what happens with this region is ads H and B H 2 across the double bond so where you have a double bond I'm going to add 8 Shh under more substituted carbons and I'm going to this had allowed and on on the less
substituted carbon and that immediately different from the addition of HCl HBO are when United HCL arranged yard added to the last substituted carbon so this gives us a way To achieve the opposite Regio chemistry and then after this next step step to hear you who makes hydrogen peroxide and sodium hydroxide together on and you will always use this to reagent combination when you follow Idaho Operations action there's never a time when you don't use that as a pair at least in the camp 51 series so ultimately at the end of what we've achieved after this oxidation step we've replaced and I'm not going to draw that each year for you we've replaced the the boron with hydroxy and this is the opposite overall it's hydration but it's the opposite we geochemistry as sulfuric acid and water if you use sulfuric acid and water on the on the substrate you would had to await them or substitute position ,comma of where that double bond OK so let so was practicing here's another out clean and thereby apply this two-step sequence step 1 and make and boring really reactive stuff and I'm not going to draw the intermediate and instead do we do this oxidation step with hydrogen peroxide and sodium hydroxide you can buy those reagents Albertson's they
sell hydrogen peroxide around bottles of the saliva cleaning clogs LID but sodium hydroxide and so remember what I told you the end result is that you put the hydroxy group at the least substituted position and I draw the age there you know you don't really have to and that's the end result interviewed used sulfuric acid and water you would have gotten the opposite regional industry that's powerful you need to remember this reaction I'm going to use this on you as a way to test whether you know this way to achieve absence staring the opposite region focus its talk about some of the details of this 2 step sequences Hydro correlations oxidation but here's my little periodic table there the 2nd born on let's talk about Boraine Beechtree 3 hit super electrical and angry it's just like carbon in the 2nd row out on any 1 state electrons every 2nd row and 8 electrons and so if you put more rain in some sort of solution is going to pick up electrons from somewhere and about Keane's American Elkins will attack on so here born with its NTP will appear on and I'm just going to with makes the colors here should see the angry MDP were the only ones some electron density the demanded Wandis hovering over here over this double bond here and in here comes out clean and just like you saw Al-Qaeda tackle the Electra files is out in the attack HP are impeccable protons is all about Al-Qaeda attach the yard to you were sealed so I hope it's not surprising that what's going to happen is the Al-Qaeda is going to take it spirit electrons and add to that which is sold only in really wants another pair of electrons in order to achieve an object now before I finish and I'm going to draw a step here but before I do that I want to show you something that is completely not obvious to you and what I'm going to show that it's not obvious is that at the same time it is double want is attacking this born starts to realize that it's picking up a negative charge and doesn't want to do that so it really delivers this hydride group back to the most substituted carbon and that's totally different from anything that you've seen before there's 2 2 bombs that are forming into bonds a breaking were forming a born carbon bonds and forming a hydrogen carbon bonds and
we're breaking the the CEC pylon in breaking the Beechmont so this is a one-step concerted reaction additionally HBR wasn't 1 step In addition of B R 2 across a double bond was instead wasn't 1 step hydrogen was step this is a one-step concerted process and you can see because the born hostile approach from either the top place where the bottom phrase that means both agent B are delivered arts to each other doesn't make a difference to the substrate but all will see I think in the later example how that can make a difference but given just sort of parameter lies this car in here and then he draw that and going out there it is and here's my where is that this the double bond and I got this very strange-looking H 2 groups pH to and that it's not like any functional group you've ever seen it isn't it looks kind of like bromine just alphabetically but it is nothing like bromine OK so it's still a little bit angry because it's more dangerous and the other reasons why this is less reactive than the original morning in hypothetically this can keep going in and 2 more out genes with the way about that if I asking the mechanism to stop here so now this is the initial step will talk about the oxidation in the 2nd half to rationalize this year rationalize the fact that the hydride comes back in head 2 to the most substituted carbon instead of the least substituted carbon and while tell you is here the mechanism this is the mechanism I wanted to but that had we rationalize how to rationalize the real geochemistry and what I'll tell you is that the transition state as the boron is getting closer and closer resembles what I'm going to show you here the transition state reaction resembles the but as I get closer and closer and closer it as well as the born starts to form a bond if I take these electrons up from double bond and I've formed a on that door now has to pick up the negative charge 5 4 Barnstable on it will have a negative charge like a little a boring it's going to be a something with a negative charge carboxyl Aghazadeh the megachurch carboxyl late but boring Paladini will still see of species very much like this but when I took the electrons away from his other carbon I'm going to leave behind a cargo cast and there so in the would not work with get into the transition state as the transition state looks more and more like this would happen this is complicated and realizes there's this very nucleophilic BH volunteer here and that DH ponders taxes this is what the transitions they resemble so when you initially had the boron on edges approaching the transition state you want to build up cargo can and character and most substituted carbon that's what's driving the radio chemistry that's why the age always ends up at the more substituted position and the boron always ends up on the least substituted position we call this motive of additional hinting Marconnet because the regional chemistry is the opposite of those other 4 reactions that I showed you this is an intimate ,comma comparable that of additions and that's when used for anyone to achieve that OK so get this kind of TUI announced with a very complex two-step sequence with Boraine then this mix of Haydn Proctor incident dropped Back to join it 50 times I will just flow the European leaders focus was good talk about it since during the oxidation of this bull run Karbon because there is no case ever on the planet Earth where you need to make him an organic class like this would ever isolated boron super reacted stuff so we we will always take that intermediate that as a carbon bonds and converted into an alcohol In this class of this affair is an example Tom Of others reactions notice we've taken out he that's differentially substituted the top carbon has 3 constituent were addressed to substituent on than the bottom 1 has an age that I didn't draw and 1 alkyl substituent and so based on what I told you the h always adds to the most substituted carbon you should expect H to add to the top realities and that's what I've got to run over here and then the beach to good end up on the bottom because that's the least substituted now we're going to treat this with this special region combination of hydrogen peroxide and sodium hydroxide I had no idea on the again what you really doing here will work but I don't want you to draw it this way because then you'll miss half the 7 questions what you're really doing is you're making Hydra peroxide I'm using sodium hydroxide to deep-rooted hydrogen peroxide and of the reason you do this because you can't buy sodium Hydro peroxide you can buy this but if you knew that this was the point here and in In a graduate classes would allow you to just write sodium Hydro peroxide so that's really what you had not adding to the reagent you just kind making it after reagent that you can't actually buy I'm OK so the whole
point here's your oxidative including this Parliament and here's some things that you've never seen before it's yet another strange part of this reaction noticed that the born won't bomb was sent the age that we initially added when we do the oxidation we replace the boron powder this is nothing like this into reaction or any reaction you have ever seen and the book doesn't show you the mechanism for this oxidative 1 common bond cleavage and I'm not going to show it to you you don't need to know it if you want I can show that you later in secret but I will I'm not going to that to you but the point is that this is nothing like it into obviously not anything like a century the mechanism for replacing born with oxygen you replace born with retention of Styria chemistry so the net effect is that you add H N O H innocent fashion it's a two-step sequence in the O H & H always end up seemed to each other in the final product others another product that you would have gotten here and I didn't draw that unsolved would make a point about the other thing you would have gotten here is that you have also got the endangerment of this intermediate and you would have gotten the Indian Chamber of this product Plessey so in case you're wondering why did the and from the top facing up from the bottom yet with the boron would of the boring would have added from the bottom faces well a 50 50 chance OK so that a durable oration oxidation ,comma again is gives you the opposite of the geochemistry of a regular hydration reaction on the H ends up at the more substituted carbon on the mechanism involves this this season addition a concerted additional agent beach to aggressive Belmont and there's always the 2nd step that involves 2 reagents step number 2 hydrogen peroxide and sodium hydroxide and that replaces the boron with retention exterior chemistry it's not innocent to react and I'm not going to show you the mechanism on the major right down there is indication you look at these notes later and wonder what's going on at that time I won't show the mechanism not that I don't think it's important that just want to add that all the stuff OK so it's clear we're going to finish up this chapter and I'll show you just on 1 of the main themes toward the end of this chapter for the last 2 parts of the last 2 sections of this chapter basically review its here's the fire reactions you earn the more importantly its review in the context of how do you make this together with with reactions from chapters 98 men and even Chapter 7 so come on the last problems that I had some problems at the end they were multistep synthesis and this year is exactly the way pretty much exactly the way I'm going to ask you questions on exams and that of the other structures will do the same and this will happen again and 1051 seats so you can expect a multistep sent this used to be an important part of organic chemistry from here on out so what is multistep synthesis about it's about I give you a starting material and I'll give you a product and you have to figure out what steps and reagents and it's never going to be 1 step that I'm very clever I know how to pick reactions that you can't possibly do in 1 step was stuff there that you know so I ask you what how many different steps and what reagents actual chemical reagents would you use in order to synthesize that reagents that come in bottles that you can pour into your reaction so how do you approach questions like this here's how you approach in question -dash see there's 2 different directions to approach this you can move forward and start looking at the start of nutrients and what do I have to do with that or you can look at the product and say Well How many different reactions join they that can generate those kinds of functional groups and so let's try that I if you're on the exam and there's a question says how I take this condo external to undo this you have to resist the temptation to try to think of one-step wasted 2 years I would do it I would start off by saying OK let me list every single reaction I know of an alcohol I look at all the functional groups here and I'm not going to pay attention to the C 2 because nothing happens that I'm not going to pay attention to the bottom CH 2 that's still there in the final product I'm going to pay attention to the parts of this molecule that seem like something has changed and so I'm going to pay attention to the alcohol water all the reactions I know of alcohols and .period drawing them out but think of some reactions well I know tussle chloride impurity the love that reaction that allows me to make a way to do it tussling leading group you can see that this is going to depend on how many reactions you know and have memorized and practiced with what's another reaction I know about swelling of vinyl chloride as host sealed to period I love that reaction "quotation mark all that puts a chlorine and I noticed now already thinking well there's chlorine to my product right there unfortunately that leaves me with this H and no way to function so maybe that's the right direction maybe it's the wrong direction and reactions with PBR 3 but there are
only now and I'm looking at that I'm thinking well want of bromine and my final product so maybe that's probably is not leading off often the direct right direction but who knows but I know some dehydration reactions so here here's 1 P O L 3 purity so your goal is to try to imagine every single reaction you know that eliminates particles 3 Imperial avoids some cobble Canon's net was an important part of this citizen reactions and and just kind of listing amount and so maybe for somebody with obvious that 1 of these I can convert in a single step to the final product that made you can see that sometimes these involved 3 4 steps so if I'm stuck here I can't immediately see how to convert this into that or the task into that then oftentimes go now go backwards OK I can't figure out where to go from here so many try working backwards many think of every single reaction I know that put either this chlorine or that chlorine Wells both Korean's at once and some minister OIC of chlorine and right there maybe I could have made their lists and I think if I took this alcohol maybe would help define angle that chlorine down students it I took this alkali treaty with buy new fluoride impurity that would replace the sewage with the chlorine atom or media had something similar here maybe well maybe not so so maybe I hadn't how keen and I added HCl across that Al-Qaeda long and laconic fashion that would give me that so you have to try to think backwards and think that every single reaction you can would put 1 chlorine or the other chlorine but here's 1 reaction it's fresh in my mind because we just finished Chapter 10 year bond were finishing up Chapter 10 and that is that if I'd taken out Keenan and C O 2 across a double bond I can actually quarantined at the same time and that's exactly the same thing that I just drew here so I've already got exact two-step synthesis fine where g if I take the out commentary with POC Austrian reappearing Our followed by similar to that and it's a two-step synthesis and there may be 3 steps in the cities that you could get to write the star of what's at stake an example let's suppose I took this PBR 3 and then I eliminated that this would be yet another way you could have made it you could 1st convert the alcohol call into an alkyl bromide and then doing elimination reaction was some kind of side here and I'll try to pick a bulky 1 because I wouldn't want U.S. into it that centers all take on tasks in 0 minus the booklets to draw TV talks like this so in
theory could also not like this to make the algebra mind you do need to elimination and then you take that treated with chlorine and get you there there may be longer syntheses count all those correct as long as each of the individual reactions efficient sets an example of how to approach multistep sentences and you can see how important it is to know lots of reactions To know lots of reactions and practice with lots of reactions again was that of the students disconnection here the G-8 have made this by having HCl across the double bond ,comma OK let's take 1 more example distant should get a little bit of extra practice so that's how you approach these multi steps and this a problems again there will never be anyone step free agent that allows you found that allows you to but To do those kinds of problems you will always require multiple steps and real chemical reagents not age plus that's that's not a real chemical what usually the wording I put problems sets and exams suggest they just a series of steps and reagents to efficiently carry out the following transformation underage steps here that the it's clear that I'm not asking you a single reagent that there's no 1 step will do this and of course when drawing this out I I don't necessarily have to make it easy for you I can spin it around a little bit just freak you out right and it's not because I'm being a jerk but that's just the way it oftentimes when you're looking at how to solve the problem the problem is not presented new in exactly the way you memorized you have to be good at orienting molecules reorienting them in your brain so obviously these 2 carbons here are the same ones from him you and so were back at this this kind of strategy had we I we do this maybe you can see right off what you're supposed to do 105 reactions about
and you do too we just finished talking about finding reactions of Al-Qaeda sold immediately you should be able to sit down and write 5 different things that you could do with that Al-Qaeda cost when I look at this before I started drawing of those 5 things I would tend to look over the product and say you know I only know so far 1 reaction to make epoxy what I know lots but you only know 1 reaction to Nikopol' oxides so when we start that way 1st and the reaction that you know over how to make a pot sides is to take a halo on the London
Stock Kenya because that it's almost invisible vessels and reaction you know that apart is to take and I'll make this clear that it's supposed to be the take some sort of a halo and it can be hydroxy in Bromide about dropping glory and to treat that with sodium hydride that's the only reaction you have so far learned sodium hydroxide produced the alcohol and then snaps shut into reaction intramolecular kind of and to on to make a boxer 1 home free now because I I started off at the end because only knew 1 apart said reaction it made more sense to start off at the end so now it's kind of easy it's as I look at this yeah I know lots of things that I can do with our team but I can immediately see there's 1 region combination that in a single step will give me this promo Iger announced the addition of B the R 2 In what and if you had started working in the 4 directional problems but maybe you just couldn't see where to go and see you draw these other things out maybe you're really excited about this kind of oration in this this tends not working for and so maybe you started drawing out all 5 reactions in history saying well Maureen that's OK do an extra stuff out and interviews it's that awaited in alcohol least that that's an oxygen atom molecule but would leave the southern region substituted knew would be able to make a rain so again you know 5 different reactions 1 2 3 4 5 use it it's helpful before you start drawing all these reactions ought to look at both sides of this synthesis starting John product to fear may be it's simpler if I work backwards OK so strategically that's how you should approach these multistep synthesis problems but that's all for Chapter tendinitis this is
what will be on our exam on Friday exam on Friday will cover chapters on 9 10 on we have another election coming up on 11 and I'm going to say a little bit about all kinds just to get prepped for that but before we we walk away here but that's the end of the exam each year the exam on Friday not cover all kinds of things so it's a something about our conferences our next because all of the beginning of chapter there's a certain general stuff thank you some cool stuff about kinds but most of it is not the kind of questions that I put on my exams and you're still expected to know those things because they they give you some background and I just posted these lecture notes online and I found so I realize that many many of you don't have these things printed out to write some stuff that's OK because we're not going to do very much OK so chapter Chapter 11 that this and all this stuff would double bonds now
Oregon into a bunch of stuff with triple once and it's the same stuff it's the same stuff we just finished 10 same reagents and the only trick here is that now that the there's to double bonds and all kinds functional some missed by just contrasting some bonding in geometry on in allocating Keynes in all kinds of just good out out cane or and just remind you of stuff that I think you may already know so there would be a prototypical arcane functional group showing up in various cities but I want you to home in on is the fact that this as S P 3 hybridization the soldiers bonds you can think of is being made from 3 parts the recipe is 3 parts orbital 1 sort on and that key character tells me something about basis in nuclear felicity of electrons so when you look at the angles and sp 3 hybridized allocating functional requirements ,comma its 109 . 5 degrees were 109
. 5 making difference there is no denying is not well drawn there we go and that interest that come within Ltd curve so if you have an Keene New jobless the bonding arrangement on them I'm trying very hard to make diesel good nice 102 degree bond angles all of these models here here here and here in green they're all about 120 degrees "quotation mark so there all about 120 degrees in each of the carbons and now out he was S P 2 hybridized things but finally with this chapter is about this chapter you can see what's happening is the angle is getting larger as we increase the amount of this character we throwing so there's is my kind functional groups and now the bond also for the for the bonds attached that carbon 100 and I hope it's obvious 180 degrees there's nothing you couldn't have figured out just by looking at the list as the hybridized carbon this is going to be the focus of this chapter on what's what's happening in general there's something that's happening that you can see on that maybe I can just try to distort this so freakishly distorted so that you'll remember what's happening here with with key characters the more pink characterized I used to make these bonds the longer those bonds are so if you look at the bonds allocating carbon like this the bonds along when I when I use a little less P character the bonds get shorter and then I didn't do a good job here on the bonds to 1 S P hybridized carbon a really short shorter than the other 2 I'm not doing a good job of really distorting the but I want you to remember so that's why I'm making it so crazy distorted area so now hopefully looks at the Elkind both on both sides the single bond in the trip along those bonds are much shorter on the other kinds leasing the Tennessee a much shorter time it's a little shorter but that little that little bit of a length difference here is huge in terms of reactivity focus about the implications here for for chemistry as far as the bonds on His 1st the bond length is the overall some of what's going to happen said 1 of the I'm contrasting at that an Al-Qaeda alkaline so they good draw out and this just try to imagine a money-making look kind of long here because the analogy to try to remember this impact of bond lengths is my house keys and over here I'm going to join our time and I'm purposely going to make it look really sure was pure models are right next to each other making a really strong 5 on a pair of really strong advance forces might help ease carbons are like a mile away from each other and the pure vanilla trying to reach over and there just not quite regional the way over this would imagine some sort of electrical comes close to each 1 of these pies systems so hero drawings and Ajax doesn't matter what taxes could be bromide or chloride that's just imagine what we should expect as this Al-Qaeda attacks that electrified and they can be br to it could be boring because this is gone down neared because this hulking bond is longer at the time what that means is that because of this this bond is longer the PRI electrons on the pipe behind is not as strong and what that means is that the pipeline is more reactive it's intrinsically more nucleophilic and basic and that's an effective on like nothing more you don't need to know anything more than bond linked to know that the national interests that these pilot transfer this very nice I In the bonds just the right length here the orbitals adjust overlap
in making a super stable pipe bombs and then dangle the same electrified above its all-time high bond let's imagine coming in that attack and working on initial you guessed look at all this electoral process one-of-a-kind violent but the end result of this Of this shorter bond with them and control that green is is a shorter time longer piled on this and because of the shorter pipeline it is less nucleophilic and let's face it so that's the effect all you needed to know is that the bond lengths at different and you could have predicted so that's 1 effect of the outcome now it's taken a completely contrasting effect happening but he would draw out kind of a John so we can try to imagine what's it like From electrified to approach this without the use of the the conservation of on faced every Ltd nothing attacks from the side where that were the alkyl groups sticking out it either top creative and those are the only 2 choices Fleming label 2 phases things can attack from the top down so the double wanted edits electrons or things can come in from the bottom and those of that said
without choice number 1 choice number 2 but now that try to control that an alcohol and I'm going to try to make this look really wacky in three-dimensional here like were it's really coming out of the water area well I look at that time stylish With 3 D glasses the whole point here is within alkaline and this is hard to imagine what it's like a cylinder of electron density electoral whilst can approach from every single possible orientation from another In attack the side on the other side of the time the bottom line the squadron over here the attack over here there is no limit on to the orientations of which you can attack and all kind of on triple by Regina Tabcorp Ivana outcome so there is no talk of everybody can attack from all directions and I hope that you can see in addition to that there's fewer substituent a macabre outcome How concept to substituent Sunyich each Carbonell kind of only 1 so intrinsically and how kind is less hinges and so hard on this matter but the on the 1 hand up here I told you that kind triple bonds or less reactive because the bond insurers but the number low I tell ye all but it's less hindered and more accessible yes react so the Pinelands themselves less reactive but the overall functional group is left-handed so as a result those kind of counteract each other as a result CC double-bond CC bonds or about as reactive SEC trip along this this symbol of the was something happened with my father that supposedly a triple behind their CDC triple loans so this is confluence of 2 contrasting effects Al teams have more nucleophilic private he endured all kinds have less nucleophilic firearms bitter but a less on so as a result of that people but the same reactivity so that's why all the same reactions we just showed in Chapter 5 we're getting ready to do all those reactions alkaline and is going to be some subtle differences because obviously if we take the electrons away from 1 of these cartons we're going to leave behind on the Cook of very strange-looking Koble cattle but this is what we're going to be doing starting on Wednesday's election minister running through the same set reactions a case over again remember to an exam on Friday and you need to be studying like crazy hopefully that this weekend studying like crazy about the problem said Sabine homework problems for Chapter 10 is due tonight this because we just finished the electorate can also make sure you finish that on
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