Lecture 12: Addition of Borane

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Lecture 12: Addition of Borane
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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: 00:09 - Addition of Bromine and Chlorine to Alkenes 07:43 - How is the enantiomer formed? 13:11 - Important points about halogen reaction 22:52 - Regiochemistry in this addition 29:14 - Addition of Borane: Hydroboration/Oxidation
Area Computer animation Halogenation Reaction mechanism Addition reaction Lactitol Chemical reaction Chemistry Columbia Records Chemical reaction
Bromine Computer animation Brauwissenschaft Chemistry Stuffing Carboniumion
Ionenbindung Calcium Setzen <Verfahrenstechnik> Reaction mechanism Columbia Records Chemistry Chemical reaction Ammonium Havana (film) Halogenation Hyperpolarisierung Colourant Mortality rate Medroxyprogesterone Metabolom Wear Essig Agar Bromide Carbon (fiber) Ethylene-vinyl acetate Chemistry Carboniumion Lone pair Scanning transmission electron microscopy Computer animation Functional group Pipette
Chlorofluorocarbon Left-wing politics Chemical bond Quantum chemistry Atomic number Chlorine Chemistry Chemical reaction Ice Molecule Electron Halogenation Dichloromethane Polonium Library (computing) Medroxyprogesterone Doppelbindung Chemical reaction Addition reaction Freies Elektron Rosenöl Medical history Famotidine Ionenbindung Bromine Reaction mechanism Mantle (geology) Hydroxyl Columbia Records Ammonium Active site Monoamine oxidase Metallmatrix-Verbundwerkstoff Metal Bromide Starvation response Rearrangement reaction Carbon (fiber) Mutilation Chemistry Carboniumion Water Hydrogen Computer animation Functional group Solvent S-Adenosyl methionine Atom Ring strain
Epoxidation Ionenbindung Chlorofluorocarbon Reaction mechanism Hydroxyl Set (abstract data type) Collision Acid Sodium Chemistry Ammonium Solvent Hyperpolarisierung Halogenation Tin foil Active site Oxide Atom probe Reaction mechanism Bromide Concentrate Starvation response Walking Minimale Hemmkonzentration Carbon (fiber) Kohlenstoff-14 Chemical reaction Chemistry Water Lone pair Hydrogen Connective tissue Computer animation Addition reaction Functional group Hydroxybuttersäure <gamma-> Chemical compound Can (band) Chemical structure Methane Thermoforming Pipette
Ionenbindung Bromine Resonance (chemistry) Carbon (fiber) Hybridisierung <Chemie> Kohlenstoff-14 Wursthülle Chemistry Water Computer animation Electron Resin Chemical structure Electron Biomolecular structure
Operon Finings Alcohol Atomic number Chemical reaction Tiermodell Halogenation Colourant Borane Waterfall Redox Resonance (chemistry) River source Chemical reaction Alcohol Electronic cigarette Addition reaction Molecule Tetrahydrofuran Thermoforming Sense District Ethylgruppe Biosynthesis Bromine Hydroxyl Hybridisierung <Chemie> Columbia Records Methylgruppe Ammonium Methylglyoxal Ageing Magma International Nonproprietary Name Setzen <Verfahrenstechnik> Sodium chloride Kohlenstoff-14 Chemistry Carboniumion Amrinone Ice Hydrogen Gesundheitsstörung Computer animation Acid anhydride Functional group Anaerobic digestion Sodium hydroxide Boron Electron
Übergangszustand Lebensmittelfarbstoff Boron Fluorwasserstoff Operon Chemistry Chemical reaction Electron Hyperpolarisierung Addition reaction Cobble (geology) Reaction mechanism Hydride Redox Doppelbindung Walking Elektronenpaar Chemical reaction Alcohol Hydroxide River mouth Acid Addition reaction Molecule Tetrahydrofuran Cobaltoxide Lymphangioleiomyomatosis Thermoforming Biosynthesis Ionenbindung Reaction mechanism Chemical plant Hydroxyl Hydrogen peroxide Wursthülle Lewisite Acid Columbia Records Ham Functional group Ageing Elektronentransfer Faserplatte Mixture Mineral Oxide Peroxide Darmstadtium Carbon (fiber) Protonation Kohlenstoff-14 Chemistry CHARGE syndrome Alkene Hydrate Water Heck-Reaktion Hydrogen Computer animation Functional group Sodium hydroxide Boron Electron Hematopoietic stem cell Base (chemistry)
Curry Ionenbindung Biosynthesis Lebensmittelfarbstoff Boron Reaction mechanism Sunscreen Operon Chemistry Grade retention Chronic (medicine) Chemical reaction Hydrogen Molecule Functional group Ameisensäure Oxide Mixture Redox Starvation response Walking Carbon (fiber) Kohlenstoff-14 Chemical reaction Chemistry CHARGE syndrome Hydrogen Computer animation Sodium hydroxide Molecule Orlistat Horizontaler Gentransfer Sieve Cobaltoxide
right let's see where we left off I sold we my dinner last time Millard Madam from inNational keen cannot go through Carver Academy Iowa intermediate we look we learned that because of this experiment right here we you run this experiment and you didn't reaction with bromine it there was a common Caroline intermediate you would get on tight and this is in addition that we don't get seen edition so it means that our proposed a mechanism that we came up with on the previous page is incorrect because it was correct to naked ,comma Qatar were going against imports and soldiers that we only get in time you need to remember that so back to this area centers were really getting into Mir's Romans on opposite sides so the entire edition so let me show you a mechanism that is consistent with this ,comma steer chemical output and I think I don't know why did
that weird stuff moving around so you got that right on your page so we're just going to keep going to what we talked about was in the vicinity of the pipeline that's something a little crazy that primarily want gets some polarized and so on so what's going to happen is it I will probably have to redraw this down here could you not prevail see what happens already dropped down here and you can it'll look good on your page Our excellence redraw lies at doing that OK this try that again no I
don't say installed come on now right now we've
got we're already we can have this happen again right also look at that OK so I have to
redraw this you don't I think it's designed to be spaced out because things got worse growing right didn't realize it would do that are right so we a polarization of the bromine bromine bond all boy hiding leave enough room for this but let's work on this year's OK of metabolome Perez on this bromine on 1 of the lone pairs on this sprawling so go ahead and add already have that on their and our money in a different colors so we can see what's going on a little more clearly here this pipe bombs going to attack this bromine Oregon a break the bromine bromine volunteer here and then 1 lone pairs on this growing that's closest to the AL team is going to come down and attack on the other side that's what the Aero pushing should look like so basically what we're doing is we're adding an extra arrow to the previous mechanism that we were proposing and what that does is when you do that now I get to go back over here it makes a new function group that we have not talked about it's called Aber ammonium ion I'm initial starting to keep stirring chemistry here of the Alpena right tilted the opting to make this a little easier to see alright so this is a this is what we call a cyclic for ammonium ion or you can just call the ammonium ion on so this is a cyclic for ammonium ion and so then what's going to happen next is the bromide ion that we just have to leave here on the 1st day of the or minus it's going to do backside attack and just like what we it's in what's going remind you of his inner Parkside bromides gonna do backside attack and so on have vinegar inversion of configuration at the carbon being attacked I'm going to have relied on Communion attack from the opposite side on the landing on the
left-hand side so boom is going to come here and have a attack on the left-hand side with all sides are equally substituted so it doesn't really matter matter which side we attacked on all sides have methyl group and if you're able to draw Osteria chemistry from a Parkside so this will be very easy for you so the bromide comes in from the opposite side story of the hour here we're going to have the are here on the left-hand side the hydrogen moves up but it's still going back on the left-hand side the metal also moves up will just you and me here and I'm on the right hand side it stays exactly the same so overall that's inversion of configuration some students are still having trouble with why that's inversion and all we did of course was to move this novel up in this hydrogen up but you can see that it's in Virgin because I'm in this product right here and abroad means on this site and over here it's on the opposite side so that is inversion just like converting neurologist like we did with into reaction back in Chapter 7 and so on that mechanism accounts for the fact that we get an entire edition only we will also give the name there's not there's 2 ways you can from the here will show you both ways that we on the next page interest Bromby comes in from the bottom let's see what that looks like so we have still tilting the opting to make history chemistry a little bit easier to drop and so we can have a brolly in command from the bottom instead we had the brawling coming into the talk is remembered this emptiness plenary and so the Roman concluded from the top as we show the previous page you can also come from the bottom so that's what we're showing here so this would give us another opportunity to practice for mechanism for this reaction Serbian attacked the sprawling we're going to
break the bromine bromine bonds and then 1 of the left and 1 of long Paris from bromine I usually just do whatever is closest goes right here and attacks the carbon on the other side so very very very reminiscent of a pop sites so there's your cyclic polonium which has a positive charge on bromine and that's going to behave exactly the same as appropriate Parkside in Italy have relied on income and check on the left-hand side again so that's what I want to get the to another way programs including an attack from the opposite side so I always start the incoming group summed in the plane and then that makes it easier to draw the steric chemistry here there's a hydrogen here's the Mathilde hydrogen here there's the Mosul so that's Union sure that's 1 way to get the unions were the other way to get the manufacturer is to have bromine attack on Jarvis ceremony in mind we did on the previous page but have bromine come in from the right hand side since this is equally substitute on both sides there is a 50 per cent share of the bromine spin tackle on the left-hand side and there's a 50 per cent chance it will tack on the right-hand side tackle the left it can tackle the right from this 1 here so I had this coming in on this side we can also have a coming from the opposite side so I'm going to redraw the bemoan Eli on from the previous page summary should have a formal so from the previous page and then I can have relied on in coming in from the right hand side we break occur Romine politic electrons of quantum bromine and will look like this hydrogen going back just moved up a little bit Neville coming forward just moved up a little bit over on the left hand side we have the on the top and we have hydrogen going back and Nestle going there this tour the same they don't look like it there but they're the same that the sensory countries the entrance of the 1 on the left I guess they do look the same note that it's not obligated again following differences are only in of appeared exactly the same molecule so that's the way that we would show the mantle of UK questions anybody I 1 Want about how information like a knockout retain all the objects are satisfied in the bemoaning a mind of ammonium mine has considerable restraint however and there is a positive charge on the bromine atoms so this is a reactive intermediates unstable just like that ,comma carriers and stable this is also stable because the program is not form his reaction no rearrangements are seeing not forming a copycat account solving can because the steric heresy tells us we know we can't recover kind the product results mysterious selected and tied dish into the double bond reaction does not work with F 2 it reacts explosively nor with I to it's thermodynamic unfavorable so we're really going to see this mostly with bromine or chlorine the rights of the or L to only if the reaction is running water rather than methylene chloride in different product is obtained as the major products let's drawbacks so we got to possibilities let's see where we get those 2 possibilities from ah notice this is not and this is no longer a symmetrical is it the previous example Wintermantel on both sides this is no longer symmetrical we have 1 group on the right and we have to our groups on the left so let's look at what our possibility what we reforming we use bromine and standing in water rather than in a solvent is we get a Bromo hydrants so bromine 1 carbon hydroxyl on the other there's 2 possibilities here hydroxyl on the left hydroxyl on the right so 2 possibilities hydroxyl on the left on the right and parishioners we would get so those more possible products here study this person insurer this plus interest and when we actually get in this reaction we get only this product right here closets in ensuring we don't get any of this and this is called a Bromo hydrant Rome over the bromine in hiding for like duration for the hydroxyl alright so this is going to be alone we had
explained that result away were also uniform of ammonium ion in this reaction just exactly like just when you go with regular Bollywood in form of ammonium ion In the 2nd step rather than over modern bromide attacking mortar attacks instead when it's otherwise it looks the same so if you think about it we make the ammonium there are 2 nuclear files president 2 of those present they attack that ammonium ion there is water and there's a bromide ion if the line I and opens up the Parkside you get a died Bromo compound if water open up the park site if they thought the Rome II and opens up the Ramon EMI on you get a dive Brummel compound if water opens up the Romani mind you get a brawl hydrant since it was since we're using water as a solvent here the concentration of water is much much larger than the concentration of worldwide since a H 2 0 is a solvent concentration of H 2 0 is going to be much much greater than the concentration of bromide ion so the nuclear file that's going to be mostly attacking is on the question draw that line will fix that what concentration here so that means that collision with the water is more likely so therefore grow hydrant is the major product even we have the possibility of forming a visible dive reliably don't tend to get that because we've got so much more water from their life here so lighter is a major problem so let's draw the mechanism for this and what really similar once again further To help us was staring chemistry and then it toppled the so it's perpendicular to your page and we still have remained coming in and we're going to still be a polarization of the bromine in the vicinity of the pipe so the pylons been attacked we're going to break the bromine bromine bonds and 1 of the lone pairs remaining on the closest from going attack ,comma whatever side as convenient as there was coming from the LAT left so I have the air coming in on the right hand side so at along the left going back methyl coming forward on the right-hand side hydrogen going back before coming forward this bromine asked you won't Pearson 2 sets of all pairs and a positive charge and we saw we got the product with the hydroxyl only came in on the most substituted side so that the women a show this the water's coming in on the most substituted size at reminding you of something yes just like impregnated apart side in this is going to behave exactly like a pro needed a Parkside so if you know Europe oxides on this is going to be easy mechanism for you so we have water here coming in Romania's and tied to the water that just came in staring chemistry on all of the groups attached to the Alpena stay exactly the same so that'll still going back still coming forward and then in the last hour waters Kennedy programming the lighter so if I put this mechanism on the test which I have many many times in the past it's a possible mechanism on the non returned to if I put it on the test I'm I would only have you show the mechanism for forming 1 in Incheon where you don't need to form the other 1 if you don't do it once you know I'd do it again and there's no reason for you to do it twice OK so but the question is when will happen we get the Indians were here as uniformly naturally have to pursue started with a cardinal reagents everything's acquire will you have to get permanent insurers hardly get the onions you were here so we certainly can water attacking on the other side to get the ensure because that's we don't get any water and outside yeah yeah from command from the bottom that's how we formed the union she on right plus III the arterial comes in from the bottom Our so this is
very similar to appropriated the Parkside ends we explain why we get this Regio chemistry and explanation is still just like the explanation from the Parkside alright so let me money just isn't just a jog your memory so if if you I'm crammed the day before the midterm you forgot this already taken you only get 1 if Ukraine the only retain like 1 5 per cent or something OK so recall its competitors I want you to say I want everybody to see the connection here so when we have a permeated of Parkside and I said this is going to behave just like approximated a side water came in from the most substituted side hopefully you did that on your chest so this is looking just like that and what we have in common is we have a three-member terrain here that has a positive charge on it so this is old here so that we had water and then in the last step we had a DUI deeper meaning so hopefully you will see the similarity here we the 1 to dial OK so I can enact was so we went through an elaborate explanation for why that happens with the top sides what we did is we drew residents structures for the probe needed the Parkside and we saw that there was more powerful positive charge on the carbon that was more substituted really use the same exact explanation here Blairite so 2
possibilities were doing something a little bit unusual here were breaking signal bonds which we don't usually do and were drawing resident structures by is legal as long as all Adams stay exactly where they are just moving electrons it's legal so that would give us the structure right here alternatively we can break the bond on the other side if we do that we get the cover pattern on the right hand side and so then what we did was we drew the hybrid of the 2 best so we took this 1 and we took this 1 and I was embarrassed because this is a tertiary cover Academy and here this is a secondary credit so on there we do the higher-end so that we have a hybrid here and we just to die but of the 2 best and so we have a dotted line right here that's a partial 1 we have partial positive on the bromine partial positive and we have partial positive here and so the nuclear file out in this case only the files and water water spin attack on the most electron deficient carbon so that's do here just like this spin attack on the most electron deficient carbon then again this is the hybrid but the 2 best resin structures are in it turns out that and when you
have 1 symmetrical of Keane and you're just using bromine bromine without water same thing happening is thinking is happening the nuclear file is attacking on the most substituted side it's just that we can't detect it please could detected because since both bombings in the city status delivered to his head back reaction but but it's a hydroxyl we certainly can't sold also saying is is that when we have and on symmetrical team which we do here we're still going to form of ammonium ion so what have the ice appropriate here going back and would have hydrogen coming forward we are still attacking on the most substituted side it's just that there's no way to detect that since both Adams are going to be the same questions on rumination anybody yes Oh yeah that's like so-and-so reacting differently now that forgot that on this what is it on your version is that a hydrogen and this is the NFL change back to an Apple methyl ethyl Apple think you so much for noticing that because I completely forgot about Sonia version Apple after otherwise when you go back and look at that that's not going to make any sense at all but if the item to the bomber like this 1 are and talk about in Andersen synthesis so we're moving very quickly into synthesis I opened up sapling chapter it's here in the last 10 problems are difficult synthesis problems so I want I want I want you wait until you're ready to go with those 10 problems and you want a really honestly try them if you get stuck trying to get help rather than I know what he do guys go online to find the answers on Facebook page likeness of mice mice and filled me in on all of us so that that's not going to help you because it's something that you need to be able to understand on your call and if you don't understand it you're not going to understand it on the matter when it's slightly different itself I will get that at the end of last month limited to it today but I want to talk about acquired operations of probably Friday so you may want to wait until Friday just to do those last 10 problem welcome additional worried so boring is another waterfall that adds to help the when edition is complete you add peroxide in and the boron is turned into a hydroxyl so this is another way to make alcohols the difference with this not granted is there were rehydrated now keen we we have a mark on accommodation when we use either operation it's what we call in time Marconnet it's the opposite Regio and so both of those reactions are going to be really important to us and said this is because sometimes we want the hydroxyl on the least substituted side sometimes in 1 of the most so we've got need these we need these 2 reactions to be able to do that our excellence is getting a little background here so what would be
a story in ths and it turns out we don't really worry too much about the story geometry here but this is a three-to-one ratio so we have 3 options for everyone the age 3 and so the beaches in ads the keen and then down in and so then when it looks like it's gonna look so so here's what it looks like I'm encircle the atoms that we just added over in actually when this fine in a market right here the original and Ltd those are the 3 cartons In a mark that right here so you can see that that's the original team and then the groups so we added on Let's circle those ominous circle the first one here what type of condition is that the borrower and the hydrogen are added to the umpteenth it's the same edition and this happens 3 times so here's the bore on the and the and and in that do a different color here for this 1 this is the boron here and that's the hydrogen here say dishes and I'm having too much fun mixing colors here this is there's the boron here and there's a hydrogen sin additional 3 times so that we don't always drawn all out it's a little bit looking all its current spidery and it's not a little difficult to see on this is often written in a shorthand way often written as VSV you here's the hydrogen that just came on here's the boron and rather than
drawing all 3 groups we just draw at once and there are 2 means that there's 2 other groups like that it's a shorthand way of writing so this is our means that 2 groups identical to the 1 shown so this is the 1st step a year is the Hideaway oration this 2nd step and really important that when you do this as a synthesis and your filling in reagents that is separated into 2 steps 1st you do the right operation and the 2nd step is basic hydrogen peroxide and what you get in zone 3 of the alcohols again on drawing enough hydrogen on the carbon where it just came in so what we've done is we've done this season edition of water to the AL Keenan do you see that the hydroxyl substituted side rather than the most substituted side hydroxyl somberly substituted side so this is an on-time mark on accommodations in has the opposite radio chemistry of hydration if you did a hydration then on the hydroxyl would be on this side right near the most substituted side so this is not on our knees substituted so this is an entire work on accommodation fans not going to go off into the papers said just go ahead and do little in there but I left off in Timor chronicle accommodation alright let's look at a temple ,comma reaction creates ths How you make a straight you take me to wait 6 which is a gas in your identity example talk about that in just a minute but that doesn't step 1 step to basic hydrogen peroxide so what I'm going to be looking for leaving you can leave the water off that I wanna see H 2 O Tsuen Wan hydroxide for step 2 and as you can see overall we have edition of the hot water across a double bond after those 2 steps so this is a hydration across the double bond and we can see if we circle the group said just came on we've got this this hydrogen and this hydroxyl seen edition hydroxyl on the least substituted side so this is not our chronicle of his entire comical Will we get an answer here and we know we get so what we said is if you start with things that are a Cairo and all reagents a Cairo when there's no crime influence if you form used ministerial centers in your product you will get a receipt that mixture you absolutely have to come so out Keane is a car this is a Cairo peroxide oxides as a cobbles so you don't get of the Union shorter and we have graduated now we're allowed to write just classy on the test rather than drawing out the ammunition this is because you guys are so mature now I know that you're ready for that big step Be careful what you we'll do that policy because on some reactions don't have an answer so the review right the correct product in the EU in you write policy you don't get any points because you there international and somebody draws the wrong enhanced when they get it wrong so why should you get it right when you write OK so be careful where you put policy some people put it on every single problem and I can cost you said make sure you know what you're doing so the highly regional selected violence serious selected reaction in a colleague of additional water to annul came and so it's opposites the radio chemistry Page 2 Page 3 plus In addition and so and so no arrearages are observed now this is what I'm going to show you the very 1st part of the mechanism I will not show you the oxidation if you're curious as a heck about the oxidation you can come to my office and I'll show you fight so I'm not going to ask you this mechanism on the test you didn't do we need to know this reaction you will this reaction over and over again and synthesis problems so I'm just gonna show you the 1st part of it because 1st some of you it will help you remember why it's in addition case that's why I'm showing you Paul
alright so MBA Teresa Lewis acid and therefore an elective files of eating B 2 8 6 plus is GHF by the way Tetra hydrofluoric steering then you can certainly use the abbreviation for th use th offering new mechanisms now what this is going to do is break apart the beach age sex In 2 ph Story so will will have a positive charge on oxygen will have a negative charge on board and that's equivalent CO on the H 3 . th so that's the shorthand way of writing so what was happening here is born is accepting electron pair from the oxygen atom of th so boron accepts electron pair classic Lewis acid-base reaction From the oxygen atom of ths then what happens such show right here 5 on grounds this hydrogen and when we do that again I myself and part in this particular reaction a we don't have the Bible attacking were actually transferring hydrogen with its pair of electrons so is H minus is that a nuclear flowery electrified it's it's it's it's it's it's it's an electric plants electorate so what's going to happen is and if you look at the polarization response 5 on does not grab the hydrogen the pie bond and constant attacks the boron they and the hydrogen on bond is going to break the arrows coming from Nov . hydrogen on board on bond in a hydrogen is being transferred with it's a pair of electrons so like a hydride so I'm hydrogen transfers this is not a proton transfer this is a hydride transfer transfers where it's a pair of electrons so as each miner this as age minors not age for us I write this is what the transition state looks like again you're not going to have to show that's on the test but I want you to see that how we get hysterical entry here that's what the transition state would look like and if you do this I'm missing my 2nd hero here are my 1st year on missing this like that we have a partial negative charge on board we have a partial positive charge on common how would you get those charges if we did step Weiss if we did it stepwise and we have this bond form 1st that would leave a positive charge here and then the hydrogen is attacking the positive charge pesos that's 1 way to think of it again and you don't need it .period but yeah as you can see and the boron in the hydrogen have to come in on the same side there's not room for this hydrogen to come up here and the board of the appeared allergy geometrically impossible so the hydrogen economy and on the same side and down that's how we get our Sterry chemistry we call this a center transition state but to the transition state looks like and then I'm so so so we have the here's our sin edition and we can see that if we look at the group's adjust the monarchy and on the same side and although we did is 2 times more and that's what we got so that's the height operations .period 3 things to notice a positive charges on the carbon that will lead to the most stable ,comma retiree if we were going to form a Catherine the bulkier BHC trade group is on the
least substituted side so that's a good way Anambra stereo chemistry here "quotation mark the moral on Lee's substituted side so low that alliteration there to help you remember born on the substituted side and unwarranted writer generated the same side of the molecule so it's a sin edition because of the fact that the boat Dearborn is on the lease substituted side means that steric factors are important sorry guys are changing pages page account I a watch that elected and because we have a passer-by was in charge of the carbon that leads to the most able Curry can we know that electronic factors are also important so there's many things going on here In this step to of the oxidation of their variable-rate I'm not say the mechanism again you can come to my office if you wanna see that but let's look at the overall steered chemical outcome because that is very important for us here's the math all years the hydrogen when Lee oxidize we were placed the born with oxygen exactly where the border there's no inversion its retention of configuration so on this bonds going to become an OH so important points about this is that the low-wage replaces borrowing With retention of configuration and Please skip this mechanism I will not ask you hide aeration as the 1st part I will not ask the 2nd part will not have hide operation mechanism you will have to learn this very important that reaction for synthesis you will use it many many times but skip mechanism for oxidation recognition to however I found that
a great starting point will continue this on Friday