Lecture 11: Addition of Water, Bromine & Chlorine to Alkenes

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Video in TIB AV-Portal: Lecture 11: Addition of Water, Bromine & Chlorine to Alkenes

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Lecture 11: Addition of Water, Bromine & Chlorine to Alkenes
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11
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26
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CC Attribution - ShareAlike 3.0 USA:
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2015
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English

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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. Index of Topics: 00:25 - Carbocation Intermediate 06:38 - Stereochemistry of Electrophilic Addition of HX 15:03 - Addition of Water to Alkenes 35:14 - Addition of Bromine and Chlorine to Alkenes
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Radon Chloride Hydrochloric acid Atomic number Chemistry Chemical reaction Ageing Addition reaction Yield (engineering) Sunscreen Library (computing) Active site Molekülorbital Mixture Periodate Mixture Hydride Bromide Walking Rearrangement reaction Chiralität <Chemie> Chemistry Electronic cigarette Hydrogen Computer animation Tiermodell Iron Freies Elektron River Medical history Biomolecular structure Isotopenmarkierung
Chemical bond Growth medium Hydrochloric acid Alcohol Chemistry Chemical reaction Molecule Tiermodell Homeopathy Water Addition reaction Marl Elimination reaction Waterfall Reaction mechanism Doppelbindung Mineral hydration Walking Topicity Chemical reaction Stockfish Death Neoteny Acid Molecule Bromine Medical history Thermoforming Reaction mechanism Sunscreen Radon Wursthülle Acid Ageing Lactitol Sunscreen Aage Mixture Area Flame Setzen <Verfahrenstechnik> Mixture Bromide Starvation response Chiralität <Chemie> Chemistry Alkene Hydrogen Gesundheitsstörung Computer animation Functional group Chemical structure
Methyl iodide Starvation response Ionenbindung Species Reaction mechanism Chemical bond Hydroxyl Alcohol Wursthülle Acid Chemistry Chemical reaction Tiermodell Ageing Water Mortality rate Active site Micelle Atom probe Reaction mechanism Doppelbindung Mineral hydration Starvation response Asset Carbon (fiber) Chemical reaction Solution Chemistry CHARGE syndrome Alkene C-Jun N-terminal kinases Water Hydrogen Acid Computer animation Functional group Molecule Library (computing) Thermoforming Stereoselectivity
Reaction mechanism Mineral hydration Starvation response Chemical reaction Chemistry Alcohol Chemistry Electronic cigarette Chemical reaction Altbier C-Jun N-terminal kinases Hydrogen Tiermodell Acid Computer animation Mortality rate Library (computing) Medical history Halogen
Chemical formula Reaction mechanism Octane rating Mineral hydration Starvation response Walking Chemical reaction Chemistry Solution Chemical reaction C-Jun N-terminal kinases Tiermodell Computer animation Tiermodell Lactitol Azo coupling Mortality rate Zellmigration
Prion Reaction mechanism Mineral hydration Starvation response Chemical reaction Chemistry Chemical reaction C-Jun N-terminal kinases Tiermodell Gesundheitsstörung Computer animation Mortality rate Locus (genetics) Carbokation
Transition metal Starvation response Walking Gezeitenküste Alcohol Chemical reaction Chemistry Chemistry Chemical reaction Computer animation Mortality rate Gemstone Carbokation
Chemical reactor Transition metal Dehydration reaction Octane rating Mineral hydration Walking Alcohol Chemistry Chemical reaction C-Jun N-terminal kinases Computer animation Mortality rate Magma
Reaction mechanism Dehydration reaction Alcohol Chemical reaction Tiermodell Mortality rate Schweflige Säure Elimination reaction Carbokation Transition metal Reaction mechanism Mineral hydration Starvation response Chemical reaction Chemistry Alcohol Alkene Psychological trauma Electronic cigarette C-Jun N-terminal kinases Hydrate Computer animation Functional group Aage Dehydration reaction Screening (medicine)
Famotidine Bromine Dehydration reaction Chemical bond Hydrochloric acid Metabolic pathway Alcohol Acid Multiple chemical sensitivity Chemical reaction Wine tasting descriptors Road surface Gesundheitsstörung Mortality rate Schweflige Säure Delicatessen Carbokation Halogen Hydrofluoric acid Reaction mechanism Concentrate Mineral hydration Starvation response Walking Asset Gene Chlorine Chemical reaction Chemistry Alcohol Alkene Wine tasting descriptors Homöostase Hydrate Process (computing) Temporary work Acid Gesundheitsstörung Computer animation Metabolic pathway Molecule Dipol <1,3-> Electron Dehydration reaction Halogen Screening (medicine) Atom
Lebensmittelfarbstoff Chemical bond Chlorine Jade Chemistry Chemical reaction Atomic orbital Molecule Electron Hyperpolarisierung Addition reaction Colourant Carbokation Dipol <1,3-> Reaction mechanism Doppelbindung Octane rating Deep sea Solution Chemical reaction Molecule Bromine Medical history Stereoselectivity Ionenbindung Bromine Blood vessel Reaction mechanism Atom Halogen Setzen <Verfahrenstechnik> Bromide Acetylcholinesterase Starvation response Rearrangement reaction Carbon (fiber) Chlorine Kohlenstoff-14 Chemistry Alkene Hydrate Taxis Drop (liquid) Computer animation Dipol <1,3-> Chemical structure Electron Halogen Atom
Methyl iodide Metal Ionenbindung Reaction mechanism Reaction mechanism Octane rating Starvation response MicroRNA Chemistry Chemistry Chemical reaction Atomic orbital Hypobromite Dairy product Computer animation Match Electron Hyperpolarisierung Colourant Tool steel Bromine Sieve Baryte
so last time we were talking about age they are additions to our team and we had an example where we could form of primary ,comma Qatar and we had an example where we could form a tertiary Ellie and for many the primary it we just want the tertiary so I'm not question here is what happens when 2 approximately equal macabre kinds of so this is what I mean here this example right here where we have and on and after 1 1 side and another 1 the other but also science are model substituted right if we may have reformed Inc ,comma Catalan underside reformers secondary ,comma can if we formed the cover Cannon inside the secondary ,comma can so there are approximately the same but not identical so let's go through that right now would have error going right down here let's Strother 2 possible Carver Academy in certain ever high jingles alongside her recounting those on the other OK and or informed and the hydrogen you go on the left-hand side ,comma can will be on the right hand side and and the problems is both secondary so you got to secondary car Caroline's misses a secondary Carver Catherine and this is a secondary current In the 2nd step bromides and I'm going to attack so in bromide attacks here when they go here just like that Oh bromide 19 attack this provocation in any will do both and end because those uncover cancer-free much of not exactly the same but very very similar to our inner probably get approximately equal amounts of both on products OK so let's try the product there that's productivity 1 and then the product number 2 under the bromine cynical in the and we get about approximately 50 50 mixture here are right so and many of the really big difference between the the 2 possible sites where we can proud made of many get just 1 product we have 2 that are about the same we're going to get a mixture of both products so important .period because the intermediate distractions a cover calendar always have to watch for rearrangements especially in the secondary carrier and so here's another example this would December using hydrochloric acid so let's just go through this year there's originally formed and secondary ,comma can and should always be alert every secondary ,comma accounting to rearrangements and so if chloride a lion attacks that have a :colon unlike initial arrows to that when show different heroes for their for the rearrangement of but the other thing that can happen is that we can't get a 1 2 hydride shift that's going to be a beneficiary arrangement because we're going to go from a secondary Carver Qatar into a tertiary so 1 2 I'm hydride share after 1 too hard drive rearrangement so here's our 2nd possible Carver definitely more stable it's label those so here's a secondary ,comma then we go to a tertiary which is definitely more stable much more stable and so then if chloride iron Texas needed the tertiary accounting reform from were always going to be on the lookout for cover tenants yes we I like to think so what we don't label it from where it is and we just mergers we're just looking at those 2 2 atoms so they could be 100 chain and with so-called 1 to articles that history chemistry of Ajax edition that's 1 of the things we're going to have to know
in this chapter 2 factors important Lincoln considers sterile chemistry of to fill condition rejects to the number 1 thing we have to remember a Cairo reactants sealed a car or a scenic products so we can take in a car reacted in and out and form of car rescinded products when everything you're reacting as they can in order to form a single in history you have to have some Manantial America we have to have some on something here that has this Kiraly in the reaction medium to do that so I'm a chemical reaction of a car react Insulza car product a product with the hysteria center the product will be overseeing the mixture automatically and so we are starting a new start with enough Keane that doesn't have any stereo centers it is a car and a car mechanics repertory agents from the top or the bottom with equal probabilities so let's look at an example here definitely starting material near a car HBO are a car if we go through that addition we see that we form of Tyrol products we have a new stereo censure right here so if we're forming a new stereo center and we have no Cairo influence at all here Everything is a it's reacting that means it must be rescinded mixture are so and this is easy to see if you consider the mechanism so let's considered the mechanism I would actually draw this how keen rather than flat on the page and then a tilted like that it sometimes makes it easier to see the product stereo chemistry some disconnect instead of being flat on the page and then it just tilted back this so from your perspective it will be flat analytical like this so that means I'm dead molecules delegates it's that's a little bit strange way to drop stockings but it works here I thought I found this really helps students a lot when coming up with the Sterry chemistry for these fees ,comma these types of reactions so it's just like that so on a Kiraly plenary correct an Aragon react that with each art analysts label will reactants a car or player and age is also are in so I was going to do is among Fulmer ,comma Council I'm going to find that out the hydrogen on the right-hand side to make the most stable ,comma Academy so this will look like after that and then over on the right hand side this Ethel is going back her molecule was still turned this hydrogen is coming forward and then actually in the plane of the paper is that on hybridized to your relieved get from that Cobb account so as you can see we learned about the structure of the Aqaba Caroline in 51 areas still keep using that every all year long far-right so on and so that means that that communist later to end it has appeared on the topic has if you on the bottom and that means that the when the bromide comes in it can attack on the top and working attack on the bottom half the the time it'll tackle the top half the the time will check on the ball so there is coming from the top here it is coming from the bottom let's draw the 2 products that we get if it comes in from the top would look like this and I'm on and whatever I idea drawing an incoming groups on in this chapter I always draw them in the plane then it's a lot easier to see for you to see what happens I encourage you to do that to prison your answers will know right away if you're getting something right or wrong because it will match what I'm doing alright so that would be if it came in from the opposite side an ETA came in from the top if comes in from the bottom with straw that product so incoming groups I have the flame and um groups that are on the team I have it dashes and wedges so let's look at what's happened here we have this is it this is the incoming hydrogen we added in the 1st step right there and so circle that hydrogen from for both of these vast the backing came from here that's this hydrogen right here and now the roaming came in here from the top and hear the bromine came in on the bottom so on this 1 here the B or the hydrogen but on opposite sides we call this an entire edition I need to know that terminology In the 1 on the bottom the bromine in the hydrogen have command on the same side analysts in addition so those terms are not new to you remember in the amount of the 2 elimination and has to be antiterror acquainted so leaving group and the bromine have to be on opposite sides and we also showed youths in addition said that that usually doesn't take place and will take place in this class so that terminology that means they just coming on the same side saying for St. an and tied for opposite sides Our questions anybody but they said
that this year different d edition we know the mechanism and we know this very chemistry which addition let's look at additional water to all teams it's very similar to HBO when water is added to an no reaction takes place because waters not elected Philip enough to add to the Al-Qaeda double bonds so we have to add an acid catalyst but generally H 2 SO 4 or a hydrochloric acid and I don't usually use hydrochloric acid because that usually throws you often makes you think of other reactions long I only use H 2 SO 4 I use a H 2 S 0 4 H 3 0 plus those are the only ones that so if you are a catalyst than you can actually get drew water to add across the double bond case and it turns out that the only at the only acids that we read that can be appropriated buyer I mean that they can was
a Proton to apply bonds have negative the case so must have negative and that's a must for this reaction takes place so we start with 8 yards fears of the gambling in my 9 something like that alright so here's the wears reaction here to answer for catalytic we also have water as a reagents and then I'm going to do what I've been doing already before where I'm going to draw the skeleton and then I'm going to show you workers just came write so we have a hydroxyl by the way I'm not trying to show chemistry here we will talk about Stary chemistry this reaction in minute undiscovered try to show you what's happening here each of the 2 groups that just came right on here the these are hydrogen goes on the lease substituted carbon to get the most stable Caracalla Water this attack the the most stable ,comma cannons so the hydroxyl is that the most goes on the most substituted carbon so very much like HBO addition greatly vision that jingles on the substituted side and make them more stable ,comma can bromine goes on the most substitute sites it's exactly like that so distracted Regis selective and falls are more general form of work on a cultural tradition of an answer magic electrification to a double bond major product comes from the more stable lower energy ,comma Cannon in the face of that that that that more general Marconnet proper rule allows us
to use it for more than 1 reaction alright let's go through the mechanism so this is not possible mechanism for mid-term too make sure you take a look at your mechanisms a lot of people and we're leaving off along Paris and charges and those cost those constant points he got a really watch those charges and peers look and leaders hiding I'm going to use age 3 0 plus in my mechanism rather than H 2 SO for and that's because I know from GE camp H 2 0 plus H 2 SO 4 essentially completed different all strong acids essentially completed their probe when you put them in water and since dilute acid I know that my mode the most common asset I haven't solutions H 3 0 plus an adjuster for minus but the equilibrium very strongly favors under the high drawing a line so this is the species I'm going to use all right so inappropriate that I under probably the pylon remember to properly pylon even at peak in an acid with the PKK that's negative and so I join you mind definitely fits that bill I'm also going to something
different is reversible errors for this reaction box so I make a ,comma account and I'm not attempting to show in history chemistry here I want to make the most substitute Aqaba so that means that the hydrogen has to go on the end here so there's a hydrogen that I just added on in here's my secondary Carver Catherine Water comes in attacks just like that so served so after the 1st that of looks like it looks very similar to adjust the as and when reaction right justness and 1 the only difference here is that we're getting the curb account in a slightly different way it has and 1 we get the coveted by the by the halogen leaving here we get the car :colon by adding acid to the Alt all right and then we have to have happen now is we need a different made to make the alcohol so there's our secondary alcohol
and we also have regenerated catalyst ceiling well tiny amount of acid here for this to happen so we started off with a
majority model this is a regenerated catalyst alright couple things important points about the
knows that the 1st step of migration ,comma cannons is the rate-limiting step so far in the reaction were before the ,comma Karin formula ,comma cannons the rate-limiting step is the because of is the rate-limiting step the rate of reaction is increased when the rate the step is increased so that means if
you add up the linking it to the restore occurred but not but bad kingmaker make at secondary ,comma time orders magnitude on fast so therefore Elkins therefore more stable car academies will undergo the reaction faster How much faster Let's take let's take a look at these guys here the best ,comma carried conform with the 1st King a secondary or tertiary so this 1 when you prune needed it forms a tertiary Carver can the 2nd 1 on when you brought me the best cover can you can make is a secondary so we would expect the 1st reaction to the faster how much faster is actually a thousand times faster that's pretty fast OK so we as much
faster just like with electrical condition rejects the hasn't won any 181 reaction whenever cover carries a want her rearrangements that sweet we keep saying that but it's easy to miss so long on 1 when there was a rearrangement and in the mechanism I told you was for arrangement that can help to have another was going to tell you OK so you're right from from here on out you need to know that we're going to get rearranged States to attacks occur McCain equally from
the top and the bottom so we have the same stereo chemistry as a spear edition so that means we get CNN +plus Inside Edition HP are we get since entice edition so that these guys are very closely related as a community diagrams is actually a three-step reaction to 3 months in our current this is step 1 "quotation mark culinary Moreira this is step to and
this last at a step 3 so the rate determining step is the the step that has the highest is the highest mountain that has to be climbed in order to go from reactors to product so this is the rate determining step right here step 1 down we have a catalyst year that's catalysts and this is regenerated catalyst alright fought for 1
inmate notice that hydration and is the reverse of dehydration and alcohol the names are on opposite ends actually the office completely opposite reaction so let's go through this distraction and that we learned in chapter 9 right dehydration so we got whenever you do please make sure you do look at your exam some people don't look at it if they done poorly they won't look at they think they don't correlate they will look at the score and will look at the but when I'm writing the final and I'm looking for ideas to funds to put the final I'm look at old exams all I might if there was a problem that a lot of people missing might put it right on the final OK so it's really important that you do that OK so let's go through this mechanism on the test you couldn't use federally mind could sulfuric acid I believe I probably used sulfuric acid we accepted both answers so it's still pursuing the greater of great this properly you should have gotten credit so we from created the hydroxyl and since it can make a secondary or tertiary ,comma account and that's what's going to happen this group is going to leave notice some easy reversible errors steadily getting elimination are at for both those on the screen at the
same time now because it's on a different page OK
well and if you have both of them on the screen at the same time what you're going to see is when we went in the opposite direction OK the just learned this the reaction we learned in Chapter 9 on the other action that we learn here today was a day Canal keen you've probably made it with Pedro airliners is the opposite in the forward direction going starting from keenly instead of deep rotating froze and then you go to the century meeting here when water attached Aqaba patterns you doing the exact opposite thing every step and in the last step on you have appropriated alcohol and you on different here you probably saw doing the exact opposite thing in every step if you look at the intermediates if you go back and take a look at the intermediate see that we have the exact same intermediates all the way through so same intermediates the same number of steps same reaction pathway but in opposite directions so that means that you could be running this reaction in this direction and you can form on this ,comma guarantee could go back the other way or it can go from this step to this definition is a step and then go backwards they could go here and here this year and they go back years ago back here ago go back here in the back and then somehow go here so all of the steps a reversible so it it's so it's an equilibrium reaction and you're going to have to be really careful fun to drive equilibrium to build the park or yes what prevents the Hallett halogen we don't have any allergens president so we knew what we do 1 avoid that's why it said 1 of the acids hydrochloric and not not uses hydrofluoric acid let's go on the next page here and since latest to the principal microscopic irreversibility of forward reaction and the reverse reactions taking place under the same conditions as is an equilibrium must follow the same reaction pathway not in microscopic detail so in 1 direction or culminating in the opposite direction were differently so we're absolutely have to drive the equilibrium here and so here's how we drive the equilibrium to favor dehydration well let's look drawn-out out what's right out the reaction here it doesn't matter which direction we write it out and we put real plus above the hero too it's just catalyst so do we want the Al-Qaeda do we want the alcohol if we want that out keen we want a favor dehydration and so the way you do is concentrated acid and heat so the concentration of water is kept very low the other way to do this in his arm removed Al Qaeda as its formed that's what you're doing a lot this week so this would be 51 lb this week so how has concentrated sulfuric acid help their reaction to drive to the right will concentrated sulfuric acid is about 96 per cent sulfuric acid in about 4 per cent water so if you have 1 concentrated sulfuric acid you don't have a whole lot of water around if you have a lot of water around you drive the reaction to the left so you knew you have very little water around you keeping the concentration of water to unpaved bright duration of NL team Yemeni used delude assets wiring used alone arson because if we if we freeze the conducts international law order there we derive the equilibrium in the in a way that uses up the wall so for want that alcohol use dilute acid if we want the Al-Qaeda we use concentrated acid and so here the dilute acid is that so that Hong Kong treasure of water is questions on hydration anybody that is a stew edition of
bromine sir following all those addition reactions in order here so halogen bromide bromine and chlorine also add Al Keynes's may be surprising since it's not obvious that Romeo career Electra files in there acting like an elector from this reaction on allergens added to buy bonds with halogen and apply bonds because held Interpol rise the electorate's double bond induces a dipole an approaching halogen molecule making 1 halogen atom electron deficient and the other electric rates in the polarization of that want to Caldera's that attracted to the nucleophilic double bond making addition possible so lonely show you what that looks like and we'll talk about what we mean by this polarization so this is a and actually and back in the day when they used to use chemical tests this was a chemical test for all things you can take it at colorless Elkins and on bromine is a deep red solution I should write met with red tape deep red solution for care and you add in the bromine drop clean it instantly to call arises which means that it's adding to the AL keen your product is a vessel died alive which just means the bromine there and John adjacent carbons now these are new structures on drawing on I'm not attempting to Shuster chemistry here at all OK so what what we get here is rapidly colorization avenues deep deep red here further that Rapide colorization Our excellent based on the mechanisms that winter already talked about in this chapter it's pure addition edition of water you might think that we have a similar mechanism happening here OK and so let's try that with studs postulate here's a prediction something like this so the bromine goes on 1 side reformer ,comma catering just as our our our prediction here and then it was exactly the same as HP on water then bromide on would attack Our assume that seems like about prediction and if we have if we actually were going by that mechanism what type of edition with this year's FA Zumstein and Tiebold they would be both CNN and Thai that OK if this prediction is correct we will get synonyms hydration and what I want when we get if we were forming a 2nd secondary ,comma countering we get rearrangements so really easy to tell this mechanism is right or not because we will that we have to look at the stereo chemistry of our product and littered the streets history product and Arnold tell us whether writer not so that's our prediction error far-right when taxi about engineering you need to turn back but only talked about was the time of the polarize ability here was so amended army others bromine cloud here that you know what should also it later was shown on the next page erected things are
inconsistent ,comma confirmation number 1 there never rearranged products and we know that Rotarians like to rearrange very rearranged to become more stable on the other thing is that the reaction history selective in other words we don't get synonym tight OK and so if you if there was a ,comma Catalonia we know that catamarans Rob player and as Africa's occurs equally on both sides so that means that this cannot be the mechanism so please don't write this as a mechanism on the tests so this means that this news and this be the mechanism all right so let's do an example that's showing staring chemistry so you can see what I'm talking about in
this I was going through the operated on OK so what do we know if we start off with a carnal and we had never aimed at all regions are Kiraly ,comma Lizzie coral and coral everything that means that we have we've organized Arizona you have to have a pair of an interest rate we know that much so they Cairo a car it turns out that we've got to possible products we've got this close it's an insurance that would be the Inside Edition product costs and insurance and we also could possibly have this since plus it's shortages actually for possible products here In his 1st products that would be 2 new stereo centers therefore you will get any insurers and the bromine are on opposite sides so this is on Thai editions are right and then over here I'm bro means are on the same side that would be a sin edition it turns out that we don't get any unseen edition at all we only get inside tuition so big X through this only inside that means that we better come up with a different mechanism Kansas certainly does not match HBO certainly does not have a match what so let's talk about a mechanism here on Monday did the same thing I do with spirited until the came back I'm tilted back and I drove like this I so I had the metals are are both coming at them so this would be floating above your page we don't normally dry out things this way but it says it's OK it's enough just to see this very chemistry in the park alright so that we have this bromine coming here so it's going so far as looking just like the mechanism we predicted that was wrong but see what happens here so we've got this very um electron Rich Pilon I want here right 1 of electron density in a room at the electorate 5 1 this bromine has long pairs on on that ruling so what's going to happen when those 2 and electron rich clouds electron clouds approach each other they're going to repel right so what somewhat so this is very similar to 1 vendor walls attraction so what's going to happen is that bromine being a dairy polarize
it's going to move some electron density to the further roaming so long as they approach it's going to move electron density away so there's less electron repulsion and so what we end up getting there's a temporary induced dipole so this bromine here is a little bit electron density that deficient because we moved electron density to the other rolling and so then this is partial negative and so there is our color color and those are theirs are polar Elektra filigree agent didn't look fuller in the in the the 1st is OK so I'm in understanding the let's write that down in the vicinity Of the pie electron clouds the bromine bromine bonds becomes polarized right G-8 said that's time will continue this next time
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