Lecture 17: Green Chemistry

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Lecture 17: Green Chemistry
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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: 00:45 - Asymmetric Epoxidation 02:11 - Oxidative Cleavage of Alkenes: Ozonolysis 09:13 - Oxidation of Alcohols: Oxidation with Chromic Acid 20:10 - Oxidation with Pyridinium Chlorochromate 24:49 - Green Chemistry 29:08 - Designing Syntheses: Part 2 40:04 - Radical Reactions: Introduction
Setzen <Verfahrenstechnik> Growth medium Redox Chemical reaction
Stop codon Ozone Biosynthesis Alcohol Ionenbindung Reaction mechanism Nitrogen fixation Complication (medicine) Spaltfläche Wursthülle Molecule Dichromate Ageing Dike (geology) Human body temperature Redox Orange juice Mineral Chromium Process (computing) Gas cylinder Gas Walking Potassium dichromate Carbon (fiber) Deep sea Solution Chemical reaction Amrinone Water Hydrogen Agriculture Sodium Gesundheitsstörung Acid Computer animation Functional group Covalent bond Carboxylierung Cobaltoxide Wasserwelle <Haarbehandlung> Thermoforming
Stop codon Semiotics Alcohol Precipitation (chemistry) Ionenbindung Species Reaction mechanism Hydrochloric acid Wursthülle Organische Verbindungen Quartz Chemistry Alpha particle Molecule Solvent Cycloheptatrien Colourant Data conversion Redox Active site Elimination reaction Chromium Process (computing) Hydrocarboxylierung Setzen <Verfahrenstechnik> Octane rating Gas Walking Hydrogen bond Carbon (fiber) Solution Chemical reaction Wine tasting descriptors Water Hydrate Hydrogen Song of Songs Acid Computer animation Curing (food preservation) Functional group Covalent bond Chemical compound Chemical structure Carboxylierung Mixing (process engineering) Cobaltoxide Thermoforming
Alcohol Containment building Chloride Operon Chemistry Data conversion Ocean Benzene Trauma (medicine) Octane rating Walking Solution Chemical reaction Chronic (medicine) Stockfish Electronic cigarette Carcinogen Acetylene Acid Iodide Chemical compound By-product Acetone Polymer Zunderbeständigkeit Bromine Medical history Bottling line Stuffing Ozone Biosynthesis Green chemistry Nitrogen fixation Bromoethane Wursthülle Origin of replication Lead Ageing Common land Controller (control theory) Redox Ausgangsgestein Chromium Process (computing) Metal Area Golgi apparatus Atom probe Bromide Carbon (fiber) Sodium Computer animation Separator (milk) Bromomethane Screening (medicine) Satellite DNA Ammonia RWE Dea AG
Setzen <Verfahrenstechnik> Biosynthesis Ionenbindung Reaction mechanism Transport Atomic orbital Carbon (fiber) Chemical reaction Food additive Systemic therapy Combustibility Computer animation Electron Functional group Radical (chemistry) Lactitol Azo coupling Valence (chemistry) Common land Redox Verwitterung Periodate Isotopenmarkierung
Computer animation Radical (chemistry) Resonance (chemistry) Carbon (fiber) Katalase Food additive Isotopenmarkierung
Area Ionenbindung Species Reaction mechanism Rearrangement reaction Spaltfläche Spawn (biology) Atomic number Combine harvester Computer animation Electron Radical (chemistry) Valence (chemistry) Azo coupling Freies Elektron Wound Bromine Atom
OK questions anybody you may finished up Chapter 12 and starts after 15 pace is picking up these chapters are shorter and so this is the point where you start to get behind if you're not careful OK so I don't that happened right media were called during his long weekend right now that's OK I wanted cleric something what we talked about the sharpness oxidation and told you that you can make a single and handsomer and now you can choose the catalyst that he is the 1st time variable territory you get 1 insurer to use my is to get the other an insular and what I said is that I will not ask you to predict the correct mentioned for that reaction some people interpreted that is you don't have to predict any answers for this chapter that's just 1 type sold for example the
here's an example mere words predict the product and and there's a there's you can get me out of parts that this is mentioned you can also get the Parkside this is -dash if you use the miners traveled territory you get this dashed and applies to get that wedged you need to know that I'm not going to ask you to draw the single and ensure that you get what I want you to be aware of is that this is a way to get a single inch question yeah that would be and that we will be using the other territory you will have to to do that Lukic are excellent where we leave off last time we talked about dying hydroxyl Asian sits
and send on time and on my left water of the age to all of this should be aged 209 to so people go back and fix that sorry and then we want to talk about ozone also this but after their retirement oxidation alcohol so reaction of came with ozone the deal products a double bond cleavages called analysis and there's 2 different what we call workouts so step 1 will be ozone Primack process not critical you include the method also critical that you with the 60 if just right over 3 unhappy and then depending on your 2nd step in the 2nd step is the work you can get different products depending on what your seconds deficit if you do an oxidative work up and in oxidative and this is a familiar reagents year you would use H 2 0 2 you're going to get a carboxyl a gas on 1 end and you're going to get a key torn on the other and Stephen again you're breaking your molecule into 2 pieces and each piece has has a smaller number of carbon so we started was we start up with 2 cartons here and now each side gets 1 of the carbon so were breaking a molecule into smaller pieces and the and and right now there's only 1 way to do this and that is those in Alsace so when you're doing synthesis if you count carbons and you have less carbon than you started with that means have duos in Alsace somewhere in that process so on during this reaction you get in shows idea there is a mechanism to get those owes 9 which you're not going to need to know so I'm not condition and the rejecting mortgages 2 ways to do productive work up number 1 is sink in water lawyer dimensions sulfide so this would be like dinosaurs except we have a soul for instead of the oxygen you can use either 1 of those methods for reductive work and as you see as you can see from the products that they keep town on side is still exactly the same here but on this carbon right here and that's the difference here this carbon right here this is oxidized to 108 here its status as a hydrogen so productive work out if we take this apart from forward basically what we're doing in this reaction in his work cleaning this double bonds right here and each side becomes a so I'm just going online in exactly the right thing the way they are each side gets an oxygen if both sides have an hour if if 1 side has to our groups you'll get a Quito if 1 side has a hydrogen I'm going to just I'm just going to make this act if 1 side has a hydrogen L. a if you use a reductive work up the hydrogen will stay as hydrogen if you do not sedated work at the hydrogen will be oxidized to Italy OK so that's what you wanna keep straight here was analysis also works with our clients With outlines we don't have an oxidative work aboard reductive work that we just use water in a 2nd step so this is step 1 and is a step too so without finds no warlock sedated or reductive workout just water and so on in and not to view of carboxyl like acid well actually carboxyl Aghazadeh on the left-hand side and I when there's a hydrogen for an outline on the right-hand side UK carbon-dioxide which of course is aghast and that bubbles away so we've we've basically what we've done is we've taken in terms of time and we have lopped off 1 Cochran says 1 carbon less than what we started right and if you have the Al-Qaeda and part of rink then he will you basically what you're going to do here is you're going to clean the and so this would be a course step 1 here bozos step 2 it's a reductive again for my class is not critical that you show the solvent it's not critical that you show the temperature for this particular reaction so long because we have to hydrogen here if we do our reductive work out they were those heightens will stay as hydrogen so on what we're going again looks at least 6 so likely that Al-Qaeda would put a double bond on each side and the hydrogen is going stay of hydrogen Why because I'm a doing a reductive work that looks like a strange-looking bond here so let's fix that I'm just trying to make room for this other carving here so were pleading that double bond and have each side is getting an oxygen a little bit complicated mechanism which is why showing that you can also right that this is equivalent to you can write it like this so in this case were not actually drove breaking it into smaller pieces will be brought are breaking apart the rain into and to make a change from that and really this is the only way to do that therefore instead you do we have stepped to you use H 2 0 2 the new products going to be the dike carboxyl gasses so this is always in Alsace is a way to synthesize carboxyl or you'll learn about another wave sensors carboxyl gasses in the next section also questions on those in Alsace anybody Our segment oxidation somewhere in use these regions a lot for the rest of this quarter and also for next quarter but by far the most serious region for exercising alcohols from a gas cylinder it comes in various different forms I will show you the form that I'm going to use this 1 right here so that's coming trioxide H to us so far you can also do sodium dichromate H 2 isoforms potassium dichromate H 2 SO but the 1 that I use is the chromium trioxide each to us of course I can't say what sapling Smith will use they probably will mix the 2 but they both did the same thing if you have a primary alcohol this region chromium 2 of 4 funds a carboxyl gasses so this is a really and colorful solution this is on chromium chromium 6 and that's an orange very deep orange solutions so listless urged the right Farm solution very brightly colored on solution and you do actually to oxidation steps you 1st oxidize the alcohol to an outer hide and then you keep going I'm going to put this in brackets because you can't stop here so I can't stop here where they were going ashore region that will stop there but we can't stop here in this in this reaction can't stop here
reaction doesn't stop here so this album I was going to be oxidized again to the carboxyl so the goal if you go back to the 1st part of this chapter worry talked about things being oxidize has to oxidation step so there's a Alden and then we're going to do this more 0 3 H 2 SO 4 goes all the way to the carboxyl against so this is the 2nd Way make carboxyl aghast so it should be another index cards showing how to take a firm an alcohol to a carboxyl a gasses that we could 1 have on drawl the Cyberonics ideas we do that the 1st time introduced a reaction we have this H 2 0 we have no answer for 2 minors and we have C R 3 plus and so that's year on that site reaction is complete because you get a green kind of got chromium Sauls it's actually blue-green but I don't have to good bring here I have to go into my other colors to do that you get the idea right of blue-green precipitate please stop .period solution you had the alcohol you add this to the alcohol the or solution goes color goes away blue-green precipitate the about that you have a secondary alcohol you get keep you get the so this is the reagent I'm going to use to Sierra actually unstable that's what actually forms in the reaction when you mix of from trioxide plus water H 2 SO 4 that means you H 2 see R 4 OK so but I don't usually use this this is the 1 that I so you'll be able to recognize that and your product is a key to secondary alcohols Dickey tells primary alcohols the carboxyl against so as you can see overall in this fraction were replacing the words you were getting rid of a carbon hydrogen bomb replacing it with carbon oxygen loss so we have now to carbon-oxygen bonds in a show you how this works this is not a mechanism is not a complete mechanism but under showing you how because sometimes that helps many students to build the picture what's happening in the structure and I want to be able to do that makes it easier to remember I will not be asking you this I never received no mechanisms in this chapter so H to C R 4 as a structure very similar to sulfuric acid except give a chromium in the middle instead and this is fast and reversible process that's what happened in the 1st step in this 2nd step we get in unusual reaction that you haven't seen before it's called an Alford elimination something redraw this chromium species here so water consumed so the limitations that we saw in Chapter III were buried eliminations this is an alpha story going here so it looks like that that's called an alpha elimination but it looks a lot like a baby elimination if you think about this hydrogen here if you think about this as a leading group it looks a lot like the beta writer removing this on this break to make a double bond here and now please it's still no it's cold enough elimination but you can see if you look at it from the perspective of this leaving it looks a lot like a fatal Haitians are right so that's what happens this is the slow rate determining step and you can see that's how you get the carbon oxygen double bonds all drawl aside products here so you can see where everything's coming from or going to get drawn on here and we're going to get C R 0 although look it'll look like this this is chromium for and that's reduced further to chromium 3 so it's a little more complicated than this are so why don't I go through and show you that when I said there's not going to be any mechanisms because I want you to realize why tertiary alcohols don't give any reaction may no reaction with chromium trioxide tertiary alcohols can't be oxidized and you can see online a reaction the 1st step can happen with a tertiary alcohols so we can form that so let's try that for Step 1 I'm sure most of you could draw mechanism for Publicis 1 it's been spending a very similar to making a tosser late I'm so serious so here's what we have agreed to a tertiary alcohol on the key step here the rate determines that is eliminating I'm an alpha hydrogen so that's a hydrogen that's bonded to the same carbon responded to the oxygen can you see that we don't have 1 here we don't have a hydrogen bonded to the carbon responded to the oxygen and that's why we can oxidize because there's no carbon hydrogen bond break so we have a primary interest to break and we will break both of us but we have a secondary there's 1 alpha hydrogen this 1 has none OK so that's that's the key thing here there's no awaits born to break so no I'm alpha hydrogen so there's no staff of hydrogen to eliminate therefore no oxidation can so of modern new index cards in this chapter we wanna show conversion of an alcohol to but still guessing who wanted to show conversion of a secondary alcohol to Quito case so that those are going to be really important because if you think about it we're making ,comma compounds with these reactions 51 see there we just 7 weeks of carbonyl chemistry so we need to build and make those compounds and this is of 1 way to make the our there's 1 more regionally you need to know from this
chapter and that's PCC and you can use the abbreviation for Kansas so feel free to use that using it as a reagent we should know what it looks like so if I actually drawn will know what it is and you do have to write PCC on like it I get a lot of strange answers on tests get CNN albeit his the CBS as I will do we actually got there actually written into the that's the CBS region the of the confusion but it has to say PCC Vivendi's US region and this is 1 of the ones that what I would call famous region which means we use it a lot so this is a really important 1 to know it's the famous region there really is a lot the rest of this quarter and next quarter especially all right so formation of PCC and we do with the same idea we have chromium trioxide 1 equivalent of hydrochloric acid so this is 1 of whom was and this is all combined and here it is still carried so were familiar with all of these regions and so what you get is pure Dini include Crawley so here's appeared in environments we probably purity it's pure in environment so as a positive charge we've seen that already and we get C R 0 3 C L -minus service forms assaults Peter yellow-orange crystals and the nice thing about you can dissolve it in the organic solvent and it does pretty nicely it's soluble and usually used nothing quite soluble in CH 2 C is a song that usually usurp using the CHT CLT that's all it is is a solid so sometimes that throws students are will just leave all that fear organic solvent so this is nice PCC uses an organic solvent chromium trioxide you can have that in warned you can also have acetone but this this is actually a little bit milder reducing agent then chromium trioxide so if you have a primary alcohol you can stop at the elder High and that's going to be used endlessly In 51 C OK so I had to know of a oxidation is seen by over oxidation the the primary alcohol going to carboxyl aghast know of oxidation seen dining mistakes usually that means no OK no program no carboxyl aghast 4 PCC with them secondary alcohols the exact same thing is coming from outside the nice thing about PCs is it's my older and we don't have access on acid In here leaders have wonderful work 1 will work when it will work if we use chromium trioxide H. Joseph or we have a lot of acid and we know that that can cause problems with without multinational should clients right we can get hydration Elkins all so if you don't mind if you have a double bond elsewhere in the molecule that you don't want any hydration happen I'm a better way to do this is to use PCC instead so these guys are all react with acid as we saw in chapter annoying use react with passes chapter 10 and 11 sorry luncheon 10 and 11 tertiary alcohols no magic cure it also doesn't work so tertiary alcohols no reaction I want to say
a little bit about green chemistry and you won't be doing it from him oxidation in the lab and the reason is that chromium regions have been found to be cursed carcinogen place so we used it when I was a student probably out on the on the bench with benzene resolve this first-generation somewhat because of injury but anyway but we try not to use it very much if you use chromium reagents Swiss which you can use of it goes in a separate waste container and it costs a lot of money so you you might not think about the ways that you generate laughter waste people come and take that away and they do whatever they do on the chromium has to go on a separate ways container and a lot more expensive so every bottle waste that's made in the lab has to be carted away that's part of what your lab fees go to many everything about that right but so many oxidizing agents in particular especially toxic so certainly but chromium 6 fat chromium 3 also bad chromium by-products so carcinogens special waste required so a lot has changed since I was a student here at UCI when we watched her glassware with acetone we were aware right on when I was a senior conspired with inevitably asked on the ways Botero costs and it goes right out into the ocean and I don't think the this love that during much but yet so things have got a lot stricter also sides really bad that's nasty stuff the last 4 some ozone is also bad down here it's been also June the upper atmosphere bad here written apparatus atmosphere bad here is also a person and so people are always looking for alternatives to these very common regions that are not necessarily very good special rates required and was due dollar signs here lots of money here OK so what especially nice on trade onto conventional chronic acid oxidation is something called him a lesson I can only say Tuesday 26 resonates CRO for minors you don't need to memorize that I just want to make be aware that we're doing paper chemistry in this class this is a better alternative what the difference is that with this 1 is still has just chromium but it's on a polymer support so you keep an eye on the polymer after you were after you run your reaction the chromium stays attached to the polymer and then I went to see the tightest stays attached the polymer it you wash your region off the polymer stays there and then you can oxidize the chromium back up again so it's it's reusable and so this is what it looks like we have this polymer supporters so it's going to be it's going to behave like PCC so it's going oxidized primary alcohols to come out of my eyes and on you can actually use it without solid so we states solvent when we will be doing this reaction if he also avoids the use of the strong acid became filtered often the regenerated so here's an example here of using this catalyst which we really like is it's also really expensive too which is probably why we don't use enlivened by accusing idea to try this will have to try that the announcement of 10 alright so the little green chemistry awareness all right when I move on to design synthesis party we started this at the end of Chapter 11 and now we're going the find to new reagents so now we can really expanded repertoire available the synthesized more complicated things which makes your life harder the parents alright so we we didn't reactions were reconstructed the carbon skeleton we did much of the data conversion we control of regional chemistry and now we're going to do when in-house controls of stereo chemistry the 1st example of is not stereo has history gives the 2nd 1 does OK so here's an example of a synthesis problem synthesized to probably promulgating from compounds and 2 Commons or you were OK so the waste we've learned to build up carbon skeletons are we take acetylene Media Pro namely had on carbon right we can add on a methyl bromide and ethyl bromide that tower building apartments built so 1st thing 1st for this problem with some drawbacks to roll the tape 1 2 3 4 2 promulgating a modest emphasize that there's carbon so we're going to want to make that from 2 carbon pieces so I wouldn't take this apart retro synthetically because I know that I can make back compound if I have the Altima and HBO I could make from that of killing the HP art and the saltiness I can make from the all-time and that if I had the kind and I can build up a carbon skeleton with the opined so we've learned raised to partially reduce and clients to make keen so that's so what we would do we probably use some H 2 England lost catalyst if we use to him last palace that we can get that out Keenan do HBO and so now this 1 we want now is that still got for Commons we want a break this into 2 pieces if we had d protonated acetylene and we had this should be a CH 3 by the local fix that this described and scale if we had those 2 compounds here we can build up that carbon skeleton those originals have 2 carbons and then there we can make from a satellite so do you have the picture in your mind how Hourigan due this week made a big job so for the 1st midterm was 2 steps and this is now ready to more that yes I didn't do it again because that OK thank
you now let's write up the synthesis and the word direction how this might look on a test but what I did their talisman will on a test it would could be an open-ended sentences will drop down Lionel Jospin might look on test could be the right we started off with the settlement I'm going to the that In the end or any any age 2 and then in the 2nd step I'm going to use and this time I'm not going to do that's a mistake ethyl bromide so I call these open-ended sentences because you right out the products from each step unless you have something like this were know you those 2 steps following go go together you have to show each so you give a little picture of what's happening here I don't do too many like this because they're very difficult to operate alright what's next h to land lots when large catalyst that is the arcane and our last step is HBO in a stupor be taken so that that's what I call open-ended synthesis of poor on the test it might look like this where I started off with acetylene and that gives you a little help their right not to know that's how you start and then you have a lot With an arrow in its then you go to this and then warn you I'm and warn you and I'm the 1 you again and make sure you number steps so but that would look like it is step 1 let's just pick 1 of wilted in age step to Ethyl bromide or iodide or chloride or toss whatever you like step 3 h to landlords step for HBO debts for steps that's quite a leap from what we had an interim 1 question the it there in here that if you if you do the HBR step 1st and then do the Lawrence but if you do need experienced 1st then you would you would use 1 last Palestinians Palladian everybody following saying let's show that that's a really good question for the same step 1 step to step 3 age 1 equivalent were also to the point where there's more than 1 way to do it and so of I write out the key some teenagers just only give that answer mark that correct if I don't anticipate everything that people say so what this is really important from this point forward that you look at your midterm and if you think you've done something correct it's marked wrong show it to me and get the points that you deserve a Case of You do this instead during handling the HBO are here rights this will be a and then in order to get that now we don't use won-lost catalysts is cattle stocks Adelstein then we would use H 2 and OK so that's another way to do so sometimes you got a lot of creative people in this room and sometimes I can't anticipate what you're going to come up with on the test and so really important if you do poorly on the test I don't know look at it that's not help we will look at it the witnessed and so that you make sure that you don't make the same mistake on the final borrowing this looks a lot more work isn't as Darien chemistry but it's not I'm just going to give you an outline were not going to do the whole thing was reduced news and discussion well let's do that does everybody see this right here this is what I hope can jump out at you we know how to do inside instead of bromine to announce somebody go retro synthesis here isn't overwhelmingly difficult it's really not so on bromine and 1 1 0 PM when I have persists on the trail traders apples on opposite sides that's what I so here's another 2 compounds a furor which Swiss screens that use using crime OK so we have that and then I can make that from the and then if I had that what what I used to go from the what what I used to go from here to here I'm going from here to here to get the Transall I used dissolving metal reductions sodium in liquid ammonia right and I know you know how to make this from settling acetylene we probably don't do it all at once told DEA probably both sides and add to distance you probably have a bromide to probe may affable so I know you know how to do that and so we will finish that in discussions questions anybody Our right here's your chance we're going to save that work and it takes a few minutes so so that is something maybe ask a question about the midterm next week something that's coming up yeah words somebody is area yes good good question if you use 1 large Kelsey Guinness's sulking the year to you on the 2 apples will be on the same side effect far-right Chapter 15 we were taking a big lead here worried about looking for mates chapter of this
scene is different than any other chapter we will do all quarter all year it's a radical chemistry and that's important for biologists to study it's also how we are going to take we've learned a lot about how to take a compliment has functional groups and change to another functional group Filipovic was skeletons but what we had like an Qaeda with no functional groups had we put a functional group on that this chapter so this has a couple of key reactions that we're going to need and synthesis it also has a very different pushing its radical reactions and so on but very different than anything you've seen before so let's talk
about that the radicals a highly reactive intermediate with an unpaired electron radicals are involved in oxidation reactions combustion reactions and biological reactions so electron transport system the covered the radicals involved that's so so here's a radical this is a carbon radical so we had a little preliminary do here before we jump into mechanism S T 2 hybridized plane what is that reminds you of the rest is a complicated 1 extreme weather the true if we threw 1 electron into the empty the orbital of carbon and would have a radical OK so let's compare that with the cargo Catherine so this is a complicated and it is also S P 2 and plan and now attended compare that with a program very different trickle period right so let's throw that negative charge there on that radical so let's label these guys here we have on this is it and this is a pure but all it is not empty has a single electrons this is an empty all and this isn't as care here in the car and and asking 3 so completely different structures and if you if you look here carbon cargo cargo-carrying common owns 1 lecture from each of these bonds right still owns 3 electrons here carbon carbon and I'm here 1 2 3 4 5 this carbon has 1 2 3 4 so this would be like if we took common straight off the periodic table and its underlined formats with all right so it's very sees some similarities to uncover gatherings definitely stability free radicals and prevent the
elected division also order stability exact its label these this is a and so still the golf more stable than tertiary which is more stable than secondary which is more stable than primary which is more stable than similar but not exactly the same what's different primary means of rural what's different every nor ,comma Qatar instability handout and you should know that if we didn't learn that 1 you'll see it again on the final guaranteed by what's the difference In a and what's more stable than silly Galilee Patricia tertiaries more stable for a cargo so here we have that's slipped that's the only difference everything else is the same and the like ,comma cannons radicals can be stabilized by residents so we have resonance stabilization here so if you can imagine that this was a positive charge here now idea now will occur cat and we have resonance stabilization we also have stabilization and I'm so this we we we call it something a little bit different this is a resonance stabilize not in all of the anomaly radical so just like with carbon Karan's you you can you can get products from both resonance structures if they're different and the same thing happens with radicals you can get products that we don't expect because of this resonance stabilization or so let's however radicals
called free radicals of Roman Barnes Creek will adequately disclose all always back to widen which chopper
was 1 of the earlier chapter but before we do that and I wanted say and I almost forgot to say is that we have no rearrangements no rearrangements where radicals so there similar to common carriers were not exactly the same don't get rearrangements so that makes life easier for you are actually great reponsible lately let's see what that looks like a couple years feeling a little danger Lucas we did this last quarter were not used to radical cleavage and all were not used in home liquidity worries to had a relative privilege so this is what really were lowered this is what we are used to saying that 2 electrons from applied on moved onto 1 added using the more Elektra negative ad right together long charged species so that's had relative catalytic bond cleavage for radical reactions we're only moving 1 electron you're not moving too and so these 2 shared electrons is Mama sharing kind of thing you get 1 electron and the like gets here so once the 1 that is not getting both electrons once getting 1 one's getting and when we do that we get to radicals that's what at once with and I want to point out certainly a out to the fish hook area so a doubleheader there like we're used to seeing moves to electrons can Richard arrow moves 1 electron and then compare that with the double-headed arrow wounds to electrons so when you do mechanisms in this chapter you're going to use single-handed arrows if you if you dry your whole mechanisms in it's entirely correct except you have double-headed areas would get no points after single because it isn't entirely correct because you're not moving to elections removing 1 electron so all of the nomenclature this is really nomenclature it's more like the terminology here bromide ion OK this is really difficult here for a that's bromide ion bromine added atomic Perrone this is like again and take it right off the periodic table in its and combined for so bromine atom or atomic bromine all bromine radical or bromine free radicals those are all interchangeable terms for them and then there's the molecular bromine which we just call bromine and that's just from meaning in its natural combines this is just a little bit different terminology that the perfect stopping point we will continue this and next time