Organic Chemistry Pre Lab Lecture, 9/21/2015

for this week um we will be in lab doing experiment three this week part 1 of experiment 3 is what we are going to feeling so talk to you about that in a little bit job your quizzes because number three but always been calculated to the quiz okay um discuss and her other calculations going to discuss them with one and then your experiment to your molecular modeling answers argue and last we going to be what this stargell after so the lab that you did last week those answer sheets put the printout of your working model once you are done are all doing laminate or start a lab piston okay experiments you is do business next week we will finish experiment three when you experiment your experiment one report will also be due in your notebook message so we’ll be taking your notebooks from you next week so make sure when you come to lab next week you have your report all ready to go so this week for expert three we’re going to be taking nutmeg kind of smell like cooking class Wow and a lot of nothing so much more than you would ever use we’re going to extract out hi Marissa to end the nutmeg and then we’ll kind of in at that point this week and then next week we will take that try Marissa and convert it to Arista castle so first of all a little bit about um try Marissa it is a fat about twenty percent of nutmeg is this bad okay there’s other things in nutmeg besides just the fact and this is calculated will calculated by mass okay we won’t do mole ratios or anything like that but when we do our extraction yield about twenty percent is what should come out of the nutmeg whether or not that’s that’s how much we get okay and so this is back looks like this has kind of same basic structure most bats the try a stir so all three of these guys through these chains are all linked together so drawn like this it looks like it’s a really compact molecule but keep in mind here we’ve got 12 CH choose in here so really long chain attached to these esters and they’re all attached to each other about the three of them content attached to each other um it is very soluble in ethyl ether so we’ll talk about how we’ll use that and ii sir as an ether is a you know relatively low polar solvent polarity as census compound we do have the ester groups but with these really long chains coming off of it it’s a really low clarity compound okay so when you need something good remember from Jane camel like dissolves in like so that’s when we want to use the ethyl ether which is very similar to this compound as far as blaring it is not very soluble in methanol well we will also use that so when you think of ether versus methanol the methanol is um you know higher polarity salt so that’s why we test the ch3oh group um and so we talked about this this is a homo triester because each of these

chains are the same thing so they’re all the same Esther’s being linked together and it’s a home try a stir of glycerol so this part is the part thats related to the glycerol and we’ll talk more about that next week when we look at the hydrolysis but most fats are transfers of glycerol okay so there’s a little bit of introduction to our friend Tristan now one thing i want to show you you couldn’t read it for this experiment let’s look at the lab that is in your lab me okay so you kind of pretty much have pre lab that you can use or base your prelab off of for your experiment this week and so remember even though we’re doing part 1 of this experiment when you come to the lab this week you want the entire pre lab in your lab nope as you should each time you start a new term on the entire pre lab in your phone alright so um I won’t read all of the P lab but I want to kind of out a few differences versus what we looked at for the experiment 1 and then also there are some things that you need to add to this you make some corrections to this so that it is correct while putting into your lab milk all right so purpose of the experiment is okay um then the next part and title was ok the next part is where we would show our balance reactions that are taking place in our experiment well for the first part of the experiment all we are doing is stirring the nutmeg in ethyl ether and extracting up a tremor isten so there’s no reaction that’s taking place ok that is that is more a workup step and so that is not shown as a reaction that is shown in the flowchart ok so you’ve got your nutmeg and you’re extracting it with ethyl ether and you’ll get tremor a lot of other things besides the tribal resident and diethyl ether and then you’ll have solid nutmeg residue that you filter wet so you’ll do a filtration here a gravity filtration so we’ll talk about what that means to separate these two then you’ll go through we’re going to remove the ether and we’ll talk about why and a little bit we remove posts mostly ether with simple distillation so well either that is removed and then most of this chunk here this primaris insoluble organic components and a little bit of dialkyl ether we’re going to add methanol to it that will precipitate all about our timer Istanbul filter and get our try morriston as a solid and then our filtrate will have methanol insoluble organic components and diethyl ether in okay so that whole process of how we get to actually having solid tie my wrists and we’re not going to show any reaction pull it out okay everybody understands why there’s no reaction to show the tremors and has never changed into anything else we’re just taking it away from the nothing all right okay so the second part of the experiment and the part that we will do next week does involve a reaction and there are two of them we will hydrolyze our tribe arrestin using sodium hydroxide and we will talk about the stoichiometry of this reaction next week okay so that’s one thing that’s really key to this but this stoichiometry is correct so over the week see if you can figure out what is going on here as to why we have one timer sim to every three sodium hydroxide comp molecules and then from here on out we carry the three through when we make convert it to glycerol and sodium wrist eight and then the sodium ER estate is then converted to myristic acid there’s always one time arrest in 23 23 23 23 23 to 30 km at the end so in the end next week what you will isolate is that myristic acid so you do need to show both of these reactions because these are both reactions that will not be shown in the flow diagram all right so it’s a little bit different than experiment 1 where our reactions also showed up in our flow diagram what we’re going to do for this flow diagram we’ll talk a little bit more about it next week is show what

happens after after that reaction okay so we’ve got all our pieces here we add the HCL we’re going to then after the HCL is added to a filtration to isolate our myristic acid and then all of the other impurities including the glycerol and ethanol and water and sodium hydroxide and our study employed and HCL um and then we go on to do a recrystallization where we and this this piece here is just to show you that this this is glyceryl okay so this isn’t an extra step then we go on to recrystallize this and once we recrystallize will filter and get our pure myristic acid and then all of the other stuff the methanol and all the other impurities that came half of it so make sure that you understand the difference between those two sets of procedures and why we don’t have a reaction for part one we just have a flow diagram for part two we have reactions to show and the flow diagram to show to get to the end all right um the other part of parts of the prelab you’ve got your table of reagents as well as products so you want to make sure that that completely takes care of all the chemicals that are going to be used or produced in your experiment so kind of double-check your table make sure that that is all taken care of we r talks about talk about the flow diagrams so then things you need to add there isn’t any drawing of new special equipment so two things that you will use our reflux apparatus in part 2 and you will use gravity filtration part 1 so you want to make sure you show both of those and then also make sure you update what edition of update this reference ok we don’t list dr. muggle anymore on it it’s as if I need an update to hear on there ok and then the last part i wanted to point out to you and in general with the prelab so we’ve given you a lot of information or helping you put your prelab together pretty much you have your pieces and you need to put your pieces together make sure whenever you’re putting stuff in your notebook you understand where it’s coming from okay so make sure that you understand what the reactions are you understand why that table of reagents looks like it does you understand the flow diagrams and understand this yield calculation okay by you putting it in your notebook this week any of this potentially could be free game as far as it quits okay so make sure that you understand where those pieces are coming from all right so um I’m going to talk about the specifics with the process as far as our extraction this week but also want to talk to you about in general the kind of categories of what we’re reviewing in general as far as chemistry so a use of to get to try Marissa then I solicitor my son is an example of an isolation of a natural cause and we took something that when we’re talking about natural products we’re talking about things that come either from plant material or animal material and we’re isolating something from this okay so we took the Nutmeg which is a plant and we’re isolating something from that nothing all right now um in terms of organic chemistry usually when you’re looking at something that is a natural product you then would want to we would want to go okay we’ve isolated this tremor istam now what could we use it for either pharmaceutical industry or some other industry what would we then take on this natural products to do something better for us okay we’re not going to then take on the time medicine and see you know what it tests for biological activity or something like that to be used for a pharmaceutical so we’re isolating this as a product but the on

it’s not necessarily a natural product synthesis or anything like that okay but related to this how this relates to things that happen in organic chemistry is a lot of things that we use things that make us feel better as far as medicines come from things that were derived from natural products okay um so like about half of fda-approved drugs right now come somehow from origins of natural products so whether it was the original natural product or they learn something about a lot of times these natural products a pretty complex structures the sky isn’t too bad and I’ll show you one here in a minute that fairly complex structures so then people learn more about how that structure is important into the function of what it does and can that structure be important in doing something else for another use okay um so a lot of our pharmaceuticals still come from things that we learned from NASCAR whether plan for animals on another example of something that is an apple product is caffeine right we extract either you’re drinking coffee or you’re drinking tea that those are both examples of extractions right you’re extracting from a solid to get something in a liquid solution and part of what you get out of that is caffeine we also just extract just pure you know Kathy put into like soda comes from an extraction process okay so this is an example of and then it’s also been synthetically me but this is an example of a natural product all right so the 1 i’m going to show you here tax all this was one that was kind of like the premier one of the premier compounds for learning something new for the pharmaceutical industry as far as getting something that was really useful as a medicine and then trying to learn a lot from its synthesis and how together so let me let me show you what it looks like it’s a really complex looking molecule there’s been many many groups research groups looking on it um around the world around the country and around the world to try and synthesize this guy so as you guys learn more about organic chemistry you’ll learn that all of these places where we have wedges and dashes are chiral centers in this compound to that when you look at something that has all of these when you look at a compound that has a number of chiral centers that usually means it is really hard to make okay because you have to make these and then make them stay and not change okay in the process so this is a really complex compound well it’s also a really important compound because it’s used as a cancer drug for breast ovarian and lung cancer it comes from you treat and the problem with it coming from the pacific yew tree is it comes from this Parker okay so as soon as you go and try and extract the tax all out of the trees bark by pulling the bark off the tree you’re going to kill the tree right as with any tree it means its bark you full its protective covering off it’s going to die so that’s not really a sustainable method for getting something that is such an important progress of pharmaceutical agent okay the other thing is for pacific yew trees are not like you know all over the united states that only want the region of the US along the Pacific coast and they grow really slowly so they’re they’re not going to you know you can’t just go buy yourself a farmer pacific yew trees and be able to extract all the tax all out you need okay so this was a found to be a really important rug but we had to come chemists had to figure out how to come up with a synthesis for and so over the years there have been

multiple proposals of synthesis and now of what is used to make it is they basically use other similarly related compounds that can be extracted and then chemically transform them in okay but a person that would go through this process is a natural product and so they’re not just extracting they’re not just you know going out into nature and taking things and extracting things out there’s a process that they have to go through to figure out if they’re finding something that is really useful or not so first of all the first part is they have to extract but then they have to scream when they extract out of the natural product or scream that extract and if they find something that looks useful in their screening and they’re going to separate it and then identify what what is that one of the important compound in this whole extraction books that i have and potentially if it’s not something that’s really widely available then you go on and figure out how to synthesize that they had to do with tax off um another example of pharmaceutical that came from national product is diabetes drug for type 2 diabetes IATA’s it comes from this bit of a Gila monster so they monster in its pit is this compound that’s a big macro molecule it’s a big 39 residue peptide okay and so it’s got 39 amino acids and in damage um but they found the compound in a Gila monster and it worked for other treating diabetes so then they had to go on and figure out how to make it because again you know trying to get a heel monster to let spit enough to benefit extract enough of it out to have enough to be a sustainable drug they had on figure out well how do we actually make that so they have it went on the market 2007-2008 this but other examples of things that have come from national products like your car tires originally car tires were made out of natural rubber from a rubber tree okay or any rubber that’s used is it came from a rubber tree so that’s another use of the national product so it’s not just pharmaceuticals that these natural products the wanting help improve people’s lives okay but this is what we arguing this week is extracting the natural product then we’re going on in using it for synthesis but we’re not necessarily going on in testing the timer’s tremor risks in itself or other other uses um so to isolate our time arisen we’re going to use what is called a solid liquid extracted so what would this be related to what have we already done we’ve already done the liquid liquid extraction right the first week of instrument one so now we’re just going to get rid of one of the liquids and put in a solid okay so it’s all the liquid extraction you’re going to have a solid and you’re going to have a liquid ok so our solid is our nothing our liquid is our teacher all right um now there’s a couple things that we need to keep in mind with this solid liquid extraction the first thing I’m going to do is talk about diet ethyl ether there’s some things we need to think about when we are using diethyl ether okay and first of all diethyl ether is also known as ether it’s not also known as

this so there’s lots of you could give her the guy to ethyl ether these are all the same same thing as far as what we’re talking about in in the organic lab okay the thing with the diethyl ether is it is extremely volatile has anyone done their cru lab yet what does it boil up 35 36 34 degrees really low okay so about 25 degrees so room temperature is one you know low 20s to 25 degrees it boils at 35 degrees Celsius it doesn’t take a whole lot to get it to boil and vaporize um so it evaporates really quickly on you so you have to be careful of that so we’re going to talk about precautions will take because of that the other thing is it is super flammable um it e very easily can be ignited it’s just by heat like it doesn’t need a spark it doesn’t need a flame nearby just the presence of heat could cause the easier to be on fire okay so we need to take precautions whenever we use ether we don’t want to have you know like a container of ether we don’t want to heat it directly on a heat plate just the vapors coming out of it can catch on fire once they contact had contact with the heat plate we’ve got to be careful you know obviously no flames around it no sparks around things like that so be really careful with the flammability of ether in general whenever you are using it as you should with forget any organic solvent but ethers probably the most volatile of the worms that we’ll use okay the other thing is because of its volatility it does want to evaporate on you really easily okay and so we’re going to be using saran wrap saran wrap this week to help prevent a problem with that so we’re going to cover you’re going to be using an Erlenmeyer flask when you’re storing your nothing and you’re ether you want to cover their own meijer flask with saran wrap and so there’s saran wrap in the in the lab and then when filtering you want to cover the funnel and flash cover as much of the openings as possible on all filter paper with cerebral keep it so the ether won’t won’t evaporate because it been evaporated what happens is when we’re filtering it’s going to get trapped in the solid nutmeg and precipitate out with a solid month nutmeg instead of going through with the filtrate and we want to keep it in in the ether filtrate okay so you got to be really careful to keep everything covered in saran wrap and when you’re filtering keep everything covered in surround rock so it doesn’t evaporate on you all right um so when we go to filter our nutmeg we’re going to be using around infiltration so a few of you had to use gravity filtration the experiment on all of you will get to use a gravity filtration may experiment three we don’t need the towel around our flats though because we’re doing things at room temperature it won’t be heated okay so with gravity filtration what you guys are going to learn this week is you’ll have to learn how to flew to filter paper okay so that’s a new new technique for you is fluting filter paper which is very useful to learn how to do it well okay there’s multiple multiple times that you’ll be using it in lab and you know it can kind of be therapeutic to your basically folding paper it’s kind of like organic origami but you want to do a really good job at it so you’re filtering doesn’t take too long okay so if you do a good job things will filter well if you don’t do a good job things don’t filter so well so or learn how to do the Oort origami well um but when you’re covering things you’re going to want all of this covered while you’re filtering one right and if you start seeing kind of off-white solid crashing out on your nutmeg that’s your trimmer awesome and so what we’ll have to do is everybody is going to start with two extractions so you’re going to stir your nutmeg in the ether filter it with gravity filtration with the Nutmeg back in another round of ether stir it filter with gravity filtration after the

second filtration if you see yellow or off-white solid in with your nutmeg we’ve probably lost some time arrested so i have to decide if we have to do a third extraction or if we can use some rinses to help get all that time arrested into your numbing okay want is much tremor as soon as possible from your nutmeg so that you’re good to go you have enough material for next week all right so after your two extractions if you have questions about what trimer sting is being left behind make sure you talk to your lab prof and see if you need to do more extractions it’s easier to take care of it now then in the end of lab find out you don’t have very much stuff and then we’ve got to go through the process again so what do you want for next week this week when you are done collecting your f I’m arrestin you want about something that would be nice with you about a gram and a half or so of wet tremor essence solvent wet so when I talk about wet enough water wet solid month on so you want something in that ballpark to make sure that once it dries next week we want to start with about a gram dry alright so things that we’re going to do on for any um the extraction to help things work in our favor the extraction itself depends on first of all select a solubility of what we’re trying to extract out you guys are Emerson is really soluble in the ether so that’s good but also with that solubility is the volume of salt ok this is really soluble we’re not going to have to go and tons of solid which is something that we want all right um we’re going to extract it number of multiple times okay so the number of times the solid is extracted is important so we will start with to buy on 30 miles or so we’re extracting things twice this is better and if you just said it once with one time 69 you’re using the same volume of solvent but actually going through the extraction multiple times helps you get more of what you’re trying to extract out out of that solid ok so you whenever you’re doing in the extraction like this you would always want to do things more than once right um particle size of something else that’s important so we’re not using like nutmeg is actually enough kind of like an acorn nut um we’re not going to you know take solid nutmeg nuts and put them into our take the solid you know quarter size or so and put it into the ether that’s not going to help us give much nutmeg out right so we use um i’m going to use powder nutmeg which is much better than just the solid or non-powered moment okay um the other thing with in with part of the size you could also call this making sure you have good good contact okay so by having a smaller particle size we’ve got a good contact of the powder nutmeg with the ether you want concern the Nutmeg coming together really um often and coming together well to make the instruction work all right um the other thing that’s important is make sure you have good sturdy besides our solubility number of times we’re extracting our contact or making the particle size the right right particle time and with the contact like that if you’re looking at liquid liquid extraction sand particle size that’s why you shook your sub Tory

phone so that you’ve got good contact with the two layers um we’re going to have good stirring so you want to make sure you plan your erlenmeyer flask because you’re going to need to have a really good string in that flask to make make sure you get all that extraction all that time Ernest instruct i extracted out ok so we want to have high stirring and we don’t want the Erlenmeyer flask is walking off off the halfway all right um so once we go through this extraction then what we’re going to do is we’re going to partially still they either okay using simple distillation well this partial distillation is what’s called a concentration we’re not going to move absolutely all of either what we’re going to remove part of it okay and you’re going to get down to about 15 milliliters of either okay and so um with that concentration um we’re removing the solvent that is really soluble in because now the next step is we need to get that timer stand out in some fashion as a solid and we’re going to precipitate it out with methanol so if we leave the ether in and just add methanol to it we’re not going to get as much solid out as they’re moving most of the ether and then adding the methanol club now the reason that we leave just a little bit of ether is there’s other stuff in there besides just the tremor ystem that came out of the nutmegs so we want the junk to seeing the ether okay and um end up and then they’ll be ether methanol mixture and end up having just try Morrison comes out of the methanol okay so we do this concentration first to remove the solvent that makes it that it’s very soluble in and then we’re going to precipitate with the methanol which is not very soluble in and when you add the methanol make sure it has cooled down to room temperature so you don’t want to have like hotties are trying to add than another flammable solvent on top of it let everything cool down to room temperature then add the methanol then stir it for a little bit sometimes the tremor Austin takes a little bit to crash out it may even be a good idea to put if you’re not seeing a lot of time arrestin put your flask into a cold water bath with a little bit of ice and try and see if the cold will help person state out the timer soon but don’t try and if you don’t have a lot of solid crashing out don’t just immediately go on to filtration try and get that solid to form okay um then once you’ve precipitated with the methanol this time we’re going to filter with vacuum filtration um and you’re going to rinse the solid with a 1 to 3 ratio of solvent that is ether to methanol okay make sure you hold this down in an ice bath as well all right so you want one two three ether to methanol rinse for mincing that solid rinse out the flask solid came out of and then rinse the solid itself when you filter ok and then as far as this solid you just want to make sure that you put it away in your drawer such that it’s going to drive really well until next week alright so we learn all that easier to dry off because what we do need is we need to calculate the yield of tremors and that you go all right and we need to know how much tremor assume you’re going to be using for next week okay so since we’re drying in between one thing we don’t have to calculate and your lab manual will tell you you you need to do this but we don’t have to calculate the percent loss on drying and what we would be calculating is the percent of

solvent loss after we let it dry over time so what we would have done is taken a small sample set it aside let it dry and see how much weight it lost over time and then gone through and carried on with the rest of the tribe arrested in mechanistic acid this year we’ve divided things into two weeks and so over the week things will dry we’re not going to have to calculate how much is lost on a drawing because next week you want to take the weight of your drive Emerson and you’ll know you know you’ll know exactly how much your drive try immersed in ways okay so make sure you get the mass next week of drive by Marissa the other thing you will want to do is set aside about point O 52 depending on how much you have 2.1 grams we need that for calculating milking points at the end of the experiment okay so you need the mass of all of the dried thyme arrestin and then we need to set aside about a half 2.1 grams for calculating the melting points you know one you calculation that you are going to for the trimer reston is you actually need to calculate and extraction so we’re not going to do a regular theoretical yield calculation for the try Morrison will do that from your mercy ask ask the myristic acid but we need to figure out our extraction meals for how much try Morrison you recovered versus how much nut maybe started so we’re going to divide by our total grams of nutmeg and we’re dividing our grams of tremor is sin by this number and then we want a percentage i will multiply by a hundred to get that as a percentage so y on knowing out how much trimer assume you’re using for next week which it’s really important to know how much for every single use for the second part you also need to calculate this as extraction you okay couple things for cleaning up whiskey there is a nutbag waste container in the reagent hood this is only for solid nothing okay so no don’t add any extra solvent don’t add any extra water we just want your solid nutmeg after you’ve completed the extractions let things dry out a little bit you’ll be able to scrape your cell a nutmeg in to the waste container ok so the solid not baked from your filter paper this all is not maybe that’s left in your class goes in this container but don’t try and rinse it with anything into the container the whole point of this container is what is contained in here is actually going to go in the garbage we just need to let the ether foods come off of the Nutmeg and then we can throw it away because it’s just it’s just like if we were cooking and we had too much not make you throw it in the garbage okay so no solid fill water in here otherwise that prevents us from being able to dry out the Nutmeg really easily and be able to throw out your garbage early okay the other thing this experiment is really notorious for getting stuff everywhere on the balances so please as you’re using them okay it’s a bet nutmeg spilled out on the balance we still don’t want solid all over the balances so sweep up the balances then please get all the nutmeg swept up around the area that you are weighing things out as well as the area that you’re working to any questions you guys have um no this is only new equipment so that’s why you just need to show the reflex apparatus in the gravity infiltration don’t have to use now what you want to do in your write-up

for as you’re writing your experimental on Florida German three so when you do the simple installation refer back to that page of your prelab of experiment 1 saying that it was set up like case so and so it you