Lecture 1: Introduction

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Lecture 1: Introduction
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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: 03:27 - Course Info 14:34 - Alkyl Halides and Elimination Reactions 15:40 - Nucleophilic Substitution: Review 30:59 - Elimination Reaction 34:54 - Alkenes: Structure and Stability
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I'm welcome 251 they were going to be starting with Chapter 8 of which I think is chapter I think Chapter 18 Chapter 9 are the 2 most difficult chapters that we have the whole year in my opinion other people feel that way also so I'm really happy that we moved Chapter 8 to the beginning of 51 B I think it's going to make it easier to learn the material and we move spectroscopy 51 A was a little bit rushed but on this quarter was much more rest before we made that move and we had 10 chapters to cover this quarter now we have 9 chapters and we have to holiday so we were really really rushed and a lot of students feel like this is the most difficult quarter on some people say 51 B is the most typical quarter some people say 51 states so I just wanted to give you a lot of little warning so you can get started early on Chapter 8 and Chapter 9 and new idea I don't want you to going into a panic thinking Oh my God this is really terrible idea you know I this is awful OK so I think it's a difficult chapter of we will be using and saplings this quarter it's going to be 10 per cent of your grade and so sapling and this being it's not something that really raised it doesn't raise your grades the points because I would say 95 to 99 per cent of the people in this class get in the 90 percent 1994 center above so when you have a classics on a curve and everybody's getting 90 per cent of the above doesn't really make any difference so what's the difference that sapling makes for you is if you actually work the problems without getting answers from other people and if you get stuck then you can ask the Department tutors you can ask me can ask the chase for the class some people that I know and I know the space for pages for this class and I know there's answers out there and you know don't kid yourself if you go out and get the answers on you not going get any benefit from it so that you can choose to do Sapir European choose not to do so .period but if you actually are doing sapling in trying to work out problems on your own and that's going to give you good practice for us the test Class I also think that you need to do problems from which the back of the chapter on so that you can get an injustice is it's all about doing as much practice as possible on this quarter is for a really really different than last quarter and that we're going to be doing a lot of mechanisms and we're going to be doing a lot of synthesis sorority learning a lot of new reagents and so on at a certain point the quarter we're going to talk about cataloging reactions and that's where you make index cards with the new reactions that you're learning because you'll need these reactions all year long Lederman 51 at you as you learn them you write a on then that means you're going to be able to have the mayor everybody when when I see 1 that when students do their cat the cataloging is right before the examiner rifling through the cards just to keep all the reactions fresh online so a lot of synthesis is quarter and some students most students find the synthesis is the most difficult part of organic chemistry but it's also the most fun and creative soul and a losers are really good critical thinking skills so if you if you working a lot of problems I think you're going to find that synthesis can be fun so I'm here and links here there's a sapling quick links on the side department tutoring Chile could tutoring chemistry better program Office lecture part has our right I don't overdo it I don't think we're doing stem study this quarter you did not mean that molecular models this quarter we will be doing some reactions that had hamsters chemistry so you may like it when we talk about a park sites in Chapter 9 you might like having models but they're not required this here the additional problems in the back of the book and do as many as you can so and 1st of all you want is sapling I had Stewart's take different approaches to their sold some students do the Sapling 1st and then they were problems at the end of the chapter some students were to come to the end of the chapter and then to saplings so it's completely up to you are my son had my class last year and he would do sapling 1st and he honestly would sit there and would mean that you would never ask me questions unless he absolutely was at his wits end it didn't know the answer so really asking the questions that he would sit there and go through all that that himself and he would do that 1st with immediate problems at the end of the chapter and interior figure it out for yourself what you need to do to do well in the class and I don't know if you can just a sapling in getting in the class I don't know if that's possible I've had students before they did that and I think they were just kind of borderline ABB fuel the class I'm pretty sure that you're going to have to work comes at the end of the chapter especially this quarter OK let's see during terms and a final I have them on Friday the 4th week Friday at 8 weeks you can read through this academic honesty wall we do have so sometimes we have problems with academic honesty on exams I do design my exams to catch people are looking at other people's exams so I encourage you not to do that for this class we also had people that were involved in academic dishonesty on sapling and I will tell you how that is that people do that but I I will tell you that I mentioned to have somebody in the past had cheated on sapling and 1 student guidance and got a little light bulb went off in his hands that I can do that too and he did it he said you gave me the idea eventually sapling and then pursue got caught cheating and I whatever anyway so but those are the main thing is that we see and again you're not fooling anybody in this class is a 100 percent continuing so if you change your way through this class we will achieve everything you learned in 51 I will come back and keep coming back and keep coming back and everything you are 51 B will come back and keep coming back coming back so it doesn't it doesn't doesn't do you any good parts of this discussion sections the way they stand right now very likely that the 8 AM class will be gone because students don't like to come in at 8 AM right who is going to be coming to the Indian class we have a few of you OK early birds I admire early birds I'm not I'm nite Albert I admire people this is so the morning such a nice time and sleeping through it but the morning is a really nice time so that was what the *asterisk are ones that I am planning on teaching I'm trying to get rid of this classroom social science trailer 100 air-conditioning doesn't work it's really it's really get out there and it's going to be too small so I middle-American on that all announced it so we're still keeping all these discussions sectors for now if this is a special section were only 1 or 2 or 3 people are showing up there we we try to have moved to a different 1 we do not take enrolled you can go to any discussion you can all discussions it's completely up to the impact are right now I talk to students about how to do well in carrying in organic chemistry and what it was Stinson told me is there in 51 you can kind of get by with memorizing and get through 51 but then that would be end 51 billion 51 C it's impossible to memorize everything so am that's not going to do you any good so on the way out of the way you want to read this classes like the math class parties study for math exam you were problems right that's how study because we take the examining the afterward problems that's exactly the same thing here I think is the most brilliant lecture and you can understand everything I say and then on when you come and take the test you will have absolutely no idea of solving the problems because you haven't done it and so on you know eyes so that's why I got this call from year I forget I see it I remember I do and I understand so that's really what it's about far-right and can't talk about a study that was done about
organic chemistry here and you can read through this but and they were talking about didn't study on students who do well in consumers do don't do well what what are the things that those students who do well having common What things systems that don't do well having common and so I have a couple of points from the study found study was similar between the 2 groups however high-achieving students engage in certain behaviors earlier this semester at guns such as seeking instructor assistants and engaging in practice problems in contrast low-achieving students waited until later in this semester was studied more intensively actually surpassing high-achieving students in frequency and duration of practice problems during the 3rd and 4th points of the summer nights so that the words you this system don't do well actually end up studying more than the students who do do well because the students who do well stop working problems right this so that's the best advice that I can give you you wanna jump right in and hit the ground running and you're going to be right on top and you feel great about it because it's a really we do a lot of really fun chemistry this this quarter alright read chapters before coming to lecture good advice you that you can't always do that I know you have midterms on certain days or have worked about as much as possible he told to try to do that work promises of the chapter as you're reading it the additional assigned problems at the end you know and you know when you get to hang out the SEC you've actually done these problems when you get to the problems at the end some reliable challenging then you need and you don't have to do that you know what I mean you can kind of you know you you want you definitely want to get to the problems where there at the end and they're mixed up with all the things from the chapters and previous chapters you want to be able to get to those because of a larger reading a chapter you know you talk about nucleophilic substitution and they have problems that are just xactly geared to that and then at the end of the chapter there's problems that tell you it's that section C continent where it's what you wanna do is you might get to the point where usable in the house were everything's mixed up because that's what the test is going to be like so you won't know what section it is and that would require you to integrate all the knowledge that you've just learned in the previous chapter I like my example structured tester understanding of material not on your ability to regurgitate facts so really what I want when I try to do as I have you had think on exams but I don't think I don't feel like I ask outlandish questions that you've never seen before when you look at my example if you've gone to discussion sections and Yovonnda lecture they'll look very familiar there's nothing going to be very out of left field anything like that but I do tweak it a little to see if you really had just memorize a if you're actually learning during critical thinking so and so why am I so big and critical thinking because it's so important for you no matter what you wanted doing review and of being a doctor adjusting your normal everyday life critical thinking this is exactly it's going to help you out no matter what and certainly if you're you know knowing it when we do organic synthesis what you learn as you learn a bunch of different reactions and now you're given a compound to synthesize and you have to integrate all those reactions and figure out exactly what to do what about what reactions to I use which ones are not going to be useful it's exactly the same process I know a lot of you 1 of the doctors you go to medical school you learn a million different diseases and all the symptoms and the tests that you have to do than any other patient come in and they give you your symptoms the symptoms and now you have to figure out what they have some of those symptoms might be due to 1 disease so there might be due to another you have to figure out which ones are important which ones are not important is exactly the same thought process so if you know if you're not going to be a doctor it doesn't matter critical thinking is in a healthy and that's what I'm I'm all about in my class so it's been it's going to help you matter what you end up doing Our rights from and so that's what this is all about why the no camp remains in organic chemistry community that never gives you some useless that that's why oral Kim was written by a doctor and he thinks it's the single most important class had as an undergrad to prepare for being a doctor so I'm something Stary vigilantes recommendations so I do write a lot of letters of recommendation and I usually get my biggest grouping in this Brink foreign Medical School Dental School of pharmacy school is ,comma sprinkled around the year throughout the year because they most of them have rolling in enrollment but that's it I have some certain things that I ask of you 1st of all ,comma senior person don't you know me I get hundreds of e-mails hundreds of e-mails and so it's difficult for me to keep track I wanted you can apply to medical dental school I must have all materials used in guidelines below by the end of the 5th week of spring quarter and then I look at your material might tell you fucking write strong letter and so this is what I had orchestrated letters direct questions for a recommendation letter those are the things you want in there so there's a questionnaire that asks you to fill out really helps me making right stronger letter free-associative it's worth your time I'm so this is going to be up on every website I have so see you know if you're going to be asking for a letter recreational probably see you in about a year or a year and a half and so just you know you can always come back and look at this questions on background anything like that alright I think we're ready to search after the 8 Tokay opulence and elimination reactions so old Chapter 7 recovered substitution recovered as 7 1 we cover destined to and we shall we talked about the fact that those 2 reactions compete with each other but we tried to figure out when we have Anderson 1 1 Yemenis into an hour just going to complicate matters matters completely for further we're going to add to the 1 elimination reactions all for those reactions are in competition with each other so we're going to have to be aware that there really have a good background so that we can figure out what's the reaction it's going to take place so what I notice when it what I was doing this discussion worksheet on this week I looked at my review problems from last last quarter and I notice that some of the answers on that we didn't have revealed as the correct for Chapter 7 those are no longer going to be corrected Chapter 8 because Nour and add a little element of complication here and you're going to see that those answers are wrong so honored put those answers Jack again on the special worksheet for next week so you'll see what I'm talking about answering to start with a little bit a so what I'm doing is writing on Word documents because every idea do abiding wanted do a PDF and not a power point because I like to keep the previous page up a little in case somebody slower writing things down as a writing at the PDF you click and that boy that caters gone so I think people would not be very happy about that Our rights over substitution and an understanding of factors that affect substitution reactions that can help determine which mechanism will predominate so you wanna go if you haven't seen this already there is in essence to hand out there under the practice link of our website because it's so practice links in essence to hand out and it talks about the factors that affect as and when it gets into American history that right now on the you can take a look at that so important factors structure the outfield deliver primary do we have a secondary to have tertiary strength the nuclear file talked about what makes a strong in what makes a week nucleophile there was also solvents on polar project for a project so this right here if you did news out of radiation last quarter project and this 1 here is polar a project and both of those on the affects the strength of the nuclear file so can know the idea to go back and review this if you forgot a lot of this and the other thing is leading group ability or right so let's do 2 examples here in this first one here we have a primary I'll
kill him so we look at the outfield here lies the structure the article here like we also looked at the strengthening could fall as I think is a stop good the fall such such a great if you don't remember what makes a great nucleophile what makes abandoned good filed in either that there's a nucleophile strength handouts under the practice like so I left a bunch of those things are already on their website for this course you can take a look at that if you don't remember that and so on Estrada product for this reaction and we have are leaving the only thing that was going on whatever reactions as if you could turn out often Aventis Vickery who is a citizen awareness and to ascend to fantastic this engine parts and that senescence you reaction other primary article headlined Adams are electrifying OK so you know when you have something like that going after all of the whole world is going to see that when this goes on open courseware hope a really committed and I think the term the painting a foundering became alright so OK cool Is it going on thank you so much OK elective father al-Khalayleh we have a great nucleophile again take a look at the new good fostering out of you don't know what it is that Britain would as this 1 hears a church area killer life alright so what can we do understand to oranges Europe candlelight absolutely not so this is going to be innocent 1 family harmony about nuclear file here what is more makes abandoned the founders has a very very slow rate of reaction so it's about the and so instead of having an arson 1 we have innocent you we haven't S 1 reaction this so strong priority is a color showing up OK no not really a riderless changes like this and then I'm going to get there I'm going to get completely alone all of this figured out however this Stephen there has been a key I know there's a race to race until I get this on the understanding no time you'll see all right so that s 1 reaction only can learn in this chapter is that that's not the only product you get you're actually going to get some elimination product there in this so so so let's let's just right added here on the 1 that will make sense later OK so anyone reaction also cited for appearing get from that reaction it will learn about this chapter
but OK belligerent actions about oneself enrollment requirements and to interview bromide requirements and 1 on the road to raise the pulse reactions to take the outturn the rate of innocent you reaction for Attleborough is exceedingly faster than the rate of innocent 1 reaction for ethyl bromide so let's review reaction frozen 1 Apple's fastest followed by primary followed by secondary followed by tertiary and tertiary no reaction foreign assets and wanly action would tertiary is actually the fastest followed by secondary followed by Mathilde followed by followed by primary followed by and what we know about this reaction is that so doing normally get on nonsense you reaction for primary metal when Anderson 1 story yeah now OK because it's very difficult to make a primaries out you'll hear is also difficult to make a muscle here lies and that'll cover Tadiran our primary coverage right so no reaction on land you have a bonds also hello former Thaksin Mathilde the lied these form from residents stabilized ,comma cannons all right so if you have no idea what I'm talking about where I write that Denzel Alabama toxic methyl here like what you wanna do is what you want to do is you want tickling could take a look at Carver can instability there's a handout called can instability some the practice link website absolutely wanted to take a look at that that will be assumed a knowledge of foreign in the 1st versus only for the upcoming mission are excellent compare here what we have energy daggers innocent reaction the primary and tertiary I'll kill him life Bob this 1 here is a primary so let's just use Neville as the bromide here for example and then will just use Turkey it'll bromide for this 1 all right so don't reactions are the actions they can take place because they have to hiring energy activation so hopefully you will remain recognize the has to halfway right here that's of the energy diagram looks like an essential and over here that's the essence pathway and then we have right here the blow and 1 pathways now there's someone carefully can look like better sometimes there's a 3rd step so what would have 3 homes so that those that did that this is a standard of Anderson 1 pathway but if you look at the 1st example here where we have on methyl bromide you can see that there sent to pathway that is a relatively unhindered alkyl here like it is easy for the nuclear file to community backside attack so we have a lower energy of activation here right here for the into reaction for ethyl bromide Ferguson 101 1 pathway we would have to to make up finery Caroline and primary ,comma cannons are extremely unstable and very difficult to make so we have a large energy of activation here and so the reason it's diet is because none of the molecules have enough energy to overcome that higher energy very recently do not see as 1 with ethyl bromide then again the reason is is that formation of the primary ,comma :colon is too high energy yeah the my rightful that's why we don't see someone with a primary alcohol light How about tertiary Octel here like 1 now we have that we we have the 2 things flip-flop now only as someone who's actually faster for the church around here like in as until there is some way way way higher energy of activation for the until announced because of its 204 backside attacks well that's why we don't get any reaction at home for the tertiary uncle under as into conditions we actually get another reaction taking place and that's going to be an elimination Oregon was about that in this chapter questions so far antibodies hopefully this is all coming back to you the impression they're not OK Barcelona
happens only have a secondary Opel here like those the kind of as you can see from this energy diagram of both reactions are possible so I didn't .period either 1 of them so we still have more we still have a you here and we still have a S O 1 8 and will we notice the difference here for this 1 here is that the rates a reaction a very competitive rates of 2 and S & 1 they are very competitive so it's the secondary uncle here was the cause good causes a lot of problems on deciding what reaction take place in case so that's another 1 certainly the most difficult are right so I we summarize this sort of this strategy here on the next stage secondary arguments react with good nuclear players into reactions it was secondary in a good ionizing solvents so again this tedious Paula Froelich Paula Protich if a 2nd priority is in a good ionizing solid-color chronic and no good Goodman good files present as and 1 reactions will prove predominates so examples of polar products solvents these are ones where have you you've taken hydrogen-bond Peony do a really good job of salivating ,comma catamarans in Aqaba carriers where you need to make an innocent reaction so exist for example we have Water methanol ethanol these are the most common so ethanol comments on OK so that pretty much summarizes the so substitution reactions would definitely take a look at that substitution handouts now ready to talk about elimination reactions we saw when a primary opulence reacts with the topside I'm innocent to reaction takes place when a tertiary outgoing I'd reacts with the same nuclear file very different reactions occur so here's our on tertiary kill the light and we have more powerful nuclear file the ,comma degrading the file and I sometimes abbreviated with flowers and you see with but the colon so great if the file ignore the sodium that's just a spectator on Iran what happens is a completely different reactions Will we end up doing is if we call the Coronet spell was bonded to the halogen Alford and the carbon that's adjacent to data In case of the Alpha is the carbon attached to the colleges are we can just let's make it more general carbon attached to there which I usually abbreviated algae for leading Group that's Alpha in any adjacent carbon is beta us so we actually have 3 Bader carbons Delaware right next door is beta and what we find is that what happens really a beta hydrogen and our leading Group so bromide ion and data hydrogen are lost so what our product we actually get to them ethanol that's a side product and we get now please so not something you would expect in public thinking Well that's difficult to figure out what that's happening but we by selling at the end of the chapter you will be able to draw the products other than elimination reactions so that's what you actually get In elimination animals also 2 groups reducing carbon says called debate elimination so this is an example of a beta or elimination we will see other types of elimination but this is the first one that will see nuclear father also strong bases promote the baby elimination reactions so nuclear files that are also strong bases so we're going to have to get that straight ahead what makes a good nucleophile what makes a strong base most of the time good nuclear files are a strong basis but there are some excellent weekly falls Italy faces worrying after really pay a lot of attention to that because we have nuclear files that a strong basis it promotes elimination reactions we have to really keep and keep an eye on them all right so elimination is also in competition with a nucleophilic substitution for all al-Khalili lights would be the hydrogen noticed
this reaction provides a way to synthesize Elkins so we're going to be learning and synthesize all teams in this chapter and so before we before
we move on to talk more about elimination we need to know a little bit about so we already know some things we know that this would be our simplest we know that both Carpenter sp to hybridize so there's Chapter 1 coming back I promised I would have all the chapters coming back and you'll see them so that's Chapter 1 but we have it's a trivial parents triple sorry thank you it's struggle .period we have approximately 120 degree bond angles all right so I kind of John this sort of disjointed King here because we're going for them to fill in the different areas here so we have this area in the center here that is where the electron density from the sigma bond is so that's where Fiore signal bond circular cemetery about the bond the line connecting the 2 nuclear so there would be a signal bonds then we have high is in the area that's not occupied by by that secures here's the fireball and we have electron density on top in electron density on the bottom so that's the part I volunteered and we also have some of the top so that's what we know from Chapter 1 and so long as it turns out that this this pipeline the I'm electrons are farther from the nucleus right on the same upon electrons are closer to their emphasis to the sigma bond for all just to OK so the same electrons are closer to the nucleus and therefore the helpless held more tightly the close electrons into the new clues that could the of the stronger the attraction between the Nicklaus and electrons so the held more tightly which means a 1 when electrons around mortality the less reactive the pylon on the other hand want to do that the rights of the apartment lectures are farther from the so we say they're more aware more loosely held and so on we'll continue this down here so therefore the pipelines were reactive supply wonderfully reactive would learn a lot about the reactivity about teens in Chapter 10 ,comma but we do need to know something about reactivity right now questions so far about Keane's inviting right soap on energy for carbon-carbon double bonds about 146 that's just around the number it's going to depend on what exactly the details of that particular carbon-carbon double Bombay by about 146 83 K cows from all for that for the sake of bonds 63 K Gazprom from all of the pipe bombs so they definitely the pie recovered there isn't any more reactive because they carbon-carbon double bonds of the we need to know about 1 Keynes'-a as it does not undergo rotation at room temperature the barrier to rotation in this and this is not a coincidence 63 K cows from all so that exactly matches this number right here so in order to rotate a pipeline we need to break apart so remember we have applied on we have keep your bills of overlapping in the adjacent to each other if we rotated into your bills are no longer adjacent there's no overlap and so you have to in order to rotational team you have to actually break the pie so that that's what this this is what this looks like but this is an overlap here on the talk and on the bottom if it rotates 90 degrees you see we no longer have a role in don't ever will no longer have any overlap so we break the so no overlap between the 2 orbitals the cheaply orbitals because they're perpendicular to each other alright so as a result of that we can have on licenses about him so but these 2 molecules are here are not the same these are actually stereo isolated musical the cisterns isomers so these 2 molecules are not the same they have completely different physical properties there is no rotation about the AL and so what we notice here in Europe remember this from Chapter 1 we have a dipole for their carbon chlorine we an adult dipole for this carbon chlorine bomb and those exactly cancel each other out so we have a dipole moment for this molecule is 0 0 0 but the bond IPOs cancel out so this is this is the amount the trans isomer and we also have this serious completely different molecules here's the dipole for that carbon chlorine born here's the dipole for this carving Korean-born in those do not cancel each other out they had together and so we actually have a dipole moment for this molecule is 1 . 9 device so the sterilize resident of each other then completely different physical properties was poor ones uncle incorrect so that goes back to Chapter 1 all right
so that is the perfect stopping point and we will continue this on Wednesday