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Topics: Newman Projection, Conformational Isomers, Energy Diagram Practice: Draw an energy diagram for the rotation about the C2-C3 bond in 2-chloro-2,4-dimethyl pe...

Question

Topics: Newman Projection, Conformational Isomers, Energy Diagram Practice: Draw an energy diagram for the rotation about the C2-C3 bond in 2-chloro-2,4-dimethyl pentane. Draw Newman projections for each local maximum or local minimum energy. Label each structure with anti, gauche, eclipsed, and/or staggered:

Topics: Newman Projection, Conformational Isomers, Energy Diagram Practice: Draw an energy diagram for the rotation about the C2-C3 bond in 2-chloro-2,4-dimethyl pentane. Draw Newman projections for each local maximum or local minimum energy. Label each structure with anti, gauche, eclipsed, and/or staggered:



Answers

Draw Newman projections for the staggered and eclipsed conformations of pentane for rotation about the $\mathrm{C} 2-\mathrm{C} 3$ bond. Which conformation is lowest in energy?

This problem will take a little bit of time. So I've gone ahead and drawn the first example in an energy diagram. I'LL explain it, and then we could do the second one together. So keep in mind it's first compound or this first confirmation is the same as the last. This is increasing energy following this line and pathway all the way back and down, so thes connect on either end if you were to make a loop out of it, and what I'm trying to show is the back carbon. If you follow, The Ethel Group is going all the way around three hundred sixty degrees, so if it moves up a little bit, then you get the eclipsed comes around your gash again, comes down its cliffs with the Method group comes down. It's gosh agan eclipsed with the hydrogen and then back up where it started. So let's look at the energy of each of these positions and see why some are greater than others. So this is the lowest energy confirmation because Thie F group is one hundred eighty degrees from the Method Group, there's far apart as possible, whereas if we were to look att. The positions where Their couch to one another. The Ethel. In the methyl group, there is still some Starik interaction that occurs here. So this is at a higher energy than this confirmation. So these two will be equivalent and energy because you have girls hydrogen sze all around the ring and one Ethel Ethel Goshen direction. You could physically do these calculations if you wanted to, to figure out the actual energy in the system. I chose not to just based on experience, But that is something you could do if you didn't want to work on intuition. If you actually wanted to calculate it, This works If we look at the Eclipse versions now, here we have a method all and a hydrogen eclipsed and Ethel in a hydrogen clips here to hydrogen is eclipsed. And the same is true with this energy level. So these two energy levels really the same. This one's at a higher energy because you physically have the apple and the methyl group eclipsed. So if we look at doing the next example, it's opened up a new page here. This was actually a little bit different in that you're gonna have to higher energies there. Just about this name. I think we're gonna want to draw something that the flake like this? Yeah, a little bit of an energy difference there. Thes to the same and then going back to our starting position. So here to draw the easiest form. Now we have an ethyl group and and that the group on our back Carbon our friend Carbon, I believe, stays the same. Hey, Trajan. Hydrogen. The lowest energy confirmation is goingto have thie ethel group opposite of the methyl group. Just because it's a larger side chain. Then if we go ahead and move around the rain here, I like to keep my front carbon the same conditions here. Now we're gonna have the ethnic group eclipsing the hydrogen. This hydrogen moves down to behind the methyl group eclipsed, and this metal group will be eclipsing this hydrogen if we move down into the energy. Well, now we're moving this ethnic group over one. So here's the group. Gosh to the metal. The hydrogen is now going down. That was over here, and the methyl group in the back is now appeared. So the reason this is at a higher energy is now because thie ethel group is gosh to the method group. Maybe not a huge difference. And energy, but they're definitely should be some difference in energy. I may have exaggerated a little bit, so yeah, well were added ish. Probably. Also draw some units here. This is an energy diagram here and here. We still have a hydrogen going up. Now. Our effort group is going to be eclipsed with the method. This should be one of the higher energy forms. The hydrogen here should be eclipsing this hydrogen. He and the method is going to be eclipsed with the top hydrogen. In the next case, we're gonna lower an energy a little bit coming back down to a garish position. This Ethel and we have these air. So hydrogen sze don't change anything about the front. Carbon just moved the carbon in the back. And now we have a hydrogen up in this position. So I'm really just rotating the back carbon in a counterclockwise direction. Now, arm Ethel group is there. So now we have two interactions with that are gouged to alcohol interactions that air gassed. Those fish should be higher energy than this couch interaction. Then if we move to the other way, go back to an eclipsed form. Now your method group is coming down this direction. The group is over here and the hydrogen is over here. Thes to energy should be fairly similar. If anything, the ethnic group might be a little bit greater than energy. But not by a whole lot. Just because alcohol chains a t least s p three alcohol change should be fairly similar. And then that takes us back. Teo, our starting position, assuming and Ethel Group is the same as a method group. As faras energy confirmations. I did go ahead and also calculate a little bit of the high energy states. So at these three positions, the three eclipse positions. So here you have two hydrogen carbon interactions, which the book says is well and eh, you have three. Sorry, you have three carbon hydrogen interactions, which is about four point two K cows per mole of energy. To be in the eclipse form like this For this form, we have an eval siege too. Hydrogen, hydrogen and a carbon, A metal hydrogen overlap, which, if you add all that up, comes around five point O. And then for this one. If you add up all of these, it comes at just about five point o again, assuming that in Ethel's just about the same size is a metal group, which isn't one hundred percent true.

Let's draw the Newman projections for the standard and Eclipse confirmations for two metal panting for rotation about the carbon to and carbon three bond. So let's take a look at to muffle Pantene and identify carbons two and three So we'll have that h three c c h ch three ch two ch two ch three. And if we identify, this is the carbon to carbon three. So we're gonna identify the rotation about the carbon, too. Carbon three bond. So let's start by drawing the eclipsed confirmations. We have ch three each three each. One, 23 and the eclipse configuration. Yeah, a little bit better here with one to three coming across this way. Here each H c h two c h three. This will be ch three h three c h. They're equipped with be each he ch two ch three and the third eclipsed confirmation will be each age ch two c h three are staggered confirmations way will have th 38 h three c and then they're staggered. We will have sure h h ch two ch three h three h d c c This confirmation here would be h each ch two ch three and ch 38 age three C that each each c two c h three. So there would be our eclipsed and staggered confirmations for two methyl painting about the C two C three bond rotation. Which confirmation is lowest and energy. So the staggered confirmation in which one methyl group is opposite the folk group. Yeah. Mm hmm. Um, em mother group is nothing. Nothing. Um, in both, um ghost and And he there's two of them are the most stable and the lowest energy confirmations. And those two staggered confirmations that would be the most stable would be these two here.

Okay. This problem is having us draw the Newman projections of a painting specifically on the carbon to and carbon three bond. So I have my painting here. This is my carbon number two. And this is my carbon number three. Okay, somebody rotate alon this axis, get and then let's represent that in your projections. So whenever I draw Newman, projection is the first thing I do is just go ahead and draw my circle because that circle is going to represent basically where my bonds are attached so we can get a different perspective on where the bonds are relative to those carpets. So the circle on the front side, the one that's facing me, I'm gonna have the circle that is going to represent carbon number two. Okay, So carbon number two attached that have my two hundreds coming in a wedge and coming in a dash. But from this perspective of my new in projection, they're going to come out to the sides like that. So 100 in there and hydrogen there and then coming down along this bond, I have my ch three. So I'm going to write that right here, so ch three okay, and then going on to cover them, too. So I'm gonna way to think about Newman. Projections is if I draw the circle over here, right. This arrow, we can kind of think of that circle as if I just continued it all the way. It'll be where minute projection is. So this circle right here corresponds to this circle. Okay, so moving back along. Okay? So carbon number three right here That corresponds to the back side of this circle. This Newman projection. So Carbon number three attached to that. I have these 200 is coming off, so there's gonna be right here. Okay? And then also on the topside, I have that ch two connected to my ch three. It's a ch two ch three. Okay, so that is the first human projection. But of course, we have to go through all six because we have to rotate along the sea to sea. Three axis. Okay, So what I'm gonna do is again draw my circle, okay? And then let's just keep one side constant. So keep my two side, the front side constant. So seize three here. And then I have my h and my other hydrogen. Okay. And now we're just gonna rotate my ch two ch three bond or start my access so that I get my ch two ch three in a different position as well as my head regions. Okay, so if I rotate it, um, I believe this would be 60 degrees. Then I would have this were out, Have my ch two ch three over there. Okay? And then on the side, I would have my hydrogen. And right here I have my hydrogen. All I did on this one was I just moved my stage two over right here, okay? And then, of course, we have the movement of 60 degrees because we go from here and then this would be the next 60. So 60 and then 1 80 Because right here, that is all, Um 1 80 we keep going. Keep going. Keep going until we get back to 3 60 So at each turn is gonna represent 60 degrees editor. And then, obviously, I just wrote out this a little bit in front of that 100 same with the president, but in reality, they should be directly behind the hydrogen. And that is representative of a very particularly unstable representation of that bond because normally they would want to be in Diskant, former, where I have my ch two ch three directly on the opposite side of my ch three. That's just the most able conform, er, that's called Staggered. And then this is called eclipsed. Okay, so next up, I'm gonna draw the next 60 degree rotation, which is where my ch two ch three is gonna be next to my siege. Three. So, for example, dry out my anyone projection, starting with a circle draw out my, um, compound where I have my hydrogen and then my ch three. So, of course I'm keeping the front side of my compound, um, on the same position, and we can choose to do that. And you're either the front or the back, whichever is easiest for us. I just prefer to keep my front the same. Okay, so my ch to stage three is not gonna be over here. So siege to stage three. Meaning it's Hodgins are gonna be on the opposite sides like this. Okay, so this is considered to be staggered because it's not equipped anymore. So each around this bond this bond between my carbon number two on carbon number three, The corresponding subsequent off of that. They're all not on the eclipse side. They're just in a staggered confirmation. Okay, so that's three so far. And to do the other three. So the other three starting off with this circle, I'm gonna keep my front side Constant associate three here and then hydrogen and hydrogen. My ch two ch three is now directly eclipse of my ch three to see it too. Ch three. Okay. And that means that my hydrogen is here and my other hydrogen is right here. So this is considered to be eclipsed. And this would actually be considered to be the most unstable Because we don't like these to be interacting with each other. They're too close. We have too much stare kindred on it. So this is the This is the most unstable form. Okay, so next up, I have the next rotation, the next 60 degree rotation. So, circle, how do you do? How did you and then my group three and now it's not going to be an eclipse. It's going to be staggered, So ch two years, three. It's little messy, but I think we get the picture. Nitrogen and hydrogen. Okay. And then last but not least, is the last rotation until I get back to the 3 60 So I have my circle. How did you hydrogen and then my muscle groups? And now it is going to be an eclipse, because right now it staggered. I need to go 60 degree rotation so that I get my ch two ch three directly behind that. How did you so seems to seems three. And then I have my hydrogen in the eclipse with this 100. And then I have my other hydrogen eclipsed with that series three. Okay, so these air my six different conformers of my plantain. If I did a rotation on the sea to secret bond, OK, but now I have to draw the potential energy diagram. So by potential energy diagram, it is a potential energy potential energy on the Y axis going up. And then I have my degrees of rotation on the bottom. Okay, so let's start off with the, um with the most unstable. So the most unstable of these is going to be this conformers. It is the equipped eclipse conform. Er, and then we also have my ch three and my ch two ch three. They're interacting on the same level, so I'm gonna draw that one out. In fact, I'll just go ahead and circle this, and we can just duplicate it. That and I'm gonna move it over here, and then we can actually go ahead and condense that so we can fit it onto the same graph. Okay, so my potential energy grant diagram is going to follow a basically a wave following some like this. So we start off right here, and we're gonna go way up there, okay? And then let's go ahead and move that a little bit over, or I could just re drawn my line. Okay, so this is gonna be way up there, and then it's gonna start to go down. As I approach the next degrees of rotation right here. It's a 60 degree rotation. This would actually just called this zero, and then the next 60 degree rotation is gonna be somewhere right there, and then it should go down. So I'm gonna show it like this in which we have on the next, um, we're going from this conform er And then we did the next rotation, which would be this one. Okay, so that's this Conformers is considered to be relatively stable, but not ideally stable, because ideally stable would be this conform er, in which we have my ch two ch three directly opposite to my ch three. So this is gonna be considered stable because it's considered staggered, but it's not as stable as we'd like to be. So I'm gonna go ahead and circle this one, and then I'll duplicate it, and it's gonna go somewhere right there. And it's not gonna be completely low and potential energy because the complete lowest and potential energy would be this one. So I'm gonna put this little wave my bet. I put it right here. Hit and next step. Next up, we have the next rotation, which is this one. Okay, so that rotation is considered to be eclipsed, and that is, um, not not the worst stability, but it's pretty bad because it's eclipsed. Okay, but the obviously the worst, but eclipsed one, it would be this one, because that takes the most energy to be in that confirmation. Because we have the eclipse of the CH three and ch two ch three. Okay, so on this one, my ch two ch three is a little bit of ways for my ch three. So that is not ideal, but it's it should be much better than my 1st 1 So I'll go ahead and I like this one, and then I'll duplicate it. Sorry, I just shorten it and move it in a position lower than my 1st 1 It's right there. Okay, so right here. It's a little bit lower and potential energy than this one right here, because this one takes more potential energy to get into this confirmation than it does for it to be in this confirmation. Even though this is bad because it's considered to be eclipsed, it's not as bad as my 1st 1 Okay, next up, I have the next rotation over, which is where my ch two ch three is directly opposite to my, um, ch three. So this one Oh, I like that. And then duplicate it, move it down here. And this is considered to be the most stable. So moving, actually pretty down and it will be very low and potential energy. It's always done there, and then we start to move up again. And this one is because we're going into this eclipsed version. It's not Eclipse version similar to the previous one or two previous ago. We have the CH two ch three relatively close to my stage three, but it's not close enough to be considered a very unstable. So this is considered to be high and potential energy, but not as high as possible, some of it down and put it in the same area as the one right beside it. Okay, so that means that this is gonna be right at the same level as this one. Okay, Okay. And then moves down again, and I should get this one. So this one is considered to be staggered. It's pretty stable, but not ideally stable. Ideally stable would be this one right here, right there. Okay, So I'm gonna move this one over here so that it's considered to be that's I move this up and then I move this a little bit down case in all the way. And then, of course, this goes back up again. Okay, so that is the potential energy dear diagram and I'll go ahead and mark these, um, as such. So 1 20 1 80 This would be to 40 and then this one will be 300 3 60 would just be back where we started. So that is a potential energy diagram. And then I already highlighted the Newman projections and put them down below. But hopefully you're following along so we could actually get the process to step by step process.

Hi guys. Live some problem. 42. We need to run human projection off the most stable and lets the stable confirmation off to me. Tiger Beauty in. So we know that always the most stable conformation is the Gulch confirmation. And to meet held it in his to publish information, let us draw the two confirmations. Police. It's one and into that of the bunch. Confirmation is this one. So what? We see that in confirmation. One there are to We tied me, tell interaction. And in confirmation, two days only one will have had confirmation interaction. Therefore, this is confirmation to ease Morris table, then confirmation one. And it is the most stable one. This is the most stable information off when we have a beacon. No, we know that the list is stable. Confirmation is the information which is eclipsed. My visit gives information. Leaves us Mr Straight. We just drove them a clips confirmation for title Lieutenant. This is the least a stable confirmation. Do me title mutant. No time problem. We need to draw the energy profile when we don't get off on two and three, so laters. Draw older confirmations. Let's just start with groups to information. Now if we'd voted six tragically really get about information. If you don't read a in another 60 degree, we'll get eclipsed for information. Island of ultra information. Then another eclipse for information. And finally we will return to the emission groups trumps domination. Now we need to draw the energy pro find what? Before that we need to the government Who is going to give the highest energy? What we see here we have Do we have any time eclipsed your direction? And one hydrogen hydrogen It gives to direction Want me 10 hydrogen Eclipse your direction So this come this confirmation is highest energy the energy propane So why excesses? Energy and X six is his angle approbation And we have the highest energy for the tipster information Because if we and to these numbers these values are given in the problem intermittently clips just live in collegial for more on me telling me I got a chance Street 0.8 killers from one meantime, hydrogen a close to 600 and hydrogen hydrogen equips transport religion 11 latents and enter these numbers for me 10 mentality cleaves to 11 individual form one 400 hydrogen eclipsed for villages. 11 410. It keeps to six religion from one of you since 21 individual for more energy for this confirmation. Then from the 2nd 1 we have do you take any pain, Welch directions. So the energy in this case is going to be 3.8 plus 3.8, which is 7.6. Imagine for more for the hard won again, we have to meet any time. I want me. Tell me time one me tell hydrogen one hydrogen hydrogen interaction. So again, the energies went to read 21 Oculus. Next we have only one. We take me time interaction, which is culture directions. So the energies on the 3.8 emerging from one in the next one we have, we have. This one is Yeah, we have on the three main title any time interactions. Middle hydrogen eclipse Redirection. So what we need to do is on six. They're having 636 killed Japon ones. So in this case, 66 plus six Villagers upon one gives us 18 individual for moon in the next storm. Again, we have on the one we tied me tired interaction, which is going into election. So the energy is in this case 3.8 religion and one final one again. One retained. Retained when we 10 hydrogen and one hydrogen hydrogen eclipsed in connection. So doing do on religion Formal is the total energy. So now leads place on this energy. Energy burns in the plant. The farce really is having highest general damages strength, you on. Imagine 11 Then we got 7.6 which comes here. Then again, 21. Next, we're going to 3.8 28 e d g. Then again we go to 18. Pleasure for more to 40. Didn't you going date again? Finally again. We've got 21 on one. No, we need to draw the energy pro. Fine. So this is how then it just goes up and down. This one is trying to eat. This one is 18. Reach France here. So it goes up to 18. De Gaulle was down and we need to pull some. And this is the energy dragon for this on these confirmations. Off to me. Time built in


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