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Consider the following isomeric structures of isoleucine, an amino acid Use this for Q6 and QZ COOH COOH 70 NHz NHz OH OH CH; CH; NHz NHz CH CH; CHCH; 8...

Question

Consider the following isomeric structures of isoleucine, an amino acid Use this for Q6 and QZ COOH COOH 70 NHz NHz OH OH CH; CH; NHz NHz CH CH; CHCH; 8

Consider the following isomeric structures of isoleucine, an amino acid Use this for Q6 and QZ COOH COOH 70 NHz NHz OH OH CH; CH; NHz NHz CH CH; CHCH; 8



Answers

Which of the following amino acids are chiral: (a) $\mathrm{CH}_{3} \mathrm{CH}\left(\mathrm{NH}_{2}\right) \mathrm{COOH}, \quad$ (b) $\mathrm{CH}_{2}\left(\mathrm{NH}_{2}\right) \mathrm{COOH}$ (c) $\mathrm{CH}_{2}(\mathrm{OH}) \mathrm{CH}\left(\mathrm{NH}_{2}\right) \mathrm{COOH} ?$

Hey, guys. So in this question were given three amino acids and were asked to find which one of them are Cairo or a Cairo. So when we determine Kyra Ality, one of the key features in a Cairo molecule is what's called an asymmetric carbon or a stereo center. And asymmetric carbon has four different attachments to it and will determine if that is Kyrill or not. So an asymmetric carbon is in Cairo molecules. And if it doesn't have on asymmetric carbon, it is probably not Cairo. So, looking at our first compound, we have Alan mean and when we look at this, we have four different attachments on our Allan ing. So we can say this is a symmetric. This middle carbon is asymmetric. Thus this carbon or this compound itself is Cairo moving on to glazing. We see that this carbon has to hydrants on it. Thus, it makes it have not four different attachments. So it's not symmetric or it is symmetric. Excuse me. So this compound is a Cairo and lastly we have searing we have again four different attachments to it. So this middle carbon right here is asymmetric and thus this compound his Cairo

All right, so we're asked to draw the this fitter on it Forms of, ah, couple different amino acid residues. Of the first is trip to Finn. All right, so starting pretty simply, with just my mean, I'm gonna leave it right there and another oxygen that I'm gonna draw the our group. I'm gonna draw one to Oh, but so that is tripped if in. Um, so now we gotta figure out we gotta worry about this fitter ionic form. Ah. So a speaker Ryan just means there's basically no charge. Um, and the the way that's gonna do that, like a neutral pH is this is gonna be hydrogenated. That is going to be Ah, deep resonated. And then you're gonna have an age three. Plus, you'll see that the positive charge on the age three of the negative charge on the car, boxy cancel out to form a neutral I on. So this is this foot ironic form, all right. Moving on to Isil Lucy, and we're gonna have basically the exact same start. Ah, and his three plus in a draw. That's ah. And then that just like I would for any other amino acid Now the reason I immediately just drew initial three as opposed to waiting to drop the charges, is another. The I solution is ah, hydrocarbon side chain. So it's got no no charge, no nothing that might affect the overall charge. So I can just draw my solution right here like that. And that's the form for that one. All right, so we got Sistine up next. Um, I'll keep my NH my oh, my. Oh, then, my ass. All right, so if I leave, this s deeper. Nated. That will have a negative charge. Um, it same as if I leave the oxen. Gee, deeper unaided. Um, so basically, what we need to figure out is which is gonna department first the oxygen or the sulfur? In this case, the car books look, acid is a better acid. So this is going to be the one that has a native charge. First, eso in order to keep up positive charge, I'm gonna label this with a positive and then just tack on my ha jin to make that file group for the Sistine. All right, last we've got histamine, which we know is another one of the potentially charged amino acids. Some believe my NH there show my oh, same thing I've done for everything. One move here. Ah, Introgen on two. That's a nitrogen. And here. Okay, so out of these two nitrogen in the ring, this one on the bottom, that one underlined in red. That's gonna be the one that's more important. Determining charge. I'm gonna make a pretty similar argument I did with the Sistine example. Right. Um, since both of these night sessions here and here can have a positive charge, but we only have one molecule right here they come. Negative charge. Only one of them's gotta be appropriated. Ah, and just based on pH values, it makes more sense for this to be our positive charge into this. Just have an age this to be negative, all right? And knows where this figure on it forms of those four amino acid residues

This is the answer to Chapter 19 problem number 65 from the Smith Organic Chemistry Textbook. And in this problem, we're asked to draw two amino acids at their neutral, positively charged and negatively charged forms on were asked which form predominates at Ph. 16 and 11. Um, and then we're asked, what is the structure of each amino acid at the ice? So electric point. Um Okay, so first for asked about me thiamine on, and we're told that decide chain of Bethany ch to see h two s c h three. So, uh, to start, you can draw. Um, Okay, well, so we'll do. We'll do a, uh, on this top line. So let's start with the neutral form. Um, and neutral form is going to be, um, this winter I on. So we have a central carbon. We have the card box doing acid, which is going to be deep throat nated. Um, we have a hydrogen on our central carbon. Then we have the mean which is going to be protein ated in this winter. I on form on. And then we have our side chain searching. Here was ch two ch two s C H three. So that's, uh that's our sweeter eye on our neutral form of this molecule. I'm actually gonna move this over just a little bit. There we go. And so, uh, the positively charged version of this molecule is going thio have the protein ated mean. Um, but we'll also have the car box cilic acid protein ated. So here's our carb oxalic acid protein ated. So there's no charge there. Here's our mean protein ated. That's where the positive charge comes from. Ah, and then our side chain, uh, is unaffected year. So that's going to look exactly the same. The negatively charged version of this molecule is going to be exactly the opposite. So we'll have the deep resonated carb, oxalic acid. Um and then we will have the not protein ated mean so in each to with no positive charge on it. C h to see h two ch three. All right, so then for be weaken D'oh! You know the exact same thing So we can eso what's be be were asked to draw. Sorry. So, for severing the side chain is C H 20 h um, okay. And so we can do exactly the same thing. So the neutral molecule, it's gonna be the sweater I on central carbon carb, oxalic acid de protein ated protein ated a mean so's Witter I on positive charge. Negative charge in the same molecule on our side chain for serene. We said with C h 20 h eso again, The positively charged version of this molecule is going to have the not deep throat nated carb, oxalic acid, You mean will be pro donated. And then again, the side chain is just the side Jane ch two Ohh. Um and we'll do exactly the same thing. Um, the negatively charged form of this molecule car box. Silly gas. It has been deep protein ated. Ah, and the mean has not been pro native. And there's the side chain. Okay, s o, uh, left to right again. These air, the positively charged versions, the neutral versions on the negatively charged versions of each of these molecules. I'm so we're asked, uh, see exactly what we're asked. Um, which foreign predominates at Ph 16 and 11? Um, OK. And so ah, at p H one, we're gonna have the positively charged versions of these amino acids s O P. H one at ph six. We will have the neutral versions, and two ph. 11 will have a negatively charged versions. Um, And at the Isil Electric point, we're gonna have the neutral versions of these molecules. So I so electric point, we will have this winter ions. Okay, so that's Ah, that's everything that we were asked about these two amino acids. Uh, and so here they all are. And that's the answer to Chapter 19. Problem number 65.

Problem. 13 is asking us to draw structure for amino acids and when the pH is less than one. So you have to remember that when the pH is less than less than the P I, that the overall charge of the moment of the amino acid will be plus one. So in that case, the amino group B positive on the Horrocks look acid group will have ah, hydrogen. Overall, the net charge is plus one for Sistine again, the P I is greater than the pH, so that should have a positive charge. And again, it's the same basic structure with a backbone of all of these amino acids. I mean, a group and then the carb oxalic acid. So the Sistine eyes carbon and then the it's over. And this will also have hydrogen attacks to attach to the curb oxalic acid group. And so this one will also have a charge of plus one tyrosine. Same basic structure. We have a positive, you know, group a couple oxalic acid group. This is our our group. That's actually this is a benzene ring and having ohh going off the top. This will also have hydrogen attached to the carb oxalic acid group. And then this one has in that charge of plus one as well. For this last one again, the same basic backbone were you know, acid for this one will also have hydrogen, a text attached to the curb Oxalic acid group. And so this one is also gonna be a plus one charge.


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