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29-46. Complete the organic reactions with indicating stereochemistry[1] NaNHz equiv}NaNHz OTs[1] NaH[21 8 [3] HzOHO[2] CHzlHzONaPdlcNH;Lindlar[1] Os04 [2] NaHSOz[1...

Question

29-46. Complete the organic reactions with indicating stereochemistry[1] NaNHz equiv}NaNHz OTs[1] NaH[21 8 [3] HzOHO[2] CHzlHzONaPdlcNH;Lindlar[1] Os04 [2] NaHSOz[1] 9-BBNPCC[2] HzOz, OH"

29-46. Complete the organic reactions with indicating stereochemistry [1] NaNHz equiv} NaNHz OTs [1] NaH [21 8 [3] HzO HO [2] CHzl HzO Na Pdlc NH; Lindlar [1] Os04 [2] NaHSOz [1] 9-BBN PCC [2] HzOz, OH"



Answers

Give the stereoisomers obtained from the reaction of 2-butyne with the following reagents: a. $1 . \mathrm{H}_{2} /$ Lindlar catalyst $2 . \mathrm{Br}_{2} / \mathrm{CH}_{2} \mathrm{Cl}_{2}$ b. $1. \mathrm{Na} / \mathrm{NH}_{3}$ (liq) $2 . \mathrm{Br}_{2} / \mathrm{CH}_{2} \mathrm{Cl}_{2}$ c. $1 . \mathrm{Cl}_{2} / \mathrm{CH}_{2} \mathrm{Cl}_{2}$ 2. $\mathrm{Br}_{2} / \mathrm{CH}_{2} \mathrm{Cl}_{2}$

In this problem, we are asked to evaluate the stereo I summers obtained from each of the following reaction paths of two butin. So starting at the top, we first react with hydrogen and lenders, catalyst, poison catalyst reactions always result in CIS Calkins. So we have sisters to beauty in from that and then a reaction with roaming and die plural methane will add two equivalents of roaming to the compound. But we have to remember that this hello donation reaction is always resulting in anti edition across the double bond. And so we might have one come out of the page and the other co into the page. But we would also have its mirror image, also known as it's an anti armor form an arrest Simic mixture. The second problem rest first for the dissolving metal reduction, which results in a trans O keane. And thus we might draw again the carbons planer and we'll have anti edition across the double bond, one grooming out the other rooming into the page. And we might consider what nancy more this compound would look like. If we were to draw one, we can have the first carbon go the first roman go into the page, the second remain come out of the page. You'll notice that if we were to rotate this 180° that we would actually have the exact same compound. So this is not a compound within an anti um er And thus this is the only product that we obtain. Mhm. For the reaction of first chlorine will have a Trans Alpine assuming one equivalent. So we'll have one chlorine on one side, one chlorine on the other side, and then again roaming and declare a methane will have anti edition. So we'll force draw the bro means to make sure we get that anti edition 12 1 growing out of the page, the other booming into the page, leaving the chlorine only one spot to occupy. And once again, if we were to draw on an anti emerges compound, it would have rotational symmetry and be identical to our previous compound. So this is the only stereo system are obtained.

Let's take a look of different reactions of all kinds. Now the first one. We have a terminal kind and we're acting reacting one equivalent of Romy. So because of this, what will end up producing is is this molecule Now? We don't know where this last roaming will lie, but it's probably going to be actually going to be hope here because there is an anti addition of Romy. So be this product. Most likely. What about HBR? Well, similar story mark optical product. Same rules. Apply. I was keen, except think of an AL kind as two out Kean's on top of each other. That's largely of what the reactions of all kinds are all kinds relative. For most of the time, all kinds do the same reactions as Al Keane's. But say, if you want to produce and in Al Cane, for example, or a halo cane, you would only do the reaction. Wants to announce keen. But you do the same thing twice to an out kind, because if you think about it, it's more of like just to out kings on top of each other. So it's like a layer kind of thing. Speaking off we have to equivalents of HPR. Now our first reaction produced and I'll tell Keane like this. Now we react another molecule of HPR. And really, this is a situation where the rich get richer and the carbon that is the most stable is still the carbon that would have that, bro Me. So you end up getting the bombing on the same carbon and hydrogen will be on these carbonates on this carbon. The hydrogen would be on that carbon H two and access. And with her catalyst, well, that will just produce an al cane H two nickel boron or nickel to born P two. Well, this is a large mess, and really, it's not really anything of that we dealt with before, and it would not be a reaction if Instead there was levelers catalyst, which is lend Lars Catalyst, which would be palladium O C O C h three, um, three C A CEO three and cuenta lean, which is an organic molecule. I mean, this is all organic molecules Crenna lean, which is an Amin. Um, that would produce A says our cane, but we don't need to worry about that for terminal out kinds So because of this, there is no reaction because nickel isn't really involved in al kind reactions. Suppose we have any NH two in an H three liquid, and we followed up with a hail out came Well, we start with a terminal. I'll kind and really, you can kind of think about this as just adding a chain. You can think about it as though you were making the first one into such an electron deficient or well electron rich molecule by adding a base to it that you can just add an electric file and we get this molecule. So here there was a hydrogen. Now here there's a train. Similar story. We would add our carbon. There's just adding carbon carbon double abundance like you're using green yards without actually using a key toe. You're adding it to an al QA im. So that's kind of the story that's being told by these reactions

This question asked us what stereo I summers are obtained when two butin reacts with each of these combinations of region. So I first wanted to identify whether these things adds inner anti. So, um, issue with the littler catalyst will add sin. And then br two will add Aunty So and the best way that I have found to draw out these types of stereos MERS is to start with your carbon carbon bond, and we know that we're gonna have two things in the plane, and then we'll have something on a wedge and something on a dash on each side. So something about a wedge and something on a dash, and then we'll start with the last thing that we added. So we added, be our last, and those were opposite each other. So we're gonna put them in the plane opposite of each other. And then we know that the H to the two ages from the little are catalysts added sin. So those have TB either both on the dash or both on a wedge. Either way is fine, so it will just put them on a dash here, Um and then the only thing left over is the methyl groups. So we add those in this box that are left over. Um, and so this is one of anti murder. And we will also get the other in an seamer of this where the metal and the Asians would be switched. Either one. Well, we'll get both, actually. And these are 30 an anti MERS Rio and Anne Sumers. Um, and we don't really get those when we add sin to a transport keen, which is what happened. Um, we're so sorry. We add anti to assist Al King either right, and send you a trains or at anti to, um, ASIS and you got knees. Oh, when you add synthesis or, um, Antigo trance. So it's just the opposite of that in part B. If we start with theme sodium liquid ammonia, this will add anti. And then the BR two will also add anti. So when we draw this out again, start with that. See, um, in our bonds in the plane and then our wedges and dashes. Um, so the last thing we added was bro me. And so I'll put those right here apples each other in the plane and then we have ages that are opposite. So one wedged and one dash and then arm full groups will fill in the blanks. Um, and this is actually a miso compound on, and there's a couple ways to know that we can a know it because we added anti it to a trans El Keane. This gave us a trans El Keen also works if you add, um, sin to a cysts Al Keen or if you want, you can do the stereo chemical work, and you can rotate one side of this molecule to put everything in the same planes. Um, and you'll see that everything matches up and you'll get a line of symmetry. And then for part C um eso, we have chlorine, adding anti and grooming, also adding anti so here we're also going to be adding anti to a trans El Keane. This will give us the trans El Keen, so if we draw that out, we'll have our seas with our in the plane and wedges and dashes on both sides. Um, our last thing added was bro means I'll put that here and then our seals have to be exit each other and will add those metal groups in to fill in the blanks groups. Um, so this will be a me so compound as well.

Let's take a look at more reactions of al canes. Well, let's take the first one with each 20 in each to us of four. Well, we know that that will produce the Markov Makov product in an alcohol so well, which carbon involving the, uh the l keen four carbons adjacent to the Al Cain will contain the alcohol. Well, the most stable carbon is that one. So that will be where the alcohol will be. And that will be your product stick. It will get the next one. Here we have this out keen with brahmi and water. So we know that that will produce the mark optical product relative to the alcohol. The alcohol would be the most stable. Be at the most stable carbon, and the Bruning will be at the last stable carbon. We know that boring nation produces the anti Markov Nukaga alcohol, which means less stable al keen or less stable alcohol of the Al King. So the less stable carbon is that one because a tertiary carbon is very, very stable. So that will be where alcohol will be produced, bro Ming. Now, this doesn't produce a carbo cat ion. So We're kind of just limited to a bro. Mean Adam here and abroad. Ming Adam. There those analysis. Well, this will cleave this double bond producing to Aldo hides. And from the looks of it, this molecule symmetric relative to that out keen. So it will just produce to molecules this Aldo hide, and that will be your final product.


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