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What organic product would be formed from the reaction of 1-bromo-2-methylpropane (isobutyl bromide) , (CH3)CHCHzBr; with Mg, EtzO,then then H30 ? H,cDraw Your Solu...

Question

What organic product would be formed from the reaction of 1-bromo-2-methylpropane (isobutyl bromide) , (CH3)CHCHzBr; with Mg, EtzO,then then H30 ? H,cDraw Your SolutionWhich diene and dienophile would vou employ in a synthesis of the molecule below?Diene:CH,Edit DrawingDienophile:Edit DrawingIncorrect:Note: Do not need indicate stereochemistry with the dash and wedge convention:Product:Edit Drawing

What organic product would be formed from the reaction of 1-bromo-2-methylpropane (isobutyl bromide) , (CH3)CHCHzBr; with Mg, EtzO,then then H30 ? H,c Draw Your Solution Which diene and dienophile would vou employ in a synthesis of the molecule below? Diene: CH, Edit Drawing Dienophile: Edit Drawing Incorrect: Note: Do not need indicate stereochemistry with the dash and wedge convention: Product: Edit Drawing



Answers

Reaction of 2,3 -dimethyl-1-butene with HBr leads to an alkyl bromide, $\mathrm{C}_{6} \mathrm{H}_{13} \mathrm{Br}$. On treatment of this alkyl bromide with KOH in methanol, elimination of HBr occurs and a hydrocarbon that is isomeric with the starting alkene is formed. What is the structure of this hydrocarbon, and how do you think it is formed from the alkyl bromide?

Okay, let's try to predict the product of various reactions of our kings. Well, if we look at the first one, we're taking the same Al King and just running different reactions to it. And if we take the first one, we know that well, the hydrogen will go to this carbon. Let me redraw that arrow, this carbon and will give the electric to that roaming and the bro Ming will take them and move it to that carbo canton which conveniently would be stable. So we end up getting this product, let me re draw that looks cleaner would be this product the next one. Well, it says basically the same story. We have a acid involving a halogen, and it will follow the same mechanism just with iodine instead of roaming. And we get the same product, the next one CEO to. While we know, that's adding to uh, cl Adams, just an anti addition of chlorine. And you may be wondering, Well, what about the CH to seal too? Well, that's just a solvent that we use that honestly just does. Nothing other than just catalyze is the reaction makes it go a little bit faster requires a little bit less energy. It doesn't really do anything other than that if we use water, there's more complications in a different product, but we'll get that with this one. This is those analysis. So this is just going to split open our AL Keen cut it right down the middle. And on either side you get a carbon eel. We've got an acetone and a methanol for this one age to over palladium. Well, that's just hydrogenation, and we just get in. Al came a, um, a good way to think about hydrogenation in terms of like addition ing or adding additional. Adding hydrogen is if you think about it, this is going to be sin addition. We're adding those hydrogen on the same side, and one way to think of it is you have this palladium sheet and you've got a bunch of hydrogen on this palladium sheet like imagine you have this desk right. You're on a desk and you take a sheet of paper and the sheet of paper is your molecule, and you have the desk that is palladium and there's imaginary. Hydrogen is just sticking out of it. And what you do is You take that sheet of paper and kind of just like, press it onto the desk, right, And it picks up those hydrogen is when you put it there, but it picks up those hydrogen on the same side as each other. Those hydrants are going to be on the same side of each other because there really isn't a way to unless you fold the paper. But you're not gonna fold a molecule on an owl Keen. It will just go straight down and up. And it's a sin Addition of those hydrogen M c p B A is a proxy asset, so we know this will make and a pock side h 20 h two s 04 While this is going to add alcohol now, common the and it'll add it to the most substituted carbon. And commonly we use age to us before, but you can see it be each F or H three p 04 And the reason is this reaction occurs in a non nuclear filic acid, non new Cleo Filic acid and what I mean by this is you want to use an acid that won't interfere with the water you want an acid That's not nuclear, Felix, So that you don't get nasty side products. You just get an alcohol. You don't want to use HCL because you could get the C l somewhere if use h 20 n c l. It'll be this molecule, but where you don't want that you want something that will not interfere with your product. You want something that will do the job of an acid but not impose itself and insert itself into the molecule. So non nuclear Filic acids and these air the three most used to non nuclear filic acids B R. Two with ch two c l two. While we decided earlier that ch two c l to doesn't really do anything to the actual molecules, this is going to be an anti addition of roaming B R. Two with H 20 This kind of goes off to what I said earlier about using a non nuclear pilic acid. In this case, we're using a nuclear file as a solvent. Ch two c l two is not nuclear filic in any way, shape or form. H 20 is So what you end up getting is you start off with this little intermediate from the bro Mean? And what happens is instead of the another, bro Ming Adam, pushing and making anti edition. You get the water to do that, and then the last roaming takes up that hydrogen from the water and you end up getting this product. The alcohol will concert itself into that carbon because the alcohol will choose to be in the most substituted. Carbon alcohol is more nuclear filic than are rather oxygen is more nuclear Philip than roaming, and therefore that's what it will do the morning we feel like, the more likely it is going to go to the most substitute carbon B R two ch 30 h While that Tables tells the same story as the previous problem except this time maken either instead of an O. H, you get O C H d. Same story, though, and finally hide operation. Well, we know this makes the anti Markov nick off alcohol product. So between this carbon and this carbon people, this carbon is the less substituted and therefore the anti Markoff Nichol of carbon. And this will be the anti McCartney called alcohol product.

In this podcast reconciling ourselves with products on the stereo chemistry. So in the first example, we have the treatment assist to beauty Was HCL to generate to claure butane. We have one stereo center so we have to end where and equals one. So we have to stereo. I stammers c c e o an s. I'll chain hydrogen onda missile. Secondly, we have C l c and we just switch these two groups Now on to the second example we have the trans to Boutin and we generate to chloral butane again and were able to generate the same products. So next we can take a look boring And how it can react with our keen to form an intermediate. Why the CIS and Trans can be used is starting materials on DSO. What we generate is the awe Pete on to all generate the ass butin to all Well, the two is the placement of our H. We can have s and r butin to all also generated both using our cysts on Trans. So in the next example, we can have the addition of our proxy assets assist you Boutin as well as trans tribute een to generate the following products where we have to s three aw 23 dynamic style boxer rain That is when we use our CIS. And then if we were to use our Trans, we can get the two s three are what is the two s three s product Using the trans to beauty mean as starting material Next week we generate is the addition of b R two r Rossi Mick mixture off two s three s on to our three are off to three Diab Roma Butane that is using the six and we get Rosie MK mix. However, if we used the Trans we generated to our three s where we generate me so compounds following up on this we have the treatment obsessed to beauty with B R two, followed by the addition of H 20 What we're able to form is to us three us onto our three are three promo Butte on to all and the next we can have the trans where what we can generate is he to all re ass. I need to ask three off. Start moving on. Here We have the treatment of sister Beauty with H two on what we're able to generate using these six, is he following? We have two different products that we can generate and then we can use the Trans. And now we start getting some trends groups in the final product where, as you can see here, we've got a plane of symmetry. Now we're gonna start having thes symmetry flipped. We can also generate second product. So following on from nest you have the treatment of sex to be a team with H 20 in the presence of H two s 04 So what we can generate here is the are you turn to all on the ass button to all using the cysts on the trends following on from this example we have the treatment assist to beauty with C H 30 h. Why we generate the s on the are to meth oxy, butane

So here we're just gonna be drawing reactions. Games. We have three sets of starting materials up on the screen and we're just gonna be drawing out of products. So your 1st 1 we have to bro my propane. This is a more Kafelnikov product and that is because our proton adds to the carbon that already has the most protons, which is this one in our starting material. Next, we're looking out to different starting materials A and B and they both generate to me thought to beauty Not when we add water so we can draw that structure. Now. Well, we have a full carbon chain for Buta and then on a second carbon we have an alcohol group and also in a second carbon We have a missile on the this structure applies to the example below is world where this also generates to me filed two beautiful

With this cyclic Am I also known as they liked him reacting with Ethel continued. So this ethical inured can be thought of as a carbon nuclear file with simple cat ion. The first step, the nuclear file will attack the car venue. Oops to generate this. That's how he drill Intermediate. Of course we have this counter cat eye on at this point, the lone pair of the nitrogen can actually kick in to cleave off this group. It's now will generate with these earmarks side which actually follow the convention truck's this way. So is this the medium? Of course, has the from I can't try on because we are in excess a flickering you'd we can have another equivalence Come in, open up this new medium leasing the lone perv electrons back to the nitrogen accessing our tertiary. I mean, the second step we have acid do not do anything Tio r product, but it can help to protein ate any of the byproducts in this reaction. Really, As we know from our acid based chemistry, the second step, we'll simply protein e army


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