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Calculations to determine amounts of material to Use in the synthesis. All calculation are based off 0.0150 moles ofthe carbonyl starting material. NOTE THE YOU MU...

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Calculations to determine amounts of material to Use in the synthesis. All calculation are based off 0.0150 moles ofthe carbonyl starting material. NOTE THE YOU MUST DO BOTH SETS OF CALCULATIONS: For your caleulations it is important to note that the ketone react with onc equivalent of phenylmagnesium bromide but the ester requires two phenyl magnesium bromide equivalents (4.5 pts) 6~| Synthesis using benzophenone as the carbonyl staring material When using' benzophenone you will form your

Calculations to determine amounts of material to Use in the synthesis. All calculation are based off 0.0150 moles ofthe carbonyl starting material. NOTE THE YOU MUST DO BOTH SETS OF CALCULATIONS: For your caleulations it is important to note that the ketone react with onc equivalent of phenylmagnesium bromide but the ester requires two phenyl magnesium bromide equivalents (4.5 pts) 6~| Synthesis using benzophenone as the carbonyl staring material When using' benzophenone you will form your Cirignard reagent using 25 molar equivalents (25 percent excess of the bromobenzene (relative to the carbonyl compound) and 4,35 molar equivalents (35 % excess) pLmaghesium Olearly label all caleulations and use the letters below to label each calculation; moles of lYk benzophenone grams of benzophenone moles of bewzophenone moles of Mg Oc} Lnksls moles of Mg grams of Mg ISO mbs 8P moles of benzophenone InJ &P moles of bromobenzene moles bromobenzene t BB grams of bromobenzene 0 Urhut BP x grams of bromobenzene mL of bromobenzene ndRP



Answers

The reduction of aldehydes and ketones with a suitable hydride-containing reducing agent is a good way of synthesizing alcohols. This approach would be even more effective if, instead of a hydride, we could use a source of nucleophilic carbon. Attack by a carbon atom on a carbonyl group would give an alcohol and simultaneously form a carbon-to-carbon bond. How can we make a C atom in an alkane nucleophilic? This was achieved by Victor Grignard, who created the organometallic reagent $\mathrm{R}-\mathrm{MgBr},$ with the following reaction in diethyl ether: $$\mathrm{R}-\mathrm{Br}+\mathrm{Mg} \longrightarrow \mathrm{R}-\mathrm{MgBr}$$ The Grignard reagent is rarely isolated. It is formed in solution and used immediately in the desired reaction. The alkylmetal bond is highly polar, with the partial negative charge on the $\mathrm{C}$ atom, which makes the C atom highly nucleophilic. The Grignard reagent $(\mathrm{R}-\mathrm{MgBr})$ can attack a carbonyl group in an aldehyde or ketone as follows: Addition of dilute aqueous acid solution to the metal alkoxide furnishes the alcohol. The important synthetic consequence of this procedure is that we have prepared a product with more carbon atoms than present in the starting material. A simple starting material can be transformed into a more complex molecule. (a) What is the product of the reaction between methanal and the Grignard reagent formed from 1-bromobutane after the addition of dilute acid? (b) By using a Grignard reagent, devise a synthesis for 2-hexanol. (c) By using a Grignard reagent, devise a synthesis for 2 -methyl- 2 -hexanol. (d) Grignard reagents can also be formed with aryl halides, such as chlorobenzene. What would be the product of the reaction between the Grignard reagent of chlorobenzene and propanone? Can you think of an alternative synthesis of this product, again using a Grignard reagent? (e) The basicity of the $C$ atom bound to the magnesium in the Grignard reagent can be used to make Grignard reagents of terminal alkynes. Write the equation of the reaction between ethylmagnesium bromide and 1-hexyne. [Hint: Ethane is evolved.] (f) By using a Grignard reagent, suggest a synthesis for 2 -heptyn-1-ol.

All right, so in this question, we're talking about Grenier three agents on their re activities. Eso starting with a We're asking what is the reaction after the final step of water between ethanol and a grainy region of Roman Benzie? Eso. In other words, we have these two things reacting. All right, let's say we have this program. Benzene. All right. And now the second step is we're gonna add water, so I'm just gonna write to H 20 down here. All right, So what the final product is going to be is essentially, we're just going toe have a, uh, benzene group off the complex that, like, acids We have something. It looks like this, right? Except instead of a car box, Little we just have, you know, age. All right, So for part B were asked a pretty similar question, except B is reaction of two beauty known and the Grenier and region off. Um, two propane. So for B, starting with the two beauty known, uh, pretty simply just looks like this. Next we're adding. Ah, this region. Alright. What that's going to do is lead to the formation of this product, right? Where I have my always here and then my propane off the edge there, moving on the sea. This is asking. I'm sorry. This is basically saying that oftentimes taken use different methods to do these things. And we're asked to propose a different method for producing the same process. A. So again, there are a lot of ways you could do this. Ah, the one that made sense to me immediately to produce the same product is just use bends out of Hyde as our starting material, and then add the ah kind of a metal grey beard. Right. And that should produce. Ah, the same thing after treatment of water. Um, where I just have that. All right. So to move down a little bit, uh, he's asking us Ah, what type of reaction re agent do you need to use if you want The always group at the end of the carbon chain. And what you need to do for that is you need use an al the hide on. The reason for that is if you were to used me just right out of high, right? So if you were to use, for example, a key tone where I haven't argue appear and ardor of here. Obviously, the product is going to have a or group on this side and our group on this side and alcohol in the middle. Ah, but I'll say a change one of these to a hydrogen by which implies, is at the end of the chain and immediately after the reaction. This is no longer in our group again. This is 100 meaning that my alcohol now is at the end of a carbon chain. All right, on and then for E says what Grenier, the agent and Carbonell compound would you used to prepare on gives us the chemical which, uh, I have right here as to muffle, uh, propane or butane? Other two. Metal. Beautiful. So what we can do from here is I'm gonna do I'm gonna draw a retro synthetic era. So this arrow means that the things to the right of it are not products, but said there the re agents that you would use to form the thing to the left of the era. Eso to me. What made sense was to first draw what this would look like before. So I'm just gonna leave my my, uh, butane kind of intact. And I have two options, right? So obviously something is gonna be coming off of this carbon right here. And the reason I can tell that is because if you look at the structure, I've gotten alcohol right here. What that means is I have to stoop potential ways to do this. I can either draw, um a very small out of Hyde. I guess I'd be method now, or I can make this my oxygen group here. Both are equally valid. It doesn't really matter. Ah, but what I'm have to do now is add again. That same sees three MGB are that I added earlier. Ah, the other solution is I could just have, um something that looks I mean, there are a lot of other solutions to this eyes, which is the cool thing about organic is that you can kind of be a little creative about it. But another, another potential solution is to have something that looks like this with a, uh, a slightly different Ah, catalyst. And you'll be creative. Just make sure you keep track of your carbons and that you just kind of all the rules of thes things for activities

Okay seriously the products and the following reactions. And the first one is reacting Burma Benzene with ethanol and this is don't over water. So Burma Benzene. Benzene is an aromatic ring with alternating double and single bonds. And this is wrapping with is that a broom in here ethanol is so if he and his two carbons in the A lending and positive and out a hood she looks like this. And um we react these structures. It's going to so the green or region of Burma Benzene is actually Benzel magnesium bar, ahmad or some other metal rafting with an ankle Gilad. And because the magnesium is a selector film from the carbon, the carbon could be the nuclear file. And this is going to attack the carbon carbon because the oxygen draws action density away from the carbon of the AL to hide and make some more electric milk acceptable to attack. So if we um and when reacting with water, it's gonna turn out cox that ion, which is oxygen with three lone pairs into an alcohol. We're going to add the benzine ring too. Substitue it. So if we redraw this, we have this and we're gonna have two carbons here. You can draw like that and carbon want us alcohol, me that structure. The second one is Russian between two Buchanan and the graveyard region of to burn propane super pains. Three carbons and the government is on carbon too. And the green our region of that is going to be um the structure and start acting with two Buchanan beauty is four carbons. The urn giving us a cartoon and again, that's going to make this carbon nuclear film. So it's going to attack the carbon carbon, which is very electric. Filic and water will give some alcohol. You can also use an asset to like H three plus or some other strong acid. It's going to get alcohol here in addition to the group which is added, which is um, this uh through carbon statue actually who you re draw this. So we have one to the carbon to is attacking carve it three for and five. It's over five carbon tune and carbon too has a massacre bread here. Carbon three became an alcohol which is this one right here and four and 5 as Carbon three also has this method group right here as well. So in reality it can be the structure, its name. This would be 23 dimethyl three panel. You see we have um, it's a different combination to give product in a and we could also do okay. So we want to create the structure and we obviously can't use the same reactant as before. But we're gonna start with benzene and we know we know we know we need to use either key to enter an al to hide and some granola region to attack it. And um if you use an outer heard and react this with vessel, a museum for Ahmad over other water or an acid, it's going to make this carbon nuclear fill And 200 South Carbon Carbon and gives the products. So this will be The CH three group that we added and this is the hydrogen that's right here. And another another note for B is that it's hard to create green are regions with secondary alcohols which is used to create to burma proof in. It's a lot easier to use um primary alcohol. So if we react another way to create The structure which is 2, 3 dimethyl three panel to start with fencing at a methyl group right there and gives a key tune and every act this with Bethel, magnesium bromide, primary alcohol load and I'll get the same result. That's just a side note. And um, for day the carbon carbon reacting with a green yard too, Gibson O. H. At the end. Okay. So the only car bottle compound that would yield a primary alcohol Got to be a one carbon alga hood. So you need the alcohol functional group and that's the only one carbon and the only structure would be formaldehyde and we're acting with some Granada region like ethel, a museum burr mod. And if we compare this with another al to hide like ethanol, the A lending and both are dawn with or ever the presence of some assets or water. If you look at this reaction, this is going to attack the carbon carbon and this would give us a secondary alcohol to be um, one, two and 3, so a three carbon chain and carbon tilbian alcohol. And this is the hydrogen that's right here To speak carbon 1, 2 and three. And this carbon one. So without this method robert here, we would have just a um, a primary alcohol. So the only structure that can react with, the only structure that can produce primary alcohol would be a one carbon atom head in this case from childhood. After the next. We want to create two methods to beautiful General structure. Butane is four. And with the metal and alcohol on carbon too, it's our indicates that we're going in reverse. So let's start with a key tune. And I'm going to use a primary alcohol in this case, we need one method group Sony's method of magnesium burr mod. And it's going to attack carpet of carbon. Yeah. And over water or some assets. Yes. Our structure and this can also be created by reacting. Um so this this can also be created by reacting a to carbon Graveyard reagent with another two carbon um in alba hood because we need for Parkinson title for Britain a reactive these structures. So it's going to attack e carbon or carbon and for a start like this. So the alcohol from react with other water acid and the addition of the Elf interpreter And still be carbon one carbon to carbon one attacked carbon too. And this is three to carbon to has the alcohol and um three is the Method Group and Carbon one has this method right here. So we can also use ethel magnesium Vermont and ethanol as well.

So we were taking a look at retro synthetic reactions are essentially given a target molecule and we're just having to like backwards. So we take a look at our first structure, my gosh, and that it can't draw actual synthesis. Arrow on. Now we draw our components where we have two missile Prepon, One island Bremer bending so sort of re agents that we're gonna be needing here is we're gonna be needing MGI andi e t 20 for this conversion to get to Phanom, magnesium bromide, new P, C, C and C H two c l to to get from our alcohol to our alga hide. Then we react these two together in the presence of e. T 20 on h 30 plus a Proton source than in the second step. We have PCC and ch two c l two. So in the next example we have we're making to synthetic cuts. It's moving straight onto our next example just to save a lot of time here. We've already discussed the sort of re agents that we need for these types of chemical reactions. So all we're going to be focusing on is the structures themselves to make us. And that's a cut green yard region on. This is generated using a alcohol starting material. Andi was a starting material. Also contains an alcohol. So I just chemically transforming our starting target molecule that we have into a primary alcohol. Because we can't achieve this chemical transformation here in Rabat to make a make or chemical cook. Now we can think about drawing are starting materials by one of our starting materials is in a box side. You just insult in a page and then on to our next example here in first of a chemical transformation into an alcoholic and we make our synthetic cut. Now we'll draw our materials ended up oxide. Well, we've seen this step before. We go from magnesium burn mind to just a bromide containing molecule. And then we used the alcohol form. Next example make a synthetic. It draws retros. And this is our Oh, and now we start to look at starting materials that we could use and this chemical transformation. So we know that we have to work backwards. So we start with our alcohol containing structure, convert this to grow me and containing structure that we combined to our green yard with the other material. We start with our alcohol containing structure and then we convert to Akita. So we have the next reality. Firstly, the chemical transformation from our key tone Thio alcohol We don't make a synthetic cup Another retros. And this is Sarah. Now we have our starting materials, but we need to work backwards for me. So of course we go via remain containing compound and then the alcohol containing compound. So this whole group was replaced with an alcohol group. In this the material that we have we are working with a primary alcohol final example. I believe we have a molecule that contains a foreman atom. It contains our benzene ring. So the first thing we do we draw our structure with appropriate functional group make us and data card here we're making to on our hydrocarbon chains. Well, as always, we go via berman containing molecule on any alcohol containing molecule

Okay, So rescue the products for the following reactions. And in the first one, we are reacting, starting with oxide. I'm sorry. Diethylene obtained diet with city with oxide and HCL. 23456 123456 Okay, so starting with oxide and HCL. So starting with oxides going to deport me at the alpha hydrogen, and this is going to attack the carbon or carbon. So an intra molecular all doll reaction. So this is going to be carbon blanc. I'm sorry. Hold on. It's gonna department the carbon leading to the most stable ring. Which the six carbon ring. So if we depart in eight, this hydrogen will have a 1234567 If we depart in eight, this one, we're gonna have a five carbon ring and five carbon blank is more stable than six. So it's gonna be pretty this carbon. So we got a carbon. I right there. This is going to attack the carbon carbon. So 12 five, carbon ring and carbon one is attached to this CEO Esther here. And this is carbon one. Carbon five. Where's the carbon heel? Is that a cock side eye on. It's also bound to an Ester as well. So this bond is going to reform. It's gonna expel the Esther, and we're going to get structure. So for B, we have, um, pet no gases with PBR three and PR two. This is over water. So, um, PBR three is going to replace the ohh burning and another Bernie Adams going to add to the alpha carbon of the Carbonnel. So this is the hell full hearts on secure action. Do you get that product? And for C, we have, um, ask 10 with Ethel. Astute. So as soon and at last, it sit with Syria meth oxide. And second step is to reacted with HCL. So you're gonna It's gonna deep for any of the alpha hydrogen and we can get to products. So structure one, get a tax structure, two or two can attack one. So if you wanna text to deeper into this hydrogen, let's go outside the carbon or carbon, and it's going to reform to expel the Esther. So car in two is the carbon in carbon three is the cartoon, and it's bouncing this method as well. So we get um the structure suffered day. We have Di Athol to hack cell two ethyl excellent diet. So 123456 and on carbon to even Ethel. So this is going to urinate the alpha hydrogen when reacting with soon with oxide and HCL. So we're going to urinate this carbon, and it's going to attack the carbon carbon. So 12345 five carbon ring and on. So carbon one is attached to again this this group and carbon 51 five Carbon to is the Ethel. Carbon five is going to be a key tune once it kicks out the Esther. So you're that structure. So for E, we're reacting di ethyl marinate with, um Osama dockside, Isobe, debris, mod and HCL. So diaphragm Allen It is actually the melodic Esther. So that name for it. So regardless will be left for the two carbon car box like acid. And we're reacting the structure with, um against the meth oxide and then alcohol. I'd So this is going to department the alpha hydrogen. This is going to attack? Yes. This is going to attack the alcohol it and it's always good to use a primary alcohol out because I'm accessible and then once reacted with HCL water and heat. We're gonna do carb oxidation reaction, and the one Esther will be will be turned into a alcohol so we'll be left with eight save one, 12 three, 45 So if it's to carbon carbon stock acid and we're gonna add through my carbon step So 345 and on carbon four, we have a method and the leading group is gonna leave to Is it for D or from ref? We have a set of fun in with dimethyl carbonate. Yeah, and this is reacting with, uh, again soon with oxide nature feel so we don't have the alpha hydrogen on ethyl carbonate, too React with. So it's gonna attack. It's gonna be pretty interesting. Afternoon. This is going to attack the carbon carbon. Um, regenerate the cartoon. Expel one Esther. So drawing a set of unknown first carbon three is the cartoon that's bound to its Esther. See that structure and for um, is the next one. We have 13 cyclo hexane dying with Albert Ahmad and sodium hydroxide. Just cyclo hexane dying. Two key tunes 13 to 1 other and reacting with Alber mod and soon my drug side. So the first step is for staying. Hydroxide was a strong base the deeper into the alpha hydrogen. And this is going to attack Alber mode and against going to attack the alcohol, I explained, leaving group surrounding a three carbon chain without kids. I'm sorry. Should be like this should be like that. This is excellent. We have, um, die bends or ketone with metal, vinyl cartoon and access to a madrassa to die Benzel cartoon. And this is reacting with metal vinyl cartoon and sit in my drug side. Two Methyl vinyl Heaton is an Alfa Beta and saturate cotton, so the first step is departing at the alpha hydrogen. Second step, reacting with an alpha beta unsaturated ketone. Do you have a Michael reaction? It's going to attack the data carbon so county from the carp until we have 12 three, 45 and six Mhm. So we're adding a four carbon chain 1234 and on carbon five relative to the carbonnel. So 12345 It's a key turn. And if you react this with more cities hydroxide It's going to, um, so deeper into the Alpha Harsha and this can attack the carbon carbon. Do you have us a ring structure? Okay, so if 123 for five and six So six carpenter ring and carbon six attached to a method to speak carbon six and reacting with water will turn the a cox dot ion into an alcohol sits on carbon six. It's getting away as well. Okay, so the next one we have Gamma Butera last tune or I'm sorry. Psych Lapetina Just cyclo pennant grafting with pure Ledeen and Catholic hydrogen. So it's like this. So this strapping with Ethel Byrne mod and hcl. Okay, so this is similar to the, um So Pirro Dean is going to act as a strong base deep party at the alpha hydrogen and just go into attack the ACA. He lied. So adding to the alpha position, we had to carbon chain. We got our products. This is with them each cell in your studio. So it regenerates the regenerates pure golden. And for for J, we have gamma Butera last tune with L d A t h f with methyl iodide to be at this structure. And this is reacting with L d a. T h f with methyl iodide because the first step is deeper near the alpha origin. And this is going to attack the alcohol in, which is metal, I dad. So it's going to attack the carbon expelling the Ida Look at that. And for for um kay 27 octane Diane. So octane is eight and to seven. Dikky turns reacting with, um soon hydroxide. So if we just reacted with sort of hydroxide will get an intra molecular reaction. This is going to attack the carbon or carbon and to counter from the carbon. And we have 12345 carbon one is attached to this group right here. And carbon five is the A cock side on. It's gonna become an alcohol. It's attached to a method as well. Don't forget that. And then for l, we have cycle Hexindo with some metro oxide and the dude deuterium G to, uh, just cyclo hexane. Noon case in the first step is going to deeper into the alpha hydrogen. And once it reacts with with, um, deuterium, we'll get the Let's go on a deeper donate did you see him? Some of your victrola? Yes. Uh, you're gonna get the structure. That's the product. And for for em, we have di ethyl 12 Benzene die carb oxalate. See the structure have a It's the Benzie ring. So 12 and these are bound to hold on. So I get that, okay? And this is attacking. Reacting with Ethel. Estimate so with sodium oxide at HCL. It's going to be part of the alpha hydrogen, and it's going to attack the carbon carbon are so many redrawing over here. So this is going to reform and expel one of the esters. So counting from the car ban on, we have one two and carbonized attached to Key tune and the Astor Do you get the structure? Can we put on Do you want me to enter? And it's a


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