Show how you would accomplish the following synthetic conversi...

Question

Show how you would accomplish the following synthetic conversions.

(c)

Accepted Answer

Hey everyone and welcome back devise a synthetic route for the following conversion. Notice that they're given a conversion involves an L kill chloride. Right? So we have our chloral cyclo propane. So that's our L kill chloride, that's our starting material. And we want to produce a key tone. Notice how looking at this reaction, we are forming this new carbon carbon bond, right? We're essentially replacing our chloral group with our key tone. So now how would that work? Let's recall that one of the most efficient ways to form that carbon carbon bond is via the Gilman wage. And Gilman Reagent essentially corresponds to the following structure. We will have to l kill groups. So we can say our to write to L kill groups bonded to copper, lithium and essentially the Gilman region would react with an acid chloride. Right? So we can say our bonded to carbon L group and there will be chlorine bonded to that carbon L group. So that's our asset chloride. In such a reaction, we are going to form our key tone. Right? Essentially, noticed that we're going to replace this chlorine with the blue our group and this reaction scheme will allow us to understand what kind of steps we can take in the formation of the desired product. So we can throw our carbonell group and now essentially we're going to add two substitutions, one of them will be the al kill group in green and the other one will be the alcohol group in blue. Right? Essentially the blue one is replacing chlorine. This is one possibility for us to form the desired key tone. So if we essentially break it down, we can essentially understand that if we break this carbon carbon bond because because our starting material involves cyclo propane ring, we can essentially think of cyclo propane forming the Gilman Regent, meaning this would be our our one of our our groups. So let's suppose that this one that we are thinking about correspond to the blue are so let's label it us. Are now looking at our key tone, we still have a methyl group bonded to our carbondale group. So that would be our green are right. So we can just label this as our green are. Okay, so we broke down our problem and we can now understand that in order to form this key tone in the world. Last step, we're going to use the Gilman reagent where we are going to have copper lithium. Right recall that copper has a negative charge, lithium has a positive charge in this region. And now we already said that there will be two R groups or two cyclo propane rings. Wanted to copper that would correspond to our Gilman region. Okay, and now this Gilman Regent R. T copper lithium must react with our acid chloride. We already know what the green are is we just need to draw a corresponding asset chloride. So that will be our chloral substitution for the green. Are we are going to choose a metal group. So let's do it, that will be our final stop. But now we have to go backwards. And now we have to think about the formation of the Gilman Regent, we definitely understand that this will be our reaction in the final reaction. But now how to reform the Gilman Regent. If we think about our starting material, our l kill chloride, notice that first of all, we want to make sure that we are replacing our chloral group with lithium. And to do that we need to use two equivalents of lithium. So we can just say that if we use this as our starting material, our chloral cyclops propane, let's draw it out. We can treat it with the equivalence of lithium. There's no need to include the equivalence. We can just think of it as access However, in general for this reaction we need two equivalents of lithium and then we are going to produce our organa lithium region. Right? We're essentially replacing flooring with lithium. Now when we have this structure we essentially want to produce the Government Regent out of it. And there's a simple way to do that. We have to recall that. We have to treat it with copper one bromide. So see you be all right. Whenever we treat it with copper one bromide, we get our gilman reagent in this form. And then when we have our Gilman region, we treated with the acid chloride and then we get our kid zone. So now let's put everything together. We already have our separate bits of information and we understand that because chloral cyclo propane is our starting material. We are going to begin by trying chloral cyclo propane. So that's our starting material. We want to replace our chloral group with lithium to produce our organic lithium region. So let's draw a reaction arrow and clearly illustrate that in this step, we are adding lithium two equivalence or basically access Now we are going to produce the desired organ analyst um Regent from here. This will allow us to get the Gilman region that we desire to have if we use copper one bromide in our reaction. So we're going to include copper one bromide. Now here when we treat it with copper one row might we get our Gilman reagent which essentially corresponds to copper negatively charged. Right? Because it essentially forms These two bonds with our cyclo propane rings. So let's draw our two substitutions and now we have lithium with a positive charge. When we get our government regent. Going back to our reaction scheme, we understand that we need to use a corresponding acid chloride to replace this chloral group with cyclo propane. And for this purpose we're going to use this acid chloride. Let's include this in our reaction scheme, meaning for the final reaction, we're going to use the following assets chloride. Let's throw it out. That will be our carbonell group, our metal group and then chloral group And based on what we analyzed before this is how we get our final key tone. Okay, so that indeed corresponds to our found product. We may now label all of this synthetic approaches our final answer, right? We are going to indicate that this reaction scheme is our final answer. And based on the synthesis scheme, we may conclude that the correct answer to the multiple choice question is B. However, if you have any questions, don't hesitate to leave your comment down below. Thank you for watching.

Show how you would accomplish the following synthetic conversions.
(c)

Key Concepts

Nucleophilic Substitution

Electrophilic Addition

Functional Group Transformation

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