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

Question

Show how you would accomplish the following synthetic conversions efficiently and in good yield. You may use any necessary additional reagents and solvents.

(e)

Accepted Answer

Everyone and welcome back in today's video, we're going to show how the following conversion can be achieved with good yield and we are going to use any necessary regions. The starting material is an asset, this is acetic acid, you may notice that we have two carbon atoms. So our starting material is a car broke cilic asset. The final product is actually a conjugated key tone. You may notice how we are getting a key tone. There are a total of 1234 carbon atoms. We have our pi bond adjacent to our carbon in group. That's why it's conjugated. Now this is a bit of a problem for us because the starting material only has two carbon atoms, the final product has four carbon atoms. We cannot think about any kind of easy conversion here because we need to make sure that we have some sorts of carbon atoms. So let's think about this reaction in general. There are several aspects that we have to keep in mind assets are not really reactive, right? So assets not really reactive. Okay, we need to solve this problem. One of the solutions to make our asset more reactive is to convert it into a corresponding acid chloride. And to do that. Let's recall that whenever you have an asset in a form of our C H, you can use chloride which essentially is S. O. C. L. C. That's final chloride. And using this reaction, we are going to change our wage group into chlorine and this gives us a corresponding asset chloride acid chlorides are more reactive. They have a good leaving group ride essentially If we think about the electra filic attack at the electra Felix center. So if we have our acid chloride, that's really good for us because we can lantern our parent chain using the Gilman region. Right? This is a very easy way for us to do. So let's recall that we have Gilman region that allows us to produce a longer chain. The general sequence of this reaction involves the following. First of all, we have to think about our acid chloride. So if we start by drawing our asset chloride, let's indicate that our substitution in blue. Okay, that's our original are bonded. See the acid chloride. And then whenever we treat it with our organic Q prate region, right? Which is the Gilman reagent. In this case we have to make sure that we are using a corresponding are. So we want to make sure that we are replacing this glory with some alcohol group. And let's suppose that this alcohol group is given in greed in Green S. R. And we want to make sure that we're using two of these bonded to copper lithium, right? Copper has a negative charge, lithium has a positive charge. So now this is our Gilman reagent. And the outcome of this reaction. If we combine them together is basically the fact that you're replacing chlorine with that green are and you're able to get your key tone and this would really work for us. Let's see how we finish this scheme. So we would have our carbon group on the left, we would have that original are in blue and then on the right, we are going to add D are in green. So this is exactly what we want to think about. If we get our assets chloride, we clearly see that on the left, we still have our metal group. So that's our blue are we can say that this one is our blue are in each case and that we are essentially thinking about changing this situation to chlorine And then replacing it with the green are so we can clearly see that this would be our green are which would belong to the Gilman region. Now everything starts to make sense. So let's draw the reaction sequence. But before we do so let's draw the structure of the Gilman region that we're going to use first of all in this case. Let's keep in mind that our is our metal group. So let's just add c. three. Now, for the green one, we already understand that we are going to use our final group. So that would be our green are So let's throw our final group. We want to make sure that We start with a double 1 1st And then we are essentially forming our two of these bonded to copper, but a negative charge lets him has a positive charge. So we clearly see what the art here is and then we are just bonding this vinyl substitutes are carbonell group and this is exactly what we are seeing right performing this carbon carbon bond. Okay, so let's create our scheme. So we can clearly see what sort of steps we're referring to. And if we scroll down, our starting material is an acid. As we previously mentioned, we are going to first of all convert it into an asset chloride. And to do that, we need to use vinyl chloride, S O C L T. We're going to replace our oh age group with chlorine. So let's see that we got our asset chloride and now we want to perform the Gilman reaction. We already said that the substitution for the green are would be our vinyl substitution. So we want to make sure that we use this Gilman region for our reaction. Let's indicate that there will be T vinyl groups. Okay, wanted to copper with a negative charge. The lithium is adjacency, that's our positive charge. And then we are replacing chlorine with our final substitution. So we're getting our final key tone. Let's draw it out on the left. We have our blue our that's our metal group on the right. We have our vinyl substations. So let's add that. Well done. We got our reaction scheme. Let's label this is our final answer And based on our synthetic sequence, we may conclude that the correct answer to the multiple choice question is a. However, if you have any questions, don't hesitate to leave a comment down below and thank you for watching.

Show how you would accomplish the following synthetic conversions efficiently and in good yield. You may use any necessary additional reagents and solvents.
(e)

Key Concepts

Aldehyde Reactivity

Imine Formation

Reaction Conditions and Catalysts

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