Show how you would accomplish the following multistep synthese...

Question

Show how you would accomplish the following multistep syntheses. You may use any additional reagents and solvents you need.

(b)

Accepted Answer

All right. Hi, everyone. So for this question, you must describe how the following synthesis can be carried out. Um use any required reagents and solvents. So let's get started, right? And let's get started by first noticing the fact that we are going from an All Keenan are starting material to a carb oxalic acid in our end product. So now the question becomes, how can we go from an all keen to a carb oxalic acid? And so before we figure out our plan, right, recall really quickly that um you can convert a grin, you'd re agent to a carb oxalic acid using a car box elation reaction, right? So you react, agreed, you're re agent with carbon dioxide to get a carb oxalic acid at the end. So that's something that we can use, right? Because we do need a commercial asset at the end. But the question becomes, how can we get from an all keen to agree new free agent? Right? And in order to do that, recall quickly that we can convert an all keen to an ocular Haley, right? And if we can convert this all keen to an actual bromide in particular that ocular bromide can be converted to a green, you'd re agent, which can then be converted to a carb oxalic acid via car box elation. So this is going to be our plan of action, right? We're gonna convert are all keen to an ocular hate light and then to a green, you'd re agent before car box elation can take place. So with that being said, I'm gonna go ahead and I'm gonna redraw our starting material on the bottom here so that we can go step by step, right? So this is our starting material. And what I want to bring to your attention before we proceed with the first step is that when you compare this all keen to the placement of your carb oxalic acid, the crab oxalic acid is on the more substituted carbon, right? Where you're all keen used to be. So that's indicative of a Markov Nikon edition, right? So that means that your actual highlight must be in the more substituted position relative to the All Keen and recall that the addition of HBR to an All Keen is an example of a Mark colony called edition. So when we go ahead and we react this all Keen, our starting material with HBR, we're going to get blooming on this tertiary carbon where all Keen used to be. And that's perfect because now we have an all kill bromine that we can go ahead and convert to a Grand re agent using magnesium in the presence of ether. So now we can do that and we end up with our magnesium bromide are green, your agent. Yeah. So this is our green yard free agent. And now that we have a green yard re agent, we can go ahead and proceed with our car box elation reaction. So when we're talking about car box elation and we'll green your reaction in general recall that the magnesium bromide group is going to have a partial positive charge associated to it. That means right, that the carbon is attached to is going to have a partial negative charge which is going to make it nuclear filic, right? So in a granular reaction, what you're going to see first is the nuclear filic attack of this partial negatively charged carbon. And in the case of a car box elation reaction, it's going to go ahead and attack a molecule of carbon dioxide. So this nuclear file here is going to attack the carbon of carbon dioxide and that's gonna cause one of these double bonds in carbon dioxide to become a single bond. And so from there, right, you're going to end up with a car box elite an aisle. So I should also mention before I go ahead and draw the rest of the molecule that your magnesium bromide group is going to leave, right? It's gonna detach from that carbon. So once that happens, we're gonna end up with a car box late and I am like I talked about before and your magnesium bromine is gonna serve as a counter ion because now it has a full positive charge. So once that happens, we need one more step, right? Because the car box late ion is not a carb oxalic acid. And so this is where our acidic work up comes in because recall that the resulting car box away and ion must be treated with acid afterwards to make sure that it gets protein ated and converted to a carb oxalic acid. And I realized that I drew that arrow in the wrong color. So let me just fix that before we move on to the next step. So in our next step, after that acidic workout, we're going to end up with our carb oxalic acid at the end. So here is our card box like acid and this is exactly what we have at the end of this process as your final product, right? So in order to go ahead and recap what we just did, I'm gonna go ahead and I'm going to write out our steps on the bottom, Right? So our 1st 1 was the conversion of an all keen to an alcohol bromide using the Markov Markov edition of HBR. And then that resulting ocular bromide was converted to a green, you'd re agent using magnesium in the presence of ether. And then from there, right, was our car box elation reaction. But the car box elation reaction was actually a two step process because we needed to go ahead and protein eight um the product of the green your reaction, right? So our first step Was the addition of co two followed by acidic work up. So from there, these are going to be all the steps that we need to take for this transformation. And your answer is going to correspond to choice, be in the multiple choice, right? So here's your answer. Yeah. And if you stuck around to the end, thank you very much for watching. And I do hope you found this helpful.

Show how you would accomplish the following multistep syntheses. You may use any additional reagents and solvents you need.
(b)

Key Concepts

Carboxylation

Cycloalkenes

Reaction Mechanisms

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