Organic Chemistry Multistep Synthesis

In summary, the student is trying to figure out how to make the desired product from the starting materials, but is not sure how to do it. He is aware of stereoisomerism and understands that umpolung and Wittig are two reactions that can lead to racemates.
  • #1
coppersauce
12
0

Homework Statement


http://i.imgur.com/H8p56.jpg

2. The attempt at a solution

I'm not quite sure how to start this one... I would assume organolithiation could get me started for the two combining, but I'm not quite sure how to get the 3' carbon to spout that ehtyl group or how to eliminate the oxygen. Any help?
 
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  • #2
My organic chemistry book says to always think backwards: ask yourself, "what compound undergoing what reaction would give me my final product?"

In that case, I'd be tempted to consider ozonolysis as the final step...
 
  • #3
I can't imagine that would be the final step... We definitely have not used that in any of our synthesis problems yet, and I looked it up and I can't see how ozonolysis could lead to that...

Did you see that it goes Desired product --> Starting materials?
 
  • #4
No... I saw an arrow and assumed that the stuff it was pointing to was the product.

Nevertheless, the principle holds. First think I'd do is remove (or add on in the last step) your methyl ether. Of course, it's also possible, as your first step, to use a... actually, I know of no reactions that reverse the effect of alkene cleavage...
 
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  • #5
I would do that, but I'm not good enough at it yet where I can see ten steps in reverse =/.

Okay I don't even know if I'm beginning right, but let's say we add Et2CuLi with an H+ workup to the one on the left to get the ethyl on the bottom... I'm not quite sure how to swap out the oxygen w/ the other reactant. Getting the methyl on the reactant on the right is easy at the end, I'm just not sure...
 
  • #6
I'm not saying it's the right way, but a couple of words spring out when I try to do the question. Wittig and Umpolung.

I assume that as there is no chirality shown that racemates are desired.
 
  • #7
Hmm could you possibly explain what race mates are?

And yes this is very likely; those two are on topic with what we have recently learned... I keep chuggin at it
 
  • #8
Are you aware of stereoisomerism? What do you understand by umpolung and Wittig, then?
 

1. What is Organic Chemistry Multistep Synthesis?

Organic Chemistry Multistep Synthesis is a process of creating complex organic molecules through a series of reactions, typically starting with simple molecules and building them up into more complex structures.

2. Why is Multistep Synthesis important in organic chemistry?

Multistep Synthesis allows chemists to create complex molecules that cannot be obtained through one-step reactions. It is also used to produce specific compounds for use in industries such as pharmaceuticals, materials, and agriculture.

3. What are the key components of Multistep Synthesis?

The key components of Multistep Synthesis include understanding the reactivity and properties of different functional groups, selecting appropriate starting materials, and designing a reaction pathway that will yield the desired final product.

4. What are some common challenges in Multistep Synthesis?

Some common challenges in Multistep Synthesis include low yields, side reactions, and difficulties in purifying and isolating the desired product. It also requires careful planning and precise control of reaction conditions to ensure the desired outcome is achieved.

5. How is Multistep Synthesis applied in real-world applications?

Multistep Synthesis is widely used in the production of pharmaceuticals, agrochemicals, and other industrial chemicals. It is also used in academic research to create new molecules for studying their properties and potential applications.

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