Organic Chemistry Multistep Synthesis

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Discussion Overview

The discussion centers around a multistep synthesis problem in organic chemistry, specifically focusing on the strategies and reactions that could be employed to achieve a desired product from given starting materials. The scope includes theoretical approaches and problem-solving techniques relevant to organic synthesis.

Discussion Character

  • Homework-related
  • Exploratory
  • Debate/contested

Main Points Raised

  • One participant suggests starting with organolithiation to combine two components but expresses uncertainty about how to introduce an ethyl group and eliminate oxygen.
  • Another participant proposes thinking backwards from the final product and considers ozonolysis as a potential final step, though this is met with skepticism.
  • A later reply challenges the appropriateness of ozonolysis, noting it has not been used in previous synthesis problems and questioning its ability to lead to the desired product.
  • One participant mentions the importance of removing or adding a methyl ether and acknowledges the difficulty in visualizing the synthesis steps in reverse.
  • Another participant introduces the concepts of Wittig and umpolung as potential strategies, while also noting that racemates may be acceptable due to the lack of chirality in the product.
  • There is a request for clarification on the term "racemates," indicating a need for further understanding among participants.
  • A question about stereoisomerism and the understanding of umpolung and Wittig is raised, suggesting a deeper exploration of these concepts is needed.

Areas of Agreement / Disagreement

Participants express differing views on the appropriate steps and reactions to use in the synthesis, with no consensus reached on the best approach. There is uncertainty regarding the application of ozonolysis and the understanding of certain concepts like racemates, umpolung, and Wittig reactions.

Contextual Notes

Participants demonstrate varying levels of familiarity with the concepts discussed, and there are indications of missing assumptions or knowledge gaps that may affect the synthesis strategies proposed.

Who May Find This Useful

This discussion may be useful for students studying organic chemistry, particularly those working on multistep synthesis problems and seeking to understand various reaction mechanisms and strategies.

coppersauce
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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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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...
 
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?
 
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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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...
 
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.
 
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
 
Are you aware of stereoisomerism? What do you understand by umpolung and Wittig, then?
 

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