Organic Chemistry Multistep Synthesis

AI Thread Summary
The discussion revolves around a multistep synthesis problem in organic chemistry, where participants explore methods to achieve a desired product from given starting materials. Key strategies mentioned include organolithiation and the potential use of ozonolysis, although doubts are raised about its applicability in this context. Participants emphasize the importance of thinking backwards from the desired product to identify necessary reactions. There is also a mention of using Et2CuLi for ethyl addition and discussions around the concepts of racemates, stereoisomerism, umpolung, and the Wittig reaction. Overall, the thread highlights the complexities of planning synthetic routes in organic chemistry.
coppersauce
Messages
12
Reaction score
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?
 
Physics news on Phys.org
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...
 
Last edited:
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?
 

Similar threads

What will be the product of this organic reaction?
Replies
28
Views
5K
Preparing for Grad School: A Organic Chemistry Review
Replies
2
Views
2K
Organic Chemistry: Sn2 Reactions - proposing a synthesis
Replies
2
Views
3K
Water sometimes drips from the exhaust of a running car....
Replies
5
Views
3K
Guess the Mechanism help (Organic Chemistry)
Replies
1
Views
2K
Calculating Synthesis Gas Volume for Water Heating: A Combustion Problem
Replies
1
Views
3K
What Is Fuming in Organic Chemistry?
Replies
1
Views
3K
At a Crossroads Between STEM Majors (narrowing interests)
Replies
5
Views
2K
Organic Chemistry is the study of what
Replies
11
Views
5K
Chemistry How to get moles from MO having % of mass?
Replies
25
Views
3K

Hot Threads

Recent Insights

Back
Top