Retrosynthetic Analysis Help!

May 2013
3
0
Please help me with retrosynthetic analysis. I have tried to solve different ways, but get stuck halfway through. Here is a link to the molecules.



THANK YOU!

Here are the assignment directions.
Please choose one molecule from the list of four molecules below and devise a
retrosynthetic analysis. Make sure to also provide the forward reaction
sequences for the synthesis. Use the chemistry that you have learned from all of
the chapters so far. Your only restriction is that you can only use three carbon
building blocks.
 
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Unknown008

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May 2010
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Wouldn't hurt to post the attempts where you stopped halfway, and will also help determining what reactions are permissible and which aren't.
 
May 2013
3
0
I have attached attempts I made with two different molecules. They didn't get very far. I also attached all of the reactions from this semester. The green boxes in the arrows have the section numbers, and we have gone up to section 14. So if the little green box is section 15 and above, I cannot use the reaction.

Thank you again!
 

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May 2013
3
0
Also, I'm not sure why the pictures uploaded upside down. They weren't like that one my end. Sorry about that.
 

Unknown008

CHF Hall of Fame
May 2010
1,658
37
Mauritius
The pictures are fine, don't worry :)

Okay, I'm not too good in synthesis myself, but I'll try to help as much as I can.

I'm not sure how you started with CH3-CH(-Cl-)CH... Are you sure Cl can be bonded to two carbon atoms?



Maybe you could start with the above?

Br could be used for nucleophilic substitutions with alcoholic CN^-.
 
Dec 2014
4
0
I had some ideas for 3 of the compounds, for the third one I have some doubts about whether the compound will survive oxidation with the peracid or not... For the fourth compound I had an idea, but the synthesis was way too long so I won't be posting it :)) However, I'll think more about it and maybe I have some luck.
 

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