Conjugate Addition and Ether Formation

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SUMMARY

The discussion focuses on the mechanisms of conjugate addition and ether formation, specifically addressing the role of acid in these reactions. Participants clarify that lithium methyl (LiMe) acts as a hard nucleophile, facilitating carbonyl addition without the need for acid. The conversation also highlights the challenge of producing an ether from conjugate addition, suggesting that it may require a two-step process. Key insights include the importance of understanding the initial product formed before any acid is introduced.

PREREQUISITES
  • Understanding of nucleophiles, specifically hard nucleophiles like lithium methyl (LiMe).
  • Knowledge of carbonyl chemistry and conjugate addition mechanisms.
  • Familiarity with ether formation processes in organic chemistry.
  • Basic skills in drawing reaction mechanisms and products.
NEXT STEPS
  • Study the mechanism of carbonyl addition reactions involving hard nucleophiles.
  • Research the process of ether synthesis from conjugate addition products.
  • Learn about the role of acids in organic reactions and when they are necessary.
  • Explore multi-step synthesis strategies in organic chemistry.
USEFUL FOR

Chemistry students, organic chemists, and anyone interested in understanding the mechanisms of conjugate addition and ether formation in organic synthesis.

lo2
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Homework Statement



http://i43.tinypic.com/nxvw41.jpg

Ok here it is molecule B.

http://i39.tinypic.com/333aaro.jpg

Ok and here it is problem nr. 8, second molecule.


Homework Equations



No equations needed.

The Attempt at a Solution



1)
So why is it that we do not add any acid here, as far as I know one need acid, in order to do a succesfull carbonlyl or conjugate addition, right? So how come? And because it is LiMe (which is a hard nucleophile) I think it will be a carbonyl addition, so am I right?

2)
Well I did not really get that far as I am really not sure how to produce an ether from conjugate addition... So how to?

Edit: images replaced with links; please don't post large images as they are breaking forum formatting.
 
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lo2 said:

Homework Statement



http://i43.tinypic.com/nxvw41.jpg

Ok here it is molecule B.

http://i39.tinypic.com/333aaro.jpg

Ok and here it is problem nr. 8, second molecule.


Homework Equations



No equations needed.

The Attempt at a Solution



1)
So why is it that we do not add any acid here, as far as I know one need acid, in order to do a succesfull carbonlyl or conjugate addition, right? So how come? And because it is LiMe (which is a hard nucleophile) I think it will be a carbonyl addition, so am I right?

Yes, you are correct. Why can't you draw the initially-formed product (before acid is added)?

2)
Well I did not really get that far as I am really not sure how to produce an ether from conjugate addition... So how to?

There is a hint in the previous problem. I'm not sure how to do this in one step but it's possible in two.
 

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