Reaction mechanism for ketone and vinyl lithium

In summary, the conversation discusses the product of 1-bromo-3-propanone treated with vinyl lithium. The discussion also brings up the structure of the molecule and how the organolithium compound should be treated in the reaction. The summary advises to consider both the carbonyl and bromine in the reaction.
  • #1
brake4country
216
7

Homework Statement


What is the product of 1-bromo-3-propanone treated with vinyl lithium?

Homework Equations

The Attempt at a Solution


I know that the carbonyl is attcked by the organolithium but I am having a hard time understanding how it attaches to the carbonyl since it is sp2 hybridized. Any suggestions? Thanks!
 
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  • #2
Something must be wrong. 1-bromo-3-propanone is not a real molecule: propane only has 3 carbons, so a carbonyl on the 3-carbon would make it an aldehyde, not a ketone. Can you draw out the structure of the molecule that you intended to say?
 
  • #3
I believe my study manual meant 1-bromo-2-propanone. But, here is the reaction that I have determined so far, attached below. The answer only says that the vinyl lithium would add to the carbonyl. Thanks!
 
  • #4
brake4country said:
But, here is the reaction that I have determined so far, attached below.
I don't see the attachment.

brake4country said:
I am having a hard time understanding how it attaches to the carbonyl since it is sp2 hybridized.
This shouldn't matter. Just treat the organolithium compound as approximately R-Li+, with R = vinyl, and just do the same type of arrow-pushing you'd do with, e.g., butyllithium.

The one caveat is to think about not just the carbonyl, but the bromine as well.
 

1. What is the reaction mechanism for ketone and vinyl lithium?

The reaction mechanism for ketone and vinyl lithium is a nucleophilic addition reaction. The vinyl lithium acts as the nucleophile, attacking the carbonyl carbon of the ketone and forming an intermediate alkoxide. This intermediate then undergoes protonation and elimination to form the final product, an alkene.

2. What is the role of vinyl lithium in this reaction?

Vinyl lithium acts as the nucleophile in this reaction. It attacks the carbonyl carbon of the ketone, forming an intermediate alkoxide. This intermediate then undergoes protonation and elimination to form an alkene.

3. How do ketones and vinyl lithium react?

Ketones and vinyl lithium react through a nucleophilic addition reaction. The vinyl lithium acts as the nucleophile, attacking the carbonyl carbon of the ketone and forming an intermediate alkoxide. This intermediate then undergoes protonation and elimination to form the final product, an alkene.

4. What conditions are required for the reaction between ketone and vinyl lithium to occur?

The reaction between ketone and vinyl lithium requires a polar, aprotic solvent such as diethyl ether or THF. It also requires the presence of a strong base, usually lithium diisopropylamide (LDA), to generate the reactive vinyl lithium species.

5. What are the major products of the reaction between ketone and vinyl lithium?

The major products of the reaction between ketone and vinyl lithium are an alkoxide intermediate and an alkene final product. The alkoxide intermediate is formed through the nucleophilic addition of vinyl lithium to the ketone, while the alkene is formed through protonation and elimination of the intermediate. The exact product formed will depend on the specific ketone and vinyl lithium reagents used.

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