Reaction mechanism for ketone and vinyl lithium

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SUMMARY

The discussion focuses on the reaction mechanism of 1-bromo-2-propanone treated with vinyl lithium, specifically addressing the addition of the organolithium reagent to the carbonyl group. Participants clarify that 1-bromo-3-propanone is not a valid molecule, as propane only contains three carbons, making it impossible for a carbonyl to exist on the third carbon. The correct structure is identified as 1-bromo-2-propanone, and it is emphasized that the vinyl lithium acts similarly to butyllithium in terms of arrow-pushing mechanisms in organic chemistry.

PREREQUISITES
  • Understanding of organolithium reagents, specifically vinyl lithium.
  • Knowledge of carbonyl chemistry and sp2 hybridization.
  • Familiarity with arrow-pushing mechanisms in organic reactions.
  • Basic knowledge of molecular structures and nomenclature in organic chemistry.
NEXT STEPS
  • Study the mechanism of organolithium addition to carbonyl compounds.
  • Learn about the reactivity of vinyl lithium in organic synthesis.
  • Explore the properties and reactions of 1-bromo-2-propanone.
  • Investigate arrow-pushing techniques in organic reaction mechanisms.
USEFUL FOR

Chemistry students, organic chemists, and anyone studying reaction mechanisms involving organolithium reagents and carbonyl compounds.

brake4country
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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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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?
 
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!
 
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.
 

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