How to Synthesize Alkenes Using Corey House Reaction?

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Discussion Overview

The discussion revolves around the synthesis of alkenes using the Corey House reaction, specifically focusing on the reaction of cyclohex-2-ene-1-one with dimethylcuprate (##(CH3)_2CuLi##). Participants explore the mechanism and application of Gilman reagents in this context, while addressing homework-related queries.

Discussion Character

  • Homework-related
  • Exploratory
  • Technical explanation
  • Debate/contested

Main Points Raised

  • One participant expresses uncertainty about how to proceed with the reaction since there is no halogen present in the compound.
  • Another participant requests to see the effort made by the original poster (OP) to solve the problem, suggesting that even seemingly trivial attempts are welcome.
  • There is a suggestion to compare the reactions of unsaturated cyclic rings with Grignard reagents and Gilman reagents to gain insight.
  • One participant proposes that the double bond in the compound will be attacked by the methyl group from the Gilman reagent, indicating a potential pathway for the reaction.
  • Another participant confirms the previous claim about the methyl group attacking the double bond and discusses the resonance structure of cyclohexane, suggesting that the beta carbon is electron deficient.
  • A question is raised about why the methyl group attacks the beta carbon instead of the carbonyl carbon, indicating a need for further clarification on the mechanism.
  • Participants emphasize the importance of understanding the mechanism before providing direct answers to the OP's queries.
  • One participant suggests reviewing the Michael reaction for clues related to the mechanism.

Areas of Agreement / Disagreement

Participants generally agree that the methyl group from the Gilman reagent attacks the double bond, but there is no consensus on the detailed mechanism or the reasoning behind the specific attack on the beta carbon. The discussion remains unresolved regarding the full understanding of the reaction mechanism.

Contextual Notes

Participants have not provided complete details on their assumptions or prior knowledge, and there are unresolved questions about the mechanism of the reaction. The discussion reflects varying levels of understanding among participants.

Physics lover
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Homework Statement
I came across a question which asked me to take cyclohex-2-ene-1-one and react it with ##(CH3)_2CuLi.##
Relevant Equations
Corey house synthesis
Gilmann reagent
I know mechanism and working of gilmann reagent with carbonyl compounds containing halogen but here there is no halogen.I really don't know how shall i proceed.Please help.
 
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Physics lover said:
Homework Statement: I came across a question which asked me to take cyclohex-2-ene-1-one and react it with ##(CH3)_2CuLi.##
Homework Equations: Corey house synthesis
Gilmann reagent

I know mechanism and working of gilmann reagent with carbonyl compounds containing halogen but here there is no halogen.I really don't know how shall i proceed.Please help.
Please somebody answer.
 
Per PF rules, you need to put in at least a little effort before we can help you.
 
Could you please show us what u have tried ? Even if it sounds particularity stupid, no problems. we can take it from there. Dont worry, don't give up yet, we can do this K ?

If you want a hint , try finding the difference between a reaction of an unsaturated cyclic ring with grignards reagent and gilmans reagent.
 
Sorry it can be totally wrong as i don't know anything about this reaction.According to me the double bond will be attacked by the ##CH_3## group.
 
Physics lover said:
Sorry it can be totally wrong as i don't know anything about this reaction.According to me the double bond will be attacked by the ##CH_3## group.

Well good news , you are correct , the Double bond is attacked by the ##CH_3## group of the gilmanns reagent.

This is because if you draw the resonance structure of the cyclohexane, you will get a electron deficient carbon At the beta position to the carbonyl carbon.(thats fancy english for the doyblebonded carbon furthest from the carbonyl carbon will be attacked by methyl)Now top it all up by showing a picture of the product you got
 
Last edited:
Physics lover said:
Sorry it can be totally wrong as i don't know anything about this reaction.According to me the double bond will be attacked by the ##CH_3## group.
Navin said:
Well good news , you are correct , the Double bond is attacked by the ##CH_3## group of the gilmanns reagent.

This is because if you draw the resonance structure of the cyclohexane, you will get a electron deficient carbon At the beta position to the carbonyl carbon.(thats fancy english for the doyblebonded carbon furthest from the carbonyl carbon will be attacked by methyl)Now top it all up by showing a picture of the product you got
Still not quite enough. Why does the methyl attack the beta carbon and not the carbonyl carbon?
 
TeethWhitener said:
Still not quite enough. Why does the methyl attack the beta carbon and not the carbonyl carbon?
Who are you posing the question to, me or the Op ?
 
TeethWhitener said:
Still not quite enough. Why does the methyl attack the beta carbon and not the carbonyl carbon?
Sir can you tell the mechanism of the reaction.
 
  • #10
Last edited:
  • #11
Review Michael reaction for a clue to the answer.
 

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