How to Synthesize Alkenes Using Corey House Reaction?

[Physics lover]

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.

 

[Physics lover]

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.

 

[TeethWhitener]

Per PF rules, you need to put in at least a little effort before we can help you.

 

[Navin]

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.

 

[Physics lover]

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]

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

 

[TeethWhitener]

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

Still not quite enough. Why does the methyl attack the beta carbon and not the carbonyl carbon?

 

[Navin]

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 ?

 

[Physics lover]

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.

 

[TeethWhitener]

Who are you posing the question to, me or the Op ?

Ideally the OP, since they haven't shown that they actually understand what's going on.

Sir can you tell the mechanism of the reaction.

No. That's not how PF homework help works.

Edit: Here are the PF homework rules: https://www.physicsforums.com/threads/homework-help-guidelines-for-students-and-helpers.686787/
Pay special attention to point number 4.

 

[chemisttree]

Review Michael reaction for a clue to the answer.