Corey house synthesis for alkenes

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In summary, the Gilmanns reagent is used to react cyclohexane with a carbonyl compound that contains a halogen. Without the halogen, the cyclohexane cannot be reacted. The double bond at the beta position is attacked by methyl group to form the product.
  • #1
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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  • #2
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.
 
  • #3
Per PF rules, you need to put in at least a little effort before we can help you.
 
  • #4
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.
 
  • #5
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.
 
  • #6
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:
  • #7
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?
 
  • #8
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 ?
 
  • #9
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.
 

1. What is Corey house synthesis for alkenes?

Corey house synthesis for alkenes is a chemical reaction that was developed by Nobel Prize-winning chemist E. J. Corey. It is a method for the synthesis of alkenes, which are molecules with a carbon-carbon double bond. This reaction involves the conversion of aldehydes or ketones to alkenes using a combination of a lithium or magnesium halide and a strong base.

2. How does Corey house synthesis for alkenes work?

In Corey house synthesis, the aldehyde or ketone is first treated with a lithium or magnesium halide, such as lithium diisopropylamide (LDA) or magnesium bromide (MgBr2). This creates an enolate intermediate, which then reacts with a suitable electrophile to form the desired alkene product.

3. What are the advantages of using Corey house synthesis for alkenes?

Corey house synthesis is a versatile and efficient method for the synthesis of alkenes. It allows for the selective formation of alkenes from a wide range of starting materials, and the reaction conditions are relatively mild, making it suitable for a variety of functional groups. Additionally, this method can be used to create stereochemically pure alkenes.

4. What are the limitations of Corey house synthesis for alkenes?

One limitation of Corey house synthesis is that it requires the use of strong bases, which can be dangerous and must be handled with care. Additionally, this method may not be suitable for substrates that are highly acidic or have unstable enolizable protons. It also does not work well for substrates with bulky or hindered groups.

5. What are some applications of Corey house synthesis for alkenes?

Corey house synthesis has a wide range of applications in organic synthesis. It has been used to synthesize natural products, pharmaceuticals, and other complex organic molecules. This method is also commonly used in the production of polymers and other industrial chemicals.

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