• Support PF! Buy your school textbooks, materials and every day products Here!

Corey house synthesis for alkenes

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 dont know how shall i proceed.Please help.
 

Answers and Replies

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 dont know how shall i proceed.Please help.
Please somebody answer.
 
TeethWhitener
Science Advisor
Gold Member
1,528
835
Per PF rules, you need to put in at least a little effort before we can help you.
 
113
34
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, dont 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 dont know anything about this reaction.According to me the double bond will be attacked by the ##CH_3## group.
 
113
34
Sorry it can be totally wrong as i dont 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:
TeethWhitener
Science Advisor
Gold Member
1,528
835
Sorry it can be totally wrong as i dont 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?
 
113
34
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 ?
 
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
Science Advisor
Gold Member
1,528
835
Last edited:
chemisttree
Science Advisor
Homework Helper
Gold Member
3,080
61
Review Michael reaction for a clue to the answer.
 

Related Threads for: Corey house synthesis for alkenes

  • Last Post
Replies
1
Views
3K
  • Last Post
Replies
0
Views
1K
  • Last Post
Replies
1
Views
5K
  • Last Post
Replies
2
Views
3K
  • Last Post
Replies
1
Views
585
  • Last Post
Replies
1
Views
2K
  • Last Post
2
Replies
26
Views
12K
  • Last Post
Replies
1
Views
9K
Top