[Aznhmonglor]

Alright so there's the problem, What I tthought it would make:



What am I doing wrong here?

[wanderlust]

Ah, I'm no expert but I believe this is a case of conjugate addition.  Without the double bond in the cyclohexane you would generate a tertiary alcohol but since you have a conjugated system you actually see addition of your nucophile at the third position and the retention of your keytone. 

I hope this helps.  Maybe someone with more experience can verify this or help you further. 

[Aznhmonglor]

Hmm what do you mean my nucleophile adds to the third position? so it would look something like this???


*Ketone at the top there, forgot to put the oxygen.

Not sure if I attacked the BuLi in the right place but right concept now?

[wanderlust]

No, counting your keytone as the first position and counting clockwise (you're missing your oxygen, btw) you would add butyl to the third position and remove the double bond.  The reaction mechanism is somewhat complex and ends up with a negative charge on the second carbon which grabs a hydrogen. 


In the end you have....(deep breath, it's been awhile for nomenclature) 3-butylcyclohexanone? 

http://en.wikipedia.org/wiki/Conjugate_addition

[Aznhmonglor]

Please do that would be a big help.

[wanderlust]

Sorry I modified my post if you reread my last post there's a wikipedia link there that should be very useful for you.

[Aznhmonglor]

Thank you it makes sense now. But for some reason in my notes it says that with a conjugated compound the strong basic nucleophile still attacks the carbonyl group and forms an alcohol?

[wanderlust]

With a alpha beta unsaturated carbonyl I'm pretty sure the nucleophile attacks where I said.  Possibly double check your notes or ask your teacher for clarification. 

[Aznhmonglor]

Hmmm...this method didn't work....anybody got anymore ideas? I think it has to attack the carbonyl group?

[wanderlust]

Why didn't it work what was is the actual product then?

[Aznhmonglor]

Im not sure but it didn't come out correct if you attack the alkene and let the carbonyl group stay.

[wanderlust]

This product is showing as wrong? 

I don't know then.

[azmanam]

alkyl lithiums are hard nucleophiles and therefore give the 1,2 add'n product.  tertiary alcohol is the correct answer.  Gillman reagents (alkyl cuprates) are the ones that give 1,4 conjugate add'n.

[sjb]

(picture of 3-butylcyclohexanone)

This product is showing as wrong? 

I don't know then.

Also don't forget to count your carbons

[Aznhmonglor]

So this would be correct answer?