[physstudent1]

OK I know that LDA will take off an alpha carbon.  then I will have an enolate ion I have tried making the enolate attack the carbonyl and then protonating to give the alcohol but it isn't correct.  I dont really know what to do we haven't done anything with carbonyls with ethers in them  and I don't know what that other reagent is and if it does something special?

[macman104]

OK I know that LDA will take off an alpha carbon.

Hydrogen, alpha-hydrogen. 

then I will have an enolate ion I have tried making the enolate attack the carbonyl and then protonating to give the alcohol but it isn't correct

You're very close.  LDA does form the enolate anion.  This anion is going to attack the anhydride.  However, unlike a regular ketone or aldehyde, the anhydride has a good leaving group in it, so you are not going to get an alcohol.  Can you draw the mechanism to right before the point where you protonate the alcohol?

[physstudent1]

sry I meant alpha hydrogen heh, yea I have it drawn on paper in front of me I don't see what could happen, maybe the O with the minus on it attacks the other carbonyl carbon?

[macman104]

Look at the picture below.  Also, hopefully you have been able to see that this is the product being that is going to be formed.  If you push the electrons like the pictures shows, there are 2 reasonable choices afterwards of things to do.  What do you think about the choices?

[physstudent1]

I think I got it would the bond between the O that is attached to the carbon with the new bond break leaving just  the methyl + double bonded O and the carbon they are both on attached to the original chain?

[macman104]

Yup?

[physstudent1]

I can't check anymore because I exhausted my attempts on accident ( i hate using webassign) but thanks!

[macman104]

Sorry, that was supposed to be "Yup!", not sure how I got the "?" in there.