[rcrandall]

http://imgur.com/Bi9Ked5
(Does this work better, I have no idea)

[rcrandall]

http://imgur.com/Bi9Ked5

[kriggy]

No, it seems fine. However the picture doesnt work unless I use the URL and copy it directly into browser.
Im not sure which link by imgur did you use but I always use the 2nd from bottom (BBCode (message boards & forums)

[Borek]

You can attach image to your post, click on "Additional options" below the edit field.

[rcrandall]

[rcrandall]

For the second synthesis problem, does this method work? Or have I missed something?

[kriggy]

1) your alkylation by methyliodide will not work because both parts are electron deficient
2) you cant abstract protons from C-H bonds like you did

Try to think about grignard reaction maybe?

[Altered State]

Numer one is correct.

Numer two is not, and as kriggy said, Grignard is a good way to go. You can easily obtain your final product in 3 steps

[rcrandall]

My class didn't get to Grignard, we ended with organolithiums. Is there another way?

[Altered State]

My class didn't get to Grignard, we ended with organolithiums. Is there another way?

You can use an organolithium reagent for exactly the same purpose. It will behave like a Grignard on paper.

[rcrandall]

Can you please explain that further? I don't know where to begin with the organolithium.

[Altered State]

Can you please explain that further? I don't know where to begin with the organolithium.

Well, if you look at your starting product and at your final product, you can clearly see that you need to introdue 2 carbon atoms, one of them being a carbonyl compound.
This can be achieved by the attack of an organometallic compound to an ester or anhydride, through an addition+elimination mechanism.

Now you just need to figure out what is the carbonyl compound you need and what is the corresponding organolithium reagent required, and how would you prepare it from your starting product.



Edit: Now that I think it and see the rest of the questions, you probably did not study that reaction too.
What about alkynes? Did you study them?
Deprotonated acetylene is another good way of introducing two carbon atoms. You can reduce it to an alkene and then obtain the corresponding markovnikov alcohol.

[rcrandall]

Is an alkene formed?

[Altered State]

Is an alkene formed?

You will have to be more especific, I don't know what you mean.
Is an alkene formed when?

You need to understand that there is never not only one solution for these kind of problems... And since I was not in your lectures, it is hard to give advice properly if you don't give enough details.

[rcrandall]

Should I try to eliminate the OH from the reactant, creating an alkene?