[mngo6]

I have some questions from my homework assignment that I am not quite sure where to start.

For this first question, I know that the grignard attacks the carbonyls but for the joint ester I'm unsure of whether or not it will open up the ring and if so how the product would form.

Does the formula C7H12O2 mean that it's in a linear chain? I am assuming that the grignard will reduce the carbonyls to alcohols but how do I deal with the ester O ?

Or am I being stupid and I should just put C7H12O2 down lol

for the 2nd question, I have no idea how or where to start :S

Sorry I had the wrong step in question 2, the changes have been made in red.

[mngo6]

Ok, I also figured it had a degree of unsaturation of 2 but as you posted wouldn't the excess Grignard react with the 2 carbonyl groups that are left over after the opening of the ring?

If we just go with 2 units of unsaturation all I can think of is this where the methyls are bonded to where the Ester linking O would have been. Does this make sense? I'm assuming that it's all I can do especially with the formula of the structure given :S

Any help with the 2nd question? It's given in stoichiometric amounts so I would assume that this question has some regiochem/stereospecificity to it?

[mngo6]

Anybody else with any insight into my questions?

[agrobert]

(1) http://www.organic-chemistry.org/abstracts/literature/003.shtm

Yes the lactone will open.  Now redraw your product.

(2) Amide formation with lactone opening to acid.  Reduction to terminal alcohol.  Now draw your product.

[english]

Ok, I also figured it had a degree of unsaturation of 2 but as you posted wouldn't the excess Grignard react with the 2 carbonyl groups that are left over after the opening of the ring?

Not appreciably if you have 2 equivalents of Grignard and 2 carbonyls in your molecule.

[mngo6]

This is the mechanism I get for the Grignard question so far.

I hope you can all read my writing, I would have scanned it if I had one...so I took a picture instead lol

[agrobert]

Did you look at the link?

Nothing has changed for (2)?

[mngo6]

Before for #2 it had then catalytic acid instead of work up

yes, agrobert, I took a look at the link, and it shows that the ring opens up, but it doesn't show me how to work in the mechanism of the cat. acid for the addition of the next methyl group to the tail or does it and I just don't see it :S?

[mngo6]

Here's my attempt at #2 if it is right SWEET! If not can you please help me correct my mechanism. I should probably be studying for my inorganic chem final instead of doing this orgo assignment. Classes are over yet my prof still finds that handing out assignments after lectures are complete is still ethical >_<.


Pic = attempt at #2

[english]

No, no.  Ester O's are hardly nucleophiles when you have amines!  Think amination.

[mngo6]

lol I feel so bad because your response makes me feel like I just broke the law >_<

Well I went on with amination but I'm unsure as to what the mechanism is. I googled a bit and saw that the amination of a ketone ends up with a single C-N bond. Is this where my reaction is headed? Or is my reducing agent LiAlH₄ going to attack the C=N-Et after the loss of H₂O

Are any of these ideas on the right track?

A, B, or C ?

PS: I hope I'm not annoying any of you with my stupidity >_<

[mngo6]

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

in the example

-COOH --> -CONH2

is that O there the ester linking O or the C=O

[mngo6]

Here's my progress with the Lactone and amine question, can anybody tell me if I am correct or at least on the right track?