[trinitrotoluene]

Hey Guys, I am trying to propose a reasonable mechanism for this transformation. I gave my best go at it, but it seems a little shady. Just wondering if this seems plausible or if there any other suggestions on how to go about the transformation.

Thanks!

[spirochete]

You've drawn a couple of elimination steps as concerted that I would expect to be stepwise. Protons alpha to a carbonyl group are relatively acidic, so you can make an enolate first, then expel the leaving group to form a pi bond. This is called E1cb (E1 conjugate base). 

[spirochete]

Also you magically made the phenolic hydroxyl group dissapear in the last step.

[orgopete]

I had to work through this backwards to understand it. None the less, I am concerned that only one product formed. With the proposed mechanism, the cyclopropane cold open two ways to give similar products. This is what I think happens. It does no decarboxylation initially, but now the most acidic proton is that alpha to the benzo group. Open the cyclopropane to give the enolate of a beta keto-acid. You can rationalize a path for the remainder of the steps.

[trinitrotoluene]

You've drawn a couple of elimination steps as concerted that I would expect to be stepwise. Protons alpha to a carbonyl group are relatively acidic, so you can make an enolate first, then expel the leaving group to form a pi bond. This is called E1cb (E1 conjugate base).

Also you magically made the phenolic hydroxyl group dissapear in the last step.

Thank you for the input ^_^ I suppose I should be more careful with concerted vs. stepwise. I have always been bad with that. Also, I don't know why I forgot the phenol, but it should be there.

I had to work through this backwards to understand it. None the less, I am concerned that only one product formed. With the proposed mechanism, the cyclopropane cold open two ways to give similar products. This is what I think happens. It does no decarboxylation initially, but now the most acidic proton is that alpha to the benzo group. Open the cyclopropane to give the enolate of a beta keto-acid. You can rationalize a path for the remainder of the steps.

We were given the reaction and just propose a mechanism. At first I did open the the ring differently, and got to another product. I will work out your suggestions though and see how it turns out differently

Thank you! ^_^