[ricecake]

This is part of a chain reaction if I did all the other steps correctly.
Bezonitril + H₃O⁺ (1:1)  A  + Na/Ethanol  B+ CH₃Cl (1:1)  C + (O)/H₂O₂  D

I got stuck at C
A is benzoic acid
B is 2,5-cyclohexadiene-1-carboxylic acid
C is no reaction? It should not be the case right since they still ask for D
Thank you so much for any guidance

[kriggy]

Could it be that there are missing conditions?
Maybe addition of dichlorcarbene on the double bond?
EDIT: wait how could someone make dichlorcarbene form methylchloride?
Or maybe you made a mistake in 2nd step

[Altered State]

Take a look at the first step:



Can you propose a mechanism based on the one for the Birch reduction?

If you can't, it is somewhere hidden in the Wikipedia page for Birch reduction

Source: http://onlinelibrary.wiley.com/doi/10.1002/anie.201300259/abstract

[Altered State]

Could it be that there are missing conditions?

Probably ammonia is missing from Na/EtOH
I don't know if there are ammonia-free Birch reductions, but since the OP said that B would be a Birch product, I assume that they want them to apporach it that way.



Anyway, In my opinion B is not the diene that the OP stated, it is an an ionic compound that can be worked up with another equivalent of alcohol or make it react with an electrophile to give the alkylation product.

So what would be D in your opinion, ricecake?
What do you mean by (O)/H2O2? I guess (O) should be O3?

[ricecake]

Take a look at the first step:



Can you propose a mechanism based on the one for the Birch reduction?

If you can't, it is somewhere hidden in the Wikipedia page for Birch reduction

Source: http://onlinelibrary.wiley.com/doi/10.1002/anie.201300259/abstract

I'm a bit confused. Do you mean my answer for B is correct?

[ricecake]

Could it be that there are missing conditions?

Probably ammonia is missing from Na/EtOH
I don't know if there are ammonia-free Birch reductions, but since the OP said that B would be a Birch product, I assume that they want them to apporach it that way.



Anyway, In my opinion B is not the diene that the OP stated, it is an an ionic compound that can be worked up with another equivalent of alcohol or make it react with an electrophile to give the alkylation product.

So what would be D in your opinion, ricecake?
What do you mean by (O)/H2O2? I guess (O) should be O3?

(O)/H₂O₂ was what my teacher wrote on the paper. I might need to clarify after I turn the assignment in.
So I was not sure since I'm stuck at C. But my best guess for C is 4-methyl-2,5-cyclohexadiene carboxylic acid 

D may be

[Altered State]

Take a look at the first step:



Can you propose a mechanism based on the one for the Birch reduction?

If you can't, it is somewhere hidden in the Wikipedia page for Birch reduction

Source: http://onlinelibrary.wiley.com/doi/10.1002/anie.201300259/abstract

I'm a bit confused. Do you mean my answer for B is correct?

Sorry, I cut my message in two parts and it ended up being a bit confusing.
It is not. For the reaction with CH3Cl to take place, B has to be an intermediate of the Birch reduction, not the 2,5-diene that you proposed. This intermediate would have a negative charge on the carbon of the cycle which is bond to the carboxylic acid group.

This is the answer (the F pathway)
http://en.m.wikipedia.org/wiki/Birch_reduction#/image/File:Birch-Benzoic_Mech.svg
D in this scheme should be B in your reaction

I didn't want to post it directly in case that you wanted to figure it out by yourself, but since I was not clear enough, there you go.

[Altered State]

(O)/H₂O₂ was what my teacher wrote on the paper. I might need to clarify after I turn the assignment in.

Well, (O) might just mean "oxidation", so H2O2 would give you the corresponding peroxiacid.
If it's O3/H2O2, the molecule would break apart through the double bonds and give you two separate molecules (malonic acid and a derivative of malonic acid)

[ricecake]

Thank you so much for your help. Sorry that's I was slow.
Since B is the intermediate, C would follow your diagram
D would be 

[Altered State]

Thank you so much for your help. Sorry that's I was slow.
Since B is the intermediate, C would follow your diagram
D would be 

C is correct.
H2O2 won't oxidize that methyl group.
However, carboxylic acid can be further oxidized to form a peroxyacid with H2O2:
http://en.m.wikipedia.org/wiki/Peroxy_acid

[ricecake]

Thank you so much! I should have read carefully the first time. You did mention peroxyacid in your previous comment. Thank you again!

H2O2 won't oxidize that methyl group.
However, carboxylic acid can be further oxidized to form a peroxyacid with H2O2:
http://en.m.wikipedia.org/wiki/Peroxy_acid

On the same note, would I-CH₂COOH + KOH/H₃O⁺/t°  a peroxyacid I-CH-COOOH. Should I think again?