[Rutherford]

Knowing that compounds A and B are isomers with the molecular formula C₇H₇NO and the relative molecular mass of compound M is 93, determine the formulas of compounds A to S taking in account the reactions given in the following reaction scheme that is attached.

This needs some time to be solved so I want only few tips for the beginning. I did till now: found out that A or B is benzamide or oxime (C₆H₅-CH=N-OH) and C probably C₆H₅CN, now I am stuck. Could N be C₆H₅CONH₂? I will be thankful for any tip or guideline.

[Rutherford]

Got that D is benzoic acid, G is m-nitro-benzoic acid, F is m-nitro-benzaldehyde, B is benzamide, A is C₆H₅-CH=N-OH.

[discodermolide]

You are doing great in answering your own question, keep going.

[Rutherford]

No, now I am really stuck  .
I want to finish first with the upper part, so I need some hints about N, P, E and H.

[Rutherford]

After some time, I almost finished this, but there are two issues:
1. The reactions of N to A, B and C aren't okay. N is an amine, A oxime, C nitrile and B amide. How can I get from an amine in 1 step any of these three compounds? The [H] should mean reduction, but carbon is in a lower oxidation state in the amine than in the other compounds. Should the arrows maybe be reversed?
2. What class of compound is made when oximes get hydrolysed?

[discodermolide]

Hydrolysis of oximes: http://en.wikipedia.org/wiki/Oxime
Amide to nitrile: http://www.chemguide.co.uk/organicprops/nitriles/preparation.html
Amine to amide: react with an acid chloride.
Amines to oximes: http://www.tandfonline.com/doi/abs/10.1080/00397911.2010.515339

[Rutherford]

Hydrolysis of oximes: http://en.wikipedia.org/wiki/Oxime

So it decomposes to the starting material.

Strange. The reactions N to A, B and C are completely wrong then. The rest is okay. Thanks.