I am trying to understand this mechanism for nitrobenzene reduction with Sn/HCl. I do not understand why it implies that you pull off the C−H hydrogen instead of the O−H hydrogen in the methanol. Is it actually suggesting that the resulting ⋅CHX2−OH radical formed from the methanol eliminates to form formaldehyde or do you get a rearrangement where you form (CHX3−O)X−? If the latter is the case, why not just pluck the proton from the alcohol group instead of breaking the C−H bond?
Also, it mentions that organic solvents are preferred for this reaction, why exactly is that over water?
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