Tuesday, September 25, 2018

organic chemistry - Nitrobenzene reduction with (tin) Sn catalyst: Why is C-H bond cleavage preferred over O-H bond cleavage?


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 CH hydrogen instead of the OH hydrogen in the methanol. Is it actually suggesting that the resulting CHX2OH radical formed from the methanol eliminates to form formaldehyde or do you get a rearrangement where you form (CHX3O)X? If the latter is the case, why not just pluck the proton from the alcohol group instead of breaking the CH bond?


Also, it mentions that organic solvents are preferred for this reaction, why exactly is that over water?


nitrobenzene reduction to aniline with Sn/HCl




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