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Butanol can be oxidized with pyridinium chlorochromate (PCC) yielding butanal. If the case is that butanol can be oxidized with PCC, can it be oxidized with CrO3, H2SO4, HNO3, OsO4, and other oxidizing agents? If yes, why? If no, why?



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Simple answer no.

For a simple transformation there may be many conditions that will get the same result (in varying yields), but that does not mean that all oxidising agents could be used. Nitric acid is a powerful and indiscriminate reagent better suited to oxidation of inorganic species as it is more likely to degrade your organic substrate than produce clean product. In the example you quote CrO3, if used with acid, will take butan-1-ol to butanoic acid rather than butanal. Solvent makes a difference too; PCC will give the aldehyde in CH2Cl2 but the acid in DMF. Temperature is also important; the Swern reaction for alcohol to aldehyde is routinely run at below -60C as above that temperature side products proliferate.

Selecting the right conditions for a transformation goes to the heart of synthetic organic chemistry and a knowledge of reagents is a basic requirement for any synthetic organic chemist.


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