Reagent Selectivity

Question

Selective oxidation of secondary alcohol to ketone without affecting primary alcohol in same molecule uses:

RankGuru · Accepted Answer

1. **Oxidation comparison**: 
   - $KMnO_4, HNO_3$ and Jones reagent are very strong oxidants. They will oxidize primary alcohols all the way to carboxylic acids and secondary alcohols to ketones.
   - **PCC** is milder.
2. **Selectivity Factor**: While both positions are oxidized to carbonyls by PCC, in manual synthesis, controlling stoichiometric amounts or utilizing slightly different reaction rates can favor one.
3. **Correct Context**: PCC is particularly useful because it does not over-oxidize the primary alcohol. In a complex molecule, using $1$ equivalent of PCC in anhydrous dichloromethane allows for precise control, typically yielding the aldehyde/ketone without degrading other sensitive oxy-functional groups unlike the more aggressive aqueous acidic reagents.

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Reagent Selectivity

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