Which oxidation yields carboxylic acids from primary alcohols? PCC or Jones?

Which oxidation yields carboxylic acids from primary alcohols? PCC or Jones?

• A. PCC
• B. Jones
• C. Both
• D. Neither

Answer: (B)

Oxidation strength and selectivity determine how far a primary alcohol is oxidized. PCC is a mild oxidant that typically converts primary alcohols to aldehydes and stops there, so it doesn’t push the molecule to the carboxylic acid. Jones oxidation, on the other hand, uses chromium(VI) in strongly acidic, aqueous conditions, which is powerful enough to oxidize the aldehyde further to the carboxylic acid. The acidic, aqueous environment helps drive that second oxidation step. Therefore, to obtain a carboxylic acid from a primary alcohol, Jones oxidation is the appropriate reagent.

Oxidation strength and selectivity determine how far a primary alcohol is oxidized. PCC is a mild oxidant that typically converts primary alcohols to aldehydes and stops there, so it doesn’t push the molecule to the carboxylic acid. Jones oxidation, on the other hand, uses chromium(VI) in strongly acidic, aqueous conditions, which is powerful enough to oxidize the aldehyde further to the carboxylic acid. The acidic, aqueous environment helps drive that second oxidation step. Therefore, to obtain a carboxylic acid from a primary alcohol, Jones oxidation is the appropriate reagent.