Jones oxidation of benzyl alcohol yields which product?

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Multiple Choice

Jones oxidation of benzyl alcohol yields which product?

Jones oxidation uses a strong oxidizing mixture (CrO3 in acidic acetone) to push primary alcohols all the way to carboxylic acids. Benzyl alcohol is a primary alcohol, so under these conditions the alcohol is first oxidized to the aldehyde, but the powerful oxidant continues to oxidize the aldehyde to the carboxylic acid. That final product is benzoic acid. The aldehyde would only be the result with milder reagents (like PCC), and benzyl alcohol isn’t left unchanged by Jones; toluene isn’t formed because this process oxidizes the attached benzylic carbon rather than removing the hydroxyl or generating a hydrocarbon.

Jones oxidation uses a strong oxidizing mixture (CrO3 in acidic acetone) to push primary alcohols all the way to carboxylic acids. Benzyl alcohol is a primary alcohol, so under these conditions the alcohol is first oxidized to the aldehyde, but the powerful oxidant continues to oxidize the aldehyde to the carboxylic acid. That final product is benzoic acid. The aldehyde would only be the result with milder reagents (like PCC), and benzyl alcohol isn’t left unchanged by Jones; toluene isn’t formed because this process oxidizes the attached benzylic carbon rather than removing the hydroxyl or generating a hydrocarbon.

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