Which oxidizing agent is used to oxidize 2-propanol to acetone in the example given?

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Multiple Choice

Which oxidizing agent is used to oxidize 2-propanol to acetone in the example given?

Explanation:
The key idea is using a mild, selective oxidant that stops exactly at the ketone and doesn’t overoxidize the product. PCC (pyridinium chlorochromate) is a classic example of such a reagent: it oxidizes secondary alcohols like 2-propanol to ketones (acetone) under relatively gentle, non-aqueous conditions, giving the desired product without pushing the oxidation further to carboxylic acids. Other reagents are harsher or less selective. Jones reagent (a strong chromium(VI) oxidant in aqueous acetone) is more aggressive and can lead to overoxidation or side reactions under certain conditions, while permanganate is also a powerful oxidant with potential overoxidation and less control in some contexts. Dess–Martin periodinane is milder and would alsooxidize secondary alcohols to ketones, but the example in question specifically uses PCC, which is the textbook choice for this transformation.

The key idea is using a mild, selective oxidant that stops exactly at the ketone and doesn’t overoxidize the product. PCC (pyridinium chlorochromate) is a classic example of such a reagent: it oxidizes secondary alcohols like 2-propanol to ketones (acetone) under relatively gentle, non-aqueous conditions, giving the desired product without pushing the oxidation further to carboxylic acids.

Other reagents are harsher or less selective. Jones reagent (a strong chromium(VI) oxidant in aqueous acetone) is more aggressive and can lead to overoxidation or side reactions under certain conditions, while permanganate is also a powerful oxidant with potential overoxidation and less control in some contexts. Dess–Martin periodinane is milder and would alsooxidize secondary alcohols to ketones, but the example in question specifically uses PCC, which is the textbook choice for this transformation.