What type of alcohol can PCC oxidize into a ketone?

Pyridinium chlorochromate (PCC) is a mild oxidizing agent commonly used in organic chemistry for the selective oxidation of alcohols. The unique characteristic of PCC is its ability to oxidize secondary alcohols into ketones without further oxidation to carboxylic acids, which often occurs with stronger oxidizing agents.

When a secondary alcohol undergoes oxidation, it loses two hydrogen atoms—one from the hydroxyl functional group (−OH) and one from the carbon atom to which it is attached, resulting in the formation of a carbonyl group (C=O) that characterizes ketones. Secondary alcohols have the general structure R2CHOH, where the carbon bearing the hydroxyl group is bonded to two other alkyl groups. The presence of these alkyl groups stabilizes the ketone product, making it more favorable for oxidation to occur.

In contrast, primary alcohols are typically oxidized to aldehydes and can be further oxidized to carboxylic acids, while tertiary alcohols cannot be oxidized to any kind of carbonyl compound because the carbon bearing the hydroxyl group is bound to three other carbon atoms, making it impossible for the necessary oxidation process to occur. The term "saturated