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16.6: Alcohol Oxidation

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    Many simple ketones and aldehydes can be purchased, but more complicated structures require reactions for their formation. Alcohols are useful functional groups for the formation of ketones (2° alcohols) or aldehydes (1° alcohols), which occurs via oxidation (the opposite of reduction). Oxidations normally occur by reacting a 1°/2° alcohol with a metal at a high oxidation state.

    The two most common transformations are the Jones oxidation and the Swern oxidation.

    A) Jones oxidation

    Screenshot 2022-12-30 at 9.59.53 AM.png

    While secondary alcohols react with Jones reagents to give ketones, primary alcohols react to give carboxylic acids. Why? Well, the reaction first forms the aldehyde, but because H2O is present in the reaction, a gem-diol can form which is susceptible to further oxidation.

    Screenshot 2022-12-30 at 10.00.04 AM.png

    The Jones reaction generates toxic byproducts, and overoxidizes primary alcohols, so other reagents have been developed to circumvent these two problems.

    B) Swern oxidation

    This reaction converts 1°/2° alcohols to the aldehyde/ketone, respectively, without overoxidation. The reagents are oxalyl chloride, dimethyl sulfoxide, and triethylamine.

    Screenshot 2022-12-30 at 10.00.08 AM.png

    mechanism:

    Screenshot 2022-12-30 at 10.01.13 AM.png

    C) Pyridinium chlorochromate (PCC) oxidation

    This is an anhydrous form of the Jones reagent, so using a primary alcohol will not result in overoxidation.

    Screenshot 2022-12-30 at 10.01.25 AM.png

    16.6: Alcohol Oxidation is shared under a not declared license and was authored, remixed, and/or curated by LibreTexts.

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