Predict the product when benzyl alcohol is oxidized with PCC in dichloromethane, followed by aqueous workup.

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Multiple Choice

Predict the product when benzyl alcohol is oxidized with PCC in dichloromethane, followed by aqueous workup.

Oxidizing a primary alcohol with PCC in dichloromethane is a mild method that converts the alcohol to an aldehyde rather than to a carboxylic acid. The alcohol (benzyl alcohol, a primary alcohol) is oxidized by forming a chromate ester, then a hydride is transferred to the chromium, yielding the aldehyde and Cr(III) species. Because the oxidant is mild and the conditions are not strongly aqueous, the reaction stops at the aldehyde rather than continuing to the carboxylic acid. The aqueous workup helps remove chromium byproducts and isolates the aldehyde. Therefore benzaldehyde is the expected product, not benzoic acid, benzene, or the starting alcohol.

Oxidizing a primary alcohol with PCC in dichloromethane is a mild method that converts the alcohol to an aldehyde rather than to a carboxylic acid. The alcohol (benzyl alcohol, a primary alcohol) is oxidized by forming a chromate ester, then a hydride is transferred to the chromium, yielding the aldehyde and Cr(III) species. Because the oxidant is mild and the conditions are not strongly aqueous, the reaction stops at the aldehyde rather than continuing to the carboxylic acid. The aqueous workup helps remove chromium byproducts and isolates the aldehyde. Therefore benzaldehyde is the expected product, not benzoic acid, benzene, or the starting alcohol.

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