Oxidation of a benzylic secondary alcohol typically yields which product?

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Multiple Choice

Oxidation of a benzylic secondary alcohol typically yields which product?

Oxidation of an alcohol changes the oxidation state at the carbon bearing the OH. When that carbon is secondary (attached to two carbon groups), oxidation stops at forming a carbonyl, giving a ketone. For a benzylic secondary alcohol, the carbon next to the benzene ring becomes the carbonyl carbon, producing a benzylic ketone (for example, Ph-CH(OH)-R oxidizes to Ph-CO-R; if R is CH3, that’s acetophenone). Primary alcohols would yield aldehydes (and can go further to acids under strong conditions), while a mere oxidation to an alcohol isn’t the outcome.

Oxidation of an alcohol changes the oxidation state at the carbon bearing the OH. When that carbon is secondary (attached to two carbon groups), oxidation stops at forming a carbonyl, giving a ketone. For a benzylic secondary alcohol, the carbon next to the benzene ring becomes the carbonyl carbon, producing a benzylic ketone (for example, Ph-CH(OH)-R oxidizes to Ph-CO-R; if R is CH3, that’s acetophenone). Primary alcohols would yield aldehydes (and can go further to acids under strong conditions), while a mere oxidation to an alcohol isn’t the outcome.

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