ACS Organic Chemistry Practice Test

Swern oxidation of a primary alcohol yields which product?

Alcohol Carboxylic acid Aldehyde Ketone

Correct Answer:

Aldehyde

Explanation:

Swern oxidation is a mild, non-aqueous method that converts primary alcohols to aldehydes. The oxidant is generated from dimethyl sulfoxide (DMSO) and oxalyl chloride under cold conditions with a base. This setup oxidizes the alcohol to an aldehyde and then, under these conditions, there isn’t leftover oxidizing power or water to push the aldehyde further to a carboxylic acid. That’s why a primary alcohol ends up as an aldehyde in Swern oxidation. For a secondary alcohol, the oxidation stops at a ketone, reflecting the difference in hydrogen removal at the two possible sites.

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