Alcohol 2 :

Problem

Solution

The oxidation of n-butyl alcohol (1-butanol) under these conditions (Jones oxidation) is complicated. In Problem 1 in Alcohols, the oxidation of a secondary alcohol stopped at the ketone. Although n-butyraldehyde 1 is formed, it forms hydrate 2 with the water present in the Jones' reagent. Intermediate 2 "thinks it is an alcohol" and the reagent treats it as such by oxidizing it to butyric acid 3, the end of the line for oxidation of primary alcohols. The oxidation of 2 is competitive with the oxidation of n-butyl alcohol. Thus, it is difficult to terminate the oxidation at 1. What change in the reaction conditions will prohibit the oxidation to the carboxylic acid? Think about it, then try Problem 3 in Alcohols.