An Oxidation Puzzle

Oxidation of alcohols Infrared spectroscopy Critical thinking application 

Sodium hypochlorite in acetic acid is an oxidizing agent capable of oxidizing alcohols to the corresponding aldehydes or ketones. In this experiment, you will oxidize a diol, 2-ethyl-l,3-hexanediol (1) and then use infrared spectroscopy to determine which of the alcohol functional groups was oxidized. 

You will determine whether the oxidation occurred selectively (and which functional group was oxidized) or whether both functional groups were oxidized at the same time. The possible outcomes of the oxidation are shown in the figure. If only the primary alcohol is oxidized, the aldehyde (2) will be formed if only the secondary alcohol is oxidized, the ketone (3) will be the product. If both alcohol functional groups are oxidized, compound (4) will be observed. Your assignment will be to use infrared spectroscopy to determine the structure of the product and decide which of these three possible outcomes actually takes place. 

Glacial acetic acid is corrosive it can cause burns on the skin and on mucous membranes in the nose and mouth. Its vapors are also hazardous. Dispense it in the hood and use personal protective equipment. Avoid contact with skin, eyes, and clothing. Sodium hypochlorite emits chlorine gas, which is a respiratory and eye irritant. Dispense it in a fume hood. 

All aqueous solutions should be collected in a container specially marked for aqueous wastes. Place organic liquids in the container designated for nonhalogenated organic waste. Note that your instructor may establish a different method of collecting wastes in this experiment. 

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