An Oxidation Puzzle Abstract: 2-ethyl-1,3-hexanediol was stirred in an ice bath with glacial acetic acid and an excess of sodium

hypochlorite for 1 hour. The mixture was tested periodically to ensure there was an excess of hypochlorite. The mixture was then added to an icesalt mixture and extracted with diethyl ether. The extracts were washed with sodium carbonate and sodium hydroxide, tested to ensure that the solution was sufficiently basic, and dried over magnesium sulfate. The ether was removed and an IR spectrum obtained for the resulting product. Introduction: In addition to its utility as a selective oxidizing agent for mind-bending organic chemistry experiments, sodium hypochlorite is also useful as a reagent for the removal of arsenic from water as described in a paper1 by researchers at the University of Bresica. The purpose of this research was to examine the efficacy various oxidizing agents on arsenic in water with various pH levels. The reason behind this is that methods for removal of arsenic, precipitation or chemical absorption, are much more effective when the arsenic is first oxidized. The researchers found that sodium hypochlorite was a good oxidizing agent for these purposes, with yields eventually reaching 100%, independent of the pH of the water. Data & Calculations: 2-ethyl-1-hydroxy-3-hexanone: clear, oily liquid; FT-IR (neat) 3400, 2900, 1700, 1450 1350 1100. See attached spectra. 2-ethyl-1-hydroxy3-hexanone Mass actual 0.0312 g Mass expected 0.4605 g % yield 6.78%

Sorlini, Sabrina, and Francesca Gialdini. "Conventional Oxidation Treatments for the Removal of Arsenic with Chlorine Dioxide, Hypochlorite, Potassium Permanganate and Monochloramine." Water Research 44.19 (2010): 5653-5659. Web. 3 May 2011. <doi:10.1016/j.watres.2010.06.032>.

Conclusion: The purpose of this experiment was to determine if elective oxidation occurred when 2-ethyl-1,3-hexanediol was reacted with sodium hypochlorite. Three possibilities were possible: oxidation of the primary alcohol group, oxidation of the secondary alcohol group, and oxidation of both alcohol groups. The presence of a broad alcohol peak at 3400 cm-1 strongly indicates that both alcohol functionalities were not oxidized. This, along with a characteristic carbonyl group peak at approximately 1700 cm-1 leaves two of three possible products, oxidation of the primary alcohol resulting in an aldehyde and oxidation of the secondary alcohol resulting in a ketone. Further examination of the IR spectrum reveals a lack of medium peaks at 2690-2840 cm-1. The absence of any peaks in this region seems to suggest that the product contains a ketone and not an aldehyde. The product is therefore most likely 2-ethyl-1-hydroxy-3-hexanone. The identification of the oxidation product in this reaction could have benefitted from additional analysis, such as proton NMR or testing with Tollens reagent.