University of Alabama, Birmingham CH 238 Oxidation of Isoborneol and Reduction of Camphor

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Oxidation of Isoborneol and Reduction of Camphor Lead Author: Leena Patel Reviewer: Andrew Rowe Editor: Dalton Williams CH238 – A8 Introduction: Camphor is naturally occurring and chemically... manufactured. It is one of the active ingredients in Vicks VapoRub and is used to reduce pain and inflammation.1 Camphor is a model compound in its ability to produce isomeric secondary alcohols, such as isoborneol and borneol, when it is reduced. Oxidation is the gain of oxygen or loss of hydrogen and reduction is the loss of oxygen or gain of hydrogen.2 When isoborneol is oxidized, a hydrogen is lost and the resulting compound is camphor. The oxidizing agent used in the oxidation of isoborneol was hypochlorous acid which was created in situ from sodium hypochlorite and acetic acid. Hypochlorous acid was used instead of common reagents such as CrO3 and KMnO4 because while the common reagents are effective, they are also toxic to humans and the environment.3 Camphor is the only product formed when isoborneol is oxidized. However, if camphor is reduced by a reducing agent such as NaBH4, then it produces two products: isoborneol and borneol. In this case, isoborneol is the major product. Isoborneol and borneol are conformational isomers which form depending on if the hydride anions from NaBH4 attack from the top or bottom [Show More]

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