REACTION: Oxidation of an Alcohol TECHNIQUES: TLC, Extraction, Recrystallization

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REACTION: Oxidation of an Alcohol TECHNIQUES: TLC, Extraction, Recrystallization In this experiment, we will explore the oxidation of a secondary alcohol to a ketone using an oxidizing reagent, sodium hypochlorite, which is a readily available and commonly used household cleaning product. We will use thin layer chromatographic (TLC) technique to monitor the progress of oxidation reaction. NaOCI, CH3CO2H acetone 9-fluorenol READING ASSIGNMENT: This handout for procedure Review any appropriate techniques. Supplementary information in Janice Gorzynski Smith (2nd ed), Chapter 12 BACKGROUND: Sodium hypochlorite solutions (approximately 2 M) sold as liquid bleach are often described as having i 1.5. 12.5% available chlorine. The term "available chlorine" compares the oxidizing capacity of the solution relative to that of the same weight of chlorine, Cl. Sodium hypochlorite solutions are used extensively in swimming pool sanitation, and as bleach in the pulp and textile industries. A less-concentrated product (5% available chlorine) is used in laundry and as household bleach. It is reported that 210,000 tons of sodium hypochlorite were consumed in the United States in 1982. The reaction described in this experiment illustrates the use of liquid bleach as an oxidizing agent in the organic laboratory. Sodium hypochlorite is prepared commercially by passing chlorine gas through a solution of aqueous sodium hydroxide (eq 1). In acidic condition, a rapid equilibrium is established between A part of this procedure is adopted from an article published by CS. Jones and K.Albizati in the Jourmal of Chemical Education 1994, 71, A271 Chem 242, Lab Sectiorn Reviewed 1-20-14 hypochlorite anion and hypochlorous acid (HOCI), which produces the "Cl"on equivalent (eq Cl2 NaOH NaOCI NaCl eq 1) (eq 2) The actual oxidizing agent in the present experiment is believed to be the chlorine ion .-CI equivalent (HOCI), which is reduced in the reaction to chloride ion (Cl). The 9-fluorenol acts as a reducing agent, and thus becomes oxidized to 9-fluorenone. Please note that "CI" is not actually floating around in the reaction mixture.

Explanation / Answer

here the solvent they are using is acetone

the 9-fluorenol is the reactant which gets oxidized.

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