EXP31 - 1 Layla Fijany Chem 12B M/W 10-3pm 1/18/2012...

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1 Layla Fijany Chem 12B M/W 10-3pm 1/18/2012 Experiment 31: Oxidation Reduction Scheme Purpose : Initial compound of borneol will be oxidized to camphor then will be finally reduced to isoborneol. Introduction: The initial compound borneol will be oxidized then reduced to isoborneol. The first reaction will consist of borneol reacting with Sodium Hypochlorite NaOCl and Acetic Acid CH3COOH. However, the Sodium Hypochlorite NaOCl will react in situ with the acetic acid CH3COOH to produce HOCl + CH3COONa . The exact mechanism of borneol to camphor is not completely clear; it is thought that an elimination reaction occurs between H2O and O-CL, leading to a ketone. Camphor then is reacted with Sodium Borohydride NaBH4 to produce isoborneol. Isoborneol is produced instead of the initial borneol compound due to the sterricly hindered digeminalmethyl group impeding the Hydrogen addition in the exo position. Hypothesis: Borneol will successfully oxidize to camphor. Camphor will successfully reduce to isoborneol. Set Up/Reaction:
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2 List of Reagent: FW (g/mol) BP (˚C) MP (˚C) Density (g/cm 3 ) Other (hazards, uses, etc) Methylene chloride (CH 2 Cl 2 ): 84.93 39.6 -96.7 1.33 - clrless lqd, high volatility, inhalation hazard, metabolized by body to CO (poisoning), carcinogenic; used as paint stripper, degreaser, aerosol spray propellant and to decaffeinate coffee/tea Sodium Hypochlorite (NaClO): 74.4 101 25 1.17 - used as a disinfect, also known as ‘bleach’; biocide substance killing germs, micro-organisms, algae, etc; highly unstable salt which becomes sodium chlorate easily Anhydrous sodium sulfate (Na 2 SO 4 ): 142 1429 884 2.66 - white crystalline solid, stable and unreacting to reducing agents at room temperature; dust can cause temporary asthma or eye irritation Acetic Acid ( CH 3 COOH): 60.05 117 17 1.05 - commonly associated with vinegar; used to manufacture a wide range of chemical products, such as plastics and acetobacter Borneol (C 10 H 18 O): Melting point: 208 °C, 481 K, 406 °F, Boiling point: 213 ºC. Camphor (C 10 H 16 O) Melting point: 180˚C, Density (g cm -3 ): 1.63, Water solubility: appreciable. Acetone ((CH 3 ) 2 CO) Melting point: -95˚C, Melting point: -95˚C, Irritant. Liquid may cause permanent eye damage (corneal clouding). Procedure
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EXP31 - 1 Layla Fijany Chem 12B M/W 10-3pm 1/18/2012...

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