OChemIIBerkeleyExp11 - The Magtrieve Oxidation of...

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The Magtrieve Oxidation of 4-chlorobenzyl Alcohol, A Solvent Free Reaction Purpose: The purpose of this experiment is to perform a completely solvent free oxidation reaction in which a primary alcohol is converted to an aldehyde under environmentally friendly conditions. Procedure: 1. Add 1mmol 4-cholorobenzyl alcohol and 700mg Magtrieve to 30mL beaker (use spatula) 2. Mix with glass stirring rod making sure to break up clumps and spread mixture evenly throughout bottom of beaker 3. Place in sand bath with watch on top of beaker 4. Place ice on top of watch glass (remove water when ice melts and replace ice appropriately) 5. Heat system at low temp (<110 ° C) while taking measurement at bottom of beaker 6. Heat for 30 minutes then remove from sand bath and let cool to room temperature 7. Carefully remove ice/water from top of watch glass then carefully lift watch glass and dump crystals onto a second watch glass, which has already been tarred. Also add crystals that had formed on side of beaker. 8. Record weight. 9. Obtain second crop of crystals with remaining product then combine yields. 10. Perform more crops if necessary 11. Measure melting point of crystals 12. Dissolve from product and starting material in acetone then spot on a TLC plate 13. Develop the plate in 60:40 hexane: ethyl acetate then use UV light and iodine visualization techniques. Prelab Checklist: Balanced Equation: Additional Calculations: Physical Data: Compound Structure Molecular Weight Melting Point Hazards Magtrieve 83.99g/mol >375 ° C Irritant
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4-chlorobenzyl alcohol 142.58g/mol 68-71 ° C Flammable 4-chlorobenzaldehyde 140.52g/mol 46 ° C Harmful, Danger to Environment Data/Observations: First Crop of Crystals: Weight of watch glass: 32.574g Weight of watch glass + first crop of crystals: 32.576g Weight of first crop of crystals: 0.002g Second Crop of Crystals: Weight of watch glass: 32.556g Weight of watch glass + second crop of crystals: 32.583g Weight of second crop of crystals: 0.027g Percent Yield: Net amount of crystals: 0.002g + 0.027g = 0.029g = 29mg Percent Yield = [(actual yield)/(theoretical yield)]
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This note was uploaded on 02/16/2011 for the course OCHEM 112B taught by Professor Sarpong during the Spring '11 term at Berkeley.

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OChemIIBerkeleyExp11 - The Magtrieve Oxidation of...

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