Lab 9 - Sodium Borohydride Reduction II

Lab 9 - Sodium Borohydride Reduction II - Sodium...

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Sodium Borohydride Reduction: The Conversion of Benzophenone to Diphenylmethanol Chemistry 0330 Hikmat Daghestani Lauren Allen 11/12/07
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Introduction The purpose of this experiment was to reduce benzophenone to diphenylmethanol with the use of sodium borohydride, re-crystallize the final product and then use IR and melting point to determine the purity of the substance. Reactions/Mechanism/Theory Reduction reactions are those that occur simultaneously with oxidation reactions and are the opposite of them. Reduction reactions are reactions in which an atom gains electron density and reduces its oxidation number. (Recitation) Reductions can be seen through a loss of an oxygen atom across a bond, addition of a hydrogen atom, or a replacement of a more electronegative atom with a less electronegative atom (ex: chlorine replaced with hydrogen). If a reduction reaction occurs, there must always be an oxidation reaction occurring as well. (Recitation) There are several different reduction reagents. H 2 and Pt (the metal catalyst) will form an alcohol from an aldehyde and an alkane from an alkene. In this reaction, the hydrogen atoms are added as “syn” to the molecule. (Recitation) This means that they are added from the same side of the “flat / double-bonded” molecule. (Dr. Wilcox) This couplet reagent requires high temperatures and high pressures and is sometimes unusable due to this because sometimes the molecule meant to react will decompose first. (Recitation) This reagent is also not selective between carbon-carbon double bonds and carbon-oxygen double bonds. So a molecule with both a double bonded carbon-oxygen and a double bonded carbon-carbon cannot be used. (Recitation) Another couple of hydride transfer reagents include Lithium Aluminum Hydride (LiAlH 4 ) and Sodium
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Borohydride (NaBH 4 ). Lithium Aluminum Hydride is the stronger of the two and is explosive with water. Lithium Aluminum Hydride will take a carboxylic acid to an aldehyde to an alcohol and a ketone to an alcohol. Sodium Borohydride will take an
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This note was uploaded on 04/14/2008 for the course CHEM 0330 taught by Professor Forget during the Fall '07 term at Pittsburgh.

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Lab 9 - Sodium Borohydride Reduction II - Sodium...

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