Lab 8 - Jones- Oxidation of Borneol to Camphor

Lab 8 - Jones- Oxidation of Borneol to Camphor - The Jones...

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The Jones Reaction: The Oxidation of Borneol to Camphor Chemistry 0330 Hikmat Daghestani Lauren Allen 11/5/07
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Introduction The purpose of this experiment was to oxidize borneol (producing camphor,) explore purification of a substance via sublimation, and then determine the purity of the substance via an IR spectroscopy graph of the final product and determination of its boiling point. Reactions/Mechanism/Theory Two types of reactions of major importance include oxidation reactions and reduction reactions. Reduction reactions are classified as the gaining of electron density and a reduction in the oxidation state of the atom (8). (In organic chemistry this atom is usually carbon – recitation) Oxidation reactions generally result in the loss of electrons and an increase in the oxidation number of the atom. Another way of determining whether one of the above reactions has occurred is by looking at the mechanism. If an oxygen is inserted into a bond, a hydrogen is lost across a bond, and then a more electronegative atom replaces a carbon or a hydrogen in the molecule, most likely an oxidation reaction has taken place. (8) To determine an oxidation state several things must be considered. In organic chemistry, carbon is usually the atom of concern. For each hydrogen atom bonded to a carbon, subtract one because it is less electronegative than carbon. For each atom that is greater in electronegativity than carbon, add one per bond. And for each carbon-carbon bond, add nothing (they are of the same electronegativity.) (8) In general, carbons oxidation states will only go from -4 to 4, this is because carbon usually only accepts 4 bonds.
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Many mistakes are often made when determining whether an oxidation reaction has occurred or not. The reaction is not one with characteristics of an oxidation reaction if one electronegative atom is replaced by another. (Recitation) It is also not an oxidation reaction if a hydrogen and an electronegative atom are both eliminated across a bond. (Recitation) This is because the -1 and the +1 from both will cancel each other, thus retaining the oxidation number. There are five important reagents in these types of reactions.
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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 8 - Jones- Oxidation of Borneol to Camphor - The Jones...

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