OCHEM The Jones Reaction 8

OCHEM The Jones Reaction 8 - The Jones Reaction: Oxidation...

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The Jones Reaction: Oxidation of Borneol to Camphor Lindy Hilpert Brad Hutnick Organic Chemistry 310 November 7, 2007
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Introduction: The purpose of this lab is to oxidize borneol to camphor, to purify it using sublimation, and characterize it by melting point and IR spectroscopy. Theory, Reactions, and Mechanisms: Oxidation reactions involve the loss of electrons and gain in oxidation number. This can be accomplished by inserting an oxygen into a bond, losing a hydrogen across a bond, or replacing hydrogen or carbon atom with a more electronegative element. Reduction reactions involve that involve the gain of electrons and the reduction in oxidation number. Jones oxidations involve the use of different forms of chromium as an oxidizing agent. The three commonly used Jones reagents are CrO3/H+, H2CrO4, and Cr2O7(2-)/H+. By using a Jones reaction, primary alcohols and aldehydes will form carboxylic acids, and secondary alcohols will form ketones. Tertiary alcohols do not react because they are too bulky for the Jones reagents to attack them. If PCC is used, the primary alcohol will stop being oxidized at an aldehyde instead of going all the way to the carboxylic acid. Extraction is a way of separating two immiscible solutions by way of their differences in polarity. Polarity is a measure of how electrons in a bond are shared. The more electronegative an atom is, the more the electrons are attracted to that atom. When one atom in a molecule is more electronegative than the other, the electrons spend more time close to that atom than the other. This action results in dipoles, which are partial charges. The more electronegative atom obtains a partial negative charge, and the less electronegative atom obtains a partial positive charge. Dipoles create a polar molecule. If the atoms of a molecule have similar electronegativities, there is equal sharing of the electrons, no dipoles, and a non polar molecule. Chemical extraction is the process of chemically changing the polarity of one substance so that two substances can be separated. The two immiscible solutions are mixed together in a separatory funnel. When the solution settles, two layers form, one is polar (aqueous) and the other is non polar (organic). One of the layers can be drained off, separating the polar and non polar components. Volatile solids can be purified through sublimation. Sublimation is when a solid on a warm surface goes directly to the gaseous phase and reforms on a cold surface. The rate of the procedure is increased when pressure is reduced so that the molecules can escape the solid phase faster and travel farther before colliding with one another. This allows them to reach the cold surface more quickly. The warm surface is produced by the steam bath and the cold surface is produced by a cold finger. The pressure is reduced by putting a rubber stopper in a filter flask that is attached to a water trap that is attached
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OCHEM The Jones Reaction 8 - The Jones Reaction: Oxidation...

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