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The ketyl radicals derived from the reaction of sodium and benzophenone is a common laboratory desiccant.Ketyls react quickly with water, peroxides, and with oxygen. Thus, the deep purple coloration qualitatively indicates dry, peroxide-free, and oxygen-free conditions.
Benzophenone is a naturally occurring organic compound with the formula (C 6 H 5) 2 CO, generally abbreviated Ph 2 CO. Benzophenone has been found in some fungi, fruits and plants, including grapes. [4] It is a white solid with a low melting point and rose-like odor [5] that is soluble in organic solvents. Benzophenone is the simplest ...
The first step in the reaction mechanism is a one-electron reduction of the carbonyl group by a reducing agent —such as magnesium— to a ketyl radical anion species. Two ketyl groups react in a coupling reaction yielding a vicinal diol with both hydroxyl groups deprotonated. Addition of water or another proton donor gives the diol.
Benzophenone is often used to generate such a soluble drying agent. An advantage to this application is the intense blue color of the ketyl radical anion. Thus, sodium/benzophenone can be used as an indicator of air-free and moisture-free conditions in the purification of solvents by distillation. [6] [7]
The ketyl radical from sodium and benzophenone can also be used for removing both oxygen and water from inert solvents such as hydrocarbons and ethers; the degassed solvent can be separated by distillation. The latter method is particularly useful because a high concentration of ketyl radical generates a deep blue colour, indicating the solvent ...
Toluene is heated under reflux with sodium and benzophenone to produce dry, oxygen-free toluene. The toluene is dry and oxygen free when the intense blue coloration from the benzophenone ketyl radical is observed.
In 1976, he reported the first example of a comparatively rare phenomenon: electronic energy transfer, mediated by electron exchange, from a triplet donor to a double acceptor; in his experiments, the donor was the benzophenone triplet and the acceptor was the benzophenone ketyl radical.
Many ketones contain the benzoyl group. They have the formula C 6 H 5 CO–R, an important example being benzophenone. Benzoyl esters and amides are common in organic chemistry. The esters are used as a protecting groups in organic synthesis, [4] which can be easily removed by hydrolysis in dilute basic solution.