Oxidation is a common practice in organic chemistry. By this means alcohols may be converted
to aldehydes, ketones, or acids, depending on the structure of the alcohol. Similarly, aldehydes
may be converted to acids. Oxygen is the one of the most common oxidizing agents. Strong
oxidizing agents for the organic laboratory include potassium permanganate (KMnO4),
potassium dichromate (K2Cr207), and chromic acid (CrO3).
In this experiment, 9-hydroxyfluorene is oxidized by chromic acid to yellow 9-fluorenone and
the experiment is written up for this case. However, other hydroxy compounds may also be used.
An alternative is benzoin, which is readily oxidized under identical conditions to give the yellow
benzil.
The chromic acid oxidizing agent has been incorporated into an ion exchange resin. The
compound to be oxidized is dissolved in toluene and then heated under reflux with the chromate
impregnated resin. The hydroxy compound diffuses into the resin where the oxidation takes
place and the product ketone diffuses out. The advantage of using a solid phase oxidizing agent
is the easy by which the product can be separated from the oxidizing agent. The separation is
accomplished simply by drawing off the solution from the resin using the micropipette. The
oxidation of 9-hydroxyfluorene is shown below:
Oxidation is a common practice in organic chemistry. By this means alcohols may be convertedto aldehydes, ketones, or acids, depending on the structure of the alcohol. Similarly, aldehydesmay be converted to acids. Oxygen is the one of the most common oxidizing agents. Strongoxidizing agents for the organic laboratory include potassium permanganate (KMnO4),potassium dichromate (K2Cr207), and chromic acid (CrO3).In this experiment, 9-hydroxyfluorene is oxidized by chromic acid to yellow 9-fluorenone andthe experiment is written up for this case. However, other hydroxy compounds may also be used.An alternative is benzoin, which is readily oxidized under identical conditions to give the yellowbenzil.The chromic acid oxidizing agent has been incorporated into an ion exchange resin. Thecompound to be oxidized is dissolved in toluene and then heated under reflux with the chromateimpregnated resin. The hydroxy compound diffuses into the resin where the oxidation takesplace and the product ketone diffuses out. The advantage of using a solid phase oxidizing agentis the easy by which the product can be separated from the oxidizing agent. The separation isaccomplished simply by drawing off the solution from the resin using the micropipette. Theoxidation of 9-hydroxyfluorene is shown below:
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