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Home Page Life Alcohol Hypochlorite Oxidation of endo-Borneol to Camphor Essay Example
Hypochlorite Oxidation of endo-Borneol to Camphor Essay Example
Hypochlorite Oxidation of endo-Borneol to Camphor Essay Example

Hypochlorite Oxidation of endo-Borneol to Camphor Essay Example

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Topics:
Alcohol, Chemical Reaction, Chlorine, Organic Chemistry
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It is believed that the positively charged chlorine (Cl+) originated from the heterolytic bond cleavage of chlorine during the first step of the hypochlorite oxidation reaction mechanism, which converted endo-borneol to camphor. The initial step involved the replacement of a hydroxyl proton with positively charged chlorine, followed by an E2 elimination of HCI from alkyl hypochlorite to form ketone. Although Cl+ was added to the alcohol during the first step, it was lost in the subsequent step, resulting in a net decrease in two electrons and oxidization of endo-borneol that donated these electrons. To ensure complete reaction, starch-iodide test paper was used periodically to confirm an excess of hypochlorite oxidizing agent. However, the experiment yielded unsatisfactory results due to low product yield (24.5%) that resulted from incomplete conversation of endo-borneol to camphor and significant ma

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terial loss during crystal transfer.

When swirling endo-borneol in acetic acid, it was noticed that some crystals adhered to the flask wall and were not oxidized by hypochlorite. To minimize crystal loss during transfer, careful handling was recommended. However, complete prevention of loss was impossible. The melting point of the product was significantly lower than expected, indicating impurities were present. Analysis of the infrared spectrum revealed a hydroxyl stretching libration at 3500cm-1, indicating the presence of unreacted alcohol. The presence of unreacted alcohol was supported by the persistent peak at 800 :m-l, as it should not have been present in a pure ketone product.The sample contained a significant amount of the desired product, camphor, indicated by a strong peak around 1750 cm-l between 1600 cm-l -1800 cm-l, confirming the presence of a carbonyl group. To enhance the experiment, one can prolon

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the oxidation reaction time to ensure complete reaction and carry out the sublimation experiment on a larger scale with careful control. One could examine the intensity of the peak at a specific absorption frequency characteristic of endo-borneol but absent in camphor to determine the amount of endo-borneol present in a camphor sample. The stepwise reaction mechanism for hypochlorite oxidation of endo-borneol to camphor is also an answer to the questions.

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