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Synthesis of Camphor - lab report
Organic Chemistry (CHEM 261)
University of Nebraska-Lincoln
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Kaung Nyi Partner(s): Olivia Thompson, Thara Lab TA: Jacob Jones Section: 001 Lab 12: Synthesis of Camphor 4/5/
Purpose The main objective of this lab is to synthesize camphor by oxidation of a secondary alcohol, which in this case is isoborneol. Afterwards, the purity of the newly formed product will be determined.
Theory Camphor can be found in numerous plants; it is extremely abundant in the wood of the camphor laurel tree which is found in Asia. Camphor is used in a variety of household items such as deodorants, wood finishes, and preservatives. In this experiment, camphor is synthesized by oxidation of isoborneol, which is a secondary alcohol. In order to achieve this, bleach containing sodium hypochlorite is used. Some amounts of acetic acid convert it into hypochlorous acid (HOCl), which acts as the oxidizing agent. Since the reaction is exothermic, it must be kept below 40 to prevent unwanted byproducts, such as camphoric acid. At the end of the reaction, °C any excess HOCl may be destroyed by sodium bisulfite, which acts as the reducing agent. Sublimation is the process of a solid changing directly to a gas, bypassing the liquid state. Due to its molecular structure, camphor can be easily purified through sublimation. While the process much quicker, it is unfortunately not as accurate as recrystallization chromatography.
Reaction
Isoborneol Camphor Percent Yield=
4 g 3 g x 100%= 124% yield Melting Point= 151-153°C
Percent of Isoborneol=
179 °C − 153 °C
40 °C
kg mol
x
1 kg camphor 1000 g camphor x
154 g isobroneol 1 mol isoborneol = 0 g 0 g isoborneol x 100% = 10% isoborneol, 89 % camphor
Methods/Procedures The experiment was followed verbatim from the lab manual on pages 99-101 with no exceptions. It is important to note that sodium hypochlorite and glacial acetic acid solution can irritate the skin, eyes, and respiratory tract, so avoid contact with both and avoid breathing in their vapors. The reaction may generate chlorine gas, which can irritate the eyes and respiratory tract so be cautious about standing directly over the reaction and breathing in any vapors produced by it.
Results After the experiment was performed, the actual yield of the product came out to be 4. grams, which is more than the theoretical yield of 3 grams. This could be due to the product not being dry enough when its mass was taken. In addition, it may contain slight impurities. The melting point range of the product was 151-153 , while the actual melting point of camphor is °C 179. Therefore, we know the product is not purely camphor. Assuming isoborneol is the only °C impurity within the synthesized product, its percent composition is calculated as 10%, meaning the product is 89% camphor.
Discussion/Conclusion Since the percent yield is above 100%, it cannot be a determining factor in determining the success of the experiment. Since the product has a melting point lower than camphor’s actual melting point, we can conclude there are impurities within the product. However, since the reaction was kept under 40 at all times, we can safely assume isoborneol is the only impurit°C y. When calculated, isoborneol makes up 10%, leaving the remainder of the product to be 89% camphor. Given the high percentage of camphor, we can conclude the reaction occurred properly with little error.
Exercises 2) The melting points of the two compounds should be different. More specifically, 179 and 212 for camphor and isoborneol, respectively. °C °C
3)
- The OH would be in an exo position.
Synthesis of Camphor - lab report
Course: Organic Chemistry (CHEM 261)
University: University of Nebraska-Lincoln
