INTRODUCTION Camphor is a trepenoid compound, meaning that it is derived from five-carbon isoprenes. Common uses of Camphor include insect repellent, fireworks and culinary purposes. In acetic acid, a secondary alcohol is converted to camphor following an oxidation reduction reaction. Sodium Borohydride is then used to give an isomeric alcohol, meaning that it has the same chemical formula as another molecule but has a different chemical structure. Since ketones can be easily reduced by metal hydrides such as LiALH4 and NaBH4, they are often used in reducing carbonyl groups. For this experiment sodium bromide is used as the reducing agent, which will reduce camphor to produce two products, namely borneol and isoborneol. For the reaction to …show more content…
Figure 2: Illustrates the NMR of the Isoborneol/Borneol. Area under curve represent ratio of % bornol vs % isoborneol
As shown in figure 2, the percentage of each isomeric alcohol in the mixture had been determined. The hydrogen atom on the carbon atom with the hydroxyl group appear at around 4.0 ppm for borneol and 3.6 ppm for isoborneol. The product ratio has been determined by integrating the peaks. A ratio of 6:1 for the Isoborneol/borneol ratio was expected and is validated by the calculations shown above, with isoborneol percentage at 83.82% and 16.17% of borneol. A CHCl3 group noted at around 7ppm and a CH2Cl2 at around 3.5ppm.
Figure 3: Represents the gas chromatography of the isomers Borneol/Isoborneol.
As shown in figure 3, the isoborneol accounted for roughly 35.51% of the compound with a peak at 12.515, while the borneol which peaks at 12.619 accounts for roughly 8.67% of the mixture
...icted α-methyl-2-naphthalenemethanol. Probably the most obvious clue that corresponded to this secondary alcohol was the seven integrated hydrogens within the aromatic region of 7.5-7.9 ppm. This compound was the only one that had seven hydrogens belonging to naphthalene. The other two secondary alcohols 3-methoxy-α-methylbenzyl alcohol and 4-bromo-α-methylbenzyl alcohol have only four aromatic hydrogens.
The goal of this experiment is to determine which products are formed from elimination reactions that occur in the dehydration of an alcohol under acidic and basic conditions. The process utilized is the acid-catalyzed dehydration of a secondary and primary alcohol, 1-butanol and 2-butanol, and the base-induced dehydrobromination of a secondary and primary bromide, 1-bromobutane and 2-bromobutane. The different products formed form each of these reactions will be analyzed using gas chromatography, which helps understand stereochemistry and regioselectivity of each product formed.
The actual amount of crude product was determined to be 3.11 grams. The percent yield of the crude product was determined to be 67.75 %. The actual amount of pure product formed was found to be 4.38 grams. The percent yield of the pure product was determined to be 95.42%. Regarding the thin layer chromatography, the line from the solvent front is 8 centimeters.
The product was made from 4-methylcyclohexanol. The chemical, 4-methylcyclohexanol is used in industrial settings. In 2014, West Virginia was exposed to this chemical in drinking water. Since this chemical is used to wash coal of its impurities, it was unsafe to drink the water as well as take a shower (CNN). Similarly, 4-methylcyclohexanol has a strong smell which may cause people to have symptoms like vomiting, skin irritation, and trouble breathing. Diesel is also replaced by 4-methylcyclohexanol (National Geographic).
2-ethyl-1,3-hexanediol. The molecular weight of this compound is 146.2g/mol. It is converted into 2-ethyl-1-hydroxyhexan-3-one. This compounds molecular weight is 144.2g/mol. This gives a theoretical yield of .63 grams. My actual yield was .42 grams. Therefore, my percent yield was 67%. This was one of my highest yields yet. I felt that this was a good yield because part of this experiment is an equilibrium reaction. Hypochlorite must be used in excess to push the reaction to the right. Also, there were better ways to do this experiment where higher yields could have been produced. For example PCC could have been used. However, because of its toxic properties, its use is restricted. The purpose of this experiment was to determine which of the 3 compounds was formed from the starting material. The third compound was the oxidation of both alcohols. This could not have been my product because of the results of my IR. I had a broad large absorption is the range of 3200 to 3500 wavenumbers. This indicates the presence of an alcohol. If my compound had been fully oxidized then there would be no such alcohol present. Also, because of my IR, I know that my compound was one of the other 2 compounds because of the strong sharp absorption at 1705 wavenumbers. This indicates the presence of a carbonyl. Also, my 2,4-DNP test was positive. Therefore I had to prove which of the two compounds my final product was. The first was the oxidation of the primary alcohol, forming an aldehyde and a secondary alcohol. This could not have been my product because the Tollen’s test. My test was negative indicating no such aldehyde. Also, the textbook states that aldehydes show 2 characteristic absorption’s in the range of 2720-2820 wavenumbers. No such absorption’s were present in my sample. Therefore my final product was the oxidation of the secondary alcohol. My final product had a primary alcohol and a secondary ketone
Once the mixture had been completely dissolved, the solution was transferred to a separatory funnel. The solution was then extracted twice using 5.0 mL of 1 M
It could have been lower than 100% because some product was lost during the recrystallization process, or due to an incorrect separation of the impurities when cooling the mixtures. The melting point data confirmed that the synthesized crystals were likely identical to the methoxybenzyl phenol ether because the mixed melting point was the same as the purified crystals. If the products were different or the synthesized product had to many impurities in it then the mixed melting point would have been lower than that of just the crystals, by themselves. The TLC made sense, after looking at the TLC plates under UV light and the calculation of the Rf values, it was confirmed that the 4- Methoxy-phenol was present in the unknown.
head group is attached to one of the glycerol hydroxyls with addition to the two hydrocarbon fatty
..., and is immiscible with water. Since there was not clear distinct two layers after steam distillation, extraction was used to separate the eugenol from water thus, steam distillation is not an effective way to isolate eugenol by itself. In order to determine how pure the isolated eugenol was, TLC was performed and compared to the standard and 1H NMR of the isolated eugenol and standard were compared to conclude that the extracted compound was eugenol with some impurities.
...bromebutane. Unfortunately, our group was only able to obtain the chromatograph for 2-bromobutane and the rest of the three chromatographs were provided by our T.A. Some possible reasons why the chromatographs for 2-butanol, 1-butanol, and 1-bromobutane were unable to be displayed properly is due to the malfunction of the syringes. If the syringe is not air-tight, the gaseous products can escape before being inserted into the injection port. In addition, the collection tube may have had a minor gas escape from the rubber septum, resulting in less concentrated gaseous products being inserted into the injection port. A possible solution is sealing the collection tube with parafilm. All in all, the provided data chromatographs and the rendered chromatograph by the 2-bromobutane in the lab session did match the expected results for the distribution of gaseous products.
Since 1-octanol was the least polar among 3 alcohols used in this part, so it was found to be insoluble in water but soluble in hexane. This was due to the longer chain of carbons makes compounds more hydrocarbon-like.
Based on the Rf values, the isolated samples can also be considered pure. The Rf value for the reference benzoic acid was calculated to be 0.33, and the value of the benzoic acid was 0.52, there is a difference in these two values, but this was due to smearing or streaking, but there are similarities in the spots. The Rf value for the reference benzocaine was calculated to be 0.31, and the Rf of the benzocaine was 0.29, which indicated very similar vales, which indicated that the isolated sample was indeed pure, and very similar to the reference compound.
Alcohol is an ethanol containing substance that is a common beverage in many social and private settings. Alcohol is also a teratogen, therefore alcohol co...
...heir chemical composition (Bevelacqua et al., 2011; Rodushkina and Magnusson, 2005; Ros et al., 2007; Tangahu et al., 2011).