Camphor Reduction Reaction Lab Report

The experiment yielded a mass of 0.32g of dibromostilbene thus a difference of 0.6g from the theoretical resulting in an 85% yield. A result in less than 100% yield may be due to the solvent used during the filtration process. The solvent could have dissolved some product and thus resulted in the loss of product during filtration.

Before the start of this experiment, the theoretical yield was calculated. Based off the data, it was found that the limiting reagent is 3-nitrobenzaldehyde. The theoretical yield is determined by relating the moles of the limiting reagent to the moles of the anticipated product by a ratio obtained from the overall equation. The theoretical yield was calculated to be 1.3 g. However, the actual yield obtained was greater than the theoretical yield; in other words, the actual mass of the product was higher than the theoretical mass. This led to an abnormally high yield of 320% and an impure product.

6. Purpose: to clarify the mechanism for the cycloaddition reaction between benzonitrile oxide and an alkene, and to test the regiochemistry of the reaction between benzonitrile oxide and styrene; to purify the crude product of either trans-stilbene, cis-stilbene, or styrene reaction.

A & C: MEASURING THE OPTICAL ROTATION OF CAMPHOR SAMPLES AND CAMPHOR OBTAINED FROM OXIDATION OF ISOBORNEOL

The reaction created in the lab was a condensation reaction, specifically a fischer esterification reaction. This reaction is created by combination of a carboxylic acid and alcohol group with loss of water. A very noticible property of ester products are the oders they produce, which is usually described as fruity. For example, propyl methanoate is described as smelling like apples. Butyl heptanoate has a distinct sent of coconut. Also pentyl ethanoate has a banana scent when created. Lastly propyl butanoate is described as smelling like pears.

The crude product was identified as 3,3,5 trimethylcyclohexanol based on an analysis of the 1H NMR and IR spectra (Figure 1 and Figure 4). In the IR spectra, a distinct broad OH peak (3356 cm-1) indicates the presence of an alcohol. The peaks of C-H (2952 cm-1), and C-O (1706 cm-1) was hard to identify the crude product due to it being in the fingerprinting region. Using the integration values of 1.11 and 3.27 from the crude product’s 1H NMR spectra, the diastereomeric mixture was identified as a 1:3 ratio of cis-3,3,5-trimethylcyclohexanol to trans-3,3,5-trimethylcyclohexanol. The TLC results from the flash chromatography of the product fractions (fraction 4-6, Fraction 11-13) showed two distinct products based on the differing Rf values of 0.66 and 0.50, supporting the claim that the product exists as a diastereomeric mixture (Figure 5).The fraction set of 4,5, and 6 were identified as trans-3,3,5-trimethylcyclohexanol while fraction set 11, 12, and 13 were identified as cis-3,3,5-trimethylcyclohexanol by 1H NMR spectra (Figure 2-3).

This is due to the fact that the hydride more readily “attacks” from the axial direction, making the equatorial alcohol the major product, hence trans-4-tert-butylcyclohexanone. Sodium borohydride is not a sterically hindered reducing agent and can attack the 4-tert-butylcylohexanone from the top. Overall, this gives the more energetically stable

In the chemistry world, there are thousands of known chemical reactions that either occur in living systems, in industrial processes, or in chemical laboratories. Few of the types of reactions include Combustion, Synthesis, Decomposition, Precipitation, Single-Replacement, Double-Replacement, Acid/Base, and Redox. It is useful to be familiar with the different types of reactions, because it allows one to know what they are dealing with in a reaction, as well as being able to predict what might happen in additional chemical processes. The first basic type of reaction is Combustion.

The total percent yield for this experiment was 6.98 %( figure 1). The yield for the ortho isomer was 4.75 %, and 2.23 % for the para isomer. The total percent yield was very low because some errors may have been coming from isolation of product. Also, it could have been from the column chromatography when we took each fractions of the

To begin the reaction, 1.008g of Maleic anhydride was added to a 25ml Erlenmeyer flask. Next, roughly 4.0mL of Ethyl acetate was added to flask. The flask containing Maleic anhydride and Ethyl acetate was shaken to dissolve solid. Then, 4.0mL of Petroleum ether was poured into the into the same flask. Finally, 1.0mL of Cyclopentadiene was carefully added to the other substances. Following the addition of Cyclopentadiene produced an immediate but short-lived boiling, along with the release of heat for a brief period. A white solid began to form, signaling that recrystallization was underway, and the flask was left to cool to room temperature to continue this process. A Cloudy white liquid with sediment appeared to form after about 15 minutes.

The objective of this experiment is to synthesize triphenylmethanol using a Grignard reagent. A Grignard reagent is a carbon-magnesium halide, where the carbon acts as a nucleophile. As shown in Mechanism 1, it is formed by reacting an alkyl halide, in this case a bromide (bromobenzene), with magnesium metal in anhydrous ether. During the preparation of the Grignard reaction, another by-product, biphenyl, will be formed; this is caused from the rapid addition of bromobenzene to the Grignard reagent solution. However, the by-product will later be removed with petroleum ether. It is also important to have no traces of water as the Grignard reagent is very reactive with water. A reaction between the Grignard reagent and water will result in an

DMSO (5 mL) was added to (10mL) round bottom flask with the product. Kt-butoxide (10% molar excess, 12.79mmol) was added via powder funnel. The mixture was heated and distilled. In a large test tube, distillate was mixed with ether (5mL). Distilled water (3x5mL) was used to wash ether layer. The organic layer was dried with anhydrous MgSO4 and filtered. The product was evaporated to 50% in 50oC water bath. GC was taken and product further reduced by 50% to obtain NMR.

A stock solution of β-naphtol (ArOH) was prepared by dissolving the solid sample in 25.0 mL of methanol (MeOH). Further, 20.0 mL solution of HCl and NaOH were prepared by diluting the samples to 0.02 M. Once the stock solutions have been made, 12 samples with varying pH values were prepared for the experiment with each vial having a total volume of 11.0 mL. Each vial contains the sample amount of ArOH, which was 1.00 mL. In addition, the first and last vials were a mixture of HCl/ArOH and NaOH/ArOH, respectively. This arranges the environment of the ArOH to be in both low and high pH conditions. Meanwhile, the remaining 10 samples are prepared by adding different ratios of the magic buffer A and B, which is similar to the previous experiment.

For part A of the procedure we worked with the solubility of solid compounds in various solvents. The three solid compounds that were worked with during this procedure were benzophenone, malonic acid, and biphenyl. These three solids were then mixed with water (highly polar), methyl alcohol (intermediately polar), and hexanes (nonpolar). When benzophenone is mixed with water the results turned out to be insoluble because benzophenone is a pure hydrocarbon, which are very insoluble in water. When benzophenone was mixed with methyl alcohol, it was soluble because Methanol can hydrogen bond to the carbonyl oxygen of benzophenone. When

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