Synthesis of Banana Flavor

The objective of this lab was to create a ketone through an oxidation reaction using a using a secondary alcohol and oxidizing agent in order to use that ketone in a reduction reaction with a specific reducing agent to determine the affect of that reducing agent on the diastereoselectivity of the product. In the first part of this experiment, 4-tert-butylcyclohexanol was reacted with NaOCl, an oxidizing agent, and acetic acid to form 4-tert-butylcyclohexanone. In the second part of this experiment, 4-tert-butylcyclohexanone was reacted with a reducing agent, either NaBH4 in EtOH or Al(OiPr)3 in iPrOH, to form the product 4-tert-butylcyclohexanol. 1H NMR spectroscopy was used to determine the cis:trans ratio of the OH relative to the tert-butyl group in the product formed from the reduction reaction with each reducing agent. Thin-layer chromatography was used in both the oxidation and reduction steps to ensure that each reaction ran to completion.

Salicylic acid was esterfied using acetic acid and sulfuric acid acting as a catalyst to produce acetylsalicylic acid and acetic acid. The phenol group that will attack the carbonyl carbon of the acetic anhydride is the –OH group that is directly attached to the benzene since it is more basic than the –OH group attached to the carbonyl group. This method of forming acetylsalicylic acid is an esterification reaction. Since this esterification reaction is not spontaneous, sulfuric acid was used as a catalyst to initiate the reaction. Sulfuric acid serves as the acid catalyst since its conjugate base is a strong deprotonating group that is necessary in order for this reaction to be reversible. The need for the strong conjugate base is the reason why other strong acids such as HCl is not used since its conjugate base Cl- is very weak compared to HSO3-. After the reaction was complete some unreacted acetic anhydride and salicylic acid was still be present in

Alcohol dehydrations are widely used in many industries to produce alkene. In this experiment 2-methylcyclohexanol was dehydrated to three possible products using phosphoric acid as a catalyst. The main tool for this experiment is the Hickman still. First, Drierite was added to the Hickman still so that any excess water formed during the experiment will be absorbed. It also acted as a boiling stone and addition surface to increase surface area. Next, 0.75 mL of 2-methylcyclohexanol is added to the still and right after 1 mL of phosphoric acid is added. The phosphoric acid (H3PO4) acts as a catalyst in order for the reaction to occur. The mixture is heated up to between 120o Celsius and 160o Celsius. If the temperature goes above 165oC then

Independent and controlled variables: The amount of sulfuric acid used for catalysis and the amount of salicylic acid and acetic anhydride.

This reaction is spontaneous for almost all esters but can be very slow under typical conditions of temperature and pressure. The reaction occurs at a much faster rate if there is a significant amount of base (OH-) in the solution. In this lab experiment, the rate of this reaction will be studied using an ester called para-nitrophenyl acetate (PNA), which produces an alcohol,

After 10 minutes the reaction liquid was separated from the solid using a vacuum filtration system and toluene. The product was stored and dried until week 2 of the experiment. The product was weighed to be 0.31 g. Percent yield was calculated to be 38.75%. IR spectra data was conducted for the two starting materials and of the product. Melting point determination was performed on the product and proton NMR spectrum was given. The IR spectrum revealed peaks at 1720 cm-1, which indicated the presence of a lactone group, and 1730 cm-1, representing a functional group of a carboxylic acid (C=O), and 3300cm-1, indicating the presence of an alcohol group (O-H). All three peaks correspond with the desired product. A second TLC using the same mobile and stationary phase as the first was performed and revealed Rf Values of 0.17 and 0.43for the product. The first value was unique to the product indicating that the Diels-Alder reaction was successful. The other Rf value of 0.43 matched that of maleic anhydride indicating some

The possible reasons for this discrepancy were discussed as the plausible mistakes committed in the procedure, such as allowing the solution to excessively cool, as well as the possibility of having used faulty or contaminated reagents and components. In general, in order to improve the results of future experiments, as well as to have potentially improved these results, a more diligent and strict manner of performing these experiments is necessary, as well as ensuring the purity and condition of any reagents used and to ensure that no objects such as glassware are compromised. Considering this information, the experiment must be considered a failure, although the purity of the small yield could be considered pure, the yield’s sheer lack of size is evidence of the fact that the reaction did not reach completion, whether it be because of a low temperature or a lack of purity in components. Therefore, it must be regretfully reported that the objective of the experiment was not

Objective: The objective of this experiment is to use acid-base extraction techniques to separate a mixture of organic compounds based on acidity and/or basicity. After the three compounds are separated we will recover them into their salt forms and then purify them by recrystallization and identify them by their melting points.

Results: No substantial qualitative data was collected, except that the original reaction mixture turned a purple color. Upon the addition of anise oil and heat, the reaction mixture turned a brown color. And with the addition of NaHSO3 the mixture turned a white color. The mass of the final product sample was measured to be 0.08g (see Calculation 1). The melting point range for this sample was 172.8-185.4ºC in Trial 1 and 171.6-185.2ºC in Trial 2 (see Table 1). The IR spectrum of anise oil can be found attached. Peaks appear to exist at 3022.86, 3002.41, 2957.58, 2933.88, 2912.63, 2834.94, and 2723.19 (cm-1). Another set of peaks appear to exist at 1608.06, 1510.55, 1464.73, 1441.16, 1306.3, 1283.06, 1247.18, 1174.78, 1036.26, 964.58, 839.29, and 787.03 (cm-1). No other significant quantitative results were collected.

The solution that was performed in this experiment was to use sulfuric acid in order to form a protonated alcohol, so when the halogen or nucleophile back attacks the compound, water is displaced. Once the alcohol is protonated, the solution reacts in either an SN1 or SN2 mechanism.

In this experiment, the main objective was to synthesize a ketone from borneol via an oxidation reaction and secondly, to produce a secondary alcohol from camphor via a reduction reaction. Therefore, the hypothesis of this lab is that camphor will be produced in the oxidation reaction and isoborneol will be the product of the reduction reaction because of steric hindrance. For the oxidation step, a reflux will be done and then a microscale reflux for the reduction step. The products will be confirmed using Infrared spectroscopy, the chromic acid test, 2,4-DNP test and 13C NMR spectroscopy. The results of this

The reaction took place in a conical vial and .2mL of each of the reactant samples were added to it along with some 95% ethanol. Two drops of NaOH were added shortly after and stirred at room temperature for fifteen minutes. The vial was cooled in and ice bath and crystallized. Vacuum filtration was performed to filter the crude product. The crude product was recrystallized using methanol and filtered again. We made one change to the procedure and instead of using .7mL of ethanol we

At room temperature (25°C), esterification reactions are relatively slow, therefore requiring the rate of the chemical reaction to be increased for the products to be formed efficiently. This is implemented, by using a catalyst, such as concentrated sulphuric acid (H2SO4 (aq)), as well as by heating the mixture: using a heating mantle. As a result, the energy of the reactants can be greater than the activation energy, increasing the rate of reaction. Hence, as the reactants are relatively volatile, so reflux apparatus such as a pear-shaped flask and a Liebig condenser were used, to minimise the amount of reactants lost, as well as allow the reaction to take place at the highest temperature possible. In addition, boiling chips were added prior to reflux, to prevent bumping and a decrease a loss of volatile reactants, during the reflux

Purpose: The purpose of the experiment was to perform the acid-catalyzed Fischer Esterification of acetic acid and isopentyl alcohol to form isopentyl acetate, or banana oil, which is used in flavor industries. The equilibrium of the reaction was changed by adding an excess amount of acetic acid. The reaction was refluxed and product was purified by extraction and distillation. Isopentyl acetate was analyzed by infrared spectroscopy and 1H NMR spectroscopy.

An ester was synthesized during an organic reaction and identified by IR spectroscopy and boiling point. Acetic acid was added to 4-methyl-2-pentanol, which was catalyzed by sulfuric acid. This produced the desired ester and water. After the ester was isolated a percent yield of 55.1% was calculated from the 0.872 g of ester recovered. This quantitative error was most likely due to product getting stuck in the apparatus. The boiling point of the ester was 143° C, only one degree off from the theoretical boiling point of the ester 1,3-dimethylbutyl, 144 ° C. The values of the