aMicroscale Synthesis of Isopentyl Acetate (Banana Oil)
Objective: Carried out the microscale synthesis of isopentyl acetate by direct esterification of acetic acid and isopentyl alcohol. This was an acid catalyzed Fischer esterification. Both extraction and distillation were employed to obtain a pure product. IR spectroscopy and gas chromatography were used to determine purity of the final product.
Reagents:
* Compound: | * MW (g/mol): | * MP (°C): | * BP (°C): | * Density (g/mL): | * Properties/ Safety: | * Isopentyl AlcoholC5H12O | * 88.15 | * -117.0 | * 132.0 | * 0.81 | * Clear, colorless liquid, disagreeable odor, flammable. Hazardous in case of skin, eye contact and ingestion and inhalation.
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Table 1: Figure 1 summary: IR spectrum isopentyl acetate: Peak (cm-1) | Corresponding Bond: | 2959.98 | C-H | 2872.89 | C-H | 1743.38 | C=O (Ester) | 1244.50 | C-O |
Gas Chromatography (GC) Results:
The GC resulted in one peak determined to be 100% isopentyl acetate based on comparing to the results of a known sample of isopentyl acetate which had a similar peak after a retention time of 1.5 minutes. Refer to figure 4 for results summarized below.
Table 2: Figure 4 GC Summary: Retention Time (min) | Area | % Composition | Identity | 1.525 | 1.7 x 107 | 100% | Isopentyl acetate |
NMR spectrum of typical isopentyl acetate sample is also shown in figure 3a.
Discussion:
This sulfuric acid catalyzed Fischer esterification reaction used excess acetic acid reacted with isopentyl alcohol to create isopentyl acetate. Because the reaction is reversible it was necessary to use excess acetic acid to drive the reaction forward and favor the formation of product in accordance with Le
Lab 8 Purpose Using sodium borohydride as the reducing agent, to convert a ketone (camphor) to a mixture of secondary alcohols (isoborneol or borneol). The product mixture will be characterized by melting point and functional group tests (TLC and IR spectrum). Pre Lab 1. Structure of Camphor NaBH4 used as reducing agent to produce isborneol from camphor Structure of isoborneol Isoborneol with wedged and dashed lines 2. Isoborneol can be produced by reduction of camphor by using the NaBH4 in Methanol.
The GC data for the product produced graph with a signal level out-of-range in peak. This gave a retention time 2.952 minutes. This would not indicate any of the possible ester products. However, after appropriate dilution, a retention time of 1.753 minutes was obtained. This retention time indicates that the ester product was ethyl benzoate.
The purpose of this experiment was to synthesize isopentyl acetate via an esterification reaction between acetic acid and isopentyl alcohol, using concentrated sulfuric acid as a catalyst. The product was washed with sodium hydrogen carbonate, as well as with water, then dried with anhydrous sodium sulfate. The product was then distilled using a Hickman still and characterized using infrared spectroscopy. The percent yield of isopentyl acetate was 61.52%. This may have been low due to not all of the condensed product being removed from the Hickman still, some product being lost during transfer of the product from the reaction tube into the Hickman still, or the loss of some product due to evaporation during distillation.
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
Ethyl ethanoate is made from ethanol and ethanoic acid. In the reaction sulphuric acid is added as a catalyst.
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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
The products of interest within this experiment are 2-methyl-1-butene and 2-methyl-2-butene from sulfuric acid and phosphoric acid catalyzed dehydration of 2-methyl-2-butanol. The reaction mixture was then separated into its separate alkene components by steam distillation and then analyzed by gas chromatography (GC), Infrared Radiation (IR) spectroscopy, and Nuclear Magnetic Resonance (NMR) imaging. Gas chromatography is an analytical technique that is able to characterize if specific compounds exist in a reaction mixture, even if they are in low quantities, assess how much of a compound exists within a reaction mixture relative to other components within the sample, and determine the purity of an isolated product. In the case of this experiment, gas chromatography is used to analyze how pure the alkene reaction sample was and if any remnants of impurities or 2-methyl-2-butanol remained in the sample after isolation of alkene components.
The purpose of this lab was to synthesize the ester isopentyl acetate via an acid catalyzed esterification (Fischer Esterification) of acetic acid with isopentyl alcohol. Emil Fischer and Arthur Speier were the pioneers of this reaction referred to as Fischer Esterification. The reaction is characterized by the combining of an alcohol and an acid (with an acid catalyst) to yield and ester plus water. In order to accomplish the reaction, the reactants were
The filter paper, holding the aspirin crystals, was removed from the funnel and was left to dry before being weighed. Once the aspirin crystals were weighed, the theoretical yield and the percent yield of the experiment were calculated. The procedure was repeated once more using the same steps.
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
The purpose of this experiment is to prepare isopentyl acetate by direct esterification of acetic acid with isopentyl alcohol. After refluxing there is an isolation procedure where excess acetic acid and remaining isopentyl alcohol are easily removed by extraction with sodium bicarbonate and water. The ester is then purified by simple distillation and the IR is then obtained.
In this experiment, a Fischer Esterification reaction was performed with two unknown compounds. The unknown compounds, Acid 2 and Alcohol D, were identified by using the knowledge of the reaction that took place, and the identity of the product that was synthesized. The identification of the product resulted from analysis of IR and NMR spectra.
A good yield of isopentyl acetate was obtained during this experiment. Loss of the product was likely through transferring liquid from separatory funnel to the Erlenmeyer flask and residual material left in the distillation flask. Using an organic solvent like benzene or cyclohexane as a transfer agent would improve the yield, since their boiling points were around 80 oC and could be easily separated from the final product through simple distillation. However this
The objective of this lab was to synthesize an unknown ester using Fischer etherification, which involved using a carboxylic acid and an unknown alcohol as the reactants, and sulfuric acid as a catalyst. First, a reaction mixture was created using the reactants. Then the reaction product was isolated by removing the aqueous layer. After isolation, the crude ester product was purified using distillation. The final product was a clear liquid with a banana like odor. It was established that the banana like odor was coming from banana oil that is either pure isoamyl acetate or amyl (pentyl acetate). To identify the unknown ester IR, 13C NMR, and 1H NMR was obtained. IR spectroscopy, which showed prominent, peaks at 1737.54 cm-1, 1366.50 cm-1, 1228.27