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The focus of this scientific inquiry was the synthesis of isopentyl acetate, commonly known as banana oil, by employing Fischer Esterification. This chemical process involves the reaction between isopentyl alcohol and acetic acid under acidic conditions. The experiment's core involved refluxing the reaction mixture, followed by the extraction and distillation of the product. The synthesized isopentyl acetate's purity and identity were then verified through boiling point determination and spectroscopic analyses, namely proton nuclear magnetic resonance (^1H NMR) and Infrared (IR) spectroscopy.
The primary aim was to synthesize isopentyl acetate using isopentyl alcohol and acetic acid and to characterize the resultant ester through its physical and spectral properties.
The experiment was guided by the reaction where isopentyl alcohol reacts with acetic acid in the presence of sulfuric acid, producing isopentyl acetate and water as by-products.
The reaction mechanism involves several key steps, including the protonation of the carbonyl oxygen, nucleophilic attack by the alcohol on the carbonyl carbon, and subsequent dehydration to form the ester.
Adapting from the procedure outlined in the laboratory manual, adjustments were made for improved efficiency.
Notably, the use of a higher variac setting ensured optimal reflux conditions.
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The experimental setup also included multiple sodium bicarbonate washes to neutralize the reaction mixture effectively.
The experiment utilized reagents such as isopentyl alcohol, acetic acid, and sulfuric acid. Essential apparatus included boiling tubes, a conical flask, a thermometer, and a distillation setup.
| Isopentyl Alcohol | Acetic Acid | Isopentyl Acetate | Water | |
| Molecular Weight (g/mol) | 88.148 | 60.05 | 130.19 | 18.015 |
| Grams | 5.0 | 8.925 | *theoretical* 7.42 | *theoretical* 1.03 |
| Moles | 0.057 | 0.149 | 0.057 | 0.057 |
| mL | 6.173 | 8.5 | 8.47 | 1.033 |
| Density (g/mL)2 | 0.810 | 1.05 | 0.876 | 0.997 |
| Boiling Point (oC)2 | 132 | 117.9 | 142 | 100 |
| Melting Point (oC)2 | -117.2 | 16.6 | -78 | 0 |
| Solubility3 | Slightly Soluble in Water | Soluble in Water | Slightly Soluble in Water |
|
| Hazards3 | Flammable; Irritant | Flammable; Corrosive | Flammable; Irritant |
|
Throughout the reflux, a color change to brown was observed, intensifying as the reaction proceeded.
The extraction phase required diligent washing to achieve the desired pH, indicating the removal of acidic components. The drying phase, facilitated by anhydrous magnesium sulfate, indicated the moisture's effective removal as the solution cleared. Distillation yielded a colorless liquid with a characteristic banana scent, suggesting the successful synthesis of isopentyl acetate.
Table 1: 1H NMR Spectrum of Isolated Product (300.17 MHz, CDCl3)
| Compound | Protons, Hx | Chemical Shift, 𝛿 | Splitting | Integration Area (cm) | #Hs | J Value (Hz) |
| Isolated Product | Ha | 0.919 | Doublet | 9.8 | 6 | 6.6 |
| Hb | 1.511 | Quartet | 3.9 | 2 | 6.9 | |
| Hc | 1.672 | Multiplet | 2.1 | 1 | 6.9 | |
| Hd | 2.039 | Singlet | 4.6 | 3 |
|
|
| He | 4.085 | Triplet | 3.3 | 2 | 6.9 |
Table 2: IR Spectrum of Isolated Product (Neat)
| Compound | Bond Vibration | Frequency (cm-1) | Intensity |
| Isolated Product | C(sp3)-H stretch | 2959.4 | Strong |
| C(sp3)-H bend (CH3) | 1367.2 | Strong | |
| C(sp3)-H bend (CH2) | 1466.6 | Medium | |
| C=O ester stretch (non-conjugated) | 1742.4 | Strong | |
| (O=)C-O ester stretch | 1243.2 | Strong | |
| Carbonyl Overtone | 3463.7 | Weak |
Table 3: Properties and Yield Data for Isolated Isopentyl Acetate Product
| Theoretical Yield | Actual Yield | % Yield | Corrected Yield | Boiling Point Range | Literature Boiling Points | Appearanc e |
| 7.42 g | 3.594 g | 48.4% | 47.5% | 99-110 oC | 142 oC | Clear, colorless liquid with a pleasant smell |
The ^1H NMR spectrum displayed distinct signals corresponding to the protons in isopentyl acetate, with chemical shifts and splitting patterns aligning with theoretical expectations. This analysis confirmed the presence of isopentyl acetate, alongside minor impurities indicated by additional peaks.
The IR spectrum of isopentyl acetate showcased characteristic ester vibrations, including strong C=O stretching and C-O stretching bands, confirming the ester's formation.
The experiment underscored the efficacy of Fischer Esterification in synthesizing esters like isopentyl acetate. The boiling point and spectroscopic data corroborated the successful synthesis and high purity of the product. However, discrepancies in the boiling point from literature values suggested the presence of minor impurities, likely remnants of the starting materials or reaction intermediates.
Through Fischer Esterification, isopentyl acetate was successfully synthesized and characterized, demonstrating the practical application of colligative properties and spectroscopic techniques in organic synthesis. The experiment not only reinforced theoretical concepts but also highlighted the importance of meticulous procedure and analysis in achieving desired chemical transformations.
Synthesis and Analysis of Isopentyl Acetate via Fischer Esterification. (2024, Feb 26). Retrieved from https://studymoose.com/document/synthesis-and-analysis-of-isopentyl-acetate-via-fischer-esterification
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