Experiment 3: Synthesis of Isopentyl Acetate (Fischer
Esterification)
Sahithi itha
2410110285
Aim
To synthesize isopentyl acetate from isopentyl alcohol and acetic acid via acid-catalyzed
esterification and characterize the product using TLC and IR spectroscopy.
Principle
Isopentyl acetate is prepared by Fischer esterification, where a carboxylic acid reacts with an
alcohol in the presence of a strong acid catalyst to form an ester and water.
Concentrated sulfuric acid acts as a catalyst and dehydrating agent, driving the equilibrium
toward ester formation. Isopentyl acetate is known for its characteristic banana-like odor.
Chemicals Used
Isopentyl alcohol (15 mL, 0.138 mol)
Glacial acetic acid (20 mL, 0.35 mol)
Concentrated H₂SO₄ (4 mL)
5% NaHCO₃ solution
Distilled water
Saturated NaCl solution
Anhydrous MgSO₄
Apparatus
Round-bottom flask, reflux condenser, heating mantle, separatory funnel, distillation setup,
thermometer, Erlenmeyer flask.
Procedure
15 mL of isopentyl alcohol and 20 mL of glacial acetic acid were added to a 100 mL round-
bottom flask. 4 mL of concentrated sulfuric acid was carefully added with swirling. The
mixture was refluxed for 1 hour.
After cooling, the reaction mixture was transferred to a separatory funnel and washed with
cold water. The aqueous layer was separated. The organic layer was washed twice with 5%
sodium bicarbonate solution until basic to litmus (effervescence observed due to CO₂
evolution). It was then washed with water followed by saturated sodium chloride solution.
The organic layer was dried over anhydrous magnesium sulfate, decanted into a dry
distillation flask, and distilled. The fraction boiling between 134–143 °C was collected.
Observations
Fruity banana-like odor observed.
Two layers formed during extraction (organic layer on top).
Effervescence during NaHCO₃ wash.
Distillation range: 134–143 °C.
Clear, colorless liquid obtained.
Thin Layer Chromatography (TLC) Analysis
Solvent front distance = 3.0 cm
Distances travelled by spots:
Spot 1 = 0.4 cm
Spot 2 = 2.8 cm
Rf Calculations
Distance travelled by compound
Distance travelled by solvent front
Rf=
Distance travelled by solvent front
Distance travelled by compound
Rf₁ = 0.4 / 3.0 = 0.13
Rf₂ = 2.8 / 3.0 = 0.93
Interpretation
The spot with Rf = 0.13 corresponds to the starting alcohol, which is more polar and interacts
strongly with silica.
The spot with Rf = 0.93 corresponds to the ester product, which is less polar and travelled
further up the plate.
The clear separation between the two spots indicates successful conversion and good product
purity.
IR Spectral Analysis
The IR spectrum of the product showed the following key absorptions:
Strong sharp peak at ~1740 cm⁻¹ → Characteristic ester carbonyl (C=O) stretch
Strong peaks in the region 1050–1250 cm⁻¹ → C–O stretching of ester
C–H stretching peaks at ~2850–2960 cm⁻¹ → Alkyl C–H bonds
Absence of broad O–H stretch (3200–3600 cm⁻¹) → Indicates disappearance of alcohol O–H
group
The presence of a strong ester carbonyl peak and absence of the broad alcohol O–H peak
confirms successful ester formation.
Result and Discussion
Isopentyl acetate was successfully synthesized by acid-catalyzed esterification. The boiling
point range (134–143 °C) aligns with expected values for the ester. TLC analysis showed a
significant change in Rf values from starting material (0.13) to product (0.93), confirming
reduced polarity and successful conversion.
The IR spectrum further confirmed product formation through the presence of a strong ester
carbonyl stretch (~1740 cm⁻¹) and absence of the alcohol O–H band.
Conclusion
Isopentyl acetate was successfully prepared via Fischer esterification. TLC and IR analysis
confirmed the formation and purity of the ester product. The experiment demonstrates
equilibrium-driven ester synthesis and purification through extraction and distillation.