Fischer Esterification of Ethyl Acetate

Synthesizing an ester with a fruity aroma

Organic Synthesis Advanced (University) 90 min ~$20.00

Objective

Synthesize ethyl acetate (the aroma of nail polish remover) via Fischer esterification of acetic acid and ethanol, catalyzed by sulfuric acid.

Background

Fischer esterification is the acid-catalyzed condensation of a carboxylic acid with an alcohol to form an ester and water. The reaction is reversible, and excess alcohol is used to drive the equilibrium toward product formation. Ethyl acetate has a characteristic sweet, fruity smell and is widely used as an industrial solvent.

Safety Warnings

  • Concentrated sulfuric acid is extremely corrosive
  • Glacial acetic acid causes burns
  • Ethanol and ethyl acetate are flammable — no open flames
  • Work in a fume hood
  • Add sulfuric acid slowly to the mixture

Required PPE

goggles gloves lab_coat

Materials

  • Glacial acetic acid (10 mL)
    Corrosive
  • Ethanol (absolute) (15 mL)
    Excess to drive equilibrium
  • Sulfuric acid (H₂SO₄) (2 mL)
    Concentrated, catalyst
  • Sodium bicarbonate solution (50 mL)
    5% for washing
  • Anhydrous sodium sulfate (5 g)
    Drying agent

Equipment

Round-bottom flask (100 mL) Reflux condenser Heating mantle Separating funnel Boiling chips Thermometer

Procedure

1

Add 15 mL ethanol and 10 mL glacial acetic acid to the round-bottom flask with boiling chips.

3 min Handle acetic acid in fume hood
2

Slowly add 2 mL concentrated H₂SO₄ as catalyst. Swirl gently to mix.

3 min Add acid slowly — exothermic
3

Attach the reflux condenser and heat gently at reflux for 45 minutes.

45 min Ensure water is flowing through condenser
4

Cool the flask. Pour the contents into a separating funnel with 30 mL water.

5 min
5

Wash the organic layer with 25 mL of 5% NaHCO₃ to remove excess acid. Vent the funnel frequently.

5 min CO₂ gas released — vent carefully
6

Separate the organic layer (top) and dry over anhydrous Na₂SO₄ for 10 minutes.

12 min
7

Filter off the drying agent. Carefully smell the product by wafting — note the fruity aroma of ethyl acetate.

3 min Never sniff directly — waft vapors toward nose
8

Calculate the yield based on the volume collected and the theoretical yield.

5 min

Expected Results

A clear, colorless liquid with a sweet, fruity smell characteristic of ethyl acetate. Typical yield is 60-70% due to the equilibrium nature of the reaction.

Cleanup

Dispose of organic waste in the designated container. Neutralize acid waste before disposal. Rinse all glassware with acetone then water.

Details

Category
Organic Synthesis
Difficulty
Advanced (University)
Duration
90 min
Est. Cost
$20.00
Steps
8
Materials
5

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Frequently Asked Questions

What is the objective of Fischer Esterification of Ethyl Acetate?
Synthesize ethyl acetate (the aroma of nail polish remover) via Fischer esterification of acetic acid and ethanol, catalyzed by sulfuric acid.
How difficult is Fischer Esterification of Ethyl Acetate?
This experiment is rated as Advanced (University). It takes approximately 90 minutes to complete.
What safety precautions are needed for Fischer Esterification of Ethyl Acetate?
Key safety precautions include: Concentrated sulfuric acid is extremely corrosive; Glacial acetic acid causes burns; Ethanol and ethyl acetate are flammable — no open flames.
What materials are needed for Fischer Esterification of Ethyl Acetate?
The main materials required are: Glacial acetic acid, Ethanol (absolute), Sulfuric acid (H₂SO₄), Sodium bicarbonate solution, Anhydrous sodium sulfate.
What results should I expect from Fischer Esterification of Ethyl Acetate?
A clear, colorless liquid with a sweet, fruity smell characteristic of ethyl acetate. Typical yield is 60-70% due to the equilibrium nature of the reaction.