Making an ester: reflux, then distil template

A-level / AP / IB / Abitur: ethanoic acid, ethanol and conc. H₂SO₄ refluxed in a round-bottom flask with an open condenser, then the same flask fitted for distillation to collect ethyl ethanoate at 74–79 °C.

What the template shows

• Heat a carboxylic acid and an alcohol with an acid catalyst, then distil off the ester
• Water out
• 1. Reflux condenser
• Open at the top, never stoppered; reflux for 20–30 min
• Ethanoic acid, excess ethanol, a few drops of conc. H₂SO₄ and anti-bumping granules. CH₃COOH + C₂H₅OH ⇌ CH₃COOC₂H₅ + H₂O
• Mantle or water bath: no flames near ethanol and the ester
• Cool, refit the flask for distillation; collect at 74–79 °C (ethyl ethanoate boils at 77 °C)
• Crude ester
• Shake with Na₂CO₃ solution to remove acid (vent the CO₂), then CaCl₂ solution to remove ethanol; dry over anhydrous CaCl₂ and redistil. A test-tube version (warm, pour into Na₂CO₃ solution, smell) suits GCSE / CBSE
• Reaction setup

Drawn with 23 shapes – every one editable in MolDraw.

Sources

• Fischer & Speier, Ber. Dtsch. Chem. Ges. 1895, 28, 3252 Original paper
• Clayden, Greeves & Warren, Organic Chemistry, 2nd ed., OUP 2012, ch. 10 Textbook
• Furniss et al., Vogel's Textbook of Practical Organic Chemistry, 5th ed., Longman 1989 Textbook