An alcohol reacts with a carboxylic acid under an acid catalyst to form an ester and water (Fischer esterification). An ester is synthesized under reflux, the organic layer isolated with a separatory funnel, dried, and purified by simple distillation.

1. Plan your target ester (for example, ethyl acetate) and record reagents, expected boiling point, and hazards.
2. In a 50 mL round-bottom flask, add ~15 mL alcohol and ~10 mL carboxylic acid.
3. Slowly add ~1 mL concentrated sulfuric acid and a few boiling chips; swirl carefully.
4. Assemble a reflux apparatus with a water-cooled condenser; start coolant flow.
5. Heat gently (mantle or hot water/oil bath) to maintain steady reflux for ~30 minutes.
6. Allow the mixture to cool to room temperature.
7. Transfer the mixture to a separatory funnel containing ~20 mL water; stopper, invert, and vent frequently; shake and allow layers to separate.
8. Drain the lower (aqueous) layer; retain the upper organic layer (for many acetate esters, the ester is the less dense, upper layer).
9. Wash the organic layer with fresh water; separate and discard the aqueous layer.
10. Add ~5 mL aqueous sodium carbonate to the separatory funnel to neutralize residual acids; vent often (CO₂ gas forms). Repeat until gas evolution ceases; separate layers.
11. Wash the organic layer once more with water; separate and keep the organic layer.
12. Dry the organic layer over a small amount of anhydrous magnesium sulfate; swirl and stand ~15 minutes until the liquid is clear.
13. Decant or filter the dry solution into a clean, dry round-bottom flask; add boiling chips.
14. Set up a simple distillation. Heat gently and collect distillate at the constant temperature expected for your ester (for example, ethyl acetate ~77 °C).
15. Stop heating when the temperature rises above the product’s plateau; do not distill to dryness.
16. Record yield, appearance, and odor (use proper wafting technique only).

Flippin' Science- Topic 3.7 Ester Preparation Using Reflux and Distillation - MrWardScience:

📄 Synthesis, Isolation and Purification of Esters in a Direct Esterification Reaction Chemistry Tutorial - AUS-e-TUTE: https://www.ausetute.com.au/esters.html#google_vignette

• Use a slight excess of one reactant (often the acid) to improve yield; note effects on workup.
• Replace the acid with an acid anhydride (for example, acetic anhydride with ethanol) to drive the reaction irreversibly; adjust hazards accordingly.
• Microscale version: perform the synthesis in a small vial with a condenser air-cooled column and purify by microscale distillation.
• Compare different ester targets (methyl/ethyl/propyl/butyl acetates) and correlate boiling point with carbon chain length.

• Wear goggles, lab coat, and gloves; tie back hair and secure loose clothing.
• Alcohols are flammable—use a heating mantle or bath; keep all flames and sparks away.
• Carboxylic acids and concentrated sulfuric acid are corrosive—avoid skin/eye contact; add acid slowly.
• Reflux and distillation involve hot glassware and vapors—use clamps and heat-resistant gloves.
• When shaking a separatory funnel, point away from people and vent frequently to release pressure (especially after adding sodium carbonate).
• Do not inhale vapors; detect odors only by wafting.
• Collect organic waste and acidic/aqueous waste in labeled containers; dispose according to your instructor’s directions.

• Why is sulfuric acid used in this reaction? (It catalyzes ester formation and ties up water, shifting equilibrium toward products.)
• How does Le Chatelier’s principle inform your choice of using an excess reagent or removing water? (Shifting conditions to favor products increases yield.)
• During extraction, which layer contains the ester and why? (Often the ester is less dense and poorly soluble in water, so it forms the upper organic layer; check densities for your specific system.)
• What is the purpose of washing with sodium carbonate? (To neutralize residual acids, observed by CO₂ effervescence.)
• Why reflux rather than simply boil in an open flask? (Reflux allows heating at the solvent’s boiling point without loss of volatile reactants/products.)
• What does a constant distillation temperature indicate? (Collection of a relatively pure component.)
• How would using an acid anhydride change the equilibrium and yield? (The reaction becomes effectively irreversible, generally giving higher yields.)