2nd Experiment:

Aldol Condensation
1. Title: Aldol condensation

2. Purpose: To understand about aldol condensation reaction.

3. Scheme

4. Theory
① Introduction about aldol condensation
② Aldol condensation mechanism and product
③ Dehydration – acid/base condition
④ α, β - Unsaturated carbonyl compound

5. Reagents & apparatus

- Reagents: Benzaldehyde, Acetone, NaOH, EA, Ethanol, H2O
- Apparatus: 50ml Round bottom flask (RBF), Pasteur pipet, Beaker, Magnetic stirring bar, Stirrer,
Oil bath, Thermometer, TLC plate, Capillary, Rubber stopper, Büchner funnel, Büchner flask, Reflux
condenser, Petri dish

6. procedure

1. Clamp the 250 mL two-neck round-bottom flask and add 35 mL of deionized water to the
flask. Insert the magnetic stirring bar and transfer 3.2 g of sodium hydroxide to the flask. Stir
vigorously.

2. Once the dissolution is complete, add 30 mL of ethanol (EtOH). Let the flask cool down to
room temperature (around 25 °C) using an ice bath.

3. Assemble the reflux condenser on the main neck of the round-bottom flask.

4. Prepare a solution by mixing 7.6 mL (7.9 g) of benzaldehyde and 2.8 mL (2.2 g) of acetone in
a 50 mL Erlenmeyer flask.

5. Once the mixture is homogenous, gently transfer half of the mixture to the round-bottom
flask. After a few minutes, a yellow blurring appears followed by a yellow puffy precipitate.

6. After 15 minutes of stirring, add the second half of the benzaldehyde-acetone mixture
dropwise.

7. Keep the reaction medium under stirring for 15 minutes.

8. Collect the product by filtration using a Büchner funnel and wash the yellow solid three times
with 50 mL of deionized water. Let the solid dry for 5 minutes.

9. Recrystallize the crude product in ethyl acetate (20-25 mL are needed) in the 100 mL
Erlenmeyer flask.
10. Collect the recrystallized product by filtration. Let the product dry on the Büchner funnel for
5 minutes.

11. Weigh a Petri dish and record the value. Transfer the recrystallized product to the Petri dish
and let it dry in a laboratory oven (80 °C).

12. Weigh the dried product and calculate the yield.

13. Perform a thin layer chromatography using the recrystallized product report the Rf values. The
eluent is a hexane/ethyl acetate mixture (4:1).