ALDOL.

ORGANIC SYNTHESIS: ALDOL CONDENSATION REACTION

EXPERIMENTAL PROCEDURE

Ethanol is highly flammable and is toxic.

Aqueous sodium hydroxide is corrosive.

Aqueous acetic acid is corrosive and a lachrymator.

Your TA will assign you an unknown aldehyde (labeled as A-01 to A-08) and an unknown ketone
(labeled as K-01 to K-06). It is important that you are careful with the amounts of the aldehyde and ketone
that you use.
Record the code numbers of your aldehyde and ketone on your report sheet.
Using a 50 mL Erlenmeyer flask, dissolve 2.0 mL (if a liquid), or 2.25 g (if a solid) of your unknown
aldehyde in 20 mL of 95% ethanol. Slowly add 3 mL of 2M NaOH (aq.) and swirl the flask to mix. Add 0.5
mL of your unknown ketone and swirl the Erlenmeyer flask periodically for 20 minutes. The insoluble solid
product should form during this time. If the solution is only cloudy or very little precipitate has formed after
15 minutes, then heat the flask in a hot water or steam bath for 15 minutes. While you are waiting for
your product to form you should set up the filtration apparatus and prepare the solvents required
for the next step.
Cool the reaction in an ice-water bath, and collect the solid product by vacuum filtration, washing the
solid with about 10 mL of an ice-cold solution made up from 5mL of 5% acetic acid (aq.) and 5mL of 95%
ethanol. The acetic acid helps remove any remaining NaOH from the solid. Finally, wash with 5 mL of icecold ethanol and allow to dry in the vacuum funnel on the aspirator for a few minutes. Weigh your crude
product.
Determine the recrystallisation solvent by testing the solubility of a small sample (20-30mg) in 5-10
drops of the possible solvents (95% ethanol or toluene) in a small test tube (see recrystallisation
technique). Once you have determined your solvent, recrystallise approximately 50-100mg of crude solid
from a minimum volume of hot solvent (warm the solvent using a steam bath). If using toluene, you may
need to add a few drops of hexane to promote crystallisation. Collect the purified solid and allow it to dry in
the vacuum funnel on the aspirator for a few minutes.
Determine the melting point of the purified solid, and compare it to the melting points of possible
products for this experiment. Determine the identities of your starting aldehyde and ketone. Submit a
labeled sample of your product to your TA.

CLEAN UP

All organic solutions should be placed in the organic waste container.

All aqueous solutions should be placed in the aqueous waste container.

ALDOL.2

REFERENCES
1.

Mohrig, J.R.; Hammond, C.N.; Morrill, T.C.; Neckers, D.C. in Experimental Organic Chemistry,
W.H. Freeman: New York, 1997; pp 408-414.

2.

M. Jones and S. Fleming in "Organic Chemistry", Norton ,4th ed., 2010, Chapter 19, pp 932-946,
965-985
Organic Chemistry On-Line Learning Center Chapter 18;
http://www.chem.ucalgary.ca/courses/351/Carey5th/Ch18/ch18-0.html