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Aldol Condensation

Pre-Lab Assignment: Complete the pre-lab cover page and develop a procedure. Draw the mechanism
of acetone reacting with 2 equivalents of benzaldehyde. Use the arrow drawing convention to show all
bond making and bond breaking steps in the reaction.
Learning Goals:
Learn the mechanism of an self and crossed aldol condensations
Learn the technique of recrystallization as a method of purification
Introduction:
The aldol reaction is a carbonyl condensation reaction between two aldehydes or two ketones giving a
-hydroxy aldehyde or ketone, which under basic conditions dehydrates to give ,-unstaurated
compounds as shown below for acetophenone.

OH

EtOH
CH3

acetophenone

CH3

CH3

NaOH (cat)

C
Ph

Ph

C
H2

Ph

a -hydroxy ketone

Ph

C
H

Ph

an
-unsaturated compound
also called an enone

The mechanism of an aldol reaction followed by dehydration is shown below and in Section C of Chapter
16.

An aldol condensation reaction can take place between two of the same aldehydes or ketones (known as
self condensation) or between two unique aldehydes or ketones (known as crossed aldol condensations).
A crossed aldol condensation between acetophenone and pivalaldehyde is shown below. Notice that

acetophenone has only one alpha carbon (three acidic hydrogen atoms) whereas pivalaldehyde has no
protons on the alpha carbon and can only act as an electrophile in this crossed aldol.

In this lab, you will run a crossed aldol reaction using benzaldehyde and acetone. Because acetone has
two alpha carbons, it will condense with two molecules of benzaldehyde (one condensation per side),
depending on reaction conditions.

Recrytallization:
Recrystallization is a purification technique that works well for some compounds that are solids at room
temperature. The trick to recrystallization is finding a solvent (or solvent mixture) in which the product
you are attempting to purify has enhanced solubility when warm and diminished solubility when cold.
This allows you to dissolve your compound in warm solvent and upon cooling, your product slowly
crystallizes. Purification results because, at least in theory, the impurities remain in solution. When
collecting your recrystallized products using vacuum filtration, it is important to rinse the crystals with a
minimum amount of cold solvent, in this case cold ethanol, to remove any remaining contamination. You
must use a minimum of solvent so as not to dissolve too much of your product, which would result in
reduced yields.
Procedure:
Assemble an ice bath. Combine 12 mL of absolute ethanol with 5 mL of 10% aqueous NaOH solution in
a 50 mL Erlenmeyer flask equipped with a stir bar. Place this flask on the stir plate and engage the stir
motor. In a short disposable test tube, using a dispensing pipette, combine 500 L of benzaldehyde with
200 L of regent grade acetone. Using a pasture pipette, transfer the benzaldehyde/acetone mixture to the
Erlenmeyer flask containing the stirring solution of ethanol and aqueous sodium hydroxide solution at a
fast drop rate (this transfer should take about 1 minute). As the reaction progresses, a product will
precipitate out of the solution. If after 5 minutes you do not see product beginning to precipitate, turn the
hot plate control to its lowest setting for two to three minutes only. After 30 minutes place the
Erlenmeyer in the ice bath for an additional 10 minutes. Following this, collect your product by vacuum
filtration using a Hirsch funnel with a side-arm vacuum flask.
Remember to clamp your securely clamp your vacuum flask and to pre-wet your filter
paper with a small about of ethanol.

Wash the product with no more than 2 mL of ice cold ethanol. Allow the vacuum to pull across your
crude product for a few minutes in order to aid drying. Weigh your crude sample and calculate yield,
note the color of the crystals. Carefully transfer the crystals from the filter paper into a 50 mL
Erlenmeyer flask, reserving a tiny amount of your crude product in a labeled sample vial. Place this crude
sample vial in your drawer to completely dry. Collect a melting point when your crude crystals are
thoroughly dry. You will now recrystalize your remaining product in order to obtain a purified sample.
Recrystallization:
Add 3 mL of absolute ethanol to the 50 mL Erlenmeyer containing your crude crystals and a boiling stick
and carefully warm your solution on the hotplate at a low setting. Continue adding ethanol drop-wise to
the warm solution until all of the solid product dissolves. If you add too much ethanol, gently boil-off the
excess
Adding too much solvent will result in reduced yields.
When your product is in solution, remove the flask from the bath and allow it to cool to room
temperature. Do not rush this stage of crystallization. Watch your product carefully and make good
observations. Your product may begin to crystallize. After your product has come to room temperature,
place the flask into an ice bath for 4-5 minutes to complete crystallization. Isolate your product by
vacuum filtration using a Hirsch funnel using a minimum of ice cold ethanol to wash the crystals. Again,
allow the vacuum to pull across the crystals to aid drying. Transfer the purified product to a second
labeled sample vial and allow to dry overnight. Note the color of your crystals, calculate percent yield,
and determine a melting point. You will determine and compare both your crude and pure samples sideby-side.
Post-Lab:
Determine the percent yield for your reaction. This will require you to do limiting reactant calculations
for each of your reagents. Show your work in the calculations section of your lab report.
Answer the following questions separate from your conclusions.
1.
2.
3.
4.

Draw the structure of your product?


What information does the melting point give you about purity?
What a possible side products from this reaction (Draw at least 2)?
Why doesnt benzaldehyde undergo a self aldol condensation?