UNIVERSITI TEKNOLOGI MARA (UiTM) ORGANIC CHEMISTRY (CHM556/557)
(Online Assessment COVID19)
EXPERIMENT 4
THE ALDOL CONDENSATION REACTION:
PREPARATION OF BENZALACETOPHENONES
(CHALCONES)
DURATION
3 hours
Watch the video by the following link: https://www.youtube.com/watch?v=MF2baiM6zZQ
OBJECTIVES
1. To synthesize trans-3-nitrochalcone from aldol condensation reaction of
3-nitrobenzaldehyde with acetophenone in aqueous base.
2. To determine the melting point of trans-3-nitrochalcone.
3. To characterize trans-3-nitrochalcone using 1H NMR spectroscopy and/or IR spectroscopy.
INTRODUCTION
In this experiment, you will perform the aldol condensation reaction between a substituted
benzaldehyde and a ketone in the presence of base to produce an α,β-unsaturated ketone. You
will be assigned with 3-nitrobenzaldehyde as the substituted benzaldehyde for this experiment.
The chemical equation of the aldol condensation reaction of 3-nitrobenzaldehyde with
acetophenone in aqueous base is shown below:
O
O2N
H O H
NaOH C C
CH3 C H2O
H C
NO2 O
3-Nitrobenzaldehyde Acetophenone trans-3-Nitrochalcone
OCT-FEB 2021_COVID19
UNIVERSITI TEKNOLOGI MARA (UiTM) ORGANIC CHEMISTRY (CHM556/557)
(Online Assessment COVID19)
APPARATUS
Erlenmeyer flask (50 mL)
Beaker
Measuring cylinder (5 mL, 10 mL, 50 mL)
Bulb pipette (if any)
Glass pasteur pipette or plastic Pasteur pipette
Stainless steel spatula
Hirsch funnel
Hirsch flask
Rubber tubing
Rubber bung or rubber filter adapter
Bosshead for retort stand
Retort stand
Retort stand clamp
Filter paper
Glass rod
Aluminium foil
Conical flask (100 mL or 250 mL)
Thermometer
Sample bottle
Eppendorf tube
Hot plate
Aspirator vacuum pump
Oven
NMR Spectrometer
Melting point apparatus
CHEMICALS
3-Nitrobenzaldehyde
Acetophenone
95% Ethanol
Sodium hydroxide (NaOH) solution (6.0 g of NaOH in 10 mL of distilled water)
Ice
Methanol
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UNIVERSITI TEKNOLOGI MARA (UiTM) ORGANIC CHEMISTRY (CHM556/557)
(Online Assessment COVID19)
PROCEDURE
a. Preparation of crude product
1. Weigh 3-nitrobenzaldehyde (0.75 g) and place it into a 50 mL Erlenmeyer flask.
2. Add acetophenone (0.60 mL) and 95% ethanol (4.0 mL) to the flask containing
the 3-nitrobenzaldehyde.
3. Swirl the flask to mix the reagents and dissolve any solids. It may be necessary
to warm the mixture gently to dissolve the solids (heat the solution onto a hot
plate). The solution should be cooled to room temperature before proceeding to
the next step.
4. Add NaOH solution (0.5 mL) (prepared by the lab assistant using 6.0 g of NaOH
in 10 mL of water).
5. Stir the mixture with glass rod until it solidifies or until the entire mixture
becomes very cloudy.
6. Add ice water (10 mL) to the flask. If a solid is present at this point, break up
the solid mass by stirring with a spatula. Cooling and scratching with glass rod
is necessary to initiate crystallization.
7. Transfer the mixture to a beaker with ice water (15 mL).
8. Collect the solid by vacuum filtration on a Buchner funnel (refer Figure 3.1).
Wash the solid with cold water and allow it to air dry for 30 minutes.
9. Weigh the solid (crude product) and calculate the weight of solid. Determine
the percent yield of the solid (crude product).
b. Recrystallization of crude product
1. Recrystallize the solid (0.5 g) which was obtained from the above step from hot
methanol.
2. Measure 20 mL of methanol and place it into 50 mL beaker. Heat the methanol
on the hot plate until the temperature reach boiling point of methanol which is
64.5ºC. Transfer the hot methanol into the solid.
3. Cool the solution at room temperature and continue cooling in an ice bath.
Scratching with a glass rod is necessary to initiate crystallization.
4. Collect the solids/crystals by vacuum filtration. Wash the solids/crystals with a
small amount of cold methanol. Allow the solids/crystals to dry by sucking air
through them. Dry it in the oven
5. Weigh the dry pure product (solids/crystals) and determine the percent yield
of the pure product.
6. Measure the melting point of the pure product (literature melting point is 146ºC)
and obtain a 1H NMR and/or IR spectra of the pure product.
OCT-FEB 2021_COVID19
UNIVERSITI TEKNOLOGI MARA (UiTM) ORGANIC CHEMISTRY (CHM556/557)
(Online Assessment COVID19)
RESULTS AND OBSERVATIONS
Results:
a. Weight of crude product: 1.0500 g
b. Weight of purified product: 0.4000 g
c. Melting point of the purified product : _______________ ºC
d. Appearance of the purified product : _______________
1
e. H NMR data (in Table) of the purified product:
Chemical shift, δ (ppm) Multiplicity Number of Type of proton
hydrogens
and/or
Observations:
Write the observations such as colour changes, colour of the precipitate etc during the period
of experiment.
Steps Observations
Calculations:
a. Calculation of theoretical yield of product.
b. Percentage yield of the crude and purified products.
OCT-FEB 2021_COVID19
UNIVERSITI TEKNOLOGI MARA (UiTM) ORGANIC CHEMISTRY (CHM556/557)
(Online Assessment COVID19)
QUESTIONS
1. Draw the structure of the cis and trans isomers of the compound that you have prepared.
2. Using proton NMR, how could you experimentally determine that you have the trans
isomer rather than cis isomer? (Consider the use of coupling constants for the vinyl
hydrogen)
3. Draw the full mechanism for the aldol condensation of benzaldehyde and acetone (in
the presence of NaOH/H2O).
a. What type of elimination occur for an aldol condensation reaction?
b. What product must form before the elimination reaction can occur?
REFERENCE
Pavia, Lampman, Kriz and Engel, Introduction to Organic Laboratory Techniques 3rd Edition
(2011). page 669-673.
OCT-FEB 2021_COVID19
UNIVERSITI TEKNOLOGI MARA (UiTM) ORGANIC CHEMISTRY (CHM556/557)
(Online Assessment COVID19)
YOUR WRITTEN REPORT MUST HAVE:
Front Page:
Name :
Student No :
Group :
Experiment Title :
Date of Experiment :
Objective: (1M)
Introduction: (2M)
Summarize the experiment briefly, add mechanism here
Procedure in flowchart: (2M)
Calculation: (5M)
Discussion: (3M)
Summarize the spectrum briefly.
Conclusion:(1M)
Questions: (6M)
References:
OCT-FEB 2021_COVID19
UNIVERSITI TEKNOLOGI MARA (UiTM) ORGANIC CHEMISTRY (CHM556/557)
(Online Assessment COVID19)
Appendix 1:
1
H spectrum trans-3-nitrochalcone
IR spectrum trans-3-nitrochalcone
OCT-FEB 2021_COVID19
