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Mixed Aldol Condensation of Benzaldehyde and Acetone

Purpose

In this experiment, the compound dibenzylideneacetone (dba) was synthesized by


performing an aldol condensation of benzaldehyde and acetone. The purity of the
product was determined by measuring the melting points as well as performing
NMR and IR spectroscopy.

Results
1. Calculate both your crude and purified yields.
The initial amount of reagents used was 5.1 mL of benzaldehyde and 1.8 mL
of acetone. The density of benzaldehyde is 1.044 g/mL which means that 5.1
mL of benzaldehyde equals 5.3 grams. The molar mass of benzaldehyde is
106.12 g/mol. By dividing the grams of benzaldehyde by the molar mass, the
moles of benzaldehyde used as a reactant is calculated as 0.050 moles. The
density of acetone is 0.791 g/mL which means that 1.8 mL of acetone is
equal to 1.4 grams. The molar mass of acetone is 58.08. Dividing 1.4 grams
by the molar mass results in 0.024 moles. The ratio of consumption of
benzaldehyde to acetone is two to one, thus assuming all of the reactants are
consumed, acetone is the limiting reagent, and the number of moles of
product would be 0.024 moles of dba. The molar mass of dba is 234.29 g/mol.
Therefore, the mass of the product, assuming 100% yield, is 5.6 grams. The
crude mass of the product was 1.60 grams. Dividing this by the theoretical

yield

1.60 grams
=0.29
5.6 grams

results in a percent yield of 29%. The purified mass

of the product was 0.69 grams. Dividing this by the theoretical yield

0.69 grams
=0.12
5.6 grams

results in a percent yield of 12%.

2. Identify the major stretched in your IR spectrum and correlate them


to the functional groups in your product
There are two obvious peaks that are separate from the others. One at 3052
cm-1 and one at 3026 cm-1. These two are very close together so it is difficult
to confirm which peak represents which bond, but it is most likely that the
3052 cm-1 peak represents the carbon-hydrogen bonds on the benzene ring,
and the 3026 cm-1 peak represents the carbon-hydrogen bonds in the
alkenes. This is because in general alkene hydrogens characteristically fall at
around 3030 cm-1 a little lower than the aromatic hydrogens. The plethora of
peaks from 1600 to 500 cm-1 represent the various alkane hydrogen bonds,
carbon-carbon bonds or possible impurities in the product. The highest of
those peaks at 1647 cm-1 is characteristic of the carbon-oxygen bond of the
ketone.
3. Attach your H NMR spectrum of the product and assign all peaks.
The first peak, the doublet at around 7.0 ppm, is the alpha hydrogen of the
ketone. It is a doublet because it is adjacent to only one hydrogen on the
double bonded carbon. The hydrogen is very well shielded so it should shift
the least. The next peak at 7.4 ppm is a multiplet. There is no distinct
structure among the peaks meaning that it likely represents the hydrogens in
the benzene ring. In this case, this peak represents the three hydrogens that
are not adjacent to the junction between the aromatic ring and the rest of the
compound (the hydrogens in the ortho and meta positions). These hydrogens

are not as strongly shielded as the alpha hydrogens and so they would drift a
bit farther away. The next peak lies at about 7.6 ppm. These are the four
remaining hydrogens on the benzene rings. These hydrogens only have one
adjacent hydrogen, but the benzene ring messes with the NMR reading and
creates a multiplet. However, these hydrogens are not as well shielded as the
ortho and meta hydrogens and so they drift a bit farther from the other
hydrogens. The last peak in this range is at about 7.8 ppm This peak
represents the remaining two hydrogens on the alkene that arent the
adjacent to the carbonyl. These hydrogens drift the farthest because of its
interactions with the carbonyl. The peaks lower than this range probably
represent the hydrogens of the ethanol used for recrystallization with the OH
bond being a farther one out.
Discussion
1.

Draw the mechanism for the aldol reaction performed in this


experiment.

The same mechanism is then repeated for the other side of the ketone.
2. This experiment uses a base to catalyze the aldol reaction, but this
can be performed under acid catalyzed conditions as well. Draw the
mechanism for an acid catalyzed aldol condensation between
acetone and benzaldehyde.

The mechanism repeats for the other side of the ketone.

3. One side product of this reaction is the following alcohol. How is it


formed?
After the aldol addition occurs, a dehydration must also occur so that the
hydroxyl group is removed. However, the dehydration process will be
imperfect and so not all of the reaction will form the desired product. If a
dehydration is not performed successfully, then the alcohol will remain and
will be unable to be removed. This usually occurs during the second addition.

4.

Dra
w all the possible products from an aldol reaction between 2-butanone and
propanal.

5. How would you change the procedure in this experiment if you wished to
synthesize benzalacetone? How would the procedures change if you were
synthesizing benzalacetophenone?
In order to achieve only one substitution, an excess of acetone can be
reacted with the benzaldehyde in order to ensure that only one substitution
occurs. In addition, it is also important to keep the acetone in its enolate form
so some LDA should be added as well. The benzaldehyde should be slowly
added to the acetone so that it is less likely that the benzaldehyde will attach
a benzalacetone. Once the reaction is complete, the remaining acetone can

be evaporated as its boiling point is much higher than acetones. (260 oC for
benzalacetone, and 56oC for acetone)
In order to synthesize benzalacetophenone, a different reactant is needed
other than acetone. Acetophenone should be used as the ketone. An addition
of benzaldehyde to acetophenone in equal molar proportion should result in
benzalacetophenone. A second addition is impossible because it lacks the
alpha hydrogens necessary for a second addition.

References
Kim S, Thiessen PA, Bolton EE, Chen J, Fu G, Gindulyte A, Han L, He J, He S, Shoemaker BA,
Wang J, Yu B, Zhang J, Bryant SH. PubChem Substance and Compound databases.
Nucleic Acids Res. 2015 Sep 22. pii: gkv951. [Epub ahead of print] [PubMed PMID:
26400175] doi: 10.1093/nar/gkv951
Valerie Keller, Department of Chemistry, The University of Chicago as adapted
from: Lehman, J. W., Operational Organic Chemistry: A Problem-Solving Approach to
the Laboratory Course, 3rd ed.; Prentice: Upper Saddle River, NJ, 1999.