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Discussion for Lab #8: Aldol Condensation

The result of performing an aldol condensation leads into the formation of unsaturated
ketone products since ketones are less reactive than aldehydes in aldol condensation because the
carbonyl of the ketones are histerically hindered and is electronically not as susceptible to
nucleophilic attack. Another reason would be because the aldehyde used, dont have -
hydrogens, so they cannot react with themselves; one such example is the experiment performed.
Also, dehydration is more favorable because the product has extended conjugations and
precipitates out of the solution. The aldehyde derivative used was trans-cinnamaldehyde and the
ketone derivative was cyclopentanone. Since the ketone derivative used was cyclopentanone and
is a symmetrical ketone, it will undergo double aldol condensation since it will be able to react
with two molecules of another carbonyl compound under basic conditions. Since the product is
highly conjugated, the hydration will be facile. The reaction of cyclopentanone and trans-
cinnamaldehyde (1:2) leads into the formation of the aldol product, (2E,5E)-2,5-Bis[(2E)-3-
phenyl-2-propen-1-ylidene]cyclopentanone. The aldol product is yellow-colored due to the
narrow HOMO-LUMO gap because of the extensive conjugation which is the reason why the

falls in the visible portion of the spectrum.


The solvent used was 20 mL of 80% toluene (16 mL) and 20% ethanol (4 mL). Hexanes
and acetone doesnt dissolve the product both in room temperature and after heating. One of the
reasons why hexanes and acetone wont dissolve the product is because of the differences in
polarity. Although the product is an unsaturated ketone, acetone doesnt have conjugated double
bonds and therefore, its ability to dissolve the aldol is hindered. Since hexane only exhibits
vander waals, like acetone, it doesnt have the ability to dissolve the aldol because the aldol can
exhibit dipole-dipole interactions. However, both toluene and ethanol dissolved some of the
crude product but not completely. Toluene dissolves most of the product since it also contains a


Discussion for Lab #8: Aldol Condensation

phenyl group like aldol. Ethanol also dissolves some of the product but since aldol is not very
polar unlike ethanol, using either toluene or ethanol alone wont be sufficient. The reason why
the solvent used was 80% toluene 20% ethanol, is because the aldol product doesnt completely
dissolve in pure toluene and pure ethanol at room temperature and when heated separately (with
the crude product). By mixing both solvents together, most of the crude product dissolved at
room temperature and the rest dissolved when heated and after evaporating the ethanol. After the
solution was cooled at room temperature, most of the crystals developed and was then
recrystallized through vacuum filtration.
After obtaining the recrystallized product, an IR spectrum, m.p, and NMR were obtained
to verify the results. The melting point of the product obtained is at 234C while the theoretical
value is 235 C. Because the obtained melting point is lower than the theoretical value, it means
that the recrystallized product still has impurities. The result of the IR spectra verifies that the
product has a carbonyl peak (C=O) at ~1676

which identifies the ketone group (R-C=O-


R). Another important peak that was identified was the peak at ~1586

which corresponds
to the phenyl group (

. However, both the IR peaks identified were not as sharp and


stretched because while the IR was not performed fast enough and ketones are volatile. The
NMR obtained shows all the significant peaks that correspond to the obtained aldol product,
(2E,5E)-2,5-Bis[(2E)-3-phenyl-2-propen-1-ylidene]cyclopentanone. However, traces of
impurities can still be traced like the singlet peak at ~2.92 ppm which is not supposed to be on
the NMR. According to the coupling pattern analysis of the product, it is not supposed to have
any singlet peak because it can only contain doublets and triplets. Due to its chemical shift and
coupling pattern, the peak might correspond to ethanol, since ethanol was also used as one of the
solvents in recrystallization. If the ethanol was completely evaporated from the solution, maybe a
much better result can be obtained from the NMR and m.p.

Discussion for Lab #8: Aldol Condensation

References
Bruice, P. Organic Chemistry, 7
th
ed.; Pearson: New Jersey, 2013.
Padias, A. Making The Connections, 2nd ed.; Hayden-McNeil Publishing: Plymouth, MI, 2013.
Padias, A. Organic Chemistry Laboratory Manual, 4th ed.; Hayden-McNeil Publishing:
Plymouth, MI, 2013.