Aldol Condensation Lab

Introduction
The purpose of this experiment was to identify the unknown ketone and aldehyde by analyzing
the H NMR and the melting point of the condensation product.
Theory
An aldol reaction is a C-C bond forming reaction of an alpha carbon of an aldehyde or ketone
with the carbonyl carbon of another aldehyde or ketone. There are two parts to this reaction, the
first being an aldol addition followed by a double aldol condensation. Both parts of this reaction
can be seen in the drawn mechanism below; however, the double condensation should be
explained in more detail. A double condensation means that two equivalents of an aldehyde react
with a side of the ketone. The condensation reaction is a spontaneous dehydration of the
molecule which is driven by the formation of a conjugated system. Normally the dehydration
would not occur; however, due to the conjugation of the system, the hydrogen atom is much
more acidic and is removed easily.

Results

Mass

47.960 g - 46.760 g

Melting Point

128 - 139 C

Theoretical Yield

0.708 g

Percent Yield

1.2 g

169%

Product Identity

1,5-Di-p-tolylpenta-1,4-dien-3-one
(C19H18O)

MW: 262.35 g/mol

Starting Unknowns

p-Tolaldehyde (Aldehyde)

Acetone (Ketone)

** H and C NMR spectra are attached at the end of this lab

Calculations:
Ketone
(0.2)(0.7844) / (58.08) = 0.0027 mol
Aldehyde
(0.8)(1.019) / (120.15) = 0.0068 mols
We are using a 2 : 1 Aldehyde to Ketone ratio which means there is 0.0034 mols of aldehyde for
each 0.0027 mols of ketone therefore there the ketone is the limiting reagent
Theoretical Yield
0.0027 x 262.35 = 0.708 g
Percent Yield
0.708 g / 1.20 g x 100 = 169%

Discussion
By looking at the NRM spectra of both our starting unknowns we were able to determine that our
unknown C was an aldehyde and that the unknown B was a ketone. From here we analyzed each
structure individually and for the ketone we were able to determine the unknown to be acetone
by looking at the number of carbons in each compound. Acetone only has three while the other
compounds had five or more. For the aldehyde, when analyzing the HNMR we were able to
determine that our unknown was in fact p-tolualdehyde. After determining the starting
unknowns, determining the structure of the product was a trivial act of determining the
mechanism of a double aldol condensation. It is known that the p-tolualdehyde was to be added
on both sides of the acetone; therefore, after working through the mechanism a final product was
arrived at of formula C19H18O. The name of this compound is 1,5-Di-p-tolylpenta-1,4-dien-3one. Our melting point which was supposed to be used to help determine the starting products
was actually quite counterproductive. With the knowledge that our starting materials were pTolualdehyde and acetone, the melting point of the product should have been in the realm of 175
C; however, we obtain a melting point of around 133 C for our condensation product. Also,
when looking at our recovered mass and percent yield it is recognized that our data is skewed.
We obtained yield of 169% which is far too large. This is likely due to a few mistakes made
during lab.
Both our percent yield and our melting point data were far off the accepted values. Discussing
the error with the percent yield first it must be mentioned that our vacuum pump was not
working and we placed our product in the oven while it was still extremely wet in an attempt to
dry it. This attempt was in vain and was most likely the reason such a high percent yield was

obtained. Moving onto the poor melting point data, this error is slightly more technical. As a
double condensation reaction goes to completion, it must first react one side before reacting the
other side. This means that when the reaction was halted, it is extremely likely that some of our
product was only the single addition product thus creating a mixture in our product. As we know
mixtures will significantly decrease the melting point of a system and this is what we believe
occurred. The mixture of both single and double addition products would have brought our
melting point down far enough to make our data points believable. In order to improve both
these errors, steps could be taken to lessen their impact. For example, thoroughly drying our
product would have resulted in a more accurate weighing and therefore a lower percent yield as
more of the liquid would have been removed from the solid. Also, allowing our reaction to
proceed for a longer period of time would have ensured a complete double addition on all the
product, creating a higher purity in the product which would ultimately increase its melting point
and result in more accurate measurements.
Conclusion
Much of the results of this lab were based on pre-analyzed C and H NMR spectra provided to us
by the stockroom. This means that the majority of what we achieved in lab were to confirm what
we already had determined by looking at the spectra. Our data was skewed so initially this data
was useless; however, after closer inspection we were able to determine the cause of these
variances and reason our way through the data. In the end we concluded that our starting
unknowns were p-tolualdehyde for the aldehyde and acetone for the ketone. When these starting
materials reacted in a double condensation reaction, they formed a product by the name of 1,5Di-p-tolylpenta-1,4-dien-3-one.

Appendix