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Rodney Pujada

Jessica Brizuela
LAB REPORT No 7: The Aldol Reaction Synthesis, purification and NMR
Analyiss of 1,5-diphenyl-1,4-pentadien-3-one.

Date: December 8th, 2016


I. PURPOSE: The purpose of this weeks lab was to conduct an Aldol condensation
reaction. This particular reaction involves the joining of acetone and benzaldehyde
molecules and the loss of water. This reaction is a base-catalyzed reaction that
involves a carbanion intermediate. The carbanion is known as an enolate anion in
which the hydrogens on the alpha carbon are unusually acidic.
II. INTRODUCTION:
Dibenzalacetone, also known as dibenzylideneacetone or DBA, is often utilized as
an ingredient in sunscreen lotions and sprays because it has spectral properties
that make it capable of absorbing UV light. It is also known to possess antiinflammatory properties and can therefore be used to treat pain, swelling and
inflammation. Dibenzalacetone canal so be used as a ligand in organometallic
chemistry, and its derivatives are often utilized as polymer cross linkers. Most
importantly, the synthesis of dibenzalacetone via the aldolcondensation of
benzaldehyde and acetone is an extremely effective. In this experiment, we
carried out an aldol condensation reaction in strongly basic conditions with
benzaldehyde acting as the electrophile and acetone forming the enolation. This
reaction synthesized dibenzalacetone with a fair yield of 73.03%.
Our mechanism is the following table No 1:

Table No 2: compound specific characteristic.


Benzaldeh
yde

Acetone
C3H6O

C7H6O

Sodium
Hydroxi
de

Ethanol
C2H6O

Dibenzalacetone/
Dibenzylideneacetone
C17H14O

NaOH

Molar Mass
(g/mol)

106.12

58.08

39.9971

46.07

234.292

BP (C)

178.1

57

1,388

78.37

130

MP(C)

57.12

93

318

114

112

Density
(g/ml)

1.044

0.791

2.13

0.789

1.1

Solubility

In
ammonia

In water

Polar
solvents

Polar
solvents

Soluble in nonpolar
solvents

Refractive
Index (nD)

1.545

1.359

1.357

1.361

1.649

III. RESULT AND CALCULATIONS


3.1 DATA
Compound use to the experiment in grams
0.012 moles of Acetone * 58.08 g/mol = 0.697 g of Acetone
0.024 moles of benzaldehyde *106g/mol = 2.456 g of benzaldehyde.

3.1.1. Mass of crude product = 1.6070 g


CONVERT TEORIC PRODUCTION IN GRAMS
2 mole of benzaldehyde = 2mole*(106g/mol) = 212 g of benzaldehyde
1 mole produced of dibenzalacetone = 1mol*234.29 g/mol = 234.29 g of
dibenzalacetone
We use 2.456 g of benzaldehyde = 2.456 g
III.1.2. By balance equations calculate the weight in grams of
dibenzalacetone

= 2.456 g of benzaldehyde* (234.29 g of dibenzalacetone/212g of benzaldehyde)


=2.71 g of dibenzalacetone
Weight theorycal of dibenzalacetone = 2.71 g
Weight practical of dibenzalacetone = 1.6070 g
III.1.3. Percentage Yields of dibenzalacetone
Weight theorycal of dibenzalacetone = 2.71 g
Weight practical of dibenzalacetone = 1.6070 g
Percentage Yield = (weight of crude *100)/ weight of theorycal product.
Percentage Yield = 1.6070 g*100/2.71 = 59 %
Percentage Yield of benzalacetone =
59 %
Our Sample recovered after column chromatographic of crude product
Weight after Column Chromatographic dibenzalacetone = 0.32 g
III.1.4.

Measuring melting point of crude product

Melting point of dibenzalacetone = 109.2 C in the range of 88-113 C


Melting point of dibenzalacetone after column chromatographic = 110 C in the
ramp of 88-123 C

III.2.
COLUMN CHROMATOGRAPHIC AND NMR GRAPHS
Graph No 1 : Column Chromatographic taken before and after
purificaion

For the experimental production we obtain Rf for SM = 1 cm


Rf for CO = 1.71 cm
Rf for CP = 3.7 cm
For the purified product by column chromatographic we obtain
Rf for CO = 2.7cm
Rf for PP = 2.7 cm

Graph No2 and 3 : Our represented NMR for our product are the
following.

IV. DISCUSSION
For our experiment we synthesized
dibenzalacetone by 59 % of yield recuperation.
We have a complete reaction because in our
TLC is clear and define spots that showed by
TLC. Rf = 3.7 in our experiment, and in our final
purified product was Rf = 2.7 after the column
chromatographic. Also, our melting point
showed a m.p. before purification is 109.2C
and m.p. after purification of 110 C.
By graph No 2 we calculate the coupling
constant calculation for two hydrogens present
in the compound JHa = (7.116-7.076)*400 =
16Hz and JHb = (7.769-7.729)*400 = 16 Hz. Geometric isomerism refers to the
cis/trans orientation of alkenes within a molecule. There are two alkenes and both
can be either cis or trans. The orientation of two protons on a disubstituted alkene
uses their coupling constant. Generally cis protons will have a smaller coupling
constant between 7 to 12 Hz and trans protons will have a larger coupling constant
between 13 to 18 Hz. The two wide doublets in the NMR correspond to the protons
adjacent to the carbonyl on the alkenes because the peak are defined as neighbors
alkenes; therefore there is a trans trans configuration.
V. CONLUSION
For our experiment calculation, we concluded we had a 59 % of yield for
dibenzalacetone with a constant melting point before and after the purification by
the column chromatographic. Also, we observe in our mechanism of reaction, -OH
is known to yield the enolate, which we must generate from acetone, in small
amounts. So we must add more than a 1:1 ratio of acetone and sodium hydroxide
in order to generate more enolate. Therefore, we had to measure a exactly
amount of compound benzaldehyde and acetone to get a good results. Also, we
obtained a trans trans isomer because our coupling constant are higher. The trans
isomer will show doublets with a higher coupling constant.
VI. REFERENCES
1.
ANALYTICAL CHEMISTRY FOR TECHNICIANS. Third Edition. Lewis Publishers.2003.
Pages 337-341
2.
Laboratory Techniques in Organic Chemistry. Morhig and others. 1 st. Edition .W.
H. Freeman and Company. 2014. Pag: 142-152
3.
Table 12.1 page 425 Characteristic IR Absorptions of Some Functional Groups
4.
McMurry, John. "Organic Chemistry." Sandra Kiselica. Belmont, CA:Brooks/Cole, a
division of Thomson Learning Inc., 2008.
Abstract: brief statement of the results - product name, yield, mp, how it was
synthesized and purified

Intro- method and reaction scheme (+MW of each reactant), mechanism


Results: how much of the SM was taken, theoretical yield calculations; mass of crude %yield; mp of crude, of purified, % recovery (must know how much you took for the
purification and how much you isolated after the column - put in in the table) TLC data
(both plates - see the files posted in the last week block). For details, consult the
syllabus. Attach NMR spectrum given in the lab or download it (posted in the last week
block) with all protons labeled on the structure and on the spectrum. If you need a hard
copy - come to my office.
Discussion
1. reaction progress - complete/incomplete based on TLC
2. Purity of your product based on TLC and mp (must compare experimental values to
the lit value).
3. Yields and recovery% - account for errors and losses of the product
4. Decide whether the product is trans-trans, cis-trans or cis-cis based on NMR and mp.
formula for coupling constant calculation:
J = 10^6*(difference in chemical shift/400)
Conclusion:
Asses overall performance for this experiment and tell what you have learned from it.
Post-lab questions (extra credit - 6 pts):
1. During the column chromatography why was it important to load the concentrated
solution of the sample?
2. Why you shall never let the column run dry?
3. How can you use NMR and IR spectroscopy to monitor the progress of the reaction
you performed? Hint: think what peak will disappear and what will appear when
reaction is done.
Should you have any question - please see me