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LAB REPORT 7 Aldol Reaction Synthesis 1 5 Diphenyl 1 4 Pentadien 3 One
LAB REPORT 7 Aldol Reaction Synthesis 1 5 Diphenyl 1 4 Pentadien 3 One
Jessica Brizuela
LAB REPORT No 7: The Aldol Reaction Synthesis, purification and NMR
Analyiss of 1,5-diphenyl-1,4-pentadien-3-one.
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.2.
COLUMN CHROMATOGRAPHIC AND NMR GRAPHS
Graph No 1 : Column Chromatographic taken before and after
purificaion
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