Experiment 10

Lab Exam

Alex Zheng (10092648)

Lab Bench K1
TA: Nick
Due: April 8, 2015
Experimental:

Materials:
50mL Erlenmeyer flask

Stopper

Glass rod

Vacuum filtration apparatus

Watch glass

Melting Point apparatus

Sodium hydroxide

Aldehyde (Labeled in a bottle) [A91]

Ketone in 95% ethanol solution

Ethanol

Distilled water

Ethyl acetate

Procedure:
Please refer to the Chem 223 Lab manual[1] for the procedure. No steps were
changed in this experiment. Our reaction mixture did not appear oily so we did
not have to add additional ethanol to the mixture.
Results:
Sample ID
Mass
Percent Yield
Melting Point
Literature melting point2
Mixed melting point

A91
0.163g
23.5%
131.3-134.1oC
128-130oC
128.1-130.1oC

Percent Yield calculations:

Limiting Reagent= 4.71*10-3
Reactant
2moles 4-methoxybenzaldehyde
pentadienone

4.71*10-3 methoxybenzaldehyde *

Product
: 1mole 1,5-Bis(p-methoxyphenyl)-3-

1 mole product
2 moles reactant

2.36*10-3 * 294.34g/mole = 0.694g product

= 2.36*10-3 moles product.

Percent Yield:
Actual Yield/Theoretical Yield
0.163g/0.694g * 100 = 23.5% yield

NMR spectrum:

Also attached onto lab write-up

Discussion:
The melting point in this lab obtained was slightly higher than literature value 2.
The reason for this was possibly because the melting point apparatus was set
at too high of a voltage and was increasing heat too rapidly. Therefore when
the crystals melted, the temperature had jumped slightly higher than the
actual melting point of the crystals. The mixed melting point had a melting
point that is identical to the literature value meaning that we are certain that
the product made in this experiment is indeed (1E,4E)-1,5-Bis(4methoxyphenyl)-1,4-pentadien-3-one, and that it is relatively pure since the
crystals of the mixture of experimental and reference product melted in
uniform. Nonetheless, only 23.5% yield was obtained from this reaction
meaning that although we managed to obtain a pure product, there were some
errors that resulted in the loss of some potential product. These errors include
dirty glassware, insufficient mixing of the reaction mixture, loss of product
during transport/vacuum filtration, and/or faulty recrystallization. This

experiment proceeded very efficiently. There was little or no oil produced so no

excess ethanol needed to be added, and after 20 minutes the mixture had
formed crude crystals. After vacuum filtrating the product, a small seed crystal
was removed and the rest was recrystallized. The product was soluble in
ethanol, however there were small chunks of solid crude crystal that failed to
dissolve into the hot ethanol even as around 20mL of ethanol was added. More
ethanol was added until we were able to completely dissolve all crude product
then we allowed the solution to cool on the bench for 10 minutes until room
temperature, then in an ice-water bath. The resulting product was a nice fluffy
solid crystal that was white, but had a slight hint of a yellow tinge to it.
The 1H NMR spectrum of the product showed that the crystal was not as pure
as we hoped for. Based off of literature 1H NMR spectrums (referenced below),
we saw that there were small deviations between my spectrum and the
literature spectrums. The first shift we look at is the shift at 3.82ppm. It is a
singlet with an integration value of 3.647 and is obviously the methyl oxide
group of the molecule. The second peak to look at is the peak at 7.70. It is a
doublet with an integration of 1.00. It is very likely the C 2 of the carbon (Please
refer to the diagram [fig.1] below with labeled carbons) because of the high
shift due to it being directly attached to the carbonyl carbon. Because it is a
doublet we know that it is attached to another proton and that makes sense
since the C2 is linked to another C3H group through a double bond. The next
peak to look at is the peak at 7.57ppm. It is another doublet but has an
integration value of 2.322.0. Therefore there are two protons that form this
doublet and that means it is likely one of the aromatic protons. Because of its
high shift, it is fair to assume that it is C 6 proton and also its mirror image
proton (on the other side of the aromatic ring). It is likely the C 6 proton because
the C6 is closer to the methyl oxide group which has an oxygen that likely
causes more shielding. The final peak to look at is the peak at 6.93ppm. After
much consideration, it only makes sense that this peak is two separate
doublets however they are two close together to integrate separately. The
integration value is 3.0 and therefore the two doublets consist of one of the
aromatic protons and one of the carbons closer to the carbonyl carbon. It
makes sense that the two protons involved in this peak are the C 3 and C5
carbons as they would have similar shifts as they are not directly beside or
close to any oxygen atoms. It is important to note that this molecule is
symmetrical and therefore the peak selections apply to both sides of the
molecule.

Questions:
1. Sample ID is A91

2. The name of the product is (1E,4E)-1,5-Bis(4-methoxyphenyl)-1,4pentadien-3-one. The structure is:

Figure. 1
3. The two unknown starting materials given were: 4methoxybenzaldehyde and Acetone.
4. The percent yield of the product was 23.5%
5. The melting point of the product was 131.3-134.1 oC
6.

7. NMR analysis:

Peak

Shift (ppm)

Splitting
pattern

Integration

Assignmen
t in
Structure

A
B

3.87
6.93

2.974
2.961

CH3
CH / CH

C
D

7.57
7.70

Singlet
Two
Doublets
Doublet
Doublet

Carbon #
(to match
on
diagram)
C8
C3/C5

2.01
1.0

CH
CH

C6
C2

References:
[1] Vlahakis J. Lab 10 Lab Exam. CHEM 223/ENCH245 Organic
reactions/Applied Organic
Chemistry. Queens University Kingston, ON, 2015.
[2] (1E,4E)-1,5-Bis(4-methoxyphenyl)-1,4-pentadien-3-one. Chemspider.com.
Web. Retrieved
April 4, 2015. http://www.chemspider.com/ChemicalStructure.624639.html
Literature 1H NMR Spectrums
[3]Sing J.A., Cumming H. Aldol Condensation. Spin solve Magritek [Online].
Victoria University of

Wellington. Retrieved April 4, 2015. http://www.magritek.com/wpcontent/uploads/2013/12/Aldol_Condensation_web.pdf

[4]Schaefer C.A., Silva V.D., Stambuk B.U., Nascimento M.G. Use of
Saccharomyces cerevisiae
Yeasts in the Chemoselective Bioreduction of (1E,4E)-1,5-Bis(4methoxyphenyl)-1,4-pentadien-3-one in Biphasic system. J. Braz. Chem.
Soc., Vol. 00, No. 00, S1-S3, 2013.
http://jbcs.sbq.org.br/imagebank/pdf/aop055_13_MS.pdf