Friedel Crafts
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Friedel Crafts
Winona State University-Chemistry Department, Winona, MN 55997
CHEM 340-01, Dr. Kopitzke
April 6, 2020
Introduction:
Nuclear magnetic resonance, also known as NMR, is a spectroscopy technique
primarily used for the analysis of organic compounds.
1
NMR functions based on
magnetic fields and particle spins. The nucleus of an atom is positively charged and
creates a magnetic field as it randomly spins. Once an external magnetic field is
introduced on the sample by the spectrometer, the nuclei either spin with or in the
opposite direction of the field.
2
The machine then generates a plot of signal frequency
versus intensity depending on how the atoms interact with the current. This data allows
researchers to identify the structure of the organic compound. In this experiment, a
reaction of isobutyl benzene, acetyl chloride, aluminum trichloride, and dichloromethane
was finalized, and the product was tested using nuclear magnetic resonance
spectroscopy. Isobutyl benzene is an aromatic compound, meaning it has a cyclic
structure along with special stability allowing it to be used as a solvent for nonpolar
compounds.
3
The aromatic compound in this chemical process is responsible for the
specific organic compound created by the reaction.
The primary objective of this experiment was to employ IR and NMR
spectroscopy to determine which isomer was composed by the successfully completed
reaction.
Experimental:
All supplies were obtained for the experiment. 2mL of CH
2
Cl
2
and 0.8 g of AlCl
2
was added to a round bottom flask and a vent was created. 0.6 mL of acetyl chloride is
slowly added to the round bottom flask over a period of 2 minutes. 0.5 mL of the given
aromatic (isobutyl benzyne) was added into the reaction over 5 minutes. The transfer
was completed by using a few extra milliliters of CH
2
Cl
2
. After the reaction was
completed, 4 mL of ice cold water was added drop by drop into the solution. The
solution separated into two layers, the organic bottom layer and the acid top layer. The
organic layer was removed without disturbing the acid layer and added into a 5 mL
conical vial. 1 mL of 5% sodium bicarbonate was added into the vial containing the
organic layer. Dry the substance with sodium sulfate and decolorize with a pipette
column containing about 3 cm of Alumina. Substance was contained in a clean 50 mL
flask and dried using N
2
. A final weight was taken and the product was sealed in a flask
for use the following week.
Infrared and NMR were both done. For IR, a drop of sample was put in between
the AgCl plates and read by the computer. For NMR, 2 drops of sample as well as 2
inches of CHCl
2
was added to the NMR tube and read. Proper washing and storage of
the glassware was done to finish the lab.
Results:
Table 1: Yield
Final Mass
0.966 g
% Yield of isobutyl acetophenone
175%
Calculations:
Isobutyl Benzene (Aromatic Substrate) = 0.5 mL *
*
= 3.13 * 10
-3
0.853 𝑔
1 ?𝐿
1 ?𝑜?
136.22 𝑔
mol
Acetyl Chloride = 0.6 mL *
*
= 8.41 * 10
-3
mol
1.1 𝑔
1 ?𝐿
1 ?𝑜?
78.49 𝑔
Theoretical Yield = 3.13 * 10
-3
mol *
= 0.552 g isobutyl acetophenone
176.25 𝑔
1 ?𝑜?
% Yield =
* 100 =
* 100 = 175%
𝑎𝑐??𝑎?
?ℎ𝑒𝑜𝑟𝑒?𝑖𝑐𝑎?
0.966 𝑔
0.552 𝑔
Table 2: Infra- Red Data
Wave number(s)
Bond Type
2956.61
C - H (Sp
3
)
1683.22
C = O
1606.05
C = C (Benzene)
1267.34
C - C
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Figure 1: IR Data Plot
Table 3:
1
H-NMR Data
δppm
Int
Splitting
Assignment
7.86
1.93 (2)
Doublet (2)
A
7.22
2.18 (2)
Doublet (2)
B
2.58
2.82 (3)
Singlet (1)
C
2.52
1.85 (2)
Doublet (2)
D
1.89
1.00 (1)
Multiplet (8)
E
0.90
6.32 (6)
Doublet (2)
F
Figure 2:
1
H-NMR plot of product
Figure 3: Structure of final product, with labeled hydrogen regions supported by
table 3
Discussion:
The theoretical yield of isobutyl benzene was calculated to be 0.552 g, however
the actual yield of the product was 0.966 g, giving a 175% yield. The extra mass can be
attributed to incomplete or improper abstraction of solvent from the product.
The infrared data that was collected, seen in table 2, showed four distinct peaks
that were identified to be C-H (sp
3
) at 2956.61, a C=O bond at 1683.22 as a ketone, a
C=C at 1606.05 as a benzene, and 1267.34 as a C-C bond. In table 3, the
1
H-NMR data
shows two peaks about the benzene, both depicted as a doublet and integrated values
of ~2, are labeled as A and B with values of 7.86 ppm and 7.22 ppm, respectively. A
peak at 2.58 ppm with an integrated value of ~3 shows a singlet and identified as region
c in figure 3. The shift at 2.52 ppm had an integrated value of ~2 and split into a doublet,
labeled as region D in figure 3. The shift at 1.89 ppm had an integrated value of ~1 and
showed a multiplet, indicating to be region E. Lastly, the shift at 0.90 ppm with an
integrated value of ~6 showed a doublet peak and labeled as region F.
The
1
H-NMR data that was collected, alongside with the IR spectroscopy data
supported the conclusion that the Friedel-Crafts alkylation proceeded to some extent,
and that the major product was the para- substituted molecule rather than the ortho-
substituted molecule.
Conclusion:
Throughout this experiment, the main objective was to determine which isomer
was composed by the successfully completed reaction. After concluding the experiment
it is known that the isomer formed was para-isobutyl benzene. If this experiment were to
be done again, students should be sure to thoroughly dry the final product to ensure
accurate infrared and NMR results. This, in turn, would create a more precise percent
yield, resulting in more accurate data.
References:
1.
Reusch, W. (2013, May 5). Nuclear Magnetic Resonance Spectroscopy.
Retrieved April 4, 2020, from
https://www2.chemistry.msu.edu/faculty/reusch/VirtTxtJml/Spectrpy/nmr/nmr1.ht
m
2.
PROTON NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY (H-NMR).
(n.d.). Retrieved April 4, 2020, from
https://www.chem.ucla.edu/~harding/notes/notes_14C_nmr02.pdf
3.
Libretexts. (2019, June 5). 13.8 Examples of Aromatic Compounds. Retrieved
from
https://chem.libretexts.org/Courses/University_of_Illinois,_Springfield/UIS:_CHE_
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267_-_Organic_Chemistry_I_(Morsch)/Chapters/Chapter_13:_Benzene_and_Aro
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