CHEM 222 Lab 7
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DEPARTMENT
OF
CHEMISTRY AND BIOCHEMISTRY
CHEM 222 LABORATORY SECTION 04-L
TUESDAY AFTERNOON
EXPERIMENT 29:
BOROHYDRIDE REDUCTION OF VANILLIN TO VANILLYL ALCOHOL
Sujay Patel
40283272
Date of Experiment: November 17, 2023
Date of Report Submission: November 24, 2023
Introduction
The goal of this experiment is to carry out a reduction reaction of Vanillin into Vanillyl
Alcohol using Sodium Borohydride
1
. Afterwards, in order to determine whether the product of
the experiment was Vanillyl Alcohol, a melting point test and Infrared Spectrometry must be
used, and the results will be compared with the values of the theoretical product.
Reaction
Techniques
-
Washing/Drying Solids
-
Recrystallization
-
Melting Point
-
Infrared Spectrometry
Data and Result
Table 1: Observations
Steps
Physical Appearance
Colour
After the mixture of
Vanillin and NaOH
Liquid
Yellow
After the First Addition of
Sodium Borohydride
Liquid
Colourless
After More Addition of
Sodium Borohydride
Liquid/Fizzle
Yellow
After the Complete
Addition of Sodium
Borohydride
Liquid
Dark Yellow
During the Addition of HCl
Liquid/Precipitation
Yellow-White
After the First Vacuum
Filtration
Solid
White
During the
Recrystallization
Liquid
Colourless
After the Recrystallization
Liquid with Solids
Cloudy-White
After the Second Vacuum
Filtration
Solid/Grains
White
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Table 2: Theoretical and Experimental Data
Theoretical
Experimental
Mass of Vanillin Used (g)
3.807
Mass of Borohydride Used
(g)
0.501g
Mass of Watch Glass (g)
29.554
Mass of Product + Watch
Glass (g)
30.969
Mass of Product (g)
3.855
1.415
% Yield of Product
100
36.71
Melting Point (°C)
115
106.7-112.7
Calculations
Mass of Crude Product:
Mass of WatchGlass
=
29.554
g
Mass of Crude Product
+
WatchGlass
=
30.969
g
Mass of Crude Product
=
30.969
g
−
29.554
=
1.415
g
The mass of the crude product is 1.415g
Limiting Reagent:
Molar Mass of Vanillin
=
152.2
g
mol
Molar Mass of Sodium Borohydride
=
37.38
g
mol
Molar Mass of Vanillyl Alcohol
=
154.3
g
mol
Mass of Vanillin Used
=
3.807
g
Mass of SodiumBorohydrideUsed
=
0.501
g
Mass of Crude Product withVanillin
3.807
g
∗
1
152.2
g
mol
∗
4
moles of Vanilyl Alcohol
4
molesof Vanillin
∗
154.2
g
mol
=
3.852
g
Mass of Crude Product with SodiumBorohydride
0.051
g
∗
1
37.38
g
mol
∗
4
molesof Vanillin
1
molesof SodiumBorohydride
∗
154.2
g
mol
=
8.266
g
Limiting Reagent is Vanillin
% Yield of Product:
Mass of Vanillin Used
=
3.807
g
Mass of Crude Product
=
1.415
g
Molar Mass of Vanillin
=
152.2
g
mol
Molar Mass of Vanillyl Alcohol
=
154.2
g
mol
Molesof VanillinUsed
=
3.807
g
∗
1
152.2
g
mol
=
0.0250
moles
4
molesof Vanillin
=
4
molesof Vanillin Alcohol
0.0250
molesof Vanillin
=
0.0250
moles of Vanillin Alcohol
Theoretical Mass of Vanillin Alcohol
=
0.0250
moles
∗
154.2
g
mol
=
3.855
g
%
Yield of Product
=
1.415
g
3.855
g
∗
100
=
36.71%
Melting Point Deviation %
Theoretical Melting Point
=
115
° C
Experimental Melting Point
=
112.7
°C
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Deviation
%
=
|
115
−
112.7
|
115
∗
100
=
2%
Infrared Spectrum
Table 3: IR Spectrum
Wavelength (cm
-1
)
ID
Needles 1400-1500
Broad Absorption 3155.60
No Absorption 1660-1750
Strong Absorption 1032.88; 1123.58
Discussion
In this experiment, the goal was to carry out a reduction of vanillin into vanillyl alcohol
using sodium borohydride. The first step of this experiment was to measure 3.807 g of vanillin in
a 125 Erlenmeyer flask. Then, 20 mL of NaOH solvent will be added to the flask. The reason
NaOH was used as a solvent is because sodium borohydride, which will be added next,
decomposes rapidly when coming in contact with acidic functional groups such as COOH or OH
of a phenol. This is why NaOH which is a base can act as a neutralizer while allowing the
sodium borohydride to react with the vanillin. The reason alcohol was not used is because it
would react with the acidic functional groups in the vanillin and would not allow the sodium
borohydride to react with it.
The next step of the experiment is to add 0.5g of sodium borohydride. The reason sodium
borohydride is used as a reducing agent is because this compound is a mild reducing agent, and it
is safe to handle in its solid state. It can also be used in aqueous and alcoholic solutions, unlike
LiAlH
4
. The latter is a stronger reducing agent that can react violently with water or other
hydroxylic solvents and releases hydrogen gas. The way a reducing agent works is by breaking
the C=O bond and adding hydrogen to the missing bonds. Therefore, NaBH
4
can also be used as
a reducing agent for acetovanillone or vanillic acid since they both contain a ketone functional
group. Finally, in this experiment, an excess of sodium borohydride was used to ensure a
complete reaction with all the vanillin in the mixture. Using sodium borohydride in excess can
also increase the reaction rate.
The third step of this experiment, once the reaction is complete and there is no vanillin
remaining, is to remove the excess NaBH
4
from the reaction mixture. Since this compound is a
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strong base, the only way to remove it is to neutralize it with an acid and form a salt. In this case,
HCl will be added. This will cause an acid-base reaction and form a precipitate which will
contain the product and many impurities. Once the acid-base reaction is complete, it will be
vacuum-filtered and only the crude product will remain.
The final step of this experiment is to recrystallize the crude product in order to get rid of
all of the impurities leaving only the vanillyl alcohol. Therefore, a recrystallization solvent must
be used. In this case, the solvent used will be boiling water since vanillyl alcohol is soluble in hot
water and not cold water. Therefore, the product will be dissolved completely in hot water.
Afterwards, once dissolved, the beaker, in which the solution remains, will be placed in an ice
bath which will cool the solution down. Since, vanillyl alcohol is insoluble in water, it will
precipitate and form a solid which will be the vanillyl alcohol. Afterwards, once the
recrystallization is complete, it will be vacuum filtered leaving only the dry product to be
analyzed with infrared spectrometry and melting point.
Conclusion
In conclusion, the goal of this experiment is to carry out a reduction reaction of vanillin
into vanillyl alcohol using sodium borohydride. After the procedures and the analysis of the
crude product, it can be said that the product is indeed vanillyl alcohol. Why? Because in this IR
spectrum, it can be seen that there are needles at the 1400-1500 cm
-1
range indicating the
presence of a benzene ring. There is also a broad absorption at 3155.60 cm
-1
indicating the
presence of an alcohol group. However, what shows that it really is vanillyl alcohol without
impurities is that there is no presence of C=O bonds that can be found in the ketone functional
group of vanillin. The second reason of why the product is vanillyl alcohol is because there is
only a 2% deviation between the theoretical melting point of vanillyl alcohol and the
experimental melting point found which shows that the result is accurate since the percentage is
below 5%.
References
1.
Wilds, C.J., Robidoux, S. Introductory Organic Chemistry II: Laboratory Manuel Chem
222; Concordia University: Montreal, QC
2.
PubChem.
https://pubchem.ncbi.nlm.nih.gov/compound/Vanillic-Acid#section=2D-
Structure
(accessed 2023-11-24)
3.
PubChem.
https://pubchem.ncbi.nlm.nih.gov/compound/1183
(accessed 2023-11-24)
4.
PubChem.
https://pubchem.ncbi.nlm.nih.gov/compound/Vanillyl-alcohol
(accessed
2023-11-24)
5.
PubChem.
https://pubchem.ncbi.nlm.nih.gov/compound/2214
(accessed 2023-11-24)
6.
Schlesinger, H. I.; Brown, H. C.; Finholt, A. E.; Gilbreath, J. R.; Hoekstra, H. R.; Hyde,
E. K. Sodium Borohydride, Its Hydrolysis and Its Use as a Reducing Agent and in the
Generation of Hydrogen
1
.
J. Am. Chem. Soc.
1953
,
75
(1), 215–219.
https://doi.org/10.1021/ja01097a057.
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