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ORGANIC CHEMISTRY 2
EXPERIMENT 3: ESTERIFICATION REACTION OF VANILIN (THE USE
OF NUCLEAR MAGNETIC RESONANCE AND INFRARED
SPECTROSCOPY TO DETERMINE THE STRUCTURE)
2. Basic condition:
i.
1.5g of vanillin was added into a conical flask with 25mL of 10% NaOH
solution.
ii.
4mL of acetic anhydride and 30g of crushed ice were added into the solution.
iii.
The mixture was shaken for 20minutes and cloudy, milky white precipitate
will form.
iv.
The mixture then was filtered by using Buchner funnel with washing of 3
portions of 5mL ice-cold water.
v.
For recrystallization, 15mL warm ethanol (below 60C) was added with the
crystal collected from the filtration until it dissolved.
vi.
The mixture was put in ice bath to initiate the recrystallization.
vii.
The mixture was filtered again until dry crystal was obtained.
viii.
The weight of product was recorded and the melting point, NMR and also IR
spectra were tested.
CALCULATION:
Mass of vanillin = 1.5g
Molar mass of vanillin = 152g/mol
Molar mass of vanillin acetate (product) = 194g/mol
Mol of vanilin =
= 0.009868mol
Volume of acetic anhydride = 4mL = 4cm3
Density of acetic anhydride = 1.08g/cm3
Mass of acetic anhydride = 1.08g/cm3 4cm3
= 4.32g
Mol of acetic anhydride =
= 0.04235mol
Limiting reactant: vanillin.
Theoretical
wavenumber, cm-1
Basic
1757.50
1396.59
1599.37,1508.29
3018.77
ii.
Nuclear Magnetic Resonance result:
1. Acidic condition
Signal
1H, singlet
3H, singlet (benzene)
3H, singlet
9H, singlet
Concentration, ppm
7.7
7.0-7.2
3.9
2.2-2.4
2. Basic condition
Signal
1H, singlet
3H,singlet (benzene)
3H, singlet
3H, singlet
Concentration, ppm
10.0
7.4-7.6
3.9
2.4
iii.
Observation
1. Acidic condition
Colour change from colourless to brick red after the addition of 1.0M of
H2SO4 (10drops).
The brick red colour turn to milky white after the addition of 35mL of ice cold
water.
The solid become shiny after the recrystallization process with warm 95%
ethanol.
2. Basic condition
Reaction between 1.5g vanillin with 25mL of 10% NaOH produce yellow
solution.
Yellow solution turns to milky white mixture after the addition of 4mL acetic
anhydride and 30g crushed ice.
The solid become shiny after the recrystallization process with warm 95%
ethanol.
100%
100%
= 69.92%
Theoretical yield of basic condition = 194g/mol 0.009868mol
= 1.9145g
Percentage yield in basic condition =
100%
= 50.14%
Acidic condition
2.0425
2.9211
69.92
90
Basic condition
0.9600
1.9145
50.14
79
DISCUSSION:
The percentage yield from both of under acidic condition and basic condition lies above half
of the theoretical yield. The loss of the mass of the product may occur during the filtration
done by using the Buchner funnel and some of it may be left in the container during the
transfer into the Buchner funnel set. In order to get the higher mass of the product, the
process of adding solution must be done slowly and always stir the solution. The person in
charge also must make sure that the solid that want to dissolve must be completely dissolve
before proceeding to the next step. The melting point test was done by using the melting
point apparatus. The melting point of both products that was done under acidic and basic
condition lies in the range of the theoretical melting point by references. The theoretical
melting point of product under acidic condition is between 90-91C while the theoretical
melting point for the product under basic condition is between 77-79C.
From the FTIR test, the result obtained showed that both of the products have the same
several functional groups. The functional groups are C=O bond from aldehyde and ester that
lies between 1670-1760cm-1 wavenumber. The C-O bond of ester appears at wavenumber
that lie between 1090-1400cm-1. Both of these functional groups have a sharp shape of
peak. Weak shape of peaks appears in several at 1500, 1600cm-1 wavenumber that indicate
the C=C bond in aromatic ring. The medium shape of peak indicated in both of the
compounds is the C-H bond for aromatic ring and it appears in a very small and not strong
peak in the spectrum.
The structures of the products were tested by using the Nuclear Magnetic Resonance. Some
of the peaks are not separated well, so that adjustment must be done to know the exact
number of hydrogen at a certain signal. The higher the concentration of the signal, the
lesser the electron density around it. Both of them used to have the benzene ring with 3
hydrogen atoms around, that appear around 7ppm in the spectra. For the product under
basic condition, it has 2 same signals that are 3H, singlet that lie at different concentration.
The first signal with less concentration has high electron density than the second signal that
move to the lowfield of the spectrum.
CONCLUSION:
The percentage yield under acidic condition is 69.92% and the percentage yield in basic
condition is 50.14%. The melting point of product under acidic condition is 79C and the
melting point of product under basic condition is 76C. Both products show the functional
groups of ester and aldehyde from the result of Infrared Spectroscopy and from the NMR
result the structure of the products resulting:
QUESTIONS:
1. Write the mechanism reaction under basic media.
REFERENCES:
1. Acetic anhydride, 27/10/2014, http://en.m.wikipedia.org/wiki/acetic_anhydride
2. CHM 556 Organic Chemistry 2 lecture notes prepared by Prof. Faujan.
3. Department of Chemistry and Biochemistry University Delaware, Synthesis of
Vanilin, 24/10/2014, http://valhalla.chem.udel.edu/vanilin.html
4. T.W. Graham Solomons, Craig B. Fryhle, Organic Chemistry, Asia, John Wiley and
Sons, 2011.