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ORGANIC CHEMISTRY II
LABORATORY’S REPORT
Objective (1M)
Introduction (2M)
Procedure in flowchart
(2M)
Calculation (5M)
Discussion (3M)
Conclusion (1M)
Questions (5M)
References (1M)
TOTAL
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OBJECTIVE:
1. To synthesize esterification products of vanillin with acetic anhydride under basic and
acidic conditions.
2. To determine the melting point of the esterification products of vanillin.
3. To characterize the esterification products of vanillin using IR (Infrared Remote) and 1H
NMR spectroscopy.
INTRODUCTION:
In this experiment, you will investigate the reactions between vanillin and acetic anhydride under
two conditions, basic and acidic conditions. These reactions will produce various products. You
are given two lab sessions to complete this experiment. The first session should be used to
conduct the reactions under acidic conditions. The chemical equation of esterification of vanillin
under basic and acidic conditions is shown below:
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PROCEDURE:
a) Preparation of product
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b) Recrystallize of the product
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RESULT:
A. Basic condition
a. Weight of product: 1.68g
b. Melting point of the product: 76.6℃-82.6℃
c. Appearance of the product: cloudy white and milky solution formed
CALCULATIONS:
1 mol of vanillin + 1 mol of Acetic Anhydride = 1 mol vanillyl Acetate
𝑚𝑎𝑠𝑠 𝑜𝑓 𝑣𝑎𝑛𝑖𝑙𝑙𝑖𝑛
Mol of vanillin = 𝑚𝑜𝑙𝑎𝑟 𝑚𝑎𝑠𝑠
1.50𝑔
Mol of vanillin =
152.15𝑔/𝑚𝑜𝑙
1.68𝑔
Percentage of yield = 1.9128𝑔 × 100%
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DISCUSSION:
Aldehydes could react with alcohols to form hemiacetals and acetals by equilibrium reaction.
The essential structural features of hemiacetals were –OH and –OR attached group on the same
carbon atom. An acetal has two –OR group attached for each carbon. If some alcohol solution
passed into small amount of gaseous HCl, hemiacetals formed and the hemiacetal could be reacted
with a second molar equivalent of the alcohol to produce acetal.
In basic condition, reaction between vanillin that weighed 1.68g with 25mL of 10% sodium
hydroxide produced yellow solution. Then, it turned to cloudy white and milky solution as 30g of
crushed ice and 4.0mL of acetic anhydride were added. After the recrystallization process with
95% of ethanol, the solid product became shiny. The percentage yield that been calculated from
the product was 87.87%. It was a good result since the percentage was more than 75%. The melting
point of this product was in the range of 76.6℃ to 82.6℃. Thus, it showed that the vanillyl acetate
obtained was pure because the actual range of melting point was from 77.0℃ to 79.0℃.
For the mechanism, the acetic anhydride functioned as electrophile, undergo nucleophile
attack by the alcohol as they both reacted together for both acidic and basic conditions. The vanillin
molecule has several functional groups, some of them were alcohol, ether and aldehyde. The base-
catalyzed reaction was straightforward esterification and does not produce any other significant
products because esterification stopped as ester was the final product.
The products formed was then being confirmed by using IR and NMR. The functional group
was determined using IR spectrum and it showed that there were (C–O–OR) group present at the
peak of 1155.72cm-1 (Ester) and also (C=O) group at the frequency of 1758.36cm-1 (Aldehyde).
There were also (O–H) group that present.
During the process, there might be some error occurred. There could be some moisture in
the mass of vanillyl acetate obtained because the pressure from the Buchner funnel was not that
strong to remove all of the moisture contained in the final product.
CONCLUSION:
The reaction between vanillin and acetic anhydride under the two conditions were successfully
investigated. The products formed was then determined by using IR, NMR and melting point
comparison. The mechanism for the products formed were successfully drawn. The percentage
yield of the product under basic condition was and under acidic condition. The objectives of the
experiment were successfully achieved.
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QUESTIONS:
1. Under different reaction media, vanillin undergoes esterification with acetyl chloride
yielding two different products.
a. Based on the IR spectrum of vanillin, at what range should you observe the
absorption signal of the hydroxyl group?
= At the range of 3300cm-1 – 2500cm-1 with broad peak.
b. Based on its 1H NMR spectrum, what is the expected chemical shift value for the
methoxy group (OCH3)? What is the multiplicity?
= According to the methoxy group (OCH3), the expected chemical shift
value would be between 2.1 – 2.5 and have singlet multiplicity.
c. Draw the structures of the major products for the esterification of vanillin with
acetyl chloride in:
i. 10% NaOH solution
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2. Write the mechanism for the reaction between vanillin and the acetyl chloride in 10%
NaOH solution.
REFERENCES:
Pavia, Lampman, Kriz and Engel, Introduction to Organic Laboratory Techniques 3 rd Edition
(2011), page 863-865
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APPENDIX:
C–H
C=O
C–O