Chem 201 Nitration of Methyl Benzoate and Recrystallization TLC Lab Report completed
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Nitration of Methyl Benzoate and
Recrystallization/TLC Lab Report
Introduction
The purpose of this reaction was to perform a nitration reaction on methyl benzoate creating a product of either Methyl 2-nitrobenzoate, Methyl 3-nitrobenzoate, or Methyl 4-
nitrobenzoate. By combining nitric acid and sulfuric acid, the nitronium ion NO
2
+
¿
was generated. This reagent was used for the nitration and acted as a strong electrophile for the electrophilic aromatic substation reaction. The substitution of the nitro group (
−
NO
2
) for a hydrogen atom on the methyl benzoate ring that was made by this reaction. Electrophilic aromatic substitution occurs when a C-H bond is broken, and a carbon bonded to an electrophilic
atom is formed by substitution.
The position the nitro group was placed in, depended on the functional group attached to the ring. Methyl benzoate has the functional group ester attached to it. Ester causes deactivation due to the substituent −
CO
2
CH
3
electron-withdrawing effect. Due to the deactivation and the partial positive charges on positions 2, 4, and 6, I hypothesized the position of the nitro group to be at position 3. Position 3 is a deactivating meta group. This experimental process was simple and analyzing the data that I got after completing the experiment was simple. The data that was collected from the experiment supported the hypothesis I came up with well. The melting point of my product was close to the melting point of methyl 3 nitro. Recrystallization is a technique used to purify solids. During this process, it is possible for impurities to form. Impurities make the compound less stable, therefore affecting the
melting point. Impurities tends to lower the melting point, and the more impurities you have, the lower the melting point will be. A successful process of recrystallization starts with choosing the best solvent. To do so, we had to find the solvent that didn’t dissolve the solid when cold, but when the solvent was heated, it dissolved the solid. After purifying the solvent in the experiment,
we recorded the melting points of the crude and pure methyl m-nitrobenzoate. We then used a technique called Thin-Layer Chromatography (TLC) to determine the purity of the compound. The TLC plate will confirm a pure solid by showing one spot that traveled up the plate and confirm an impure solid by showing two spots that traveled up the plate. The experimental
process was simple and reflected by hypothesis well by getting a product of methyl 3-
nitrobenzoate. Table 1
Name
Methyl Benzoate
Nitric Acid/ Sulfuric Acids Methyl Nitrobenzoate
Formula
C
8
H
8
O
2
HNO /H
₃
2
SO
4
C
8
H
7
NO
4
Structure
FW(s)
136.15g/mol
63.01g/mol ; 98.08g/mol
181.04 g/mol
mL used
1.5
1.0mL / 1.0mL
Theoretical grams
1.62g
2.0g / 2.0g 2.17g
Theoretical moles
0.012 moles
0.032 moles/ 0.020 moles
0.012moles
Density 1.08g/mL
1 / 1
Actual Grams 1.62g
2.17g
Actual Moles 0.012 moles
0.012moles
% Yield Procedure
The materials used in this experiment was 4.0 mL of conc. sulfuric acid
, 1.5 mL of methyl benzoate
, 1.0 mL of conc. nitric acid
, and 10 g of ice. In an ice-water bath we cooled 3.0 mL of sulfuric acid and 1.5 mL of methyl benzoate in a clean, dry 25 mL Erlenmeyer flask to below 10
o C. In a small test tube 1.0 mL of sulfuric acid and 1.0 mL of nitric acid was also cooled in the ice-water bath. The cold sulfuric acid/nitric acid mixture was then added dropwise, using a plastic dropper, to the cold methyl benzoate. We then swirled the flask vigorously to mix the reagents, and allowed it to warm to room temperature, standing for 15 minutes. To precipitate
the product, we then poured the mixture onto 10 g of ice in a 50 mL beaker. The flask was then rinsed, and the water was poured in the beaker with the mixture. We allowed the ice to melt and collected the product of our reaction by suction filtration. After suction filtration, we disposed the filtrate, and collected the melting point of the crude and pure methyl m-nitrobenzoate. For the
crude methyl m-nitrobenzoate the melting point recorded was 58.8-71.9
C, and the melting point
of the pure methyl m-nitrobenzoate recorded was 68.8-76.6º C. Lastly, the theoretical yield, actual yield, and percent yield was calculated. The materials used for the Recrystallization and TLC was 0.4g of the impure compound, 1mL of water, 1mL of ethanol, and 1mL of toluene. First, we gathered 3 small test tubes and placed 0.1g of the compound in each test tube and then approximately 1mL of each of the solvents (water, ethanol, and toluene) to each of test tubes. We stirred them well and observed the solubility. The test tubes of solvent which still contained some of the solid compounds were
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