Nitration Of Methyl Benzoate

Topics: Sulfuric acid, Acetic acid, Nitration Pages: 4 (795 words) Published: April 22, 2015
Introduction:
The purpose of the lab is to go through a reaction involving the nitration of methyl benzoate, also known as an electrophilic aromatic substitution. The nitronium was formed using the reaction of nitric and sulfuric acid. The nitronium ion reacts with methyl benzoate, creating an intermediate Arenium. The Arenium later shifts a proton to the bisulfate ion, forming the methyl 3-nitrobenzoate. Experimental:

The sulfuric was measured out to 6ml, poured into an Erlenmeyer flask, and cooled to 0 °C. 3.058 grams of methyl benzoate was added, and the mixture was further cooled to 6 °C. The 2 mL of concentrated sulfuric acid was added drop wise to the solution, kept in between 5 – 15 °C when adding this. The solution was warmed to 20 °C and later poured into 40 mL of ice in a 100 mL beaker. This was filtered through a Buchner funnel, using plenty of water. The mixture was also washed with 2.5mL of cool methanol. The sample was weighed to be 3.589 g. The amount of methanol used for recrystallization was 2.6 mL. The melting points of the crude and recrystallized product were measured. TLC analysis and IR analysis of the recrystallized product was also done. The 1st TLC plate had spots 3-5 dinitro, 4 nitro, and recrystallized product, and the 2nd TLC plate had spots methyl benzoate, a co-spot, recrystallized product in ethyl acetate as the solvent. In the end, 2.893 grams of recrystallized product was formed. Results:

Table 1: TLC Rf Values of 3-5 Dinitro, 4 Nitro, Recrystallized Product, in Ethyl Acetate Spot Sample
Spot Distance (cm)
Solvent Distance (cm)
Rf Value
3-5 Dinitro
4.9,5.6
5.9
.83/.95
4 Nitro
4.86
5.9
.82
Recrystallized Product
4.80
5.9
.81

Table 2: TLC Rf Values of Methyl Benzoate, Co-Spot, Recrystallized Product in Ethyl Acetate Spot Sample
Spot Distance (cm)
Solvent Distance (cm)
Rf Value
Methyl Benzoate
4.9
6.0
.82
Co-Spot
4.6
6.0
.77
Recrystallized Product
4.8
6.0
.80

Table 3: Melting Points of...
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