Nitrification Of Methyl Benzoate

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Nitration of Methyl Benzoate
Reaction summary;

Chemicals used;
6mls concentrated sulphuric acid.
2mls Methly Benzoate.
1.4mls concentrated Nitric(v) acid
Water
Methanol
0.030g GCMS.
Calculations of theoretical yield;

Procedure
6mls of concentrated sulfuric acid were dispensed into Erlenmeyer flask. Cooled to 0˚C in
an ice filled bucket, 2mls of methyl benzoate are added. To create a nitric – sulfuric
acid mixture, 1.4mls of concentrated nitric acid were added into same Erlenmeyer flask that
contained the sulphuric acid. This was then cooled to temperature not exceeding 0˚C and 10˚C in an ice bath. Sulfuric-nitric acid mixture was then added drop-wise to the cooled
methyl benzoate-sulfuric acid mixture; swirling regularly on addition and maintaining cool
temperatures ranging between 5˚C – 15˚C. The resulting mixture was then warmed to room
temperature. After a 15-minutes stay at room temperature, 50g of cracked ice were poured in a
250mL beaker. This resulted to formation of a precipitate. Suction filtration was used to separate
solid product, by sporadic use of water wash. A solid product collected was put in a beaker and
left to dry for a 7 days. It was then dried, weighed and separated into two, one for melting point
measurement and the other for TLC analysis. The remaining product was to be used in
recrystallization.

For recrystallization, similar volume of methanol as that used in making the
product was weighed and added to the beaker containing the product, heated and the solution
waited to dissolve. After dissolution, it was cooled to 250c, then placed in an ice bath for
complete recrystallization.
Suction filtration was used to separate the precipitate, by subsequent addition of chilled
methanol . Two small samples were collected for determination of melting point and TLC
analysis as shown below;
Product analysis:

Conclusion;
Methyl m-nitrobenzoate was prepared whose hypothetical yield was 3.9852 g while the actual
yield was found to be 2.6996 g. This gave a percentage yield is 67.74%. The melting point of our
product was found to be75˚C- 78˚C. This brought to the conclusion that the product obtained
was methyl m-nitrobenzoate( Mei, Wenyi, et al.) “An efficient and green process for the synthesis of 5-methyl-2- nitrobenzoic acid.”2754).

Notes
Nitration refers to the introduction of nitrogen (iv) oxide into a chemical compound acid.
Electrophilic aromatic substitutions involve the addition of a caption on an aromatic ring with an electrophile that becomes substituent.
3. Sulphuric acid makes the methyl benzoate be positively charged creating a quality stabilized arenium ion intermediate . 4. Nitronium ion which lacks electrons combines with the positively charged intermediate meta position.
Work cited
Mei, Wenyi, et al. “An efficient and green process for the synthesis of 5-methyl-2-
nitrobenzoic acid.” Research on Chemical Intermediates 44.4 (2018): 2751-2759.