NITRATION OF METHYL BENZOATE

Mariellena P. Mendoza Human Biology 21 De La Salle University-Dasmariñas Dasmariñas City, Cavite,Philippines

ABSTRACT

Nitration is an introduction of nitrogen dioxide into a chemical compound. In the process, the methyl benzoate was nitrated to form a methyl m-nitro benzoate. The reagents were added very slowly to avoid vigorous reactions and the temperature was maintained low to avoid formation of di-nitro product. The percent yield was computed which give a result of 92.77 %. These shows how close the yield of the product to the original value. The melting point of the product was gathered with the use of melting point apparatus. This shows that the melting point of methyl m-nitro benzoate was 78 C which proved that it was a pure substance.

Introduction

The nitration of methyl benzoate is a typical electrophilic aromatic substitution reaction. The electrophile is the nitronium ion which is generated by the interaction of concentrated nitric and sulfuric acids. Figure 1 below shows the nitration of methyl benzoate and the nitronium ion generation.
H3C O H3C O

HNO3 CH4 H2SO 4 CH4

NO 2
+ +

HNO 3 + 2H 2 SO 4 Nitronium Ion

NO 2 + 2HSO 4 + H 3O

Figure 1: Nitration of Methyl Benzoate and Nitronium Ion Generation

The remaining product was submitted to our instructor. The weight of the dried product was determined. The watch glass was preweighed then transferred and dries over a steam bath. It was found with the use of melting point apparatus. The melting point proved that the product is a pure methyl m-nitro benzoate. The filtered product was washed with cold distilled water and 5% NaHCO3. Since. which is somewhat stabilized by ring resonance. protonates the methyl benzoate in the structure above. The rate of formation of the Arenium ion. The weight of the methyl benzoate was recorded. the dried product was scrape and grinded into fine powder. the nitrating agent was added in an ice bath then poured to the mixture slowly using the Pasteur pipette. The product was transferred into a capillary tube and observed in the sample chamber. After addition.The solvent which is the sulfuric acid. the vacuum filtration set-up was used to filter the mixture. just add few drops H2SO4 until the cloudiness disappear. After swirling.77% The melting point of re-crystallized methyl m-nitro benzoate was 78 C with 0% difference. The Carbomethoxy group is electron withdrawing. The percentage yield was computed and the melting point was obtained using the melting point apparatus. 10g crushed ice was added to the mixture and stirred until melted. After waiting. The mechanism for the synthesis of methyl m-nitro benzoate was shown in the Figure 2 below. the conical flask with methyl benzoate was chilled in an ice bath together with the 2ml H2SO4 then swirled. First.2670 g 92. The TLC Profile of the product was not founded because methyl m-nitro benzoate was a pure product. Results and Discussion The percent yield of methyl m-nitro benzoate is shown in the table 1 below. Table 1: Percentage Yield of methyl m-nitro benzoate Mass of Methyl Benzoate 0. The mixture was put in a water bath for 15 minutes. so it deactivates the ring relative to Benzene.2868 g Mass of re-crystallized methyl m-nitro benzoate % Yield 0. If cloudiness will occur upon addition. The flask was emptied then the solid product was washed with cold distilled water then tested with blue litmus paper to know if it¶s neutral. . Materials and Method The conical flask was pre-weighed using the analytical balance then 20 drops of methyl benzoate was added inside the flask. determines the rate of reaction. This is to show how close the measured amount of the methyl m-nitro benzoate to the expected amount. The resultant ³resonance´ structures favor ³Meta´ substitution over Ortho/Para director [1]. cloudiness did not occur we did not add anymore. The resonance stabilized arenium ion intermediate then transfers a proton to the basic bisulfate ion to give methyl 3-nitrobenzoate. After solid product was formed.

[2] Aside from methyl m-nitro benzoate. other product can also be formed.5-dinitrobenzoate because it is possible for methyl benzoate to nitrate twice. The figure below shows the nitration product that can be formed if phenyl benzoate is used.H O H N + O + O H SO 3H H O + O N + + + - O SO 3H O N + O + H 2O OH OH H3CO O H3CO O H3CO O + H2SO4 O N + O O2 N H - NO2 O SO3H Figure 2: Mechanism for the synthesis of methyl m-nitro benzoate The reaction condition should be maintained at a very low temperature to avoid production of a dinitrated product. And the reagents are added very slowly to prevent vigorous reaction especially when acids are added. O O O HNO3 H2SO 4 O O 2N O2 N Figure 3: Nitration of Phenyl Benzoate . This can be Methyl-3.

S. Essentials of Organic Chemistry Laboratory. 2nd Ed.edu/pahlavan/2425L3. Nitration of Methyl Benzoate.hccs. and Sta.REFERENCES: [1] K. Philippines. ³Experiment 3: Organic ChemistryII´. Williamson.pdf [3] Legaspi. Houghton Mifflin. Nitration. 2010. 2010. A. Ana. Macroscale and Microscale Organic Experiments. L. 1994. Retrieved from:swc2.T. Boston [2] Pahlavan-Cherif. G. (Evaluation Copy) .