Nitration Of Methyl Benzoate Lab Report
Nitration of Methyl Benzoate to form Methyl-m-nitrobenzoate via Aromatic Substitution
Linh Ngoc Thuy Nguyen
Seattle Central Community College
Professor: Dr. Esmaeel Naeemi
Date: February 21st, 2012
Abstract
In this experiment, methyl-m-nitrobenzoate, followed the electrophilic addition of aromatic ring, would be formed from the starting material methyl benzoate and nitric acid, under the catalysis of concentrated sulfuric acid. The reaction between nitric acid and sulfuric acid resulted in the formation of nitronium ion NO2+. It then acted as strong electrophile that nitrated the benzene ring. After that, vacuum filtration and recrystallization were methods used to obtain the final product with minimal impurities. The mass of product …show more content…
First, nitronium ion is made by the reaction between nitric acid and sulfuric acid, with sulfuric acid acting as a protonated reagent. The nitronium ion is a strong electrophile that can react with benzene ring to form the arenium ion intermediate, despite the fact that it can temporarily lose its stability provided by the resonances. After that, it regains its stability by deprotonating the intermediate and yields the final product, in this case is methyl-m-nitrobenzoate. This experiment will be carried out under controlled temperature of 15oC or lower, since higher temperature will result in the second nitro group addition. In this experiment, student will observe the mechanism of electrophilic aromatic substitution reaction through the nitration of methyl …show more content…
The mixture was then cooled to 0oC or below using ice-salt bath before adding slowly 1-1 ratio concentrated sulfuric acid and concentrated nitric acid (4mL). The mixture was stirred continuously to maintain the reaction temperature below 15oC for a period of 15 minutes. The acid mixture then poured over crushed ice (25g), and waited for 5 minutes until the ice was completely melted. The product, after isolation by vacuum filtration, was washed with two portions of cold water (30mL) and ice-cold methanol (25mL). Recrystallization of product was carried out with minimum amount of solvent methanol, which resulted in the final product of methyl m-nitrobenzoate (3.84g, 0.0212mol), with the percent yield of
Linh Ngoc Thuy Nguyen
Seattle Central Community College
Professor: Dr. Esmaeel Naeemi
Date: February 21st, 2012
Abstract
In this experiment, methyl-m-nitrobenzoate, followed the electrophilic addition of aromatic ring, would be formed from the starting material methyl benzoate and nitric acid, under the catalysis of concentrated sulfuric acid. The reaction between nitric acid and sulfuric acid resulted in the formation of nitronium ion NO2+. It then acted as strong electrophile that nitrated the benzene ring. After that, vacuum filtration and recrystallization were methods used to obtain the final product with minimal impurities. The mass of product …show more content…
First, nitronium ion is made by the reaction between nitric acid and sulfuric acid, with sulfuric acid acting as a protonated reagent. The nitronium ion is a strong electrophile that can react with benzene ring to form the arenium ion intermediate, despite the fact that it can temporarily lose its stability provided by the resonances. After that, it regains its stability by deprotonating the intermediate and yields the final product, in this case is methyl-m-nitrobenzoate. This experiment will be carried out under controlled temperature of 15oC or lower, since higher temperature will result in the second nitro group addition. In this experiment, student will observe the mechanism of electrophilic aromatic substitution reaction through the nitration of methyl …show more content…
The mixture was then cooled to 0oC or below using ice-salt bath before adding slowly 1-1 ratio concentrated sulfuric acid and concentrated nitric acid (4mL). The mixture was stirred continuously to maintain the reaction temperature below 15oC for a period of 15 minutes. The acid mixture then poured over crushed ice (25g), and waited for 5 minutes until the ice was completely melted. The product, after isolation by vacuum filtration, was washed with two portions of cold water (30mL) and ice-cold methanol (25mL). Recrystallization of product was carried out with minimum amount of solvent methanol, which resulted in the final product of methyl m-nitrobenzoate (3.84g, 0.0212mol), with the percent yield of