Nitration of Methyl Benzoate
Abstract: This procedure demonstrates the nitration of methyl benzoate to prepare methyl m-nitrobenzoate. Methyl benzoate was treated with concentrated Nitric and Sulfuric acid to yield methyl m-nitrobenzoate. The product was then isolated and recrystallized using methanol. This reaction is an example of an electrophilic aromatic substitution reaction, in which the nitro group replaces a proton of the aromatic ring. Following recrystallization, melting point and infrared were used to identify and characterize the product of the reaction.
Purpose: The purpose of this experiment is to synthesize methyl nitrobenzoate from methyl benzoate, concentrated nitric acid, and concentrated sulfuric acid via an …show more content…
If the nitric acid/sulfuric acid mixture is added too quickly, the temperature of the reaction would rapidly increase and exceed 15 °C, therefore increasing the formation of ortho and para isomers of methyl m-nitrobenzoate. Thus, the yield of the desired product is reduced. By slowly adding the acid mixture, the formation of the side products is greatly reduced. 4. Interpret the infrared spectrum of methyl m-benzoate.
C-H stretch of the aromatic at 3100 cm-1, strong peak near 1750 cm-1 representing the carbonyl ester stretch, two NO2 stretches at 1520 cm-1 and 1300 cm-1, and an aromatic stretch near 1600 cm-1. 5. Indicate the product formed on nitration of each of the following compounds: a. Benzene: Nitrobenzene b. Toluene: