Nitration Lab Report

Lab report for a nitration synthesis.

Course

Organic Chem Lab (CHEM 145)

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University

Howard University

Academic year: 2018/2019

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Introduction A Nitration reaction is an electrophilic aromatic substitution where a nitro group is added to a benzene ring. Nitric acid is converted to a nitro group by sulfuric acid, a catalyst, and then the nucleophilic benzene ring attacks the nitro group. While nitration reactions do not usually occur in nature, the are important steps in the synthesis of dyes and pharmaceutical agents. 1

Abstract The nitration reaction of methyl benzoate and nitric acid was carried out using techniques of vacuum filtration and recrystallization, and melting point and TLC analyses were performed. 2 Methyl 3-nitrobenzoate was formed in 71% yield, with a melting point of 75-78°C, and a Rf of 0. Experimental Sulfuric acid in the amount of mL was chilled in an ice bath and then added to 3 g (0 mol) of methyl benzoate. A cooled mixture of sulfuric acid and 3 g (0 mol) of nitric acid was added dropwise to the sulfuric acid and methyl benzoate mixture. The resulting mixture warmed to room temperature, then was added to ice and filtered using vacuum filtration. The product was washed with ice cold methanol, and a small sample of this crude product was saved for analysis. The rest was recrystallized in 3 g of methanol. The purified product was filtered again by vacuum filtration and washed with cold methanol. 2 The product was collected and weighed, with

2 g (71% yield) of methyl 3-nitrobenzoate formed. The melting point of the crude product was 71-75°C (lit. 2 74-76°C) and the melting point of the recrystallized product was 75-78°C (lit. 2 78°C). A TLC analysis was also performed, the Rf of the crude product was 0, and the Rf of the recrystallized product was 0. Reagents, Product, and Yield

Table 1

Compound MW Density Amt. Used # of Moles mp/bp

Methyl Benzoate 136 1 3 g 0022 -13/198-199 °C Nitric Acid 63 1 3 g 0 -42/83 °C Methyl 3-Nitrobenzoate 181 3 g 0 78/279 °C

Limiting reagent is methyl benzoate.

Results and Discussion Methyl benzoate and nitric acid reacted to produce methyl 3-nitrobenzoate with a 71% yield. Melting point analysis of the product showed that it was pure, as the range matched closely with the expected value. TLC analysis also led the conclusion that the correct product was formed, as

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Introduction

A Nitration reaction is an electrophilic aromatic substitution where a nitro group is added to a

benzene ring. Nitric acid is converted to a nitro group by sulfuric acid, a catalyst, and then the

nucleophilic benzene ring attacks the nitro group. While nitration reactions do not usually occur

in nature, the are important steps in the synthesis of dyes and pharmaceutical agents.1

Abstract

The nitration reaction of methyl benzoate and nitric acid was carried out using techniques of

vacuum filtration and recrystallization, and melting point and TLC analyses were performed.2

Methyl 3-nitrobenzoate was formed in 71% yield, with a melting point of 75-78°C, and a Rf of

0.5.

Experimental

Sulfuric acid in the amount of mL was chilled in an ice bath and then added to 3 g (0.022 mol)

of methyl benzoate. A cooled mixture of sulfuric acid and 3.02 g (0.048 mol) of nitric acid was

added dropwise to the sulfuric acid and methyl benzoate mixture. The resulting mixture warmed

to room temperature, then was added to ice and filtered using vacuum filtration. The product was

washed with ice cold methanol, and a small sample of this crude product was saved for analysis.

The rest was recrystallized in 3.5 g of methanol. The purified product was filtered again by

vacuum filtration and washed with cold methanol.2 The product was collected and weighed, with



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Nitration Lab Report

Organic Chem Lab (CHEM 145)

Howard University

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