Electrophilic Aromatic Substitution – Nitration of Bromobenzene
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Electrophilic Aromatic Substitution –
Nitration of Bromobenzene By: Ben Weyer
Chem 443 – Section 001
February 22, 2024
Introduction
The experiment for this lab is to nitrate bromobenzene to produce 4-bromo-nitrobenzene and separate its isomers using column chromatography.
Goal
Since the lab is split into two parts, there are multiple goals involved with this experiment. The goal of part 1 of this experiment is the nitration of bromobenzene to produce 4-bromo-
nitrobenzene. The goal of Part 2 is to separate the bromonitrobenzene isomers obtained from Part 1 using column chromatography. These products collected are then to be further characterized with methods such as M.P. characterization, TLC, % yield, and IR and 1H NMR.
Significance
In the field of chemistry, fundamental techniques like nitration, recrystallization, and chromatography are essential for creating and purifying organic compounds used in pharmaceuticals, materials science, and other industries. These skills also play a role in drug development by synthesizing and purifying new drug candidates for medical testing. The experiment also introduces techniques like Thin-Layer Chromatography (TLC) and melting point
determination, which are important in analytical chemistry for identifying and characterizing chemical substances in various industries, including pharmaceuticals and environmental monitoring. Overall, it provides students with practical skills applicable in research, industry, and
environmental science, while fostering critical thinking and laboratory safety skills.
Reaction Scheme
Reaction Mechanism
Procedure
Part 1: nitration of bromobenzene
1.
Prepare a solution of 4.0 mL concentrated nitric acid and 4.0 mL concentrated sulfuric acid in a 25 mL round-bottom flask. Cool the flask to room temperature with a water bath.
2.
Insert a magnetic stir bar into the round-bottom flask and attach a Claisen adapter, thermometer, and condenser.
3.
In portions of about 0.5 mL, add 4.5 mL of bromobenzene through the top of the condenser for 10 minutes. Maintain the temperature below 50-55°C during the addition.
4.
After the addition is complete, heat the stirred mixture for 15 minutes, keeping the temperature just below 60°C.
5.
After, cool the reaction mixture to room temperature and then pour the solution into 40 mL of cold water in a 250 mL beaker.
6.
Isolate the mixture of crude bromonitrobenzenes by vacuum filtration.
7.
Wash the filtered solid thoroughly with cold water until the washes are neutral to pH paper.
8.
Continue to vacuum until the solid is dry. Remove a spatula tip of the sample (the size of a fruit fly) and transfer it to a test tube – this will be used later as a 'crude solid'.
9.
Transfer the solid to an Erlenmeyer flask and recrystallize it with 95% ethanol.
10. Cool the recrystallization mixture first to room temperature and then further to 0°C with an ice-water bath.
11. Isolate the solid product by vacuum filtration.
12. Wash the product with cold 95% ethanol and then allow the solid 4-bromonitrobenzene to dry on a watch glass.
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