Lab Report & Lab Notes
Exp#: 7 Nitration of Methyl Benzoate
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, Chemistry Lab Report
Experiment #: 7
Title: Nitration of Methyl Benzoate
Purpose:
The purpose of the experiment is to perform a synthesis/nitration reaction of 3 nitro
methylbenzoate which serves as an example electrophilic aromatic substitution.
Procedure:
1. Dissolve 6.1g of methylbenzoate in concentrated sulfuric acid. We do this in an
ice bath because the dissolution process is exothermic.
2. Add 12mL of concentrated sulfuric acid in small portions at a time to the
methylbenzoate.
3. Check the temperature and make sure the mixture cools down to 5o or below.
4. Create a nitration mixture by mixing 4mL concentrated nitric and concentrated
sulfuric acid in an ice bath. Add the sulfuric acid at slowly with small quantities at
a time.
5. Keep the mixture on ice and continue to monitor the temperature.
6. Add the mixture of concentrated nitric and sulfuric acid very slowly over a period
of several minutes.
7. Once all the nitrating mixture has been added, remove the reaction from the ice
bath and allow it to warm to room temperature while it stirs.
8. Pour the reaction mixture over 50g of cracked ice and water in a beaker and
allow the product to precipitate. Mix the mixture.
9. Isolate the nitro methylbenzoate solid precipitate from the ice water mixture using
suction filtration. Pour the mixture through a Buchner funnel.
Data/Results/Calculations:
Mass yield of Nitro Methylbenzoate= 5.65g
Theoretical yield (from 6.19 g of methyl benzoate) = 8.23g
% yield = 68.7% (fair because >50, <70)
Visual appearance: off-white, pale yellow crystalline solid
▪ Nitro groups typically impart a pale-yellow color to organic compounds when they
are present.
Melting point data:
▪ Onset = 77.2o C
▪ Clear = 78.5o C
▪ Range = 1.3o C
▪ Spread is less than 2 degrees
▪ Literature MP: 78o C
▪ Ortho: 13oC, meta: 78o C, Para: 95o C
o Meta derivative is the major product from the reaction
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