Nitration Lab

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  • Topic: Sulfuric acid, Nitric acid, Nitration
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  • Published : May 8, 2012
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Nitration of Methyl Benzoate
Date of Completion: February 29, 2012 Date Report Submitted: March 14, 2012 Objective of Experiment: The purpose of this experiment is was to synthesize methyl 3-nitro benzoate from methyl benzoate through an electrophilic aromatic substitution reaction. Chemical Equation:

Materials:
Name of Compound Molecular weight MP/BPGrams UsedMoles Used Methyl benzoate136.16 g/mol-12.5 OC /199.6 OC0.28g2.056*10-3 Sulfuric acid63.01 g/mol10 OC /337OC 0.8g1.2*10-2
Nitric acid98.08 g/mol-42 OC /83 OC 0.2g2.039*10-3
Methyl 3-nitro benzoate181.15 g/mol78 OC /279 OC 0.107g5.906*10-4

Procedural Details
To a reaction tube 0.6 mL of concentrated sulfuric acid was added; followed by 0.28g of methyl benzoate. Using a glass-stirring rod the contents was stirred. The mixture was then cooled to 0 OC where a mixture of 0.2mL of concentrated sulfuric acid and 0.2mL of concentrated nitric acid was added drop wise. The reaction was kept on ice and stirred with the addition of each drop of acid. Once all the acid had been added, the test tube containing the mixture was taken out of ice and allowed to sit for 15 minutes after having reached room temperature. In a small beaker, the content was poured in 2.5 grams of ice-cold water. Using a filter flask and a Hirsch funnel the product was isolated by suction filtration. The product was washed with water and then with one 0.2mL of ice-cold methanol. It was finally recrystallized, with an equal amount of methanol, allowed to dry and analyzed.

Results, Summary, and Conclusions:
Limiting Reagent is Methyl benzoate.
Theoretical yield
(.28g/136.16) * (181.15) = .3725g
Actual
.107g . (.107g/.3725g) * 100 = 28.7% of methyl 3-nitrobenzoate The methyl 3-nitrobenzoate that was collected weighted to be .107g. A melting point was preformed with a temperature range of . The final range was , this value was similar to the CRC manual. Answers to...
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