Esterification and Hydrolysis: Methyl Benzoate by Fisher Esterification
Esterification and Hydrolysis: Methyl Benzoate by Fisher Esterification
Nitration of Methyl Benzoate
Jingling Li
2/16/2014
Purpose of the experiment: To understand the mechanisms for Fisher esterification reactions as an equilibrium process and hydrolysis is the reversal reaction of esterification. Nitrate methyl benzoate by an electrophilic aromatic substitution reaction.
Summary of procedures: Add sulfuric acid to the mixture of benzoic and methanol, heat up the mixture to 65 oC. Transfer the mixture to the separatory funnel and add ether, sodium bicarbonate and saturated sodium chloride-brine solution, drain the bottom layer each time and remain ether layer. Decant the solution with calcium chloride,then evaporate the ether by steam bath and cool down. The product is methyl benzoate.
Pour methyl benzoate into cool concentrated sulfuric acid and keep the temperature below 10oC. Add concentrated sulfuric acid and nitrite acid to the mixture and raise temperature to room temperature. Pour the solution into ice bath, filtrate the solution wash by methanol. Finally crystallization the product.
Chemical equations:
Results:
Percent Yield and the results for esterification: mols of Benzoic acid = 10.0 g / 122.12 (M.W) = 0.0819 mols
Theoretical yield = 0.0819 mols * 136.15 (M.W of Methyl benzoate) = 11.14g
Actual collected 8.27 g of the methyl benzoate
Actual yield = 8.27g / 11.06g * 100% = 74.8%
Percent Yield for Nitration: mols of Methyl Benzoate = 10.0 g (what we started with/from previous week) / 136.15 (M.W) = .0734mols
Theoretical yield = .0734 * 181.15 (M.W of Methyl 3-nitrobenzoate) = 13.31g
Actual percent yield of crude product = 10.80g / 12.33g *100% = 81.14%
Melting point is from 72.0oC- 77.2oC.
Conclusion:
The mechanisms of the Fisher esterification reaction is an equilibrium process that takes place over a few hours of refluxing. This reaction involves an initial protonation of the carboxyl group, an attack by a nucleophilic
Nitration of Methyl Benzoate
Jingling Li
2/16/2014
Purpose of the experiment: To understand the mechanisms for Fisher esterification reactions as an equilibrium process and hydrolysis is the reversal reaction of esterification. Nitrate methyl benzoate by an electrophilic aromatic substitution reaction.
Summary of procedures: Add sulfuric acid to the mixture of benzoic and methanol, heat up the mixture to 65 oC. Transfer the mixture to the separatory funnel and add ether, sodium bicarbonate and saturated sodium chloride-brine solution, drain the bottom layer each time and remain ether layer. Decant the solution with calcium chloride,then evaporate the ether by steam bath and cool down. The product is methyl benzoate.
Pour methyl benzoate into cool concentrated sulfuric acid and keep the temperature below 10oC. Add concentrated sulfuric acid and nitrite acid to the mixture and raise temperature to room temperature. Pour the solution into ice bath, filtrate the solution wash by methanol. Finally crystallization the product.
Chemical equations:
Results:
Percent Yield and the results for esterification: mols of Benzoic acid = 10.0 g / 122.12 (M.W) = 0.0819 mols
Theoretical yield = 0.0819 mols * 136.15 (M.W of Methyl benzoate) = 11.14g
Actual collected 8.27 g of the methyl benzoate
Actual yield = 8.27g / 11.06g * 100% = 74.8%
Percent Yield for Nitration: mols of Methyl Benzoate = 10.0 g (what we started with/from previous week) / 136.15 (M.W) = .0734mols
Theoretical yield = .0734 * 181.15 (M.W of Methyl 3-nitrobenzoate) = 13.31g
Actual percent yield of crude product = 10.80g / 12.33g *100% = 81.14%
Melting point is from 72.0oC- 77.2oC.
Conclusion:
The mechanisms of the Fisher esterification reaction is an equilibrium process that takes place over a few hours of refluxing. This reaction involves an initial protonation of the carboxyl group, an attack by a nucleophilic