Nitration Of Methyl Benzoate Lab
Lab 8- nitration of Methyl I Benzonate
Date of experiment:
INTRODUCTION:
The nitration of methyl benzoate is an example of an electrophilic aromatic substation reaction. In the experiment the electrophile was the nitronium ion and the aromatic compound was methyl benzoate and with addition of nitrating solution Methyl 3-nitrobenzoate was the product.
Methyl benzoate Methyl 3-nitrobenzoate
MATERIALS AND METHODOLOGY:
The procedures for this experiment were as followed according to Experiment 12.2: Nitration of Methyl I Benzoate: Part B. However, there were minor changes during this experiment.
We began the experiment by preparing an ice bath, that would maintain the flask cool. We then …show more content…
obtain the required amount of methyl benzoate (1mL) and concentrated (18 M) sulfuric acid (2.25 mL). We combined the two solutions on to the flask and place a spin bar. We then mixed the solution and stored the mixture in ice bath. The flask was secured with a clamp in the grid. In a separate flask prepare a second mixture. The nitrating solution was prepared by obtain the correct amount of concentrated (18 M) sulfuric acid (0.75 mL) the concentrated (16 M) nitric acid (0.75 mL). We mixed the solution and stored the mixture in ice bath. Once cooled, we slowing added the mixture of sulfuric acid and nitric acid to the mixture of methyl benzoate and sulfuric acid. The two mixtures needed to be added in a 15 minutes time frame. Once addition was over we removed the mixture from the ice and waited for the solution to reach room temperature while the solution was still stirring. Once the solution reached room temperature we let the solution to sit unstirred for about 15 minutes. In a clean beaker we measured 10.09 grams of ice, we the pour the solution on the ice. We then rinse the remaining solution with 5 mL of cold water. Once the ice melted we began to vacuum filter the product to collect the crystals that were formed from the product. We then began to wash the crystals on vacuum filter. We washed the crystals with 5mL of cold water two times and then with 1.5mL of cold methanol two times. The product was then recrystallized with the following steps. We began the recrystallization process by bringing 20 mL of methanol to boil. We then place the product in a clean beaker. At a this point the crystals were large. We slowly added the boiling methanol to the product beaker using a pipet. We then place solution in an ice bath to recrystallized the product. We then wash the crystals with only methanol. Once dry we were able to obtain the mass and the melting point, and the infrared spectrometry diagram.
RESULTS AND OBSERVATIONS: As described in the section above we began the experiment by adding 1mL of methyl benzoate with 2.25mL of concentrated sulfuric acid, and then mixed the solution and stored in an ice bath.
We then prepared the nitrating solution by mixing 0.75 mL of concentrated sulfuric acid and 0.75 mL of concentrated nitric acid. We then mixed the two solutions, the mixture of sulfuric acid and nitric acid to the mixture of methyl benzoate and sulfuric acid. When the nitrating solution was being added to the mixture o of methyl benzoate and concentrated sulfuric acid. There was a color change. The color change was from clear to light yellow. As we added more of the mixture the color change increased. The color change was due to the conversion of aromatic properties. The product from the ice and allow to reach room temperature while it was still mixing and then allow to sit still for 15 minutes. we then added the product in a beaker than contain 10 grams of ice. We then vacuum filter the product and wash the crystals with cold water and cold methanol. We then began the recrystallization process. During the recrystallization process, the product was a white chucky large crystals, when the boiling methanol was added there was a color change from white to yellow. The color change was due to the conversion of aromatic properties. We then place solution in an ice bath to recrystallize the product. At this point the crystals were sand like and white in color. We then wash the crystals with …show more content…
only methanol, the addition of methanol allows the product to dry faster. Once the product was dry we collect the results. We were able to obtain the mass and the melting point, and the infrared diagram. The mass that we were able to gather is 0.481 grams. The melting point was 69-72 °C and the infrared spectrometry diagram is shown in page 6. The black line indicated the starting reaction and the red line indicated the product.
Percent Yield: Methyl benzoate Methyl 3-nitrobenzoate
Methyl benzoate: limiting reagent because there is only one reactant
0.93g x = 0.0068 mol
0.0068 mole x = 1.23182 g Percent yield: = .7550 *100 = 75.50%
DISCUSSION AND CONCLUSION:
At the end of the experiment we had sand-like, grainy, white crystals of Methyl 3-nitrobenzoate. Our melting point was 69-72 °C, the literature melting point of pure Methyl 3-nitrobenzoate is 78°C. The variation of the melting point could is due to experimental errors. This could have been due to the filter not removing all impurities, thus causing a different melting point, or maybe we did not allow the product to completely dry.
At the end of the experiment we recovered a total 0.481 grams of Methyl 3-nitrobenzoate.
We were able to collect a total of 75.50% percent yield. Some of the loss of product could be due to the constant transfer of the solution. Throughout the experiment the solution was moved from the flask to the vacuum filter, and then to another flask some of the loss could have happen there. The infrared spectrometry results we can conclude that the substitution pattern of the product. The black line indicated the starting reaction and the red line indicated the product. For the most part of the diagram the lines line up except during the aromatic
substitution.
REFERENCES:
Schoffstall, Allen M., Barbara A. Gaddis, and Melvin L. Druelinger. “Experiment 12.2
Nitration of Methyl I Benzoate: Part B” Microscale and Miniscale Organic
Chemistry Laboratory Experiments. New York: McGraw-Hill Higher Education, 2004. N. pag. Print.
Date of experiment:
INTRODUCTION:
The nitration of methyl benzoate is an example of an electrophilic aromatic substation reaction. In the experiment the electrophile was the nitronium ion and the aromatic compound was methyl benzoate and with addition of nitrating solution Methyl 3-nitrobenzoate was the product.
Methyl benzoate Methyl 3-nitrobenzoate
MATERIALS AND METHODOLOGY:
The procedures for this experiment were as followed according to Experiment 12.2: Nitration of Methyl I Benzoate: Part B. However, there were minor changes during this experiment.
We began the experiment by preparing an ice bath, that would maintain the flask cool. We then …show more content…
obtain the required amount of methyl benzoate (1mL) and concentrated (18 M) sulfuric acid (2.25 mL). We combined the two solutions on to the flask and place a spin bar. We then mixed the solution and stored the mixture in ice bath. The flask was secured with a clamp in the grid. In a separate flask prepare a second mixture. The nitrating solution was prepared by obtain the correct amount of concentrated (18 M) sulfuric acid (0.75 mL) the concentrated (16 M) nitric acid (0.75 mL). We mixed the solution and stored the mixture in ice bath. Once cooled, we slowing added the mixture of sulfuric acid and nitric acid to the mixture of methyl benzoate and sulfuric acid. The two mixtures needed to be added in a 15 minutes time frame. Once addition was over we removed the mixture from the ice and waited for the solution to reach room temperature while the solution was still stirring. Once the solution reached room temperature we let the solution to sit unstirred for about 15 minutes. In a clean beaker we measured 10.09 grams of ice, we the pour the solution on the ice. We then rinse the remaining solution with 5 mL of cold water. Once the ice melted we began to vacuum filter the product to collect the crystals that were formed from the product. We then began to wash the crystals on vacuum filter. We washed the crystals with 5mL of cold water two times and then with 1.5mL of cold methanol two times. The product was then recrystallized with the following steps. We began the recrystallization process by bringing 20 mL of methanol to boil. We then place the product in a clean beaker. At a this point the crystals were large. We slowly added the boiling methanol to the product beaker using a pipet. We then place solution in an ice bath to recrystallized the product. We then wash the crystals with only methanol. Once dry we were able to obtain the mass and the melting point, and the infrared spectrometry diagram.
RESULTS AND OBSERVATIONS: As described in the section above we began the experiment by adding 1mL of methyl benzoate with 2.25mL of concentrated sulfuric acid, and then mixed the solution and stored in an ice bath.
We then prepared the nitrating solution by mixing 0.75 mL of concentrated sulfuric acid and 0.75 mL of concentrated nitric acid. We then mixed the two solutions, the mixture of sulfuric acid and nitric acid to the mixture of methyl benzoate and sulfuric acid. When the nitrating solution was being added to the mixture o of methyl benzoate and concentrated sulfuric acid. There was a color change. The color change was from clear to light yellow. As we added more of the mixture the color change increased. The color change was due to the conversion of aromatic properties. The product from the ice and allow to reach room temperature while it was still mixing and then allow to sit still for 15 minutes. we then added the product in a beaker than contain 10 grams of ice. We then vacuum filter the product and wash the crystals with cold water and cold methanol. We then began the recrystallization process. During the recrystallization process, the product was a white chucky large crystals, when the boiling methanol was added there was a color change from white to yellow. The color change was due to the conversion of aromatic properties. We then place solution in an ice bath to recrystallize the product. At this point the crystals were sand like and white in color. We then wash the crystals with …show more content…
only methanol, the addition of methanol allows the product to dry faster. Once the product was dry we collect the results. We were able to obtain the mass and the melting point, and the infrared diagram. The mass that we were able to gather is 0.481 grams. The melting point was 69-72 °C and the infrared spectrometry diagram is shown in page 6. The black line indicated the starting reaction and the red line indicated the product.
Percent Yield: Methyl benzoate Methyl 3-nitrobenzoate
Methyl benzoate: limiting reagent because there is only one reactant
0.93g x = 0.0068 mol
0.0068 mole x = 1.23182 g Percent yield: = .7550 *100 = 75.50%
DISCUSSION AND CONCLUSION:
At the end of the experiment we had sand-like, grainy, white crystals of Methyl 3-nitrobenzoate. Our melting point was 69-72 °C, the literature melting point of pure Methyl 3-nitrobenzoate is 78°C. The variation of the melting point could is due to experimental errors. This could have been due to the filter not removing all impurities, thus causing a different melting point, or maybe we did not allow the product to completely dry.
At the end of the experiment we recovered a total 0.481 grams of Methyl 3-nitrobenzoate.
We were able to collect a total of 75.50% percent yield. Some of the loss of product could be due to the constant transfer of the solution. Throughout the experiment the solution was moved from the flask to the vacuum filter, and then to another flask some of the loss could have happen there. The infrared spectrometry results we can conclude that the substitution pattern of the product. The black line indicated the starting reaction and the red line indicated the product. For the most part of the diagram the lines line up except during the aromatic
substitution.
REFERENCES:
Schoffstall, Allen M., Barbara A. Gaddis, and Melvin L. Druelinger. “Experiment 12.2
Nitration of Methyl I Benzoate: Part B” Microscale and Miniscale Organic
Chemistry Laboratory Experiments. New York: McGraw-Hill Higher Education, 2004. N. pag. Print.