Melting point of the product was ranged from 97-102*C what is the major product formed?

Part C: Miniscale Nitration of an Unknown Aromatic Compound Prepare an ice-salt bath in a 100- or 150-mL beaker on a magnetic stir plate. The tem- perature of the ice-salt bath should be-8Â°C Place 1 g of the aromatic compound in a 25-mL Erlenmeyer flask and add 2.25 mL of concentrated (18 M) sulfuric acid and a stir bar. Carefully place the flask in the icebath so it stays immersed and begin stirring. Pre- pare the nitrating solution by adding 0.75 mL of concentrated (18 M) sulfuric acid and 0.75 mL of concentrated (16 M) nitric acid to a clean, dry vial. Cool this mixture in the ice bath. With a Pasteur pipet, slowly add the cooled nitrating solution to the stirring solution containing the aromatic compound. The addition should take approximately 15 minutes. Adding the nitrating agent more rapidly will increase the amount of by-products and decrease the yield. After all the nitrating agent has been added, carefully remove the icebath. Continue stirring until the reaction has come to room temperature. Then let the reaction flask stand undisturbed for 15 minutes. Place 10 g of ice in a 50-mL beaker. With a Pasteur pipet, carefully transfer the reaction mixture to the beaker containing the ice. Rinse the flask with 5 mL of cold water. When the ice has melted, vacuum filter the crude crystals using a BÃ¼chner funnel. Wash the crystals with two 5-mL portions of cold water. Recrystallize the product. To select the recrystallization solvent, test small amounts of the crude product in methanol, 2-propanol, or other solvents. Alternatively, the instruc- tor may suggest an appropriate recrystallization solvent for the specific unknown. Let the crystals dry thoroughly before measuring the melting point. Record the mass of the dry product and calculate the percent yield. Determine the identity of the product based on the melting point. Melting points of the possible products are detailed in Table 12.2-1

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Miniscale nitration of methyl benzoate was performed in the lab:

Procedure below:

1. Prepare and ice bath in a 100mL beaker on a magnetic stir plate.

2. To a clean, dry 25 mL Erlenmeyer flask, add 1.0 mL of methyl benzoate via pipet.

3. Calculate the mass of methyl benzoate.

4. To the methyl benzoate, add 2.25 mL of concentrated (18M) sulfuric acid and a spin bar.

5. Carefully clamp the flask so that it is immersed in the ice bath and begin stirring.

6. Prepare the nitrating solution by adding 0.75mL of concentrated (18M) sulfuric acid and 0.75mL of concentrated (16M) nitric acid to a clean, dry vial.

7. Cool the mixture in a second ice bath.

8. With a Pasteur pipet, slowly add the cooled sulfuric acid-nitric acid solution to the stirred solution of methyl benzoate. *Addition should take approximately 15 minutes. Adding the nitrating agent more rapidly will increase the amount of by-products and decrease the yield

9. After all of the nitrating agent has been added, carefully remove the ice bath.

10. Continue stirring until the reaction has come to room temperature.

11. Then let the reaction flask stand undisturbed for 15 minutes.

12. Place 10 g of ice in a 100mL beaker.

13. With a Pasteur pipet, carefully transfer the reaction mixture to the beaker.

14. Rinse the flask with 5mL of cold water.

15. When the ice has melted, vacuum filter the crude crystals using a Buchner funnel.

16. Wash the crystals with 2 5mL portions of cold water and finally with 2 1.5mL of cold methanol.

17. The crude product can be recrystallized from methanol.

18. Record the mass of the dry product and calculate the yield.

QUESTION: What is the major product formed in this reaction? Justify your reasoning..

Hello I need help with calculating the theoretical yields. All the information are given below. The images of the equations couldn't be uploaded.

Nitration of Methyl benzoate, acetanilide and Competition

Experimental Procedure:

Nitration of Methyl Benzoate

A. Preparation of the Nitrating Agent

1. Support a small test tube in an Erlenmeyer flask.

2. Using the small plastic dropping bottles, add 20 drops of concentrated acetic acid, 40 drops of

concentrated sulfuric acid, and 16 drops of concentrated nitric acid.

3. Swirl the mixture and set aside to be used later.

B. Nitration of Methyl Benzoate

4. Place a magnetic stir bar in a 25 mL Erlenmeyer flask and add 0.2 g of methyl benzoate.

Methyl benzoate is a liquid so place the Erlenmeyer flask on the balance, zero the balance, and add drop wise until the mass is 0.2 g (record exact mass used if slightly different than 0.2 g).

5. Add 20 drops of concentrated acetic acid and 40 drops of concentrated sulfuric acid.

Place the flask in an ice bath (small beaker with some ice and a little water) and stir for several minutes to dissolve the methyl benzoate (a homogeneous solution is achieved).

While stirring, use a glass pipette to add the solution of the nitrating agent drop wise over 3 minutes.

Remove the reaction from the ice bath and stir for an additional 20 minutes.

After 20 minutes, add a few pieces of crushed ice directly to the reaction mixture.

After the ice has melted, slowly 5 mL of saturated sodium bicarbonate.

Collect the product using vacuum filtration and wash the final product with a 5 mL of cold water and allow it to dry under vacuum for several minutes.

Record the mass of the final product, measure the melting point, calculate the percent yield and obtain an IR spectrum.

Nitration of Methyl benzoate, acetanilide and Competition

Nitration of Acetanilide

A. Preparation of the Nitrating Agent

1. Support a small test tube in an Erlenmeyer flask.

2. Using the small plastic dropping bottles, add 20 drops of concentrated acetic acid, 40 drops of concentrated sulfuric acid, and 16 drops of concentrated nitric acid.

3. Swirl the mixture and set aside to be used later.

B. Nitration of Acetanilide

4. Place a magnetic stir bar in a 25 mL Erlenmeyer flask and add 0.2 g of acetanilide.

5. Add 20 drops of concentrated acetic acid and 40 drops of concentrated sulfuric acid.

6. Place the flask in an ice bath (small beaker with some ice and a little water) and stir for several minutes to dissolve the acetanilide.

7. While stirring, use a glass pipette to add the solution of the nitrating agent drop wise over 3 minutes.

Remove the reaction from the ice bath and stir for an additional 20 minutes.

After 20 minutes, add a few pieces of crushed ice directly to the reaction mixture.

After the ice has melted, slowly 5 mL of saturated sodium bicarbonate.

Collect the product using vacuum filtration and wash the final product with a 5 mL of cold water and allow it to dry under vacuum for several minutes.

Record the mass of the final product, measure the melting point, calculate the percent yield and obtain an IR spectrum.

Nitration of Methyl benzoate, acetanilide and Competition

Competition Experiment (Methyl Benzoate vs. Aectanilide)

A. Preparation of the nitrating agent

Support a small test tube in an Erlenmeyer flask.

Using the small plastic dropping bottles, add 2 drops of concentrated nitric acid, 10 drops of concentrated acetic acid, and 20 drops of concentrated sulfuric acid.

Gently swirl the mixture and set aside to be used later.

B. Competition Experiment

Set a 25 mL Erlenmeyer flask on the balance, zero the balance and add 0.1 g methyl benzoate (add this reagent first because it is a liquid).

Measure 0.1 g acetanilide (using weighing paper) and add this to the 25 mL Erlenmeyer flask containing the methyl benzoate.

Add 10 drops of concentrated acetic acid and 20 drops of concentrated sulfuric acid.

Place a magnetic stir bar in the flask and begin stirring.

Place the Erlenmeyer flask in an ice bath and add the solution of the nitrating agent drop wise over 5 minutes.

Remove the reaction from the ice bath and stir for an additional 10 minutes.

After 10 minutes, add a few pieces of crushed ice directly to the reaction mixture.

After the ice has melted, slowly 5 mL of saturated sodium bicarbonate.

Collect the product using vacuum filtration and wash the final product with a 5 mL of cold water and allow it to dry under vacuum for several minutes.

Record the mass of the final product, measure the melting point, calculate the percent

yield and obtain an IR spectrum.

Nitration of Methyl benzoate, acetanilide and Competition

Pre Lab Questions

1. Fill in the appropriate data in the tables below and calculate the theoretical yield. (Use

the amounts of materials that will be used from the experimental section above)

Molecular Weight
amount				Theoretical yield
moles
density/concentration (if applicable)
Equivalents

Molecular Weight
amount				Theoretical yield
moles
density/concentration (if applicable)
Equivalents

2. Look up the melting point of methyl-2-nitrobenzoate, methyl-3-nitrobenzoate, methyl-

4-nitrobenzoate, 2-nitroacetanilide, and 4-nitroacetanilide (and record the reference(s)

used)

3. Which product is expected from the nitration of methyl benzoate based on the directing

nature of the ester?

4. Based on the predicted reactivities of methyl benzoate compared to acetanilide, what

product is expected from the competition experiment.

This is the only info I get

Organic Chemistry Laboratory II EXPERIMENTAL PROCEDURE . Borrow a stir bar from the instructor 2. Place 3.3 g of acetanilide into a 125-mL Erlenmeyer flask and then add 5 is of p-Nitroacetanilide mL of glacial (concentrated) acetic acid (CAUTION: strong irritant). Warm the flask on a hot plate in the hood until the acetanilide dissolves. Cool the flask in an ice bath to about 20Â°C; then add 5 mL of cold, concentrated sulfuric acid. The temperature of the mixture will rise to about 60Â°C. Chill the solution to about 10Â°C in an ice bath. (The solution may become very viscous.) 3. Mix 1.8 mL of concentrated nitric acid and 2.5 mL of concentrated sulfuric acid in a 50-mL Erlenmeyer flask (CAUTION: Use extreme care when preparing this nitrating mixture), and chill the flask in an ice bath for~4 minutes 4. When both solutions are cold, slowly add the nitrating mixture, 1 mL at a time, to the constantly stirred acetanilide solution. Keep the reaction flask in an ice bath so that the temperature of the reaction mixture is maintained between 10 - 20Â°C. The entire addition requires about 15 minutes. 5. After the addition is completed, allow the reaction to proceed at room temperature for 30 minutes (keep the stirrer going). Monitor the temperature; if it rises above 30Â°C, chill the flask in an ice bath to just below 30Â°C. Should the re-chilling be necessary, allow the reaction to proceed for an additional 10 minutes. 6. Pour the reaction mixture into a 250-mL beaker containing 50 mL of water and about 15 g of cracked ice. Stir the mixture for a minute or so during this time a light yellow solid should form. [If a white solid forms, then you have recovered unreacted acetanilide. If a dark yellow or yellow-orange solid is recovered, then the product has undergone hydrolysis. Should any of these two things occur, you must start the reaction all over again - consult with your instructor if you are unsure about the color.] 7. Vacuum filter the solution. Press down on the light yellow solid with a clean 50 mL beaker or Erlenmeyer flask to remove as much of the aqueous solution as possible. (CAUTION: Nitro compounds are toxic and can be absorbed through the skin.)

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