2-Methyl-2-propanol, (12.7 mL; d=0.79 g/ml) was reacted with30.0 mL of concentrated hydrochloric acid (d=1.19g/mL).
A total of 10.8 grams of pure 2-chloro-2-methylpropane wasobtained fromthe reaction. Complete the following: (C=12, H=1,O=16, Cl=35) (show your work)
1. Write the structural equation of this reaction.
2. Calculate the theoretical yield of this reaction
3. Calculate the percent yield of this reaction?
4. Calculate the Atomic economy and Experiment Atomiceconomy?
5. Calculate E-product
2-Methyl-2-propanol, (12.7 mL; d=0.79 g/ml) was reacted with30.0 mL of concentrated hydrochloric acid (d=1.19g/mL).
A total of 10.8 grams of pure 2-chloro-2-methylpropane wasobtained fromthe reaction. Complete the following: (C=12, H=1,O=16, Cl=35) (show your work)
1. Write the structural equation of this reaction.
2. Calculate the theoretical yield of this reaction
3. Calculate the percent yield of this reaction?
4. Calculate the Atomic economy and Experiment Atomiceconomy?
5. Calculate E-product
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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 |
| Molecular Weight | ||||||
| amount | Theoretical Yield | Theoretical Yield | ||||
| moles | ||||||
| density/conc | ||||||
| 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.
Procedure: Setting Up: Add 1.0 g of p-aminobenzoic acid and 10 mL of absolute ethanol to the round-bottom flask containing a stir bar. Stir the mixture until the solid is completely dissolved. Add 1 mL of concentrated [18M] sulfuric acid dropwise to the ethanolic solution of p-aminohenzoic acid, equip the flask with a condenser, and set up the apparatus for heating under reflux using the heating mantle. Reaction: Heat the mixture under gentle reflux for 30 min, stirring all the while. If any solid remains in the flask at this time, remove the flask from the heat source and allow the mixture to cool for 2-3 min. Add an extra 3 mL of ethanol and 0.5 mL of concentrated H2SO4, to the reaction flask and resume heating under reflux. After the reaction mixture becomes homogeneous, continue heating it under gentle reflux for another 30 min. For the experiment to succeed, it is important that all of the solids dissolve during the reflux period. Work-Up and Isolation: Allow the reaction mixture to cool to room temperature and then pour it into a beaker containing 30 mL of water. Basify the mixture to a pH of about 8 by slowly adding 10% aqueous sodium carbonate with stirring. Be careful in this step as frothing occurs during the neutralization. You should calculate beforehand the approximate volume of 10% aqueous sodium carbonate that will be required to neutralize the total amount of sulfuric acid you used. Collect the crude benzocaine that precipitates by vacuum filtration. Use three 10-mL portions of cold water to rinse the solid from the beaker and wash the filter cake. Air-dry the product. Purification: Weigh the crude product and recrystallize from methanol/water pair of solvents: Place the solid in a 50 mL Erlenmeyer flask. Add the minimum amount of hot methanol to dissolve it. Keep on a steam bath. Slowly add hot water to the solution using a disposable pipette just until the solution becomes cloudy and fails to clear up when it is swirled. To the hot solution on the steam bath add hot methanol, drop wise, until the turbidity or crystals just disappear. Allow the solution to cool to room temperature and then cool it in an ice-water bath for 10-15 min to complete crystallization. Isolate the crystals by vacuum filtration, wash them with 5-10 mL of cold water, and allow them to air-dry. Weigh the crystals and calculate the percentage yield.
True or False? When analyzing the IR spectra of starting material and product, a positive indication suggesting that the product was made would be the disappearance of a strong stretch between 1690-1740 cm-1.
|
Why is it important that all of the solids dissolve during the reflux period for you to obtain a good yield of product?
A. Because everything needs to be in solution for the reaction to happen to the fullest extent.
B. Because the product will be impure if the intermediate doesn't dissolve completely.
C. Because the ethanol will evaporate off if it's not dissolved.
D. All of the above
What is the gas that is evolved during neutralization?
A. O2
B. CO2
C. SO2
D. CO3
Why is it necessary to neutralize the reaction mixture to work up the product?
A. Because it is dangerous to work with an acidic solution.
B. Because after the addition of ethanol and sulfuric acid, the benzocaine exists as ammonia and must be protonated so that it becomes insoluble and collectable.
C. Because after the addition of ethanol and sulfuric acid, the benzocaine exists as a soluble carboxylic acid and must be neutralized so that it becomes insoluble and collectable.
D. Because after the addition of ethanol and sulfuric acid, the benzocaine exists as a soluble ammonium salt and must be neutralized so that it becomes insoluble and collectable.
If you end up adding 1.5 mL of concentrated sulfuric acid (18 M), how many mL of 10% aqueous sodium carbonate would be required to neutralize the reaction mixture?
A. 1.5 mL
B. 3 mL
C. 15 mL
D. 29 mL
What is the purpose of the sulfuric acid?
A. To catalyze the reaction.
B. To protonate the intermediate salt.
C. To protonate the ethanol.
D. To increase the pH of the reaction mixture.
What is the theoretical yield of the product?
A. 1.00 g
B. 2.98 g
C. 1.20 g
D. 10 mL