1. The actual substitution of the methoxy group in methyl salicylate with the hydroxyl group in...
1. The actual substitution of the methoxy group in methyl salicylate with the hydroxyl group in salicylic acid requires one hydroxide ion, but in all actuality, a minimum of two equivalents of hydroxide ion are required for every one equivalent of the ester in order to achieve the theoretical yield. Explain why.
2.Why does the addition of sulfuric acid to the crude reaction mixture result in the precipitation of the product? Write a balanced reaction equation showing the chemistry that is occurring.
Homework Answers
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1. The actual substitution of the methoxy group in methyl
salicylate with the hydroxyl group in...
When salicylic acid combines with methanol it becomes the ester known as methyl salicylate or oil...
When salicylic acid combines with methanol it becomes the ester known as methyl salicylate or oil of wintergreen. This esterification is generally catalyzed by sulfuric acid in the presence of heat. 1.) If you couldn’t use sulfuric acid, would there be any other ways to speed up the reaction (heat, pressure, radiation, ultrasound, etc)? 2.) What other acids might work as a catalyst? 3.) Would carbonic acid catalyze the esterification? Why or why not?
PREPARATION OF PHARMACEUTICALS - Fischer Esterification Reactions Q: Calculate the expected mass of both methyl salicylate and aspirin assuming 100% yield. EXPERIMENT7 PREPARATION OF PHARMACEUTICALS...
PREPARATION OF PHARMACEUTICALS - Fischer Esterification
Reactions
Q: Calculate the expected mass of both methyl salicylate and
aspirin assuming 100% yield.
EXPERIMENT7 PREPARATION OF PHARMACEUTICALS Fischer Esterification Reactions Almost 2500 years ago, physicians such as Hippocrates recommended that patients chew on the bark of the willow to alleviate pain. The active ingredient in willow bark was found to be salicin, a compound made of a molecule of salicyl alcohol bonded to a p-D-glucose molecule. In the stomach, the bond between...
EXPERIMENT 20 CSI: SMU Part 2. Synthesis of an Ester. Esters are compounds of the form...
EXPERIMENT 20 CSI: SMU Part 2. Synthesis of an Ester. Esters are compounds of the form RCOOR'. They occur naturally in many plants and animals, and can be synthesized. They have a pleasant aroma usually described as "fruity of flowery". In a Fisher esterification an ester is formed from the reaction of a carboxylic acid and an alcohol with a strong acid as a catalyst. The OH contained in the carboxylic acid group 1s replaced with the alkoxy group (O-R")...
Question 1 What is the mechanism of the synthesis of methyl salicylate? esterification Sn1 SnAcyl AnE Question 2 Which compound is responsible for the burnt-fat odor in the test for gly...
Question 1 What is the mechanism of the synthesis of methyl salicylate? esterification Sn1 SnAcyl AnE Question 2 Which compound is responsible for the burnt-fat odor in the test for glycerol? glycerol acrolein acetic acicd o fatty acid Question 3 Which of the following reagents is NOT used for the synthesis of methyl salicylate? o acetic acid methanol salicylic acid sulfuric acid Question 4 Which of the following chemically define a soap? salt of a thoester salt of a carboxylic...
Preparation of Aspirin, Methyl Salicylate and Nylon Experiment #9 Pre-Lab Exercise Briefly describe the difference between...
Preparation of Aspirin, Methyl Salicylate and Nylon Experiment #9 Pre-Lab Exercise Briefly describe the difference between an acid and an ester. Give an example of each. 2. Show the chemical reaction for the hydrolysis of the ester, ethyl acetate, indicating the two products of this reaction. 3. Describe what is meant by an amide, showing the structure of at least one example of a compound that is an amide. Be sure to give the correct name of the compound you...
question 2 and 6 thabk you Exercises 1. (a) Calculate the volume of 6 M NaOH...
question 2 and 6 thabk you
Exercises 1. (a) Calculate the volume of 6 M NaOH required to react completely with the amount of methyl salicylate you used. How much of the 6 M NaOH that you used was in excess of the theoretical amount? (b) What volume of 3 M H SO is needed to neutralize all of the disodium salicylate and the excess NaOH present after the initial reaction? How much sulfuric acid was in excess? 2. Refer...
Calculate the theoretical yield and percent yield for experiments 7, 8, and 9. For experiment 9,...
Calculate the theoretical yield and percent yield for
experiments 7, 8, and 9. For experiment 9, determine the
theoretical yield based on starting with 0.50g of 3-nitrobenzoic
acid. Show work
Acid I (experiment 7): Weight of methyl 3-nitrobenzoate = 1.9
g
Acid II (experiment 8): Weight of 3-nitrobenzoic acid = 1.75
g
Acid III (experiment 9): Weight of 3-nitrobenzamide = 0.30 g
Experiment 7:
-2.5 mL concentrated H2SO4
-1.75 mL concentrated HNO3 (16M)
-2.1 mL concentrated Methyl Benzoate
Experiment 8:...
Exercise 7: The % Yield of Aspirin Name Date Read Exercise 7 in your lab manual....
Exercise 7: The % Yield of Aspirin Name Date Read Exercise 7 in your lab manual. Complete the Pre-lab Assignment. In this substitute lab exercise, you will watch a short video on preparing aspirin. The video is posted on the course Moodle page, and it provides the masses of the reactants and the product; you should be able to calculate the theoretical yield and the % yield from the data given by the video. Submit the completed assignment by March...
4-chloro-2-methyl-2-pentene reacts with acetic acid (solvent), two substitution products are urmea, with the rearranged product predominating...
4-chloro-2-methyl-2-pentene reacts with acetic acid (solvent), two substitution products are urmea, with the rearranged product predominating as shown in the diagram that follows. When small amounts of acetate ion are added to the reaction mixture, no increase in the rate is observed. Propose a mechanism that accounts for these results. Explain clearly why two products are formed (5 points) Minor Major
CH3OH H-SO methyl salicylate acetylsalicylic acid NaOH aq. EtoH benzaldehyde acetone dibenzylideneacetone (dba) 2....
CH3OH H-SO methyl salicylate acetylsalicylic acid NaOH aq. EtoH benzaldehyde acetone dibenzylideneacetone (dba) 2. For reactions where there is chemical equilibrium between reactants and products, a common way to increase yields is to apply Le Châtelier's Principle, and increase the amount of one reactant. This is particularly useful when one reactant is a cheap liquid that can be used as a solvent or co-solvent. Each of the two reactions shown (unbalanced) above employs a cheap organic liquid (methanol or acetone)...
PREPARATION OF PHARMACEUTICALS - Fischer Esterification
Reactions
Q: Calculate the expected mass of both methyl salicylate and
aspirin assuming 100% yield.
EXPERIMENT7 PREPARATION OF PHARMACEUTICALS Fischer Esterification Reactions Almost 2500 years ago, physicians such as Hippocrates recommended that patients chew on the bark of the willow to alleviate pain. The active ingredient in willow bark was found to be salicin, a compound made of a molecule of salicyl alcohol bonded to a p-D-glucose molecule. In the stomach, the bond between...
EXPERIMENT 20 CSI: SMU Part 2. Synthesis of an Ester. Esters are compounds of the form RCOOR'. They occur naturally in many plants and animals, and can be synthesized. They have a pleasant aroma usually described as "fruity of flowery". In a Fisher esterification an ester is formed from the reaction of a carboxylic acid and an alcohol with a strong acid as a catalyst. The OH contained in the carboxylic acid group 1s replaced with the alkoxy group (O-R")...
Question 1 What is the mechanism of the synthesis of methyl salicylate? esterification Sn1 SnAcyl AnE Question 2 Which compound is responsible for the burnt-fat odor in the test for glycerol? glycerol acrolein acetic acicd o fatty acid Question 3 Which of the following reagents is NOT used for the synthesis of methyl salicylate? o acetic acid methanol salicylic acid sulfuric acid Question 4 Which of the following chemically define a soap? salt of a thoester salt of a carboxylic...
Preparation of Aspirin, Methyl Salicylate and Nylon Experiment #9 Pre-Lab Exercise Briefly describe the difference between an acid and an ester. Give an example of each. 2. Show the chemical reaction for the hydrolysis of the ester, ethyl acetate, indicating the two products of this reaction. 3. Describe what is meant by an amide, showing the structure of at least one example of a compound that is an amide. Be sure to give the correct name of the compound you...
question 2 and 6 thabk you
Exercises 1. (a) Calculate the volume of 6 M NaOH required to react completely with the amount of methyl salicylate you used. How much of the 6 M NaOH that you used was in excess of the theoretical amount? (b) What volume of 3 M H SO is needed to neutralize all of the disodium salicylate and the excess NaOH present after the initial reaction? How much sulfuric acid was in excess? 2. Refer...
Calculate the theoretical yield and percent yield for
experiments 7, 8, and 9. For experiment 9, determine the
theoretical yield based on starting with 0.50g of 3-nitrobenzoic
acid. Show work
Acid I (experiment 7): Weight of methyl 3-nitrobenzoate = 1.9
g
Acid II (experiment 8): Weight of 3-nitrobenzoic acid = 1.75
g
Acid III (experiment 9): Weight of 3-nitrobenzamide = 0.30 g
Experiment 7:
-2.5 mL concentrated H2SO4
-1.75 mL concentrated HNO3 (16M)
-2.1 mL concentrated Methyl Benzoate
Experiment 8:...
Exercise 7: The % Yield of Aspirin Name Date Read Exercise 7 in your lab manual. Complete the Pre-lab Assignment. In this substitute lab exercise, you will watch a short video on preparing aspirin. The video is posted on the course Moodle page, and it provides the masses of the reactants and the product; you should be able to calculate the theoretical yield and the % yield from the data given by the video. Submit the completed assignment by March...
4-chloro-2-methyl-2-pentene reacts with acetic acid (solvent), two substitution products are urmea, with the rearranged product predominating as shown in the diagram that follows. When small amounts of acetate ion are added to the reaction mixture, no increase in the rate is observed. Propose a mechanism that accounts for these results. Explain clearly why two products are formed (5 points) Minor Major
CH3OH H-SO methyl salicylate acetylsalicylic acid NaOH aq. EtoH benzaldehyde acetone dibenzylideneacetone (dba) 2. For reactions where there is chemical equilibrium between reactants and products, a common way to increase yields is to apply Le Châtelier's Principle, and increase the amount of one reactant. This is particularly useful when one reactant is a cheap liquid that can be used as a solvent or co-solvent. Each of the two reactions shown (unbalanced) above employs a cheap organic liquid (methanol or acetone)...
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