what effect would the following have on the reaction between salicylic acid and acetic anhydride? Support...
what effect would the following have on the reaction between
salicylic acid and acetic anhydride? Support your reasoning by
drawing the mechanism for the reaction and incorporating them in
the mechanism.
1. anhydride sodium acetate 2.pyridine 3. boron trifluoride and 4.
concentrated sulfuric acid
Homework Answers
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what effect would the following have on the reaction between
salicylic acid and acetic anhydride? Support...
Organic chemistry -Carboxylic acid homework Question: In the general chemistry lab, students synthesize aspirin from salicylic...
Organic chemistry -Carboxylic acid homework
Question: In the general chemistry lab, students synthesize
aspirin from salicylic acid and acetic anhydride. In the lab,
students use sulfuric acid as a catalyst, but I want to consider an
alternate method for synthesizing aspirin using sodium acetate as a
catalyst:
a. Draw the structure of sodium acetate. Is sodium acetate a
stronger or weaker base than sodium hydroxide (NaOH). Explain. (1.5
pts)
b. Consider the structure of salicylic acid. It contains two
potentially...
In the mechanism for formation of acetylsalicylic acid via reaction of salicylic acid with acetic anhydride,...
In the mechanism for formation of acetylsalicylic acid via reaction of salicylic acid with acetic anhydride, phosphoric acid acts as a catalyst by O cleaving an acetyl group from acetic anhydride via protonation of the bridging oxygen O neutralizing the hydroxide ion side product protonating the carbonyl oxygen in the acetic anhydride protonating the phenolic oxygen of salicylic acid Question 10 (3 points) What would be the predicted major product from the thermodynamically controlled dehydration of the following material OH
Mass of salicylic acid: 3.112g volume of acetic anhydride: 7.40ml Density of acetic anhydride = 1.08...
Mass of salicylic acid: 3.112g volume of acetic anhydride: 7.40ml Density of acetic anhydride = 1.08 g/ml molar mass of Salicylic acid in g/mol is 138.12 1. Calculate the moles of Salicylic acid used in the reaction: Round your to 4 significant fig: 2. Calculate the mass of acetic anhydride used in the reaction in g: Round to 3 sig. figures
1) Which reactant, salicylic acid or acetic anhydride, is in excess? Show your work. 2) If you we...
1) Which reactant, salicylic acid or acetic anhydride, is in
excess? Show your work.
2) If you were to use 3.17 g of starting material, how much
product would you expect? Again, show your work.
3) Why is phosphoric acid added to the reaction?
4) A small amount of water is added at the end of the reaction
to react with the excess acetic anhydride. Show a balanced equation
for that reaction.
5) Explain the purpose of the FeCl3 test...
H3PO4 OH + OH OH salicylic acid acetic anhydride acetic acid acetylsalicylic acid (aspirin) 1. Why...
H3PO4 OH + OH OH salicylic acid acetic anhydride acetic acid acetylsalicylic acid (aspirin) 1. Why is it better to perform acetylation with acetic anhydride rather than using a Fischer esterification with acetic acid? 2. Draw a complete arrow-pushing mechanism for the reaction. 3. When an old sample of aspirin is left in moist conditions, it will begin to smell like vinegar. Draw a reaction scheme and briefly explain what happened.
3. 0.69g of salicylic acid was reacted with 0.6g acetic anhydride in the presence of concentrated phosphoric acid...
3. 0.69g of salicylic acid was reacted with 0.6g acetic anhydride in the presence of concentrated phosphoric acid to yield 0.80g of acetyl salicylic acid (see below). Determine the limiting reagent and percent yield. C-CH OH COOH CH, COOH CHC Salicylic acid MW 138.12. mp 159C Acetic anhydride Acetylsalicylic acid M W 102.09. bp 140CMW 180.15. mp 128-1370 4. How do you account for the smell of vinegar when an old bottle of aspirin opened?
QUESTION 3 Salicylic acid reacts with acetic anhydride to form aspirin and acetic acid as shown. Use the equation to answer Questions 3 – 6. (salicylic acid) ...
QUESTION 3 Salicylic acid reacts with acetic anhydride to form aspirin and acetic acid as shown. Use the equation to answer Questions 3 – 6. (salicylic acid) (aspirin) C7H6O3 (s) + C4H6O3 (l) → C9H8O4 (s) + CH3COOH (l) MM = 138 MM = 180 If we divide 180 by 138 we find that 1.00 g salicylic acid will produce a maximum of 1.30 g aspirin. 3. A student starts with 3.20 g salicylic acid. What is the maximum amount...
1. What two functional groups are found in salicylic acid? 2. For the formation of aspirin,...
1. What two functional groups are found in salicylic acid? 2. For the formation of aspirin, salicylic acid is acting as an _ acetic anhydride as a and 3. Where should you dispose of acetic anhydride and concentrated sulfuric acid? 4. The purity of your sample is determined by testing it with ferric chloride. What should you observe if your sample is pure?
Salicylic acid and acetic anhydride are synthesized with phosphoric acid to catalyze the reaction to make...
Salicylic acid and acetic anhydride are synthesized with phosphoric acid to catalyze the reaction to make acetylsalicylic acid (aspirin). How will you know if you have successfully synthesized acetylsalicylic acid? What compound will you have if you did NOT successfully synthesize acetylsalicylic acid, and how can you confirm it?
1. Mass of salicylic acid (g) 2.0089 5.10ml & 2. Volume of acetic anhydride (mL) Limiting...
1. Mass of salicylic acid (g) 2.0089 5.10ml & 2. Volume of acetic anhydride (mL) Limiting reactant is (circle one): Salicylic Acid or Acetic Anhydride Calculation for Limiting Reactant: 3. Theoretical yield of aspirin (9) Calculation for Theoretical Yield of aspirin: 4. Mass of filter paper 0.3369 N 5. Mass of filter paper + aspirin 2.471g 6. Experimental Yield of aspirin (g) 7. Percent Yield Synthesis of Aspirin An early oral pain reliever, salicylic acid, was determined to cause stomach...
Organic chemistry -Carboxylic acid homework
Question: In the general chemistry lab, students synthesize
aspirin from salicylic acid and acetic anhydride. In the lab,
students use sulfuric acid as a catalyst, but I want to consider an
alternate method for synthesizing aspirin using sodium acetate as a
catalyst:
a. Draw the structure of sodium acetate. Is sodium acetate a
stronger or weaker base than sodium hydroxide (NaOH). Explain. (1.5
pts)
b. Consider the structure of salicylic acid. It contains two
potentially...
In the mechanism for formation of acetylsalicylic acid via reaction of salicylic acid with acetic anhydride, phosphoric acid acts as a catalyst by O cleaving an acetyl group from acetic anhydride via protonation of the bridging oxygen O neutralizing the hydroxide ion side product protonating the carbonyl oxygen in the acetic anhydride protonating the phenolic oxygen of salicylic acid Question 10 (3 points) What would be the predicted major product from the thermodynamically controlled dehydration of the following material OH
1) Which reactant, salicylic acid or acetic anhydride, is in
excess? Show your work.
2) If you were to use 3.17 g of starting material, how much
product would you expect? Again, show your work.
3) Why is phosphoric acid added to the reaction?
4) A small amount of water is added at the end of the reaction
to react with the excess acetic anhydride. Show a balanced equation
for that reaction.
5) Explain the purpose of the FeCl3 test...
H3PO4 OH + OH OH salicylic acid acetic anhydride acetic acid acetylsalicylic acid (aspirin) 1. Why is it better to perform acetylation with acetic anhydride rather than using a Fischer esterification with acetic acid? 2. Draw a complete arrow-pushing mechanism for the reaction. 3. When an old sample of aspirin is left in moist conditions, it will begin to smell like vinegar. Draw a reaction scheme and briefly explain what happened.
3. 0.69g of salicylic acid was reacted with 0.6g acetic anhydride in the presence of concentrated phosphoric acid to yield 0.80g of acetyl salicylic acid (see below). Determine the limiting reagent and percent yield. C-CH OH COOH CH, COOH CHC Salicylic acid MW 138.12. mp 159C Acetic anhydride Acetylsalicylic acid M W 102.09. bp 140CMW 180.15. mp 128-1370 4. How do you account for the smell of vinegar when an old bottle of aspirin opened?
1. What two functional groups are found in salicylic acid? 2. For the formation of aspirin, salicylic acid is acting as an _ acetic anhydride as a and 3. Where should you dispose of acetic anhydride and concentrated sulfuric acid? 4. The purity of your sample is determined by testing it with ferric chloride. What should you observe if your sample is pure?
1. Mass of salicylic acid (g) 2.0089 5.10ml & 2. Volume of acetic anhydride (mL) Limiting reactant is (circle one): Salicylic Acid or Acetic Anhydride Calculation for Limiting Reactant: 3. Theoretical yield of aspirin (9) Calculation for Theoretical Yield of aspirin: 4. Mass of filter paper 0.3369 N 5. Mass of filter paper + aspirin 2.471g 6. Experimental Yield of aspirin (g) 7. Percent Yield Synthesis of Aspirin An early oral pain reliever, salicylic acid, was determined to cause stomach...
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