Aspirin Synthesis To 138 mg (0.001 mol) of salicylic acid in a dry reaction tube is...
Aspirin Synthesis
To 138 mg (0.001 mol) of salicylic acid in a dry reaction tube
is added 0.1 mL of pyridine (just sufficient to dissolve it)
while the tube rests in a cold water bath. One-tenth milliliter of
acetyl chloride (slight excess over 0.001 mol ) is added in one
portion. The mixture becomes viscous at this stage. The reaction
tube is allowed to stand in the cold water bath for 15 min. Then 5
mL of cold water is added and the mixture is shaken vigorously. It
turns cloudy. Shaking is continued until white product begins to
appear and at once separates. Crystals are filtered, washed with
cold water, and air dried. Recrystallization from aqueous ethanol
(50%) gives a yield of 33%, mp 133–135 °C.
1. Draw the mechanism of the reaction shown above (Arrow Mechanism) step by step.
Homework Answers
Add Answer to:
Aspirin Synthesis
To 138 mg (0.001 mol) of salicylic acid in a dry reaction tube
is...
a) Which products (shown above) from reaction 3 can react with HCl in an acid-base reaction?...
a) Which products (shown above) from reaction 3 can react with
HCl in an acid-base reaction? Show the mechanism for this acid-base
reaction and give the structures that would result from the
protonation of these products. Which phase (organic or aqueous)
would these protonated products be soluble in?
b) Which phase (organic or aqueous) would the
p-methylacetanilide be found in?
c) Why did we have to use hot ethanol for the
recrystallization?
d) Why did we have to cool the...
Calculate theoretical and percent yield. In this experiment, salicylic acid and acetic anhydride will be reacted...
Calculate theoretical and percent yield. In this experiment, salicylic acid and acetic anhydride will be reacted to form acetylsalicylic acid in an acid catalyzed reaction. In a reaction tube, add approx. 140 mg salicylic acid, a boiling chip and a small drop of 85% phosphoric acid. Add 0.3mL acetic anhydride, which should wash the reactants to the bottom of the tube. Mix thoroughly. Heat in a beaker of water at 90oC for 5 min. Cautiously add 0.2 mL water to...
Pre-lab Questions: Importance A one-step preparation of aspirin from its precursor, salicylic acid, via an ester...
Pre-lab Questions:
Importance A one-step preparation of aspirin from its precursor, salicylic acid, via an ester formation illustrates one of synthetic organic chemistry's most important uses, making the drugs that treat all types of illnesses. OH HOOH Background Aspirin is a prodrug of salicylic acid, the actual active drug. A compound related to salicylic acid, salicin, was first isolated from willow bark in the mid 1700's, but willow-bark extract was used by the ancient Greeks as a treatment for pain...
a) Which products (shown above) from reaction 3 can react with HCl in an acid-base reaction?...
a) Which products (shown above) from reaction 3 can react with
HCl in an acid-base reaction? Show the mechanism for this acid-base
reaction and give the structures that would result from the
protonation of these products. Which phase (organic or aqueous)
would these protonated products be soluble in?
b) Which phase (organic or aqueous) would the
p-methylacetanilide be found in?
In step 5 of reaction 3, the reaction mixture containing the products shown below in ethyl acetate is extracted twice...
SYNTHESIS OF trans-p-ANISALACETOPHENONE Prepare a table of all chemicals used in the procedure with their purpose...
SYNTHESIS OF trans-p-ANISALACETOPHENONE
Prepare a table of all chemicals used in the procedure with
their purpose
Melting point of trans-p-anisalacetophenone (with source) and
Molar mass of trans-p-anisalacetophenone (with source) (i cant find
these two things anywhere)
Procedure: 1. Carefully measure 1.0 mL each of p-anisaldehyde and acetophenone and place them in a screw-cap testtube. 2. To this add 3.0 mL of 95% ethanol. Shake the test tube gently to achieve a homogenous mixture. 3. Add 6-7 drops of 40% sodium...
PROCEDURE CAUTION!!! Nitric acid and sulfuric acid are strong and corrosive acids. For that reason, avoid...
PROCEDURE CAUTION!!! Nitric acid and sulfuric acid are strong and corrosive acids. For that reason, avoid inhaling its vapors or causing any contact with the skin or clothing. Wear your protective glasses at all times. Use the extractors to work with these acids. A. Nitration of methyl benzoate 1. Preparation of the reactants. In the extractor you will find a burette with concentrated sulfuric acid, a second burette with concentrated nitric acid, clearly identified. Familiarize yourself with the scales of...
Draw a mechanism for the acetylation of p-methylaniline in reaction 3. Reaction 3: Acetylation NH2 NH2...
Draw a mechanism for the acetylation of p-methylaniline
in reaction 3.
Reaction 3: Acetylation NH2 NH2 + NH2 (acetic anhydride) NH2 NH2 m-methylaniline p-methylaniline O-methylaniline m-methylaniline HN o-methylaniline O p-methylacetanilide Procedure for Reaction 3: 1) The solution of the three isomers of methylaniline in ethyl acetate was cooled to 0 °C. 2) An equimolar amount of acetic anhydride to the quantity of p-methylaniline theoretically present in the solution was added dropwise with stirring. 3) The stirring was continued for 15...
13. In step 5 of reaction 3, the reaction mixture containing the products shown below in...
13. In step 5 of reaction 3, the reaction mixture containing the products shown below in ethyl acetate is extracted twice with HCI. NH2 NH2 HN o-methylaniline m-methylaniline p-methylacetanilide a) Which products (shown above) from reaction 3 can react with HCl in an acid-base reaction? Show the mechanism for this acid-base reaction and give the structures that would result from the protonation of these products. Which phase (organic or aqueous) would these protonated products be soluble in? (6 points) b)...
are there any synthetic transformations produced in this lab Step 1. Preparation and Recrystallization of a...
are there any synthetic transformations produced in this
lab
Step 1. Preparation and Recrystallization of a Diastereomeric Salt - Synthesis of (R,R)-1,2-Diammoniumcyclohexane mono-(+)-tartrate: In a 150 ml beaker, L-(+)-Tartaric acid (7.5 g, 0.05 mol) is dissolved in 25 mL of distilled water. The solution is stirred as 11.4 g (12.2 mL, 0.10 mol) of 1,2-diaminocyclohexane is added carefully in one portion. (The addition of the diamine is exothermic.) A slurry is formed initially but complete dissolution is observed once addition...
That is the entire reaction and below is the question I need answered Reaction 3: Acetylation...
That is the entire reaction and below is the question I need
answered
Reaction 3: Acetylation NH2 NH2 (acetic anhydride) NH2 NH2 0-methylaniline NH2 m-methylaniline p-methylaniline HN o-methylaniline m-methylaniline 0 p-methylacetanilide Procedure for Reaction 3: 1) The solution of the three isomers of methylaniline in ethyl acetate was cooled to 0°C. 2) An equimolar amount of acetic anhydride to the quantity of p-methylaniline theoretically present in the solution was added dropwise with stirring. 3) The stirring was continued for 15...
a) Which products (shown above) from reaction 3 can react with
HCl in an acid-base reaction? Show the mechanism for this acid-base
reaction and give the structures that would result from the
protonation of these products. Which phase (organic or aqueous)
would these protonated products be soluble in?
b) Which phase (organic or aqueous) would the
p-methylacetanilide be found in?
c) Why did we have to use hot ethanol for the
recrystallization?
d) Why did we have to cool the...
Pre-lab Questions:
Importance A one-step preparation of aspirin from its precursor, salicylic acid, via an ester formation illustrates one of synthetic organic chemistry's most important uses, making the drugs that treat all types of illnesses. OH HOOH Background Aspirin is a prodrug of salicylic acid, the actual active drug. A compound related to salicylic acid, salicin, was first isolated from willow bark in the mid 1700's, but willow-bark extract was used by the ancient Greeks as a treatment for pain...
a) Which products (shown above) from reaction 3 can react with
HCl in an acid-base reaction? Show the mechanism for this acid-base
reaction and give the structures that would result from the
protonation of these products. Which phase (organic or aqueous)
would these protonated products be soluble in?
b) Which phase (organic or aqueous) would the
p-methylacetanilide be found in?
In step 5 of reaction 3, the reaction mixture containing the products shown below in ethyl acetate is extracted twice...
SYNTHESIS OF trans-p-ANISALACETOPHENONE
Prepare a table of all chemicals used in the procedure with
their purpose
Melting point of trans-p-anisalacetophenone (with source) and
Molar mass of trans-p-anisalacetophenone (with source) (i cant find
these two things anywhere)
Procedure: 1. Carefully measure 1.0 mL each of p-anisaldehyde and acetophenone and place them in a screw-cap testtube. 2. To this add 3.0 mL of 95% ethanol. Shake the test tube gently to achieve a homogenous mixture. 3. Add 6-7 drops of 40% sodium...
PROCEDURE CAUTION!!! Nitric acid and sulfuric acid are strong and corrosive acids. For that reason, avoid inhaling its vapors or causing any contact with the skin or clothing. Wear your protective glasses at all times. Use the extractors to work with these acids. A. Nitration of methyl benzoate 1. Preparation of the reactants. In the extractor you will find a burette with concentrated sulfuric acid, a second burette with concentrated nitric acid, clearly identified. Familiarize yourself with the scales of...
Draw a mechanism for the acetylation of p-methylaniline
in reaction 3.
Reaction 3: Acetylation NH2 NH2 + NH2 (acetic anhydride) NH2 NH2 m-methylaniline p-methylaniline O-methylaniline m-methylaniline HN o-methylaniline O p-methylacetanilide Procedure for Reaction 3: 1) The solution of the three isomers of methylaniline in ethyl acetate was cooled to 0 °C. 2) An equimolar amount of acetic anhydride to the quantity of p-methylaniline theoretically present in the solution was added dropwise with stirring. 3) The stirring was continued for 15...
13. In step 5 of reaction 3, the reaction mixture containing the products shown below in ethyl acetate is extracted twice with HCI. NH2 NH2 HN o-methylaniline m-methylaniline p-methylacetanilide a) Which products (shown above) from reaction 3 can react with HCl in an acid-base reaction? Show the mechanism for this acid-base reaction and give the structures that would result from the protonation of these products. Which phase (organic or aqueous) would these protonated products be soluble in? (6 points) b)...
are there any synthetic transformations produced in this
lab
Step 1. Preparation and Recrystallization of a Diastereomeric Salt - Synthesis of (R,R)-1,2-Diammoniumcyclohexane mono-(+)-tartrate: In a 150 ml beaker, L-(+)-Tartaric acid (7.5 g, 0.05 mol) is dissolved in 25 mL of distilled water. The solution is stirred as 11.4 g (12.2 mL, 0.10 mol) of 1,2-diaminocyclohexane is added carefully in one portion. (The addition of the diamine is exothermic.) A slurry is formed initially but complete dissolution is observed once addition...
That is the entire reaction and below is the question I need
answered
Reaction 3: Acetylation NH2 NH2 (acetic anhydride) NH2 NH2 0-methylaniline NH2 m-methylaniline p-methylaniline HN o-methylaniline m-methylaniline 0 p-methylacetanilide Procedure for Reaction 3: 1) The solution of the three isomers of methylaniline in ethyl acetate was cooled to 0°C. 2) An equimolar amount of acetic anhydride to the quantity of p-methylaniline theoretically present in the solution was added dropwise with stirring. 3) The stirring was continued for 15...
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