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Questions and Answers
What compound is methyl salicylate primarily synthesized from?
What compound is methyl salicylate primarily synthesized from?
- Wintergreen plant extract
- Salicylic acid (correct)
- Methanol
- Aspirin
Methyl salicylate has identical medicinal properties to salicylic acid.
Methyl salicylate has identical medicinal properties to salicylic acid.
True (A)
What is the main purpose of using vacuum distillation in the synthesis of methyl salicylate?
What is the main purpose of using vacuum distillation in the synthesis of methyl salicylate?
To purify high-boiling liquids without decomposition.
The esterification reaction for methyl salicylate requires an excess of __________ to shift the equilibrium.
The esterification reaction for methyl salicylate requires an excess of __________ to shift the equilibrium.
Match the following terms with their descriptions:
Match the following terms with their descriptions:
What effect does applying methyl salicylate to the skin have?
What effect does applying methyl salicylate to the skin have?
Methyl salicylate can be absorbed internally or through the skin.
Methyl salicylate can be absorbed internally or through the skin.
What was methyl salicylate first isolated from?
What was methyl salicylate first isolated from?
What is the primary purpose of adding concentrated sulfuric acid to the mixture during the experiment?
What is the primary purpose of adding concentrated sulfuric acid to the mixture during the experiment?
Isopentyl acetate is also known as banana oil due to its odor.
Isopentyl acetate is also known as banana oil due to its odor.
What is the general procedure for isolating isopentyl acetate after the reaction?
What is the general procedure for isolating isopentyl acetate after the reaction?
The reaction of acetic acid and isopentyl alcohol produces isopentyl acetate and __________.
The reaction of acetic acid and isopentyl alcohol produces isopentyl acetate and __________.
What safety precaution should be taken when handling concentrated sulfuric acid?
What safety precaution should be taken when handling concentrated sulfuric acid?
Match the following materials with their roles in the experiment:
Match the following materials with their roles in the experiment:
The equilibrium of the esterification reaction favors the formation of isopentyl acetate without adjustments.
The equilibrium of the esterification reaction favors the formation of isopentyl acetate without adjustments.
During the experiment, glassware should be checked for __________ before starting the distillation process.
During the experiment, glassware should be checked for __________ before starting the distillation process.
Flashcards
Esterification
Esterification
A chemical reaction in which an alcohol and a carboxylic acid react to form an ester and water.
Distillation
Distillation
A chemical reaction where a compound is heated to its boiling point and the vapor is condensed and collected.
Vacuum Distillation
Vacuum Distillation
A type of distillation conducted at a pressure lower than atmospheric pressure, which allows for the distillation of substances with high boiling points at lower temperatures.
Reflux
Reflux
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Extraction
Extraction
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Methyl Salicylate (Oil of Wintergreen)
Methyl Salicylate (Oil of Wintergreen)
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Hydrolysis of Methyl Salicylate
Hydrolysis of Methyl Salicylate
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Salicylic Acid
Salicylic Acid
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Heating under reflux
Heating under reflux
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Simple distillation
Simple distillation
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Boiling point
Boiling point
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Drying
Drying
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Acetic acid
Acetic acid
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Study Notes
Methyl Salicylate (Oil of Wintergreen)
- Methyl salicylate is an ester with a pleasant odor, used as a flavoring agent and has analgesic/antipyretic properties.
- Synthesized by reacting salicylic acid with methanol.
- Esterification is an acid-catalyzed equilibrium reaction.
- A large excess of methanol is used to shift the reaction equilibrium towards the desired product.
- Vacuum distillation is used for purification as it lowers boiling point to avoid decomposition of the high-boiling ester.
Experimental Procedure
- The experiment requires starting the lab period early for the long reflux time needed in order to effectively esterify salicylic acid and produce a respectable yield.
- Use a 5-mL conical vial and a water-cooled condenser.
- 0.65 g of salicylic acid, 2.0 mL of methanol, and a spin vane are used with 0.75 mL of concentrated sulfuric acid.
- A white precipitate will form.
- Handle sulfuric acid carefully as it’s corrosive.
- Check glassware for flaws before starting distillation.
- Combine products for the final vacuum distillation if needed.
- Dispose of aqueous extracts in designated containers.
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