Methyl Salicylate Experiment Overview

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Questions and Answers

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.

True

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.

methanol Signup and view all the answers

Match the following terms with their descriptions:

Esterification = An acid-catalyzed equilibrium reaction Methyl Salicylate = Oil of Wintergreen Salicylic acid = Analgesic and antipyretic compound Vacuum Distillation = Technique for purifying high-boiling liquids Signup and view all the answers

What effect does applying methyl salicylate to the skin have?

It produces a tingling or soothing sensation. Signup and view all the answers

Methyl salicylate can be absorbed internally or through the skin.

True Signup and view all the answers

What was methyl salicylate first isolated from?

Wintergreen plant (Gaultheria) Signup and view all the answers

What is the primary purpose of adding concentrated sulfuric acid to the mixture during the experiment?

To act as a catalyst for the esterification Signup and view all the answers

Isopentyl acetate is also known as banana oil due to its odor.

True Signup and view all the answers

What is the general procedure for isolating isopentyl acetate after the reaction?

Extraction with sodium bicarbonate and water, followed by drying with anhydrous sodium sulfate and distillation. Signup and view all the answers

The reaction of acetic acid and isopentyl alcohol produces isopentyl acetate and __________.

water Signup and view all the answers

What safety precaution should be taken when handling concentrated sulfuric acid?

Wear safety glasses Signup and view all the answers

Match the following materials with their roles in the experiment:

Salicylic acid = Reactant Methylene chloride = Halogenated waste Anhydrous sodium sulfate = Drying agent Calcium chloride = Reaction assembly Signup and view all the answers

The equilibrium of the esterification reaction favors the formation of isopentyl acetate without adjustments.

False Signup and view all the answers

During the experiment, glassware should be checked for __________ before starting the distillation process.

flaws and cracks Signup and view all the answers

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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Description

This quiz covers the synthesis and properties of methyl salicylate, also known as oil of wintergreen. It highlights the experimental procedure for esterification, including the materials used and safety precautions. Test your knowledge on the concepts of esterification and the practical aspects of the experiment.