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Fischer Esterification: Synthesis of Methyl Salicylate

 

 

Abstract

Paragraph or two summarizing the lab. Include balanced chemical equation. May include discussion about mix a carboxylic acid and an alcohol and an acid catalyst is required.

Introduction

1 page describing background of the lab, chemical equations, mechanisms, etc. Describe the lab.

Procedure

Safety glasses were worn at all times during the lab, and nitrile gloves were worn while handling chemicals.  2.76 g salicylic acid was placed in a round bottom flask.  The exact amount obtained was 2.758 grams.  1.2 mL concentrated sulfuric acid (H2SO4) and 3-4 boiling chips were added to a test tube and set aside.  Approximately 7 mL methanol was added to the round bottom flask.  Then the concentrated H2SO4 was added drop by drop to the round bottom flask.  A distillation column and connected to the reaction tube.  A clamp was used to attach the apparatus to the round bottom flask.  The round bottom flask was embedded into a sand bath.  The column was completely covered with a wet paper towel to prevent vapors from escaping. The sand bath was placed onto the hot plate in which the temperature setting was set at 6-7.  A low boil was desired and observed for approximately seventy minutes.  If the mixture turned cloudy, it was to be removed from the heat.  After seventy minutes the mixture was removed from the heat and transferred to a 100 mL beaker.  The beaker was placed into an ice bath for 30-40 seconds to cool to room temperature.  20% of Na2CO3 was added to the reaction mixture.  The organic solvent was to dissolve the product and the starting product is not desired as the reaction can be reversible.  This converts the acid to the base.  The Na2CO3 is mixed by using a pipette and was added until no effervesce was observed to indicate the CO2 has been removed from the mixture.  The mixture was then tested with pH paper.  Drops were added tot eh strip until it tested blue to indicate it’s basic.  Two centrifuge tubes were used to equally collect the product into two test tubes.  Approximately 8 mL of dichloromethane was placed in a graduated cylinder.  250 mL beaker was filled half way with water then placed on a hot plate and kept around 50-60 degrees Celsius.  The dichloromethane was split into each of the centrifuge tubes.  The centrifuge tube stopper was inverted to release the pressure.  The product was allowed to sit in order to allow the layers to separate.  The bottom layer was extracted and placed into a test tube.  Approximately 10-15% of anhydrous sodium sulfate was added to the test tube.  A clean test tube was used to measure the mass.  The mass of the test tube was 12.929 grams.  The bottom layer was removed and placed in a different test tube (not the test tube that was weighed).  The liquid was transferred to the weighed test tube.  A boiling stick was placed in the weighed test tube.  The test tube was placed into the warm water bath by attached a clamp to the test tube.  Instructed to not allow the product to boil over.  The temperature was kept around 50-60 degrees Celsius.  It test tube was held until it no longer boiled.  The final weight was 2.11 grams.

Results and Calculations

SubstanceAmount usedMolecular weights
Methyl salicylate2.11 g152.149 g/mole
Salicylic acid2.79 g138.121 g/mole

15.039 (Test tube and product) – 12.929 (test tube)= 2.11 weight of product

% yield= moles methyl salicylate/ moles salicylic acid *100

2.11 g methyl salicylate * 1mole/152.149 g= .01387 moles methyl salicylate

2.79 g salicylic acid * 1mole/138.121 g= .01998 moles salicylic acid

Theoretical yield= .01387/.01998= .6942 * 100=69.42%

Discussion and Conclusions

1 page discussing the results, describe what worked and what didn’t work, etc.

References

Williamson, K. L., & Masters, K. M. (2010). Macroscale and microscale organic experiments.Boston, Mass: Cengage Learning.

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