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This is Sample Write up. It is not a template. Each experiment will have different requirements for reporting.

See Lab Policies and Procedures for the type of information that should be included in a lab report. The Synthesis of Salicylic Acid from Wintergreen Oil PRELAB Purpose: To Prepare salicylic acid from methyl salicylate. Properties: Compound Methyl salicylate mw g/mol 152.15 Mp oC -8 Bp oC 224226 211 Density g/mL 1.174 Solubility Eth. Chl al. hazard
1 2 0 1 0 3 0 0 3 1 0 3 1 0

Salicylic acid

138.12

159

1.1443

0.20 g/100mL water, al. ace. Ether w. v. s. al. Glyc

Sodium hydroxide

40.00

318.4

1390

2.130

Sulfuric acid

98.07

280

1.841

w. al.

Equations:

OH

O OCH3 + 2NaOH

ONa O ONa + CH3OH + H2O

ONa O ONa
Methyl salicylate 152.15 g/mol 1.52 g 1.30 mL Calculations: Amount of H2O needed for recrystallization Amt of salicylic acid x 100 mL H2O 0.20 g salicylic acid

OH + H2SO4

O OH + Na2SO4

Salicylic acid 138.12 g/ mol T. Y. 1.40 g

Amount of methyl salicylate

10-3 mol x 152.1 g / mol 1.174 g / mL PLAN: I.

= 1.30 mL

Reaction 1. Assemble the apparatus for reflux. 2. Measure 15 mL of 6 M NaOH and 10 mm (1.3 mL) methyl salicylate, and combine them in balloon flask. 3. Reflux the mixture for about 30 minutes. 4. Allow the solution to cool to room temperature and then slowly and incrementally add drops of 3 M H2SO4 until a pH of 1-2 is detected using pH paper. II. Separation 1. Vacuum filter the acidified reaction mixture. II. Purification and analysis. 1. Recrystallize the filtrate using the amount of water determined necessary for recrystallization (from Calculations section). 2. Dry the product in dessicator. 3. Determine the mass and melting point for dried final product. Procedure: A 50 mL round bottom flask was tared (43.09 g) on balance # 3.. Methyl salicylate (1.32 mL) was added to the round bottom flask. 2 boiling chips were added to the flask. 15 mL of 6 M NaOH was added to the balloon flask. A white precipitate formed. A reflux apparatus was assembled and the round bottom flask was secured to it. A heating mantle was placed under the round bottom, turned on and the heat was slowly adjusted until the mixture started to boil. After 30 minutes of refluxing the apparatus was allowed to cool to room temperature. The cooled liquid was clear and colorless. 3 M H2SO4 (15 mL) was added slowly into the recovered liquid whiled stirring with a glass rod until the solution turned pH paper to dark red (pH =1-2). The flask was cooled in an ice bath. A thick white solid appeared. The white precipitate was collected by vacuum filtration and washed with 13 mL H2O. The filtrate was clear. A small amount of the crude product was set aside for analysis.

hose reflux condenser water drain hose water inlet 50 mL round bottom

The white solid was dissolved into 25.7 mL of hot H2O. There was a small amount of solid that did boiling chips not dissolve. The solution was filtered by vacuum filtration as described on page 34 to remove the solid impurities. The beaker was rinsed 2 times with 2 mL boiling water. As the filtrate cooled, white needles began to form. The filtrate was further cooled in an ice bath for 10 minutes. More crystals formed as the solution was chilled. The mixture was vacuum filtered to isolate the crystals that had formed. The crystals were transferred to a dessicator and left to dry. On Monday the sample weighed 1.32 g, Tuesday the sample weighed 1.09 g and Wednesday the sample weighed 1.10 g. The melting point range of the sample was determined twice 153-155 C and 152.5-154.5 C.

Post Lab: Reaction

OH

O 1) 2NaOH OCH3 2) H2SO4

OH

O OH

Amount of methyl salicylate used: (1.30 mL methyl salicylate)(1.173 g/mL) = 1.53 g Theoretical yield: (1.53 g methyl salicylate)(138.12 g/mol salicylic acid)/(152.15 g/mol methyl salicylate) = 1.40 g Actual yield: 1.32 g Percent yield = 1.32 g/1.40 g = 94% Melting point range of crude product 140-145 C Melting point range of purified product 157-160 C Mixed melting point range with salicylic acid: 156-160 C Error Analysis: Some product was lost during transferal steps. Impurities that weighed into the original sample were removed during purification. Conclusion: The melting point of the product is only slightly lower than the literature value. This suggests that the product is relatively pure. No significant melting point depression occurs when the product is mixed with pure salicylic acid. The following is a sample of the same procedure with typical errors. There are missing volumes, concentrations, and observations. There examples of active instead of passive tense and incomplete sentences. Can you find the errors? A 50 mL round bottom flask was tared (43.09 g). I then added methyl salicylate to the flask. 2 boiling chips were added to the flask. 15 mL of NaOH was added to the balloon flask. The salt formed. A reflux apparatus was assembled and the round bottom flask was secured to it. The heating mantle was turned on and the heat was slowly adjusted until the mixture started to boil. After 30 minutes of refluxing the apparatus was allowed to cool to room temperature. 3 M H2SO4 was added slowly into the recovered liquid and was stirred with a glass rod. Enough H2SO4 was added so the pH was measured at 1-2. The flask was cooled in an ice bath. A solid appeared. Collected solid by vacuum filtration and washed with H2O. The filtrate was clear. A small amount of the crude product was set aside for analysis. The white solid collected was dissolved into 25.7 mL of H2O. There was a small amount of solid that did not dissolve. Filtered by gravity filtration to remove the solid impurities. Rinsed beaker 2 times with water. As the filtrate cooled, white needles began to form. The filtrate was cooled in an ice bath for 10 minutes. More crystals formed as the solution was chilled. The mixture was vacuum filtered to remove the crystals that had formed. The crystals were transferred to a dessicator and left to dry. Once the solid had thoroughly dried the mass and melting point of the crystals were taken.