Experiment 17 Williamson Ether
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Experiment 17 Williamson Ether

Course: CHEM 2212, Spring 2008

School: UGA

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John Goodson CHEM 2211L/2212L Lab Report Cover Sheet Name: John Goodson TA: Omkar Dhamale Date: 4/16/2008 Experiment: Williamson Ether Synthesis of Methylphenoxyacetic Acid Prelab (40 points) Title Introduction Table of Reagents Safety Information Prelab Quiz Inlab (25 points) Procedure Data and Observations Postlab (30 points) Results and Discussion Conclusions Answers to Questions Discretionary Points...

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Goodson CHEM John 2211L/2212L Lab Report Cover Sheet Name: John Goodson TA: Omkar Dhamale Date: 4/16/2008 Experiment: Williamson Ether Synthesis of Methylphenoxyacetic Acid Prelab (40 points) Title Introduction Table of Reagents Safety Information Prelab Quiz Inlab (25 points) Procedure Data and Observations Postlab (30 points) Results and Discussion Conclusions Answers to Questions Discretionary Points ____________ (15 points) ____________ (5 points) ____________ (10 points) ____________ (5 points) ____________ (15 points) ____________ (10 points) ____________ (10 points) ____________ (10 points) ____________ (10 points) ____________ (10 points) Total ____________ (100 points) TA Comments: John Goodson Williamson Ether Synthesis of Methylphenoxyacetic Acid Introduction: In this experiment, a Williamson ether synthesis will be carried out to synthesize methylphenoxyacetic acid from a cresol and chloroacetic acid. The melting point of the product will be obtained to determine which cresol isomer was used. In the work up of this experiment, the isolation of the product from the organic layer involves the exploitation of the relatively lower acidity of phenol than the acidity of carboxylic acids. The lower acidity of phenols are due to the higher resonance stabilization of the phenoxide ion over the carboxylate ion. Reaction Sequence: Reaction Mechanism: John Goodson Table of Reagents o-cresol m-cresol p-cresol chloroacetic acid methylphenoxyacetic acid Safety: Proper attire must be worn at all times including gloves and goggles. Cresols are corrosive, KOH strongly caustic, and chloroacetic acid is strong and a skin irritant. Wash spills with plenty of water and do not allow KOH to contact glass joints. Discard remaining ethyl acetate properly. Procedure: Added 2.039 g of KOH, 4 mL of water, and 1.025 g of cresol into a small round bottom flask and swirled until a homogeneous solution resulted. Attached a reflux condenser and heated to a boil. Added 3 mL of chloroacetic acid dropwise through the condenser over the period of fifteen minutes. Refluxed for another 15 minutes. Cooled the reaction mixture and added water. Transferred the mixture to a separatory Acidified funnel. the solution with HCl Extracted the mixture with 20 mL of ethyl acetate. Washed the ethyl acetate extract with water. Extracted the organic layer with two 10 mL of potassium carbonate. Acidified the potassium carbonate extract with HCl. Precipitate was vacuum filtered and washed with cold water. Recrystalized the solid from boiling water and suction filtered. Product was allowed to dry, weighed, and melting point determined. mol. wt. (g/mol) 108.14 108.14 108.14 94.50 166.18 bp (C) density (g/mL) 191 1.048 203 1.034 202 1.034 mp 62-64 1.58 mp 152(o) 103(m) 137(p) Data & Observations: o 2.039 g of KOH, 1.025 g of cresol used in reaction mixture o initial reaction mixture was orange o crystals were white and fibrous in appearance John Goodson mass of product = 0.085 g % yield: 1.025 g cresol 1 mol 1 mol product 108.14 g 1 mol cresol 166.18 g = 1.58 g 1 mol 1 mol product 166.18 g = 4.17 g 1 mol chloroacetic acid 1 mol 1.5 mL chloroacetic acid 1.58 g 1 mol 1 mL 94.50 g % yield = (0.085 g / 1.58 g) * 100 = 5.38% bp = 122-124C Result & Discussion: The extremely low percent yield, 5.38 %, suggests that the reaction did not occur as well as it should have. Loses may have been due to conditions in which the starting material was not completely consumed, undesired side reactions, and losses in the work-up procedure. It is possible that chloroacetic acid was added too quickly to the reaction mixture. Another possibility could be some errors during the extractions performed; perhaps the wrong layer was extracted and used in later extractions. The melting point of the product (122-124C) is close to the para literature value (137), making para the most likely orientation, also suggesting that the product was almost but not completely pure. Again, this could be caused by errors in recrystallization. Conclusion: Despite the very low percent yield (5.38%) and slightly impure product (mp. 122-124C), the presence of a product suggests that the reaction did occur. The melting point also suggests the correct product was at least partially obtained, the most likely being the para oriented isomer. Answers to Questions: 1) a) John Goodson b) 2) 3) 4)

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