CHEM 242L University of Nevada Las Vegas Williamson Ether Synthesis Lab Report Hello,Please complete the lab report template attached using the details fro

CHEM 242L University of Nevada Las Vegas Williamson Ether Synthesis Lab Report Hello,Please complete the lab report template attached using the details from the experiment attached and the graph. Thank you! Notes for the Template:
1.
2.
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at now).
Remove all text inside of the parenthesis as well as the example
paragraphs. Your final write-up shouldn’t contain any parenthesis
except for the ones you choose to add. There will be point
deduction if you still have them in your final, submitted draft.
NAME: (your name)
CHEM 242L
SECTION #: (your section #)
UNLV 2020 Summer Session III
WILLIAMSON ETHER SYNTHESIS
Purpose: (Specifically state the purpose of the experiment and evaluation methods in a
few sentences.)
Procedure: (Write a paragraph of the detailed experimental procedure including
observation in 3rd person past tense. In this report, do not copy your notebook procedure.
See the following example for your understanding.)
Example:
316 mg of ferrocene (1.7 mmol) and 2 mL of acetic anhydride were placed in a 10 mL of roundbottom flask, to this mixture, 10 drops of 85% phosphoric acid was added slowly with stirring. A watercooling condenser was attached, and the mixture was heated for 20 minutes in a 90 ?C water bath. After
cooling down, 1.0 mL of ice-cold water was added dropwise to the reaction mixture. The diluted mixture
was poured into a 50 mL beaker containing about 10 g of ice. The mixture was neutralized by adding
approximately 5 g of solid sodium bicarbonate (about 0.25 g at a time) until the CO 2 stops bubbling off and
pH = 5 – 6 with the pH paper testing. The crude solid product was collected by vacuum filtration and washed
thoroughly with cold water. After determining the mobile phase by TLC, the crude product was purified by
column chromatography using ethyl acetate/hexane (1:9, v/v).
Data/Results: (Record all collected and calculated data from the experiment video. If
possible, a tabular form is preferred.)
Compounds
4-ethylphenol
Tetrabutylammonium
bromide
Ethyl
p-toluenesulfonate
Molecular
Weight
(g/mol)
Molar ratio
Actual
mass used
(mg)
Actual
amount
(mmol)
•
The mass of the pre-weighed 10 mL beaker with a boiling chip =
•
The mass of the 10 mL beaker + the boiling chip + the product =
•
The actual yield of the product =
•
The limiting reagent =
•
The theoretical yield =
(Calculation required, use the formula function of the MS word or insert your
calculation as an image)
•
The percent yield =
(Calculation required, use the formula function of the MS word or insert your
calculation as an image)
•
IR Analysis: Identify all respective peaks and assign all functional groups from the
provided IR spectrum (If necessary, insert additional rows in the table)
Peaks Position Observed (cm-1)
•
Assignment (functional group)
NMR prediction: Predict chemical shifts of all protons in the 1-ethoxy-4ethylbenzene.
(c) (d)
(e)
(b)
O
(f)
(a)
Proton groups
Predicted chemical shifts (ppm)
(a)
(b)
(c)
(d)
(e)
(f)
Conclusion: Summarize your results and draw conclusions from the experiment using
complete sentences in a narrative form. Did you prepare the proper substances or
perform the experiment properly? Always include your yield data (grams and percent) and
any other pertinent data collected (melting point, TLC Rf values, etc.). If your yield was
low, discuss any possible sources of error. Can you suggest any improvements in the
procedure? If you were given an unknown, always include the unknown code with your
analysis.
Example: “Acetylsalicylic acid was synthesized from salicylic acid. The yield was 5.32 grams, which
represents a 76% yield. The melting point of the acetylsalicylic acid was determined to be 131-134 °C which
is slightly below the literature data of 135-136 °C, indicating the presence of impurities. The crystals were
white and powdery in appearance, but did give a slight purple color on testing with ferric chloride, indicating
the presence of some unreacted salicylic acid in the product.
Post Lab Questions
1. The isolation technique used in Williamson ether synthesis experiment is
extraction. How do you determine organic and aqueous layers?
2. What is the role of anhydrous sodium sulfate in Williamson ether synthesis
experiment?
3. What is the role of tetrabutylammonium bromide in Williamson ether synthesis
experiment?
4. Why do you wash the diethyl ether layer containing the product with 5% NaOH
during the extraction procedure?
5. Outline the synthesis of each of the following ethers beginning with an alcohol
and an alkyl halide (or tosylate).
Experiment #2-1:
Williamson Ether Synthesis
INTRODUCTION
The Williamson ether synthesis is a reaction that converts alcohols into ethers. This synthesis consists of
an SN2 reaction of a sodium alkoxide with an alkyl halide, alkyl sulfonate, or alkyl sulfate. This route allows
the formation of asymmetric ethers, which are ethers with two different R groups. However, it has all of
the limitations associated with SN2 reactions. Therefore, the substrate reacting with the alkoxide must be
relatively unhindered to prevent elimination. As a result, primary or methyl substrates are best suited for
this reaction.
In this experiment, you will be using the Williamson reaction to make 1-ethoxy-4-ethyl benzene.
O Na
OH
+
+
NaOH
4-ethylphenol
H2O
4-ethylphenoxide salt
Reaction scheme 1. Formation of the p-ethyl phenoxide salt.
The first step of the reaction is an acid-base reaction, where the acidic proton of phenol is removed with a
strong base (NaOH). Sodium hydroxide is not sufficiently strong to remove the hydrogen from alcohols;
however, the protons of phenol are more acidic than alcohols (refer the pKa chart in the textbook), due to
the resonance stabilization of the phenoxide anion. The extra stability of the phenoxide ion compared to an
alkoxide ion makes reaction of phenol with NaOH favorable.
O Na
4-ethylphenoxide salt
+
O
O S
O
TBAB
O
+
130 oC
ethyl p-toluenesulfonate
O
Na O S
O
1-ethoxy-4-ethylbenzene
Reaction scheme 2. Formation of the 1-ethoxy-4-ethyl benzene
Once the phenoxide has been formed, the ethyl p-toluenesulfonate and the tetrabutylammonium bromide
(TBAB) is added and the reaction is refluxed for 45 minutes. The TBAB is known as a “phase transfer
catalyst”, which forms an “ion pair” with the phenoxide anion. This association allows the long alkyl chains
of the TBAB to stabilize the phenoxide anion with the organic phase, which contains ethyl ptoluenesulfonate. During this reaction, the catalyst (TBAB) does not react with the two reactants; rather it
acts only as an aid to bring the two components together for the desired reaction to occur.
1
PROCEDURE (experiment video, https://youtu.be/qCepnw9Yn_Y)
Part A. Formation of the 1-ethoxy-4-ethylbenzene
1. Place 1.20 mmol of 4-ethylphenol in a 5 mL conical vial with a spin vane.
2. Add 0.05 mmol of tetrabutylammonium bromide (TBAB) to the conical vial.
3. Add 1.20 mmol of ethyl p-toluenesulfonate to the conical vial.
4. Add 2 mL of 25% NaOH to the conical vial.
5. Assemble the conical vial with a water-cooled condenser, and heat the reaction flask (the
conical vial)j under reflux while continuing to stir the solution for 45 minutes.
Part B. Isolation of the product via extraction
1. After 45 minute reflux, cool down the reaction mixture to room temperature and disassemble
the condenser.
2. Add 2 mL of diethyl ether to the conical vial and identify your organic layer.
3. Place the conical vial on the hotplate and spin vigorously for 1 minute.
4. Allow the contents of the vial to settle and remove the aqueous layer by using a pipette (keep
all aqueous layers in a separate beaker until the experiment is finished).
5. Add 1 mL of water to the vial and spin vigorously for 1 minute.
6. Remove the aqueous layer.
7. Add 1 mL of 5% NaOH solution to the vial and spin vigorously for 1 minute.
8. Remove the aqueous layer.
9. Wash the remaining organic layer by using 1~2 mL of water and follow the procedure #5 and
#6.
10. Add anhydrous sodium sulfate to the vial and leave it on the desk for 5 minutes.
11. Transfer the organic layer to a pre-weighed 10 mL beaker with a boiling chip.
12. Place the beaker on a hotplate and evaporate the solvent slowly.
13. Calculate % yield of the product.
14. Analyze the IR spectrum of the final product.
15. Predict 1H NMR chemical shifts of all proton groups in the final product (1-ethoxy-4ethylbenzene).
2

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