3. Two unknown samples are found to have the same R f value under identical TLC conditions. Are they the same compound? Explain.
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1 I. Techniques in Organic Lab and TLC Analysis a. Thin-Layer Chromatography 2. A TLC plate displays the compound spot approximately 3.2 cm above the base line upon visualization; the solvent ran 4.1 cm up the plate. Calculate the R f value of the compound. 3. Two unknown samples are found to have the same R f value under identical TLC conditions. Are they the same compound? Explain. 4. A TLC plate has a polar stationary phase (silica gel) and a non-polar mobile phase (EtOAc/Hexanes). Two unknown compounds are spotted and allowed to run up the plate. The spot for Compound A traveled 1.3 cm above the base line; Compound B traveled 3.6 cm above the base line. Which compound would you expect to be more polar? Why? 5. Identify at least 3 different methods used for visualization of a TLC plate. II. Experiment 1: Extraction of Caffeine from Tea a. Vacuum Filtration
2 b. Using Pasteur Pipets c. Microscale Extraction d. Drying Agents e. Solvent Removal 2. Write the structure of caffeine: 3. What is the purpose of adding CaCO 3 to the reaction vessel? 4. When performing an extraction with dichloromethane as the organic solvent, would you expect the aqueous layer to be on top or on bottom? Why? 5. What is the function of anhydrous MgSO 4 in this experiment?
3 III. Experiment 9.1: S N 1/S N 2 Reactivity of Alkyl Halides 1. List the experimental conditions that favor S N 1 reactions and those that favor S N 2 reactions. 2. Write the reactions performed in this experiment: a. S N 1 Favored: b. S N 2 Favored: 3. Describe the mechanism for S N 2 reactions; include a description of the transition state and the resulting stereochemistry of the product. 4. Describe the mechanism for S N 1 reactions; identify the key differences between this mechanism, and the mechanism described in Question Which one of the following alkyl halides gives a stable carbocation? 6. Rank the alkyl halides above in terms of increasing S N 1 reactivity.
4 IV. Experiment 9.2: Synthesis and Identification of Alkyl Bromides from Unknown Alcohols a. Reflux b. Simple Distillation c. Microscale Extractions d. Short-Path Distillation e. NMR Spectroscopy 2. Write the mechanism of the reaction performed in this experiment. 3. What is the purpose of sulfuric acid in the reaction? 4. What is the function of the anhydrous CaCl 2? 5. In the extraction steps, why was the product washed with aqueous sodium bicarbonate?
5 6. Review the 1 H NMR spectra provided by your teaching assistant. Be sure to practice identifying unknown compounds when given the 1 H NMR spectra and molecular formula. 7. Assuming 80% yield, how many grams of the alcohol starting material do you need to prepare 2.0 moles of the desired bromide product? V. Experiment 4: Synthesis of Salicylic Acid a. Microscale Reflux b. Boiling Stones c. Heating Methods d. Microscale Recrystallization e. Melting Points 2. Write the reaction performed in this experiment.
6 3. Write the mechanism for the reaction above. 4. What is hydrolysis? 5. What is the catalyst of the reaction? 6. Suppose that you obtain 1.0 g of salicylic acid (MW = 138) from the hydrolysis of 1.3 ml of methyl salicylate (MW= 152, density = 1.17 g/ml). Calculate the percent yield. VI. Experiment 5: Analgesics and Synthesis of Aspirin a. Heating Methods b. Microscale Recrystallization c. Mixed Solvent for Recrystallization d. Melting Points 2. Write the reaction performed in this experiment.
7 3. Write the mechanism for the reaction above. 4. What is the function of the concentrated phosphoric acid in this reaction? 5. The process by which aspirin is synthesized from salicylic acid is best described as. VII. Project 4: Interconversion of 4-tert-Butylcyclohexanol and 4-tert- Butylcyclohexanone a. IR Spectroscopy 2. Write the reaction for the oxidation performed in this experiment. Identify the oxidizing agent. 3. Write the reaction for the reduction performed in this experiment. Identify the reducing agent. 4. Predict the products for the reaction shown on the following page. Draw in the mechanism arrows.
8 5. In covalent organic systems, it is easiest to think of oxidation as the. 6.The oxidation of a primary alcohol yields a(n). 7. The oxidation of a secondary alcohol yields a(n). 8. The oxidation of a tertiary alcohol. 9. Draw the cis-isomer of 4-tert-butylcyclohexanol. What is the approximate 1 H NMR shift of the methine proton on the carbon bearing the hydroxyl group? 10. Draw the trans-isomer of 4-tert-butylcyclohexanol. What is the approximate 1 H NMR shift of the methine proton on the carbon bearing the hydroxyl group? 11. What equation would you use to determine the ratio of cis-to-trans isomers based on the 1 H NMR integration? 12. What equation would you use to determine the % of cis-isomers present based on the 1 H NMR integration?
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