2510_2023Sm_Pre1

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Cornell University *

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2510

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Chemistry

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Apr 3, 2024

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18

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1 LAST NAME, First (PRINT, please) CU ID (7 digit number) Chemistry 2510 Cornell University Summer 2023 Prelim 1 DO NOT OPEN THIS PRELIM UNTIL YOU ARE TOLD TO BEGIN. Please write your answers directly on the question page. All calculated values must be supported by work presented on the page in order to receive full credit. Numerical answers should be presented with proper units. You may find it helpful to read through the entire exam and work first on questions that are quick and/or you are confident in. Once those are complete, you can return to the ones you find more difficult. Please follow the directions for each question and enclose answers in boxes where they are provided. The exam is printed double-sided and has 7 numbered questions on 10 pages. There is a separate, colored double-sided packet with a periodic table, a ruler and information needed for several problems. Sign below to affirm that you are not presenting anybody else’s work as your own. Signature:
2 Question 1 Finn Hudson struggles with headaches, so he always has Excedrin Extra Strength with him. See colored sheets for relevant information. a) (8 pts) He wants to purify caffeine, so he grinds up 4 tablets and adds 25.0 mL of ethyl acetate. After filtering out the insoluble material, he proceeds to add 15.0 mL of buffer (aq) (pH ~7.5). Below, please indicate the probable location of each compound by drawing its structure in the correct box ( pay attention to protonation state and formal charges ) . Assume each compound only exists in one of the solvents. b) (6 pts) Finn believes that the three compounds are not separable by acid base extraction because each of the three has an acidic proton (H). Is he correct? Explain briefly. c) (2 pts) If Finn obtained 0.421 g of caffeine, what was his percent recovery? 1c answer Ethyl acetate layer Buffer (aq) (pH ~7.5) layer
3 Question 2 Quinn Fabray wants to make aspirin from salicylic acid and finds a mixture of benzoic acid and salicylic acid that the chemistry teacher had prepared for a recrystallization experiment (like the one you did, except that salicylic acid was the target compound). She has a 1.5 g sample of salicylic acid contaminated with an unknown amount of benzoic acid. Compound Solubility at 0°C (g/L) Solubility at 100°C (g/L) Benzoic Acid 1.7 68 Salicylic Acid 2.17 66.6 a) (5 pts) What is the maximum theoretical percent recovery of salicylic acid? b) (5 pts) She gets distracted and accidentally adds 47.3 mL of boiling water to dissolve the original sample. Rather than start over, she boils the sample until the volume is reduced to 1.3 mL, then cools it to 0°C. What mass of salicylic acid does she theoretically recover? c) (5 pts) Quinn repeats the procedure (correctly) and determines that she recovers 96% of the 1.5 g starting sample. From this she reasons that the starting sample is 4% salicylic acid. Is her logic correct? Explain. 2b answer 2a answer
4 Question 3 Rachel Berry is analyzing the salicylic acid that Robin purified. a) (4 pts) She measures the melting point of a small amount of the salicylic acid as 160- 161.5°C (lit: 159°C). Briefly explain the relevance of this result. b) (4 pts) Rachel runs a TLC of the salicylic acid and sees a vertical smear extending for half the plate. What does this indicate about the purity of the compound, if anything? c) (4 pts) Sam Evans suggests that Rachel load less sample before running the TLC again. Is this a reasonable suggestion? Why or why not? d) (4 pts) For a TLC of two unknown compounds, when the solvent front is 8.5 cm, the two spots have R F values of 0.25 and 0.62. If the compounds are run again with a solvent front of 6.0 cm, how far will each spot travel?
5 Question 3 (cont). e) (6 pts) Quickies… i) When running a TLC plate should the lid be ON or OFF the sample chamber? ii) How deep should the running solvent be relative to the sample origin? iii) A nonpolar compound will have a LARGE or a SMALL R F ? iv) Increasing the polarity of the running solvent DECREASES or INCREASES the R F of a polar compound? v) How do you know when to stop running a TLC? vi) Which will result in a lower R F for a very polar compound 50:50 or 10:90 ethyl acetate:hexanes? f) (4 pts) Puck purifies his reaction mixture by column chromatography after the synthesis in question 4b. His grid TLC is shown below. On the analytical TLC, fill in a reasonable approximation of expected results from the indicated fractions. Fraction #: 1. 2. 3. 4. 5. 6. 7. 8. 9. 10. Analytical TLC Grid TLC of Fractions 1 2 3 4 5 TLC of Mixture Before Column Run Column Chromatography 6 7 8 9 10
6 Question 4: Kurt Hummel is performing the oxidative cleavage reaction but, foolishly, he relies on Sue Sylvester to provide the reagents. Instead of the expected diol, Sue gives him 2-methyl-1- phenylhexane-1,2-diol. Mike uses 3.5 g of the diol and excess oxygen along with sufficient catalyst. (See data on colored sheets.) a) (4 pts) What is the theoretical yield (in grams) for the synthesis of the benzaldehyde? b) (5 pts) Kurt runs a TLC and sees three spots by UV detection. One has the same RF as the starting material. He states that this means that the side product was not formed. Do you agree with Mike? Explain briefly. 4a answer
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