2510_2023Sm_Pre1

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Apr 3, 2024

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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
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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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7 Question 5: To prepare for column chromatography of the reaction mixture from question 4, Santana Lopez finds IRs of the 4 compounds of interest (the starting diol, the two products and the possible side product). However, distracted by memories of dancing with Brittany Pierce, she fails to label the printouts and mixes them in with her IRs from the other experiments. The IRs are in the colored packet. Please determine which IR correlates to each structure. Write the number of the corresponding IR in the box next to the compound. (2 pts each) OH HO O O O HO 5a answer 5b answer 5c answer 5d answer
8 Question 6 Will Schuester finds a bottle labelled “magic voice potion”. Emma Pillsbury suggests they perform some analysis on the compound to determine what it is. Using diethyl ether as the organic solvent they measure the aqueous partition coefficient of the compound at various pHs (see below). pH 2 4 6 7 K 10.8 5.3 0.03 0.0006 a) (3 pts) Is the compound an acid, a base or non-ionizable (neither an acid or base)? Explain your answer. b) (3 pts) TLC indicates the presence of impurities, so they dissolve the compound in ethyl ether. They want to wash out impurities and leave the compound in the ether. Should they use a low pH or a high pH in the aqueous layer? c) (5 pts) Starting with 7.0 g of the compound in 25 mL of ether, they extract once with 10.0 mL of pH = 6 buffer. What mass of the target compound remains in the ether layer? d) (5 pts) Unsatisfied with the results in part d, Emma performs a second extraction of the ethyl ether layer. The bottle of buffer is running low so she only adds an additional 3.0 mL of pH = 6 buffer. How much compound remains in the ether layer after the second extraction?
9 Question 7: Dave Karofsky sets up the reflux apparatus below for the S N 2 reaction, but Artie Abrams is paying close attention. What 5 errors does Artie correct? Why do these errors need to be corrected? (Explain briefly why the error is a safety or performance concern.) 1) 2) 3) 4) 5)
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10
DO NOT OPEN UNTIL TOLD TO BEGIN
Question 1 Data: Back of a package of Excedrin Extra Strength Basic nitrogen (pKa 0.7) Acidic hydrogen pKa 14 O N N N N O caffeine H O OH O O aspirin Acidic hydrogen pKa 2.97 O N H OH acetaminophen Acidic hydrogen pKa 9.5
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Question 4 Data: Reactants : 2-methyl-1-phenylhexane-1,2-diol MW: 208.5 g/mol Also, molecular oxygen and the catalyst OH HO Expected Products : O O Benzaldehyde MW: 106.1 g/mol hexan-2-one MW: 100.1 g/mol Possible side product : O HO
Question 5 IR Data: IR #1 IR #2
Question 5 IR Data (cont): IR #4 IR #3
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Question 5 IR Data (cont): IR #6 IR #5
H Be 1.008 9.012 1 4 Hydrogen Beryllium Md (258) 101 Mendelevium No (259) 102 Nobelium Fm (257) 100 Fermium Es (252) 99 Einsteinium Cf (251) 98 Californium Bk (247) 97 Berkelium Cm (247) 96 Curium Am (243) 95 Americium Pu (244) 94 Plutonium N p (237) 93 Neptunium U 238.0 92 Uranium Pa 231.0 91 Protactinium Th 232.0 90 Thorium T he P eriodic T able of e lemenTs Li 6.941 3 Lithium He 4.003 2 Helium B 10.81 5 Boron C 12.01 6 Carbon N 14.01 7 Nitrogen O 16.00 8 Oxygen F 19.00 9 Fluorine M g 24.31 12 Magnesium Ca 40.08 20 Calcium Sc 44.96 21 Scandium Ti 47.87 22 Titanium V 50.94 23 Vanadium Cr 52.00 24 Chromium Mn 54.94 25 Manganese Fe 55.85 26 Iron Co 58.93 27 Cobalt Ni 58.69 28 Nickel Cu 63.55 29 Copper Zn 65.39 30 Zinc Ga 69.72 31 Gallium Na 22.99 11 Sodium Rb 85.47 37 Rubidium K 39.10 19 Potassium Cs 132.9 55 Cesium Fr (223) 87 Francium Al 26.98 13 Aluminum Cd 112.4 48 Cadmium A g 107.9 47 Silver Pd 106.4 46 Palladium Rh 102.9 45 Rhodium Ru 101.1 44 Ruthenium Tc (98) 43 Technetium Mo 95.94 42 Molybdenum Nb 92.91 41 Niobium Zr 91.22 40 Zirconium Y 88.91 39 Yttrium Sr 87.62 38 Strontium In 114.8 49 Indium Tl 204.4 81 Thallium H g 200.6 80 Mercury Au 197.0 79 Gold Pt 195.1 78 Platinum Ir 192.2 77 Iridium Os 190.2 76 Osmium Re 186.2 75 Rhenium W 183.8 74 Tungsten Ta 180.9 73 Tantalum Hf 178.5 72 Hafnium La 138.9 57 Lanthanum Ba 137.3 56 Barium Nh (286) 113 Nihonium Cn (285) 112 Copernicium Ce 140.1 58 Cerium R g (282) 111 Roentgenium Ds (281) 110 Darmstadtium Mt (268) 109 Meitnerium Hs (277) 108 Hassium Bh (264) 107 Bohrium S g (266) 106 Seaborgium Db (262) 105 Dubnium Rf (261) 104 Rutherfordium Ac (227) 89 Actinium Ra (226) 88 Radium Fl (289) 114 Flerovium Mc (290) 115 Moscovium Yb 173.0 70 Ytterbium Tm 168.9 69 Thulium Er 167.3 68 Erbium Ho 164.9 67 Holmium Dy 162.5 66 Dysprosium Tb 158.9 65 Terbium Gd 157.3 64 Gadolinium Eu 152.0 63 Europium Sm 150.4 62 Samarium Pm (145) 61 Promethium Nd 144.2 60 Neodymium Pr 140.9 59 Praseodymium Lv (293) 116 Livermorium Ts (294) 117 Tennessine Pb 207.2 82 Lead Bi 209.0 83 Bismuth Po (209) 84 Polonium At (210) 85 Astatine Sn 118.7 50 Tin Sb 121.8 51 Antimony Te 127.6 52 Tellurium I 126.9 53 Iodine Ge 72.63 32 Germanium As 74.92 33 Arsenic Se 78.96 34 Selenium Br 79.90 35 Bromine Si 28.09 14 Silicon P 30.97 15 Phosphorus S 32.07 16 Sulfur Cl 35.45 17 Chlorine Kr 83.80 36 Krypton Xe 131.3 54 Xenon Rn (222) 86 Radon Ar 39.95 18 Argon Ne 20.18 10 Neon O g (294) 118 Oganesson Lu 175.0 71 Lutetium Lr (262) 103 Lawrencium 1A 2A 3B 4B 6B 8B 1B 2B 7B 5B 6A 3A 7A 5A 4A 8A 1 2 3 4 5 6 7 11 12 13 14 15 16 17 18 9 10 8
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