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PracticeFinalKey - WPrM-fi Ce" Final 1 Chem 2364 Final...

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Unformatted text preview: WPrM-fi Ce" Final 1 Chem 2364 Final Test Name: Vlfiw W K6 Jul-22nd-2003 Last Name, First Name 5 The exam has 8 printed pages of questions and 1 table. Check now to make sure you have all 19 questions and 9 total pages. Put all answers on these sheets. The exam is worth a total of 250 points. Multiple Choice (6 points each, 60 points total). Circle the one correct answer to each problem. 1. Circle the strongest acid. Gm CM W0 OOH M0 A B {a D E 2. Circle the strongest base. CH3CH20Na CH3C02Na NaCl Q—ONa CICHZCOZNa C9 B C D E .3. Circle the most stable carbocation. <3 6752 Gees A [email protected] D E 4. What is the correct way of disposing of sodium acetate? ’own the drain with plenty of water ) trash can c) organic solid waste d) organic liquid waste 5.What is the correct way of disposing of adipic acid? a) down the drain with plenty of water trash can , rganic solid waste ’ organic liquid waste ‘ 6. Circle the compound that would yield the following combination of qualitative tests: Positive Jones test, Positive Bromine test, and Negative Lucas test. Q—Cflon O—Cflon O-OH Q—OH CH3CH20H A B C E 7. Circle the compound that would yield the following combination of qualitative tests: Positive Jones test, Positive 2,4-DNP test, and Negative Bromine test. CHO due 5"“ c WHO 3 8. Circle the compound that would yield the following combination of qualitative tests: Negative AgN03 / EtOH test, and Positive NaI / acetone test. Q—CHZCI Q—Cl CH3CH2C1 Q—Cl 0—0 A B @ D E 9. Circle the compound that would be most easily nitrated. OCH3 CN CHO 5 5 5 5 5 Q B 10. Circle the compound that would be most easily dehydrated with phosphoric acid. OH 0 OH QCHZOH CH3CH20H <:>—OH GM A c: D E 3 11. Draw the structure for the reactant or major organic product of each of the following reactions or write N .R for no reaction. Place only one appropriate structure in each of the ten boxes. (6 points each, 60 points total) Show the correct stereochemistgz when needed! 913 NaOH CH3—(E—Cl —fi-O——> CH3 2 N02 0 'NH2 0 'NH N32520:: ’ H I —-—> NH H20 H 0 heat V 0 Cl NaI ———-> , acetone @CCIB ‘ NaOH, H20 0‘ ———-—> He at, (dehydration) ECH3 1 Room Temp. 9 f 9 C—Q—C— NH—(CH2)8- NH CHZNH2 l) CICHZCOCI, sodium acetate ———-‘-——-> NH (excess) \59 $NHCCH2C'@ o + Ag(NH3)2 ———-————> H20 at???" 12. Match the following compounds with their corresponding hazards. (10 points) _C/_ hydrazine A) Flammable A hexane B) Lachrymator L old Tollen’s reagent C) Carcinogen A xylenes ' D) Explosive _& chloroacetyl chloride . I 13. Draw a detailed arrow— ushin mechanism for the following reaction. Show every single arrow, bond being broken, bond being formed, lone pair of electrons, resonance forms and formal charges. (15 points) 2 ,i. .LEL, it H CH3 H CH=CI-I- CH3 . H20 A) Deprotonation to form enolate (4 points) . a .69 O 0 ll ‘95 L 'I Hi fT-H v—flg H/ 01-842 4‘? H/ 0: CH2. 9| I . HF :QH . B) Nucleophilic attack (4 points) .0 05 _——\\i I H H h. H ’0‘“£H2 HAG-43 H CHfélL\C’H3 M H C) Protonation to form aldol (4 po'mts) i. ~. (3’ .. ’fi :dile/O\H : 0-H 5 H l H CH7, 0H3 b— H/C\mZ/C.\ CH3 H H D) Dehydration (3 points) . . ' \ ‘ ‘ " O I .II 05* J; GH\ H<> H 5 (91.014 6 14. Assign a structure to each of the following unknown compounds and clear! indicate our assignments of all proton resonances as well: (15 points each, 30 points total) Compound A Compound B C11H160 C11H15C1 ' 1H-NNIR spectra: ’ 1H-NMR spectra: A) doublet 6 1.2 ppm (3H) A) doublet 5 1.0 ppm (6H) B) singlet 6 1.4 ppm (6H) B) singlet 5 2.0 ppm (3H) C) singlet 5 2.0 ppm (1H) broad C) septet 5 2.5 ppm (II-I) D) quartet 6 3.8 ppm (1H) _ E) multiplet 5 7.3 ppm (5H) E) multiplet 6 7.2 ppm (5H) 15. A thin layer plate coated with silica gel was spotted with a mixture of 5 compounds using a capillary tube. Determine the expected decreasing order (largest first) of Rfassuming that a good separation was achieved by using a suitable solvent. (10 points) 0012, C0211 COZH CH(CH3)2 C0211 0H 0CH3 E D>L>C>E>fi 16. a) What catalyst was used in the Fisher Esterification experiment? (5 points) DOWQV aciAiQ 10% exchange resin b) Fisher Esterification is completely reversible. How did you achieve to bring the reaction to completion? (5 points) we removed mode/r +0 ’Porce the cow \bmw +0 ‘Hflfl produd’ ' actual Jrheo. 17. From the list of compounds below circle a pair that would produce the following molecule: CN (10 points) CN 0 2. 03:: 03 (I: 02 03 18. Acetoacetic acid can be synthesized by oxidation of 1,3-butanediol with chromic acid. A) Calculate and then circle the limiting reagent in the equation below. (6 points) Show your work OH 0 o + 3Hso --> + Cr(SO) + 5110 NOE @ 2 2 Mon 2 .2 2 13-52 g “fig 20 mL 18 M 6.70 g(actual yield) MW(g/mol) 90.12 152.0 98.08 102.10 392.18 13,02 I352 3 Cliolx "‘0‘ <15" W: 0,1500 moi awioogei’ic acucl qui23cl\0\ \mo\ dwl 2‘0"”3 0’03 x midli— XW: o. 0575 m “mac mg; 152.0% 003 2. m0\ CrOa 7,50“ H750“ a.“ \ 20““ "L“ '8 "“3ng W: 0.12M“ me \L. ‘7‘ g on\ HZSOH B) Calculate the theoretical yield of the acetoacetic acid in grams. (5 points) Show your work 0,0875 moi ace’ioarel’lc acid X W: 8,q53 hnol aceioace’fic 001A C) Calculate the percent yield of the acetoacetic acid. (4 points) Shaw-year work __(o.-7O .. ’7 7 5.6133753 7 19. Use anyneeded reagents to effect the following transformations: (15 points each, 30 points) 595 NH-CCH2CH3 CH3 61/130043 (HBCHZCCI Hi ES “03> m/«g \ (M HZSOW \f CH3CHZ ON N02. NH1 CchszoH on ‘ 0 OH O 0 NoxOHlHZDO |\ Tones)“: ,4, H/Lkfi A 8 ...
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