exam 4 morr - CHEMISTRY 2212 EXAM 4 Be sure to read each...

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Unformatted text preview: CHEMISTRY 2212 EXAM 4 April 28, 2010 Be sure to read each question carefully. Partial credit will be assigned where appropriate. Only answers written in the associated boxes will be graded. Five points will be deducted for failure to write our name on eve '. a e of the exam. Relax and good luck!! 1. (16 points — problem 21.36) Write the major product of each of the following reactions: 00020H20H3 9H3 H2C=CHCHCH2C02CH3 1. CH3CH2MgBr ...._.—>.. 2. 1-130“ 1. DIBAH ——Ir 2. H30“ CHaNHz CH30H H2804 O O CHggOICIICl-g —_—>.. pyridine 1. LiA|H4 .——>. 2. H20 soc:2 1. LiAIH4 2. H20 - l HxC, : CHCH (2szka TOTAL SCORE 2. (12 points — problem 21.48) When ethyl benzoate is heated in methanol containing a small ‘ amount of HC], methyl benzoate is formed. Write a detailed, stepwise mechanism for this | transformation using the curved arrow formalism. O O ©)\00H20H3 CHaOH . HCI (cat) .JLOCHE ——).- heat ‘ ethyl benzoate + methyl benzoate C 3. (10 points — problem 21.5.6) MN-Diethyl—m-toluamide (DEBT) is the active ingredient in many insect—repellent preparations. How might you synthesize this substance from m- bromotoluene? 9 0 H3O Br 4 steps H30 ' I I ‘lTl—CHZCHa ——-—->- . CHZCHg NAME K E 7 | last, first 810# ‘ 4. (10 points - problems 20.22 & 21.32) Provide IUPAC names for the following compounds. I H O: 2 .‘ a .. ],2_C‘ICLOHE¥HNEDICAR1SOXYLIC Bab . 74002” L2.) - . HacCECCH=CHCOZH 2-— H EXEN- "i' "‘1 N 0 IC- F’rC—l b < >—CN 1 - (:JCLD'BUTENE Cfilusom t'rrau LE 0 O - | GAO ’PHENYL. BENzom-E O H OCHchzcocliHCHs Iso'PfZOPYL ’3- PHEMLMLOMNOHTE CH3 5. (10 points — problem 20.42) Show how you might prepare the anti—inflammatory agent ibuprofen starting from isobutylbenzene. —+——’ isobutylbenzene ibuprofen 6. (12 points — problem 20.52) Write the missing reagents in the boxes: JV 2. Hus;1 "OH ”OH "A /I\/\ Br 5’“ § )3 2!: 6+ ' OH COOH AA 7. (10 points — problem 22. 26) Prepare the "following compound using either the aeetoacetic. ester or malonie ester synthesis. ‘1? CH3CHZCHZCHCCH3 CH3 (9 I. N 084: “EL—9 Chat-{zei—ECFHCCH; Z CrH;CH2.(—HLBI‘ C0LE'E as once». or: 15=I1'<’.‘:a't’TUECt STEM (. N‘oa: mm 135 lNVERT—E 1. CH5?» 43?? 9WD H < 1430+ c1+3a4lafi — out CHgd-{LHLCH‘¢'C’H3 hear catt- NAME K E 7 ‘ last, first 810# | 8. (10 points — problem 22.44) Synthesize the following compound from cyclohexanone and . any other necessary organic reagent. '2 . 0:0 ‘"—l" OCHZCHZCOZH 9. (10 points — problem 22.50) Treatment of a cyclic ketone with diazomethane is- a method for accomplishing a ring-expansion reaction. Using the curved arrow fonnalism, propose a detailed, stepwise mechanism for the formation of cycloheptanone from cyclohexanone using diazomethane. ...
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