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key 3 - NAME lad firs CHEMISTRY 221 1 EXAM 3 November 4...

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Unformatted text preview: NAME ____________ lad, firs: CHEMISTRY 221 1 EXAM 3 November 4, 2613!! Be sure to read each question carefully. Partial credit will be assigned where appropriate. Relax and good lookll l. (12 points n problem 3. :8) In the adjacent boxes provide systematic (IUPAC) names for the following compounds. CEO K C “‘1‘: “c: \.. C H3 CH3 H3CCH=CCECCHCH3 HECZCHCH=CHCECH 1,3—Hexodien-5-yoe or Hem-LS-dien-S-yne (1;ch H3 0ch HgtllHCECCHfillHCI-ig CHgCHa CH3 3,6-Diethy]-2-methyl-4—oetyne or '3,6-Diefl1yln2—methyloet-4uyne CURE TDTAL I 2. [IE-points -proofems ?.24'& 126] Predict the products ofhe follooing reactions. Show both regtoehemistry and stereoehemistry where appropriate. | H H .I' ‘L 0:0. 0504 Q“ N —"—F 'H-C g H e” b=dx GHglz. Znt'CLI ‘ [ :l H 'I' 0 ‘ H H b_ ”J mefaChieroperoxybenzot-z: eeitt : .. —C ——h— H 2. Zn H30” “3 1.BI-|3 2. H202 -oH 11:5 peints— prflbfern £46) Plexiglas. a clear plastle used to make many molded articles, 15 made by poiymenzafion of methyl methaerylate. Draw a representative segment of Pl‘iglas tontaining 3 monomer units. H20 "WC/c R‘OCH; Methyl metheorylate ooon3 oozeHa. ooon W lmt, first 31th! 4. {It} points — tit-obtain 152) rx—Terpinene. Clalim, is a pleasant—smelling hydrocarbon that has been isolated from oil of marjoram. On hytirogenation over 'a palladium catalyst, a-terpinene reacts with 2 molar equivalents of H: to yield a hydrocarbon. CmHzfi'. Du ozonolysis, followed by reduction with zinc anti acetic acid, q—terpinene yieltts two products, glyoxal and burnethyl- 2.5mheptanetiione. errTerpinene does not contain any triple bonds. 0 Cl C! t a" E H H Giyorral H CH3 E—MethyI-Efi-heotanedlone a) How many degrees of unsatur'ation does cz—terpinene have? b] How many double bonds and how many rings does it have? 2 double bonds and 1 ring | c] Draw the structure for auterpiuene. 5. [12 points —.proh!em .7254) Reaction of HBr with 3-hromocyoiohexene yields trims-1,2- | dihromoeyelohexane as the sole product. Write the mechanism for the reaction at” 3— bromoeyelohexene with HBr that explains. the formation ofrra'rrr—l.E—dibrornoeyelohexane as | the only product. 1 6. {14 points n pmbfam 3.23) Prm'idfi flm reagents Ihat will carry Hut the following I tansfnrmaxiflns. H20, H2302 f HgSCb Q HJCCHQCECH ———'h CH3CH2CCH3 T? CH3CH2CH2€H HSCCHICECH H3CCH1C02H CH3CH2CH2CHQCH=CH2 ‘3 “395} {:ch HECHECHECECH ——p-— 1. Br: J" CHIC}: 2. 2 NaNflg, NH} 13$. rust .Elflfi 1(15 points — problem 3.39) Propose mucturias ffil' hydrocm‘laons that give the following / m | prnducts an oxidative cleavage by Ritual-104 or 03: | 002 + CH3(CH2}50D2H 'CH3_(CH2)5CECH GI" | CH3{CH2)SCH=CH1 ' CHEEUEH + Q—CDZH '| HQ EC ['3 H2lac'DZH ll H | CHE-CH + CH3CGHECHQCOEH + 002 D I I fl #CH HC c.1420 H2O HECHECCDZH + (:02 .3. (12 points — problem 3.3.?) How would you can}: out the following uensfortnntion? More thanone step is needed. Drew a structure for the product ofesch step and include all necessary reagents. \ ?‘ CH3 CHECHzthECH ———'—+ f;\ Htuyc —£{”’H CHgCHgCHgCHg CH3 1. Nathl, NH3 one2 2. c1133: H2 CH3CH2CHjCH3CECCH3 Lint-Her catalyst H3CH2GH20H20 CH3 9. {11] points— problem 156] Use our general knowledge of alkene chemistry to suggest a mechanism for the Following reaction. Use curved arrows to show electron movement. ...
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