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final - CHEM 3332 — Final EXAM(aH A Nomenclature Total =...

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Unformatted text preview: CHEM 3332 —- Final EXAM (aH) A. Nomenclature: Total = 12 points, 4 points each {56 an _ C a; .. L} Qhe M 3 331* O u 1 / ' OH Give an acceptable name for each of the compounds below. B. Reactions. Total: 40 points 8 points each Please provide the starting material, major product or necessary reagents in the answer box. Be sure your drawing indicates stereochemistry if applicable Partial credit Is awarded only when intermediate products are shown below the reaction. COZCHa 1 +CCN 1. Heat 2. LiAlH4 (xs) 3 H20 2‘ E? 1 MCPBA 2. CH3CH20 Na+ 3. CH31 4. NaCN IH+ 5. H3O+l heat CH3 CH3 1. KMnO4/ 'OH /heat 2. W 3. 'SOCIZ (XS) 4. NH3 (xs) 5. Bra / 'OH/ H20 (xs) 1. CHacHZO ' Na+ / EtOH O 2. H30+ ' u 3. CH3CH20 ' Na$ / EtOH ’ CHSCHz'C O H 4. CHa—C - CH=CH2 ‘EH3 ‘3 -C-CHQCH2-C-CH3 l COQCH20H3 C. Mechanism: (18 points) Provide reasonable mechanisms for the reaction below. Use curved arrows to indicate "electron flow". Show all intermediates and all formal charges. If there is more than one resonance structure, you must Show the "best" (i.e., lowest energy) structure. + NaOEt H30+ O o --———-—> —-———-> GE: EtOH A D. Synthesis: (18 points) Synthesize the molecule below using any of the following reagents: alkanes, alkenes, alkynes, or alcohols of two carbons or less, benzene, any inorganic reagents, any oxidizing or reducing agents, and any peroxyacids. E. Spectroscopy: (12 Points) A compound with the formula C10H1203 exhibits the IR, 1H NMR, and proton-decoupled 13C NMR spectra shown on the following page. Please identify this compound and draw the structure in the box. provided below. Z ‘RflNSflIIIflNCE MP C10H1203 100 MW 180 95C 66.7 %H 6.7 1439.09 1666.9! 1282.93 .5 0.0 7. 7.0 5. PPH' 4. 4.0 3. 3.0 a. 2.0 1. P9! 1.0 Prutun NMH W 160 . 140 120 100' 80 50 40 20 PPM' 0 Carbon 13 NMH . E] TABLE 13.2 Characteristic infrared absorptions of groups ________________————————-——— FREQUENCY GROUP RANGE (cm‘ ‘) IN'I'ENSI'I'Y’x __________________._.______————-—————-———-——- A. Alkyl C—H (stretching) 2853-2962 (m—s) Isopropyl, ——CH(Ci13)2 1380— 1385 (s) and 1365—1370 (s) ten-Butyl, —C(CH3), 1385— 1395 (m) and ~ 1365 (s) B. Alkenyl C—H (stretching) 3010—3095 (in) C=C (stretching) 1620—1680 (v) R—CH=CH2 985— 1000 (s) and 905—920 (s) R2C=CH2 (out-of-plane 880—900 (s) cis-RCH=CHR C’H handmgs) 675—730 (s) trans—RCH=CHR 960—975 (s) C. Alkynyl EC—H (stretching) ~ 3300 (s) CEC (stretching) 2100-2260 (v) D. Aromatic Ar—H (stretching) ~ 3030 (v) Aromatic substitution type (C—H out-of-plane bendings) Monosubstituted 690—710 (very s) and 730—770 (very s) 0 Disubstituted 735 —770 (s) m Disubstituted 680—725 (5) and 750—810 (very s) p Disubstituted 800—840 (very s) E. Alcohols, Phenols, and Carboxylic Acids 0—H (stretching) Alcohols, phenols (dilute solutions) 3590—3650 (sharp, v) Alcohols, phenols (hydrogen bonded) 3200—3550 (broad, s) Carboxylic acids (hydrogen bonded) 2500-3000 (broad, v) F. Aldehydes, Ketones, Esters, and Carboxylic Acids C=0 (stretching) 1630-1780 (s) Aldehydes ' 1690— 1740 (s) Kctones 1680—1750 (s) Esters 1735 — 1750 (s) Carboxylic acids 1710—— 1780 (s) Amides 1630- 1690 (s) G. Amines N—H 3300—3500 (m) H. Nitriles C’='N 2220—2250 (m) ‘ Abbreviations: s = strong, m = medium, w = weak, v = variable, ~ = approximately. ._.>m_.m .w.u 362053.98 908: 253.8. 4:3 llllllllllllllllllll'lllll'lllll A<wm Om ENOHOZ DIES—OZ. 9:3 3. 2:3 lalllll:||||lll|l||l|lllll|.lll 1 23.. .8? No 25.. wgrw mo 25;. 50: >525. fanning? Hr W996. ”now: by mafia—mo. Eu >02Em3n. ”ONO: >=Q_ woman. ”GEL mama. W09?” Zooror :00: ”N .25; 68350. ”GEN? >50; 951%. NO: NO— Sawzn. wannnw: SEEP ”Noun! __fl >353? >5 Zanrwan. wnm . AF Encro— Eanoxfi. ”on >330. ”la: 3550:? 20$ 0353:? W00: = o cal—b fNI TA ##qu rolfo N._IN.m NNINU ~0l9_ P_luu Value mulab mLIPa PQIVm adlmb ublug oblou which Pulwba #0190: burgh? 513a ll‘lll'lllllllllllll .. .35 2.853»— m—Eua cm 50mm @883 55. w: @522: 875:; BE «<3. 83—3328 Ea 8:83:38... ._.>w_.m a.» >Ugox§mnm 8303-3 3223. 3.3 :wm Om O>WWOZ >HOZ— Ommzwnxfix 9.54 a. 3.5V #0 25;. fig: . also No >=Qr wnmuw Elmo we 25;. ”03”» Elmo _ 25.— ero 3 8:59 Ifilx x H Q. m... 9. LTIV Siam _ 2025— on 092. [Julio 318 2559 .lnm aonwo / 2.8:». null: Son 3o \ >39 A O I: So: So 25in? .IOIHIZ Eel Go 0 . __ _ >358. .1an1. Gel :5 n__v nBcQQ—mn gnaw. 8.88. [Clo gonna MW taming. wnnoaom, IOI ‘ EMING llllllnlllllll'lllll'lllll Ema—OED .265 O." 4.1m mrmgmzd... >333 3:33».- 2.55 3.3::— >.a=..n 51%... '23.?! 4:5?! I .2 3.3» . a 3:225: >252: Atria... 23...?! . . . mu , 1.— , m: an . . . 5o; . . 3...: SSS , 3.3 .3 i = Eran. 2...... E 398 a 432...- a... :2... 53.2... :15: 1.. 5.3.. E: - 233cc: .3 132.58. .3 3-: 553.2- ... =3 3...: 3...... on ear-Sat: .58.... 1 1239.3 .733... ...
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