test_final_spring_B - CHEM 3332 A. Nomehciafiire: Total =...

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Unformatted text preview: CHEM 3332 A. Nomehciafiire: Total = 12 points, 4 points each fl Rmaf ' ‘ ‘ f. 1.,C5g1 Give .an aécefiiéble'ngme for-each of 1h¢pgmfigmasbelpw '. 1 ,2 - ' . OH EXAM (aH B. Reactiong; Total figpgims, a points each - A r _ . Pleasé'=-p'rffivj‘de lit-1e 'afiifigj‘matgriat, major-prodmt qrnecessary-reagents in theganswervbwk Bfé sureywr _ drawian indiga‘tgs " ' "eéhem'istryfi apfllicabl'e.’ Pa‘fifia‘] :urediié'is‘iiaward ed out? When ‘ifitErmédiatéVp'rz‘nd uc-Isi are shown Lb.eiQW’1fie“'-‘reaction. ' r ' - ‘ ' ' _ CH3 I . ‘ j. COcha ' 1. Heat _""——_———9" ‘ . E-LFAJHzi-Iifl) ON 3‘; H20 . CH3 0H3 I. MCPBA 3. 2. CHaCHgo ' Na + 3. CH3I j 4. NaCN IH+ ~ 5. H30+ fheat‘ C. Mechanism: (18 points) Prewide rcasonnbla mechanisms; for the reaction bplow. USE: curved arrows to indicate '"clcctton flow”. Show all intermediates and all formal -'cih3rgfas.;;_ .fllqc E5 mqge-r-Ihanr one Manages structure, you must showfiue-“bést‘” (i.e., lowest energy) stmctfi'r'c. ' ' - ‘ NaO Et H302“. .—.——p— EioH A 1.. ‘KMnfi-gi "OH / 'he'eit- 12?". ' 2. H+-' ' 8.1800! )3 4. NH3(XS) :5. .Brglfiom H2065) 1. CH50H20 I EtOH . O CH O 2., H30" ‘- 3 I! 'l 1! CHaon'Cfi'C-G HECHz-C-CHg . D. Synthesis: (18 points) ‘ Synthesifmrt’ha moieculabgiow usingirany 0f the, fallowingfmggcntsz-t alkapesa achacsl alkynes,_ or mamas-01f :two .‘carbggs Igor iesis; benzcne, any inorganic rEage'nts, any'oxidizing' by 're'duciflg agents, and any peroxyaci'ds. " ‘ -' ‘ ‘ " ‘ - . ‘ 7- . - E. Spectroscopy: (12 Points) _ A cdmpqgnd: with ppéufoflnula. txhibi‘ts. the IR1 .mfi ‘pmmmdeqoupled 13C NMR spectra shoWn on the: fdll'owifig fiége'. Plrease'iden'fify thié‘ campountiéfid draw" the " structure in the. box provided below. , MP (11331203 199 is!) 99C 56.7 fiEp—nngir x ‘ an .whmn 6. HH' m .5 BJJ Prutun NHR 20 PPM' O I 50 40 BO 106 120 140 Carbon 13 NEH 150 TABLE 13.2 Characterisric infrared absorptions of groups BRO ' WGE.{cm'-‘) . INTENSITY ' is. 1mm ‘ c—H (scratching; 2353—2962. (m—s) "Isgprppyl, —CH(CH,): 7 _ 1389—1385 (s) ‘ and 1365—1370 (is) ‘rqn-Butyl. “C(Cflj); ‘. ‘ 1335-— l395 (m) ' and -- 1.365 ‘ (5) .B} - r L r. . ‘ . 3010—3095 (In) 1620-4680 ‘ (u?) 9.8541390 ‘ (a) . I 31121 ‘ :905\—j.§20 . it I_ (g) _ r ouxawfqilanck . 330-2900 ‘ (5.) , ‘ .1 C-‘fI-Iwbgndmgs) ;_675-_730 (5.) : 960—935 {5.) C. Alkgmyl I EC—H (Saar-@333 ' ~ 3306 (s) CEC (scratching) 2100—2260 ‘ (v) D. ‘Mématic ArH-H (strctchiggg') '- 3030 (v) Aramafic substitution typc ‘ (C—H Butuof-pianc bandings) Monosubsdtutbd 690 4'10 (very 5) and 730 —770 (very 5) a Dlsubstituted 735-4170 (s) m Disubsticuted 680—725 (5) _ and 750—310 (very s) p Disubsfimtcd 800440 (very s) E. Alcohols, Phenols, and Carboxylic _ . Acids ' 0-..=I-I (Stretching) ' ' AlcoholsT phenom (dilute solutions) 35§0—3650 (sharp. v) Alcohols, phenols-(hydrogen banded) 200—3550 (broad, 5) Carboxylic‘ acids (hydrogen bonded) 2500—3000 (braad, v) F. Aldehydes. Ketones. Estcrs, and Carboxylic Acids (i=0 (snatching) 1630—1780 (5) Aldehydcs ' 7 1690—1740 (5) chncs 1680- 1750 (a) Encrs 1735—1750 (5) Carboxylic acids ' 1710- 1780 (s) Arnich 153041690 (5) G. Amines N—H 3300— 3500 (m) H. Nitrilcs CEN 2220—2260 (m) " Abbreviations: s = strong. m = medium, w = wcak. v = variable. -— = approximalclv. ...
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This note was uploaded on 01/05/2012 for the course CHEM 3321 taught by Professor Bean during the Spring '11 term at American Jewish University.

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test_final_spring_B - CHEM 3332 A. Nomehciafiire: Total =...

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