Final_J Key - Final Exam Name (PRINT) Chemistry 3332...

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Unformatted text preview: Final Exam Name (PRINT) Chemistry 3332 Signature May 4, 2005 88# Please circle class days. f. lu b, J l Last, First A- n h J36" A. Nomenclature: (15 points) Give an acceptable IUPAC name-g for each of the following compounds. Be sure to indicate the _ stereochemistry where approppate. ESHBK I I’ (“W/0 {‘31 <13" '3 - 1 . 7 6 5 ‘ Eu 0 l H N(CH3)2 r .A m: (3:541fi3fiifiymmnew- D -A fine-FEM 5 "WW5 E‘ hérwé'éiflflfi'éé {‘23) r r v ‘ m‘ .; Er"- , V, by, L t u ‘ ‘ IL. f H N- mm: — N- w -s‘ ‘szma- #‘mem a w (mg/Mg? & i i i 1:; J ‘ l _:‘m___7_¥l .____.‘—a—-“‘— 3‘6 IV? _ OJ? GE hufigf Jim-q {:7 3‘1! 51 L! 113-5. m: {J} r'r'e 5* W1 \ 3’00 #fiw" 141/5 B. Facts: 8 points 1. Place the letter of the more stable resonance contributor in the box. (2 pts.) H H 0’ +0” A 2K 1 A B 2. Rank the following compounds in order of-increasing basicity. (1=least basic, 3=most basic) (6 pts.) NH2 (m C. Reactions: Total = 32 points, 8 points each Piease provide the reagents or major product in the answer box. Be sure yoor drawing indicates stereochemistry if applicable. Partial credit is awarded only when intermediate products in a multi—step reaction are shown beiow the reaction. ‘ 1. CH3NH2/ NaBHSQN 1, ALA 2. CHsl (x3) ‘L 3. A920 I H20! heat _ 4. MCPBA “fits: 5. CH3O‘ Na+l CH30H «M s. H3O+ I‘L,‘ Note: MCPBA: m—chloroperbenzoic acid 1 w 0G.) lei-(.33 J a (A i , .f" \x .1. nix.“ A / KIN pram ‘ 53. J “LEN-L a" *3» yN-fl-‘rfi {3‘ m a ‘ X63 ‘ 1. Big (CH3002H 2. . \ o 2. I / or (CH3)3CO'Na+ ' Al/ N 3. \1 fit / __ r: OCH3 i . 4 ( {5r 3 J «t if 'lf (:5: i H '6‘) -:"‘\k._ H / KW §> /, / i ,, i“ q, NW I7: 5 ,- ~ 9 V} (Jilin 241w" n NH" G if 0 C‘ g m1. 5 “gm” 3mm" , . ‘ v 3‘. 4-3.} 001-13 OCH3 a; H— NOE ! 447;?ch H 9/ 1% D. Mechanism: (15 points) Provide a clear mechanism to explain the formation of the product. Uee curved arrows to indicate "electron. flow". : - n- u-- o n - t - o n ‘ =0 - v u - Show all intermediates and all formal charges. When more than one resonance contributor may be drawn, be sure to draw the most stable contributor. ' - O 0 “fl W + “Noe Na E I EtOH ' _ O OZN O . K r m...- C.‘ V _ ‘ l H t . . E. Synthesis: 15 Points Synthesize the molecule below using any of the following reagents: benzene. cyclohgggane, amt three carbons orvkamgsu,’ any Inorganic reagents, any oxidizing or red-ucmg agents, and any-peroxyaCIds. CH3 0 C”) II OLC-oHCHQCHE-C Q (ff-OCHZCH3 I O ‘ 0 Meat! Ema»; ' 2?: Ham” 6!“; r1 /"$Jl_l‘fi £,I 1w. , _nfifl 5\ \LNQOELr/Emtvi ‘ '2. H30 v No.0 ween Where -§* {am-1 n O - F ‘ , . a L)—‘- {3's $13...." $2.; a?“ find-«Er! we H“:- g + I {f} I . J ~ - _— ‘ _ H“ \H CW c'@ ' H 'l“ T H T . .... “M ..... m... 31.11? TA l [‘1 *5 H.__.| “if. - : / ' f I”; ,1 - CH?)- C—OH *‘s‘ Haw-EP‘CHQ "WWW a. A‘flf' é-H‘bCHga’HZ. A“ L“— J i (:9 , Mr??? E Ci?» r-MWM“1‘ B“ _-_.W_'_.._._..=. I l____ _fif ‘ .r v ' W" 4., ‘ (39145:; d){. cliffs» Cl 4” if a I P”: “fl'hf'm'; f . {3.5. [ME—MM"; .2 ,.-:-u a \ J” 052. {K + / fi’hfl’fi H20 '“f‘F-c‘ ' + ' “RH/f; L f3! PW}? H -. pm . n sic-fem 1 f ,. E E :( H.255“! I: a ,5} '"" ""‘”'W ‘1 , .. _ ‘ - .- 55¢ “INF _ \r A. a m * W2. Om WM H 5 r \‘leu M \ f _.._ / . |* m yak-3132115 I {Emirmmm {m t - r I 1}! rwfisié‘w’ .- —»——=‘r~—“"" {4/ 1 / W {H J v r. r" s 5"; H r 1;,“ r ‘ “ F. Spectroscopy: 15 Points A compound with‘the formuia C4H11N exhibits the |Fi,‘H NMR and proton decoupled 13C NMR spectra shown below. Please identify this compound and draw the structure in the box provided below. 7. mam THEE qué‘a'ti ‘3" it 2” N ‘r r" :3" clpillaI-g rm but air Pll'rls MRS mwifl‘ “92 395-3 TTLCH LO PPii (L5 3.5 3.0 2.5 2.0 1.5 From NMR “51‘5— Ei'a 11.15 15.33 1mg integrnl values 50 20 mm '1 Carbon 13 M TABLE 13.3 Approximate proton chemical shifts TYPE OF PROTON CHEMICAL 5mm“ (5, ppm) 1" Alky]. RC“, 2“ Alkyl. RC1!le 3° Alliyl. R3C1l Allylic. R2C=C-CH, lg . Ketottrz. RCCII: 0 Eenzylic, AICHa Acetylenic. RCECH Aikyl iodide. RCI-lfl Ether. ROCHIR Alcohol, HOCIhR Allryl bromide. RCHZBr Alkylehloride. RCH 2CI Vinylic. RICmCHZ Vinylie, R1C=CH ! R Aromatic. Arli Aldehyde. RC1! 0 Alcohol ltytlroxyl. ROH Amino, R—N‘i!2 Phenulic. ArOH Carbuxylin, RfiOI! D (LB—Ll] 1.2— 1.4 l.4—l..7 l.6—l.9 2tl-—?..6 2.2-4.5 2.5«3J 3.1-3.3 3.3—3.9 3.3—4.0 3.4 —3.6 3.6-3.8 4.6-6.0 5.2—5.1I 6.0—9.5 9.5—9.6 0.5—6.0" 1.0—5.0" 4.5—7.7; Ill—13“ w——______._._.———- a The chemical shiftsof Ihese protons vary in dlfierenl solvents and with temperature Ind concentral'tun. WEQUENC‘.‘ GROUP RANGE 1.211."; M fin Allryl C—H (stretching) 1853-2962 (m — s) ISOmeyl.‘CH(C}IJ)1 1380—1385 (s) and 1365-1370 E's) I tart—Bury]. —C(CH,}. 13ll_5— 1395 {m} and ~ 1365 {5) B. Alltenyl CPI-l (stretching) 30104095 (ml C=C (stretching) 1620— l680 (V) R—CH=CH, 985—1000 (s) and 9(15— 920 (s) R3C=ICH2 ‘ (out-of-plane 880—900 (s) eis-RCH=CHR C"H banding” 575—730 (s) trans-RCHHCHR 960— 975 (S) Ct Alkny EC-H (stretching) " ~3300 (S) CEC (Stretching) 2100-— 2260 (V) D. Aromatic Ar—H (set-etching) - 3030 (V) Aromatic substitution type (C—-H out-Of-plnrte headings) TABLE 13.4 Approximate carbon-13 chemical shifts _____,—_._.___..._..._ #M..._.._. TYPE OF CARBON ATOM CHEMICAL SHIFT (I5. Plum WW___W_A __ 7 l“ Alkyl, RCH, - ' - 0—40 2“ Alkyl, RCH2R Ill—SI) 3° Alkyl. RCHR2 . ‘ 15-59 I - I . Alkyl halide or amine. —$—X X = Cl, Br. or N— Ill—(15 | Alcohol nr ether, --(|3--O 50—90 Alkync, —C—=—‘ till—9!) Alkene, EC: lllll- I'lll f Mllto — Il'lll—l'l‘fl Nitriles, —CEN ' 120- |_l[l 0 ll l Amides, —C-N— ISU— IBFI (‘1 ll thuxylic acids, esters, ~C-0 I60- I L'fi 0 ll Aldelwdee, kctones. -C~— till-~25 Monosubstitute'd 690—710 (very S) and 730-770 (very s) a Dlsubstlruted 735-710 . (s) m Disubstimted 680~ 75 (s) . and 750—310 (vanr 5) p Dlsubstimted BOD—840 (vary 3) E Alcohols, Phenols, and Carbuxyl'tc Acids 0—H (stretching) Alcohols, phenols (dilute solutiuns) 3590-3650 (sharp. v) Alcohols. phenols (hydrogen bonded) 3200—3550 (brand. 5) Carhoxylic acids (hydrogen bonded) 2500-3000 (broad. v] F. Aldehydes. Retranengslers‘ and Carboxylic Acids C=O (SD-etching] 1630- 1780 (s) Aldehde . 1690—1740 [5} Hanna . I ' _ tfistt—t‘rso (s) Burs I 1735—1750 (2:) Carbnxylic acids 171071780 (5) Amides 1630—1690 (a) . Amines N—H 3300—3500 un) H. Nitrils CEN 2220—2260 (ml _______—___._._..._._..........—__——-——-— ' Abbreviations: s 2 strong. m = medium, w -= weal; v F variable. - 2 approximately. ...
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Final_J Key - Final Exam Name (PRINT) Chemistry 3332...

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