CHEM223Asum11_Final_Key

CHEM223Asum11_Final_Key - CHEM 223 1 FINAL p 1 M2 sec(20 1...

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Unformatted text preview: CHEM 223 1 FINAL ' p. 1 M2 sec (20) 1. Provide unambiguous names'for the structures shown below. Use stereodesignators as needed » . - O ‘ - S'\ (S) 07/“ floCH'S Br WHZCI‘E ' / 9.1;. z . Ia-wysneirhox -1)“2—d{nimb{n n i it renOIjl—bmmahznjéne. 3‘Li~dini‘ivéckvlisol€.. ’ _ metth 3,4-oii‘nihrvphcnjl afhei/ B‘Y 531.1%.{9‘13 . I . , 3 CL c ' (:4 CH QH CH) a's (qpt) >V\‘\L\/CH2 ‘2(..,H3\2. 65' Squ 2 2 (. 3 ’2. a? _ 5 a o ' ('R)‘Cr-broma—3’ochloro-Zjé—diwxefla theycanéja,‘ ,_' _ _ -0": _ _‘ 1‘Cblor0*.Ll,»Li-CliwleHfl L-Z- anfanwone R2265. V (16) 2. The diene starting material affords the two cyclohexenyl bromides shown in nearly equal amounts. Provide a rationale for this experimentalobservation. Also provide the structure of another product that might be expected for this reaction. ‘ HBV‘ ' g +. —“‘>. . _ B awasiséAblb' ‘ g , allji editors "unharmed 9 +’/L @6ua\ chm/ice em_ 3 . - ends ' eaner anAnleBr C51 {W althcrslwcium/ (12) 3. Rank the follOwing species as acids. Use the following scale: 1‘ = most acidic, . . .- 5 i the weakest acid [3 FL, \awier CH3NH2 HON02 F3CCH20H (CH3)3COH gab} \ / OH I 5 1 i 3 a Li /’ 2 i '34,}; 355g _ ‘ " -- ’a‘rder 3,913: " (05) 4. Which of the following, HF or BF3, has the greater molecular dipole ? ' CHEM 223 ' FINAL p. 2 2 K5 ' sec ' (08) 5. Draw Newman projections of two staggered conformers of'Z-methylbutane. It will be useful to View the molecule so that the Newman projection rotations are about the C2—C3 bond. (09): 6, Isomers. How Inany stereoisomers (cis/trans, E/Z, R/S, etc. — NOT constitutional isomers) ' . are pOSsible for each of the structures shown below. YOU DO NOT NEED TO DRAW THEM "CL ' - ' -' cL ' ' b ' “‘3 ' ' fi‘ p \ _'2,)£:fw 20:4 2ft; 4 42p1‘s) (05) 7. What product will result when a drop of sulfuric acid is added to a solution of . cyclohexanone in excess ethanol. 0 Ef V. , 0 5% . 60 E I: 60H 579% I ' I _ Zfl-x (06) Which of the following obj ectsnor substances are chiral: a) a wine glass, b) a coin and c) ' 9:0 ? “3 v _ , . £360er +3/'Z - p v- a; . (06) :9. What,_in your opinion, is the single moSt important factor that favors an E2 reaction over A, t and 8N2 reaction for a substrate that could do either ‘2 I - ' 0H, for» alwgéi’ h/(M/m/Mcfl gézacéfl'a/g/mé mower 07/75 CHEM 223 FINAL p. 3 K52 V sec (35) 10. Fill in missing reagents, starting materials and/or productsin the following synthetic“ transformations. 6 [91% (23 /V a r #2 106,, t . 50 50 - CH CH ' 3 /H2- *‘t CH /. Kfl/nfly Ho 3 COOH z 3 7—, 3r; F2313 ' CH2 3 5 m ' . ‘ B r 3/117 grid/feet 5r+v the only product H I I. 5143 05/043 .2' ; ’I/OH / _ (09) 11. A textbook problem (9.42b). Maggi: a set of reagents for the transformation below. ‘ " " r aldt’r _ V OH ‘ mm W "W “‘1 V G 43 512 H0220; Egg BK . - V. Jpfieacfilyéefl (08) 12. The example above corresponds to one way of introducing a éflw Sidechain on a benzene. There are other shorter routes in many cases. Provide an example by coming up with a short synthesis for ~ ‘I- 5’2 #25:; 7 °“ ' 2. M10 '- _ ' - /\n/ . . . o I '0)” Que/1 bafitfr - RCOCJ ' Rafi-8:!” R Mal R’ mag,» 41% CHEMzis FINAL " p.4 2 ' sec (16) 13. Using benzene(with no substituents) as your only'source of an aromatic ring, design a synthesis of the ether shown below. 4 ' @ 'l'lg‘b All“? = Z, “(LON-A \\,,\ cugci _ " ~ ' A “‘3 "f 7f, (11) 14. Indicate whether the pairs of structures shown below are conformers (C), enantiomers 7::Vrec/li7 _ (E), identical (I), or diastereomeric (D). It is possible that more than one label may apply. , CH3 “H H “I , I . 3 s a.) 1 p ‘ 'I. ' *1 $05 ‘ _ F): ' g ' . . .a t c :9) ‘Ln “Mir” - :w" am 4 6r ' )( LI~ n I A . a. _ ' . . . c ‘ . l’. 7 '(09) 15. When the dibromide shown below is treated with excess NaCN (using a mixture of ethanol and water as the solvent), one product appearsrapidly but is replaced by another after a longer time. Show the structures of the initial and final products. ’ crazer NaCN iv ‘ caged“. 1 Eton—H20 » Br , . _ we . . p r I (:nieigén ) . (05) 16. Draw the stable chair conformation of the dibromide in problem 15. I B V . ‘ ("#2 B r \ __ CHZB" 3,, \ ’7 5/0 1L5 f: . CHEM 223 FINAL p. 5 P651 sec (16) 17. Illustrate the use of three of the following reagents orvcatalysts in organic synthesis: ' a) FeBr3 , b) $02Cl , c) CH3CECNa , d) CH3NH2 (acting as a nucleophile), and/or 6) meta- chloro-perbenzoic acid. ' ‘ ‘ _ g It 'RCOZH —» racoot , 25233“ a 125026 Y _ r, \ . 7 :/\9 C10 c) (31-5620”) R—X- or W36”C / masc: + $0 “+9 "756ch (73» 1 .ao_ L b) lZOH‘*C,) 3 I. * A" Cl 34 a CI) \ISNZ riflA an‘ >- {3 a _‘ NHCFB I s or V“? ‘3” 39H W V— *5 e). growl/x1140} 6f GIW’ ' ,~ '6; .5 5' 5610 fig 1:1,)ZWLEHJ (07) 18. Carboxylic acids and peracids, for example CH3C02H and CH3C03H, differ in acidity by 104 (4 pKa units ). Do you expect the peracid to bemore or less acidic than the carboxylic acid? ' Answer (say fmore’ or ‘less’) e) [€55 ‘ [Kan ansmr Why? C ‘ : 'f . Luan (3'65. 0 O ‘ )kO/O \ V630 VlavvtcL. L I, C)" __ Qt; /0r' ’fM’W w“ “We CsO/H (4 R p, CHEM 223 FINAL p. 6' ' sec (20) 19. _ C H3 CH3 CHS The ratio of the products varies with both the temperature and NaCN concentration. (3) Which products are obtained in relatively higher yield (amounts) at the higher temperature? , . (:tZ~0H L+)—(A/ . . ' ‘ ’ . Zpts [pf (‘1) With regard to (+)-CN and (—)-CN , which will be obtained in higher yield as the NaCN concentration is increased ? , g 3‘ CM ’ 0w Cor/€5.19 anSwe-r' (13) Provide reaction course diagrams (using the same energy scale throughout) for the reaction(s) that produce (+)-CN and (—)-CN . C H”; " barrier v/O'K \_ i ' / FILM WUCé‘fJéJ 1. l £57344 I7a r‘ l . .5” J. i \_ ...
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CHEM223Asum11_Final_Key - CHEM 223 1 FINAL p 1 M2 sec(20 1...

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