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fall2008 3key - [3 Please check here if you wish to have...

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Unformatted text preview: [3 Please check here if you wish to have your exam returned to the boxes outside the classroom. Exams not returned to the boxes may be picked up at Professor Gray's office (6686 Kolthoff) during office hours (2:30 - 3:30 M-Tu-W—F). Last First Name l [(3% Name Question 1. l 0 (please pr' t clearly) 2. l2. 3. 7.0 ID. number Organic Chemistry 2301 Exam #3, November 12, 2008 4. 3 6 Professor Gary R. Gray Please answer all questions in the space provided. You may not use 6. I 0 molecular models, notes or electronic devices of any kind. The exam must be taken in ink in order to be submitted Total l 0 Q for re -grading. 1. (10 points) Give a detailed mechanism to account for the products in the following reaction. You must show each bond- forming and bond-breaking step separately. Q0222» -—»E><> COCO 2. (12 points, 3 each) Draw a s’rrucfure for each compound whose proper name is given below, being careful To indica’re ’rhe configuroTion of any double bond or The chiraliTy at any chiral center. a. (Z)-3—meThy|-2-oc’rene ® 151" Ed‘sowr [7, 3 IF] 0.43 {OHLI¢\ Z #3 c. :c\ OH? H b. (S)-3—meThyl-1-pen’ren-4—yne H \w [qr/17%] (,l KOO? 3 6) LG? lg'l-‘SDWSP >03C<§\CEc—'H H H c. (32, 65-1,3,6-ocfafriene [7'3/4'] E2) coral/t anrlreat Olleole lOOleQ. (fingfi. (JOWM 'le awe) lf‘ld lm [777%] on 3 » rule/3r \/ gag ('L) far E'tswmr' Br. (”HI—W3 3. (20 points, 4 each) Give the structure of the major organic product in each of the following elimination reactions being careful, where necessary, to correctly indicate double bond configurations. (Wd«m?sms not v13 wdwewé) P“ P Pin a Br H NaOH A\c.-;’:Z:c./ (-2-)150.» g- 0' H36 H H20 / \ {son/w- [7,m/J Ph heat 0,43 H (Ph= 0—) l Br [4 Br} Pia H 5143 H Pk r0 twig; Pl. 5H3 Pk H #DEJJ Ph B b :13: Eth ryic/l'l 69 pm, 2- Ph heat p k / \ P h v 50W; [74%] T 'B H Br + rjljh I H Br Pl‘ r0 cholze ’3'” :75 W7 Ph Hr 51:310.:5 '\_/ Question 3, continued Ph Brig C. H r' E7407 Ph 23w H NaI _ '—.———+ m acetone CH3 , heat 'OH [7“ 9% Va] 943 e. H3C—C—CHZOH fl» ' heat CH3 [’7w44fl] Pk \c i; /P E?) 10'9" S“ l4/ C\H §$0WW Br? Pk H“ Br J fl? Gr'eoal'l'ér erreof ream Lsonmr“ 0H3 H \c. g c/ / \ 0H3 “4'3 CTCfiVVWfi¢Wflt) (36 poinfs, 4 each) Give The structure of The major organic product in each of The following addifion reactions, being careful To properly indicaTe sfereochemis’rry. If The produc’r is racemic (i), so indicaTe. Ph CH3 HBr °- tc=c’ —> “Pk, cu onion-3, (i) H W—I (no _ i (D perOXIdes) B P Q) 3 - 0r __. OH (9 2. NaBH4 [54%.51 3 0“ dil:I_’r____>e H2504 / I W3 '" 20W/ E) G7 [saga] Bra on; {33"} 042.6943 63 (Fischer Projection) e. / \c=c 1. BZI—Ié Wsmga—iLS/H 0H / \ 2. H202 i 3 (i) CH3CH2 H NaOH CM 3.0”?" (D ('9 Question 4, continued 1‘. H c H [5’ a a 3 \c—c/ ii" 34 F1 / _ H CH3 9. H3C CHZCH3 [9’3462 /C=C H H h. CH Clz QM, V 7— 3 H20 ’ H M [$4.14.] W3 4) CH3CO3H 0H} W H m4 (”9 H 0H 0‘43 (Fischer Projec’rion)’} £9 a Hm LSOVVIIV‘ M; Q 323-» “$0“ m 2 2 H 01—! (0 C33 ‘44qu (Fischer Projection) (92-) inc YEW?“ 091m CnCDI/Veo‘t or not dun/r @C‘ no cruu’f Par WWW”? r-eficochomw 5. (12 points, 6 each) Show how you would accomplish the following Transformations in good yield. Please write the appropriate reagents over the arrows and, if more than one step is required, itemize (number) the steps in the order that they would be performed. HO CH3 CH3 /, ”2,5051%“? (Z3 “OH 0' _> (i) 59-ch Z. THF‘BH3Q 0r BzHé 3.14202wa0/[email protected] /. Nn/A/L/z, 0r OH b. H—CEC—H JEL‘—> H3C—é—CEC—H 9 A z. Diva-«Mg «“2 Ph I l7 ] 3. #954117 C79 (10 points) Outline a synthesis for the following compound using acetylene (ethyne) and compounds containing no more than four carbons as starting materials. You may use any other necessary reagents. H3C\ /Cl’l‘?cH3 from acetylene and compounds H /C\_/C\ H (.t ) containing no more than four carbons C H2 M4117, (9 gr» (Cal 0 M'l3 Cl'le 3 <9 5%: C H H 247/, 0 Adria/gar EM, (lad/Dyslfifijut‘no/ine) (I) W3’C EC~6HLCH3 I/I Nfl-«NM% 0V" BMLL. @ 2. 64/3 6.7423,— (5%“ M/myé/e 0 W3~C7£eCWH 0r" ddfiéede) T /. [VJ/NHL, 0r Bub: Q Z. W I ( r aft/arable, 3 0 0r" bVaMevdle) 0 #vfiécrH ...
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