EdExam3 - Jentz, Edward 810186982

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Unformatted text preview: Jentz, Edward 810186982 HIIIIIII/IHIII"IIIIIIIUIIIMIIIIIIIIIIII/Illlllfll/IIII July 15, 2009 SCORE .me €10 igé $5.20 810# CHEMISTRY 2211 Be sure to read each question carefully. Partial credit will be assigned where appropriate. To receive full credit you must answer the question completely. Relax and good luekl! 1 l. (6 pts) Provide the proper IUPAC names for the following compounds in the 2 spaces provided below: 2- .7 n4 t -_ H~ “ alf— ’ ‘ 4f)(g-4 h?” 2. (10 pts) Provide a complete, detailed and stepwise mechanism for the following reaction. In order to receive full credit vou must show all electron movement and rovide all ofthe intermediates for this reaction: Br ' \CHa BT2 . —————i> ElOH f"\ {if ‘ 6if ‘ it , 7' t l/ i -—-_—_—_ f‘\ I x“ :3 (:1- . l; .r‘ ( ('II:‘§\ ( a 1 N '“\ 1‘ ‘« ;’\‘LJJ\ Dir/fi‘ k \ ’4 L{) /I £1] Li \‘v .w‘\‘ .1, A l if" 3. (8 pts) Draw the structures for all of the possible product(s) of the following reactions. Clearly circle the major productgs) of each reaction if more than one product is formed: - i H.164 WW7 w !‘—‘ HO H2804,H20 1? THF, 50°C ' r‘ - ‘ r7 (8 pts) There are two series of reactions that will result in the transformation of1,2- dimethylcyclopentene to the trans-diol shown in the reaction scheme below. Draw the appropriate structures of each intermediate and provide the specific reagents required to achieve each transformation: Reagents Shared Intemediate A «1 \,/' Reagents Reagents Intermediate ‘\' ' 7‘ :- r ‘1‘” _ \‘1 ‘H- 5. (12 pts) Provide all of the products, consistent with Markovnikov’s rule, resulting from the addition of one equivalent of HBI‘ to the following compound: I; 1. In order to receive full credit for this problem, you must provide the structure of each final product as well as the structure of the specific intermediate that leads to each product. In addition, clear] label the ma'or kinetic and thermodvnamic roducts alon with the minor kinetic and thermodvnamic rodncts. Be clear and organized in the arrangement of your answers. You do not need to show stereochemistr E/Z or ms in vour answer 5 . Intermediates . _ __ Products "10362 ~/ ,9 / > a, u ‘4'.” 6. (8 pts) Complete the following Diels-Alder reaction schemes by providing either the appropriate dienefdienophile starting materials or all possible reaction produet(s)'. Show specific stereochemistry when appropriate: It- ’ -~- u., . L F- f 1‘ 7. (2 pts) Draw the structure of the free radical formed from the following reaction: (3 pts) Draw the structure of a two monomer segment of the polymer formed from the acid catalyzed polymerization of the diene provided below: Acid Catalyst H+ (3 pts) Draw the structure ofthe alkene monomer that forms the following compound after undergoing free radical polymerization: Free Radical Polymerization y» 8. (10 pts) \Vrite a series of steps to accomplish the following synthetic transformation. You must provide all appropriate reagents and intermediates for your synthetic pathway. No reaction mechanisms (arrows) are necessary to answer this question. w O O I] i Acetylene I::::_,> M + \/l\/U\ H H 1 mole ‘M..- f/ hf \_ . K ,-..‘ ‘ r n \ mm 9. (16 pts) Complete the following reaction schemes by adding the appropriate reagent(s), starting material(s), andlor produet(s). Make sure to indicate the proper regiochemistry and stereochemistry when necessary: *Iowlroom tem reaoent onl OK 1.) 0504 —-——-—->- 2.) NaHSO3. HZO 10. (14 pts)Comple1ethe following reaction schemes by adding the appropriate starting material(s), reagent(s) andfor produet(s). Make sure to indicate the proper regioehemistry and stereoehemistry when necessary: /\’/\ HBr 2 equivalents 1) 03 /\/\, 4. 2) Zn/Hao+ \ /\'/\“T~ I? 10 2 equivalents 11 Bonus (5 pts): A. Clearly circle all of the chiral carbons in the structure provided below: B. Draw the two enatiomeric forms ofihe following condensed formula. Be sure to use dashed and wedged lines in clearly indicate the proper spatial orientation of each group around the chiral center: Br I CH3C(NHCH3)CHZCH3 12 rmFEEMw—U‘ficgum ESE—E Eh EEE. Ecfiflnm >mkEEHIUxu=ztm 75395 .3; «32:... 2:55qu an E. 1 may...“ 8—. we. 2:. 2:. mm 3 hm mm mm mm "$3 5...: EN. EN. 33 7 :E a. SE 1 ca. n. .9: n. m. $53 3 E. E. m... an S mm mm 3 8 E on mm mm 3 a, i E a o: 3 E E n. a new 5 2,. a m. $3.: w «an: m. 322 9, (SE n. 832 n. ENE a. 32m— ? R? N. ‘3: N. E: n. as; 7 32: 9, .U<n_:_ >2 #2:? .93... _o 3.53% 9.: Es: Bu: an =3. ..m.m~ E 8:39.”. 9.: mmficmo: map 9.63 Emmet—E 982m 6 3552..» he m_onE>m was $9.2 268295 9:... .......................... a: N: F: 2: 2: z: 2: Ecmfi. 723$: 25 25 as 55 :2 m: g 3 8 55 EN” EN. EN. 25 as: m t. . . . . . n m...ch ucm mh mEmEmE .2 w.3.~a.a—. mé TwnéT e.mw.mn.m T Wm 73.5. w.n_..~m.m—. TuTmnéT “$73.3. méfiwmrmT TméTn—Lmé 3 w an mm 5 3 5:28 32;,“ _.m cm $.wa manNnéT ....E.mm.§. _..§.E.w.~ 73.3.?“ “Jo—LET?“ mm a<hv . . ‘ , www.25— w. :3 a .9: 33“ E. n— finnde .mnBofl :oEEou E mEmE 25.2 n. 50E 9: E manEzc mmmE Em E. m; wmmchmhmn _.__ EmnEzc mmmS. "202 VIN ll 5:929:00 ,5:qu D II .mnEsz EEO? 53cc _ 89? n om. :0 uwmmn Em mmmmmE EEOE m>zfiwm _an>m a I 385 coamuio uEumEm II VI _. Sin; .II mums. 2:33. o .5254 >m¥ m w mflcoEmzm 9.: .5 2an 2623a. ...
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EdExam3 - Jentz, Edward 810186982

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