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Bertozzi_Chem3A_Final_1997_Key

Bertozzi_Chem3A_Final_1997_Key - Chemistry 3A Fall 1997...

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Unformatted text preview: Chemistry 3A - Fall 1997 Final Exam - December 10, 1997 Professor Carolyn Bertozzi Your full signature 32% Professor James Leahy Print your full name (Last name. First name, Middle) Please circle the section number and name of your GSI/T A. 111 Clarke,Kristin_ 231 Grunwell,Jocelyn 341 Pindzola,Bradford 121 Schmidt,Joseph 361 Janzen,Daron 41 1 Purdy,Matthew 131 Desaire,Heather 371 Crawford,Nathan 421 Skyler,David 141 Tripp,Jennifer 381 Holland,Andrew 511 Marcaurelle,Lisa 21 1 Yin,Jun 31 1 Sadow,Aaron 521 Keet,Corinne 221 Grayson,Scott 321 Patin,Joshua 531 BIazey,Charles 331 Duncan,Andrew Making up an I-grade Indicate semester you took 3A Professor This exam has 20 pages; make sure that you have them all. We will only grade answers that are in the Do Not Write in this Box. designated spaces; please do your scratch work on the backs of the exam pages. Except in the boxes for question 3, write only 93 answer to each problem; multiple answers will receive m credit, even if one of them is correct. 1. (30) 2. (50) 3.__(100) 4 (30) 5. (25) 6 7 8 Note: This examination runs for a total of 180 minutes. No questions will be answered by proctors after the exam begins. Please write legibly; ambiguous or messy answers will receive no credit. Partial Periodic Table I II III IV V VI VII VIII He (25) (50) (90) Total (400)_ 4a. 8a. 4b. 8b. 40. Sub 4 2 Name ....... 1. (30 points) Indicate the relationship between each of the following pairs of compounds (identical, enantiomers, diastereomers or structural isomers). In addition, circle any compounds that are chiral. CH3 CHZCH 3 Identical a) Hg :H H: :H Enantiomers CHZCHS CH3 Structural Isomers Identical b) m Enantiomers Diastereomers Structural Isomers lde ntical Br Enantiomers c) Br CECH K HCEC Diastereomers Structural Isomers Identical B d) V9 8'33 HO Diastereomers Structural Isomers Identical CH3 CH3 e> “jg“ Him CI H H Cl Diastereomers CHQCHa CHZCHa Structural Isomers Identical f) “ud’\ Enantiomers Diastereomers = Structural Isomers 3 Name ....... 2. (50 points) For each of the following series, circle the appropriate answer based on the information requested. In each of the following, which is the most stable? a)» w 69 ”0” Cf H CH3 CH3 H CH3 CH3 H H H H H In each of the following, which is the most acidic? e) CF3CH2CH20H CHacFZCHZOH \I g) HCECH HZC=CH2 H3CCH3 Name ....... In each of the following sets of reactions, which will proceed the fastest? 0 O OgCH CF hue 0 CF 9 3’ ll 3 a j T 3 + CH3803 o o 0 O OgCH CBCICIIOG O 00' o 3 _.\ 3 D’ II D Y + CH3803 o 0 fl. 0 Br 0 OH ”Y /\TI/ :3: N + HCI /\I/ Name ....... . (100 points) For the following reactions, provide the appropriate starting material, reagents and/ or organic product(s) in the box provided. Note that more than one reagent or product may be necessary in a box for the answer to be correct. Be certain to clearly indicate stereochemistry or alkene geometry where necessary. Note that you may ignore water workup in these questions. a) d ‘ ' OH b) Cl /l\‘:\/ NaOCH2CH3 a Br W Bra. CHacHzOH /7/K/ I 0—\ d) CH3CECH Name ....... e) Cl /'\(\/ KOC(CH3)3 cm —— 0* \ 1) CH3CH2MgBr 2) H20 Br 0 ll 1) NaOCCHa 2) NaOH. H20 Name ....... 1) 03 00 2) (crabs Name ....... 6H 6N r) W NaH 0 Br OH ——'—'—’ 0 HBr %/ CH3OOCH3 Br Name ....... . (30 points) For each of the following reactions, provide a detailed, step-wise mechanism using the 'curved arrow notation.’ Be certain that your mechanism accounts for the formation of the product shown, including stereochemistry and / or alkene geometry. ”<1“ CE .1641, x ”is 0 (if 0 \ a 0% 4—» H’JéHQb-Hc} Name....... 10 11 Name ....... 5. (25 points) In your job at the Berkeley Chemical Company, you've found a bottle that simply has the label ”C4H80” and nothing else. In taking an infrared spectrum, you find that this compound does not absorb at frequencies above 3100 cm , but it has a strong absorption around 1100 cm . The proton and carbon NMR spectra are given on the following page. What is this unknown compound? Note that you will be graded based on the structure drawn in the box. If you feel that you can only identify a portion of the structure, be certain to put that in the box for partial credit. //\0/\ C4H80 ON CV 00 ow 00—. CE. 3, omzvo no <50QO $42 at: dc 12 13 Name....... 6. (25 points) Prenyl bromide is the common name for a useful reagent in organic synthesis. The molecular formula for prenyl bromide is C SHgBr. When treated with hydrogen in the presence of a platinum catalyst, it reacts to form a new compound with the formula CanBr. The proton and carbon NMR spectra for prenyl bromide and the new product are given on the following pages. What are their structures? Note that you will be graded based on the structures drawn in the boxes. If y0u feel that you can only identify a portion of the structures, be certain to put them in the boxes for partial credit. )Me Prenyl Bromide )wfir Hydrogenated Prenyl Bromide . iii: 5.33;; 00 ON 9: 4:2 2.? MES—0mm 4>mea m0 <m._.0mn_w W222 4 1 mo__>_Omm_ 4>men_ Dmk<ZmOOmD>I “.0 <EHOQO $22 5 1 16 Name ....... 7. (50 points) For the following schemes, each of the boxes below represents a different compound such that all of the information is satisfied. What are these compounds? 3) 0 ll 1) HQ(OCCH3)2. H20 2) NaBH4 Hao+ C9H180 - CTO3 PBra O - 1) CH3MgBr 2) H20 KOC(CH3)3 17 b) optically active optically active HBr . / Name ....... HBr peroxides At? optically active @/\/Lr<s, optically inactive 1) 03 2) M828 18 Name ....... 8. (90 points) Provide a viable synthetic route from the starting material shown to each of the following products. Where applicable, follow the restrictions listed, but otherwise, use any reagents you deem necessary. Show your synthesis in a step- wise fashion in the forward direction. a) \/O\/\/\/O\/ from cyclopentane and any other reagents with 2 carbons or less (5"). NaO :1) ‘0 _.—5r 6} A w l.) 05 0104+ (“FM-3 a) (1‘5ng (3. era». u) /\o/\/\/\0/\ 19 b) Name ....... >=C>=o from trans-4-bromocyclohexanol (6r \ \O'H +43}: {$on H’ CJ (Car) 0H .0 I) )L G 97 “WV“ .0 H5 0 20 C)/W\/\)J\ from 5-bromopentanol _..._:,» ' 6M0“ ’KJCCvfi-B /\/\/\/\/ OX f Pfir Name ....... ...
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