MS E3 Spring 11 - CHEM 241 Organic Chemistry Examination...

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Unformatted text preview: CHEM 241 Organic Chemistry Examination Ill ’ 29 April, 2011 YOUR NAME (Last, First, MI.) ENTER Your DISCUSSION Section: 61__ (4 points) Initial of last name Instructions - Please fill in your name in the space above and on the next page - Print the initial of your last name in the box above « Sign your name under the Honor Code acknowledgment - DO NOT OPEN THIS EXAM UNTIL INSTRUCTED TO DO SO - Please provide your answers in blue or black pen. Use of erasible media will forfeit your chance to request a regrade. Cross mistakes out completely o uestions in the saces rovide Notes - This exam is worth 125 points - The exam period is 50 minutes. At the end of 50 minutes, all exams will be collected in a timel fashion; there will be n exce tions 5 points) For each of the reactions below and on the following two (2) pages, provide the major -‘ anic reaction product(s). If no reaction occurs, write “NR”. Stereochemical designation is not important. 0 (Eng-CU —'——————> CI 0 EKDH ——-——>— on ' o 1)socb “27EKM¢--—-—+- OH 0 NaBH4 OEt o nimBAL 2 0‘ 3)H304 O . 1) Br2/NaOH —2)'DTBFI.——" CH3 CH3 Problem 1 Continues on Next page Problem 1 - Continued B. o 1) H2/Pd —'~—-—> \ DB 2) H3C'Mgl (x3) 3) H30+ O . \/U\ Etc- “a CB 1) (Et)2-Cu Li 2) Et-‘Li 3) H30+ 1) (Et)2NH/H+ . ——_—> 2) EtBr 3) H30+/Heat 1) LDA NCACN 2) EH 3) NaOH/Heat 4) H30+lHeat H 1 H+ 0 Problem 1 Continues on Next Page lem 1 - Continued 0 O 1) \éLH w H 2) H30+ 1 CO 5 MgBr ) 2() 2) H30+ 3) SOCI2 4) EtOH ,1) PBr3 OH 2) NH3 3) LAH 4) H30+ fl)BH§THF OH 2) H30+ 2. ’28 olnts Forth . . I mQChapnism; If inteerrtrgzgeformatlon below and the one on the next page, prowde detalled arrow-pus‘ 0 forms . [ates occur WhiCh are Stabilized by multiple resonance forms, show all resolvea \ A. For this problem, you may use as your base 4 . 4 O O ‘ 1' H+ ———-—-—————> OEt EtO' B O "\_ l <0 ' ‘ 'de reas ‘30 3. (24 points) For the transformation below, and for the one on the followmg pag,e' prof! I enable‘ r Synthetic schemes to effect the transformations. If a given synthetio step results In mu tip e products or . multiple stereoisomers, assume the major product or isomer YOU W'Sh to proceed W'th can be ISOlated' A. NH /\Br _—_—————————-—-—P* /\/ 2 Problem 3 Continues on Next Page OH O lem 3 - Continued HO ‘ 4'. (15' points) Using the spectroscopic data provided on the next pag moiec exam. e, determi uie. Draw your structure in the box provided. Table of IR and NMR inform ne the structure for the ation is at the end of the $10!!!) 3360 20m 1611)!) ‘ 1200 800 v m“: Mass Spectrum Na signmcam UV abscrpflm 2mm 22M 9- "‘ - 33 i‘ “1.3 ct,ng . 40 so 120 {so 200 240 280 mm ‘30 NMR Spact'urn E > ‘ 3 ~o— mid-ms filo £20.21 kHz. (23:1: Watch} ; two {man at I 75 right fluid 2% :60 120‘ 80 4'0 0 6mm} a ‘H NMR Spectrum [.10an <3mmlL batman) 'Z... ...
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