MS E3 Spring 12 - CHEM 241 Organic Chemistry Examination...

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Unformatted text preview: " CHEM 241 Organic Chemistry Examination Ill 27 April, 2012 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 0 Print the initial of your last name in the box above - Sign your name und_er_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 erasable media will forfeit your chance to request a regrade. Cross mistakes out completely - Answer questions in the spaces provided 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 timely fashion; there will be no exceptions j/ [if ,z‘ 1. (54 points) For each of the reactions below and on the following two (2) pages provide the major organic reaction roduct s . If no rea ‘ ~ u u . _ h t A. P ( ) ctlon occurs, write NR . Stereochemical deSIgnation is not important. 0 “ZTmmmf—-—->- 3)H30+ o C' 1) HN(CH3)2 3) H3O+ 0 OH 1)Pocg at y It mm 3) H30+ o OEt 1), O—Mgl (x3) 2) H30" 0 H30+IA 0 CH3 1) mCPBA —-———-——-—+ 2) H30+ 3) P00 Problem 1 Continues on Next page Problem 1 — Continued B. O \/U\ 1) DIBAL 25 EthuEl ’ CE 3) LAH 4) H30+ O \/U\ 1) Et'o- W DE: 3 O 1) E1 CuLi H mm 3)Jones O 1 DIBAL 0” 3) Me-l 4)Jones /\CN 4% 2) Et‘Br 3) NaOH/A 4) H3O+ NC 0 . Q \/U\ H'VA- W H Problem 1 Continues on Next Page ' Pr. ~ Problem 1 - Continued C \Vk /\Br Jk 2) Jones 3) POCI3 1) M90 3) H30+ 4) DIBAL 5) H30+ 1) I2/NaOH 3) H3O+ 1) PBI'3 3) MeLi 4) H3O+IA ) BH3-THF W and the one on the next page, provide detailed aFFOW-p'ugm (:‘tt points) For the transtm‘n‘uttlort below abilized by multiple resonance f meclmnisms. ll intermediates occur which are st forms. A. Be sure to show explicitly the formation of BOTH molecules of product 0 OH 0 H30*‘ --——-—'—” 2X H H orms, show all resona 5 . i orlllatlon be‘OW d pa e 0 de easonab e S C St CrhelilleS le a synthetic Step results il’l llr|u\lf(|'plerp OdUC SIO “lu peseeosoules aSSUHIe heul III II II Isoae . A. Problem 3 Continues on Next Page ‘ B Show each halogenation individually, and make sure to form the carboxylate O Br2/NaOH (XS) .__———————————-——-> CH3 MD significzam: W 355mm above 229 nm ‘40; 88 3‘20 160 2m 2m 2m min- “C MAR 5mm (53.0 MHz: cw; 290 >150" ‘ 1’26" 3d ‘ 43" ' a Smp} “H NMR S’pefib‘um {200 an. cm} mm: ...
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