MS E3 Fall 12 - y CHEM 241(Dr Montague-Smith ‘ Organic...

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Unformatted text preview: y/ CHEM 241 (Dr. Montague-Smith) ‘ Organic Chemistry II Examination Ill 29 November, 2012 YOUR NAME (Last, First, MI.) DISCUSSION SECTION #64 __ (5 pointS) Initial of last name Instructions - Please fill in your name in the space above and on the next page - Please put your discussion section number in the space provided. . Print the initial of your last name in the box above . Sign your name under the Honor Code acknowledgment on the following page - Failure to sign the Honor Code Acknowledgement will result in the forfeiture of your right to request a regrade - 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 questiosn inthe spaces provided (60 points) For each of the reactions below and on the following three (3) pages, provide the MAJOR organic reaction product(s). If no reaction occurs, write “NR”. If the reaction is an equilibrium reaction, assume product formation. PARTO A >p M i 1) H3O+IA 2) $0012 3) EtOH 1) EtOH 2) EC 3) EtBr 4) NaOH/A 5) H3O+IA 1) 30012 2) NH3 3) LAH 4) 1130+ 0” 1) DIBAL/‘78°C ———-————> 3) Actone/ H+ Problem 1 continues on next page Problem 1 - Continued PART B \\\]//JL\\w1)NaBH4 2) H30+IA o A 1) LDA OCH3 /—” 2) Et-Br 3) LAH 4) H30+ 1) LDA 2) Me-Br 3) LDA 4) Et-Br 5) NaOH/A 6) H30+IA '1)NaBH4 O O M 2) H30" 3 OH ) Y /H+/A o 1)Jones /\/\/\__________> OH HO 2) SOCI2 3) EtOH (x3) 4) CH3'MgBr (x3) 5) H30” Problem 1 continues on next page oblem 1 - Continued ART C 0 CI 1) EtOH 3) LDA 4) CH3'Br 4) H30+IA 1) EtOH/H+/A ——"——> OH 2) Eto- 1) H30 Li (XS) 2) H3O+ 1) SOCI2 NH \/“\ 1) Bra/PBr3 -- OH ——————‘-—> 2) H20 3) -CN Problem 1 continues on the following page PART I) lv’mlunm I - Cu'nllmuxl O H 1) Acetone/NaOH/A ~—————~—-——->- (MXS Zflfimd 3)NaBH4 4)H30+ 1) I2/H+ 2)NaBr CH3 1) Bra/NaOH 2) DIBAL -78°C 3) H30+ o /“\o/\ _1)_EtO;___> 2) H3O+IA H30+IA PART B OH OH HO 3. (20 points) For the transformation below and the one on the next page, provide arrow-pushing mechanisms. if intermediates occur which are stabilized by multiple resonance forms, show all resonance forms. PART A O O / H30+IA /“\ HN _*_____* /U\ N / OH \ PART B For this problem, use “B:-“ as your base as appropriate. OEt H+IA __—_———+ OH O + EtOH -' determlne the structure for the unk pic data provided on the followin t . nown molecules. D - 9 .WO (2) pages, Table of IR and NMR Information is at the end of the erg/myour structures In the boxes provided below. Draw your structure for molecule A in this box Draw your structure for molecule B in this box Spectral Informetion for Molecule A “c NMR Spoclmm (zooms. cw, lumen] No significant UV absorption above 220 nm 40003000 fi-i mun Specfium mo um. com:l MM 2000 _,1500 van] M*'- 14s (was) 120 180 200 min 1200 80) 240 280 j ...
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