CHM 3120 Exam 1 Answer Key 2010

CHM 3120 Exam 1 Answer Key 2010 - CHM 3120 (Fall 2010)...

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Unformatted text preview: CHM 3120 (Fall 2010) Midterm in - Saturday, October 2 Instructions: Please write all of your answers on the following pages. if you require additional space. you may write on the back pages of the exam. The last page of the exam has been intentionally leit blank. Assume aqueous work ups in all questions. Clearly denote stereochemistry where appropriate. Molecular model kits are permitted. Good lucki 1. a) Identify the most acidic proton in each of the following molecules and give its pKa value. (6 points) arise? (4 points) f Mme i0“ 1/‘\Q\ a\gj/Hfllo y NJ; wand plcfa h) /D . (Stuck qo" 1» ¢:o 1L 0 {W Ml wloil‘bl Ovukp "RM 0" . W 3.1 law Pair . I 9 k 0“ malty/«Adm Nu COM mhi aQPmC‘M" 0* \O’i" ' r / %%\”§Uhl\*t Mg: [070 2. Consnder the following reaction. “9w: y W“? NHCHa : c E CH30H2M984’ 4. § m ff}? 0“ Give the structure of the expected products from this reaction. Is there any selectivity in this reaction and if so, what is the major product? Justify your answer using appropriate models. [10 points) 3. Consider the following reaction. 0 9020M Zn(BH4)2 9H E05”? 0“ z ' ' ‘ ' / + Give the structure of the expected products from this reaction. Is there any selectivity in this reaction and if so. what is the major product? Justify your answer using appropriate models. (10 marks) OM; / Mag M)” LUA V a. u 0W 9 3—2nk'fitflxb,‘ {L a O 3/ 9‘ 09:3 /L{\/\{ OCH}, ’5 TL “ “ W W“: K W H m *4 8W“ @ /D‘:6QIAVQ 0\'\ gobuh DUB 3 Wm I 4. Consider the following unsymmetrical ketone. YK / Draw the structures of the “kinetic” and "thermodynamic" enolates. Provide the reagents and conditions necessary to form each of these enolates mm. (10 marks) W/‘§ EEO ACYCver‘sk'bgg 559%!) \K, W LBW -% $UCGH' 01 504* 3) 2’ €alvm+ (w. P\ ~31 Low «wwufin \ ’wad men Km. 00 W Kemp mm «(1‘ MN? rm “hm ‘ ' I v 5. Provide the structures of the two enolates that result from deprotonatlon of the / ketone shown below. THE-78°C V .. v I Z “>Fav‘6‘ L; ’ Clearly label each enolate as "E" or “2". Which enolate is favored? Why? As part of your discussion you should draw appropriate transition states. (15 marks) W0) W5 0 ‘m‘luackms E ' Enolalca Pb Rhea v‘tl» 6. Consider the following reactions. What ls the structure of the major product in each case? What are the transition states for the major and minor products in (b)? Clearly lllustrate why the transition state for the mlnm: Product ls disfavored. (10 marks) a) / o E”? 1) PhCH28r &(\Pk “’°‘ {3 ® *’"°°‘ Q) b) Cydohexyl é 0 6H 0' ‘Cydohexyl 1)PhCHO ' pt. \ "PA 1 [Awhm/ 2)H30* N W (I) ’ r Mk (II wk cw {x M \ 0/1!\Q1 A 1% 0 (I) M “H o "923 7. Provide a Man mechanism for the following reaction. (10 marks) 0 \N’ 013»:cha HsO’Mao / ’ , - / / .. __ in: g” #39 m0 8. Consider the following reaction. What is the structure of the enolate formed under these conditions? Why is only one enolate formed? How is the starting material prepared? (10 points) ’LI" 5 ° ° LDA.THF.-78°C o \J‘Nko —- v. ‘\ 2‘5,“ ft LI 0 (f) (Abs 5+0») 0" o 1 0 z 3 \J (D d “Babe flog. o o \,./ ...
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CHM 3120 Exam 1 Answer Key 2010 - CHM 3120 (Fall 2010)...

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