CH231 Exam 4 - Chemistry 231 Fall 2009 Dr Shaughnessy...

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Unformatted text preview: Chemistry 231, Fall 2009 Dr. Shaughnessy Exam #4 November 24‘“, 2009 / N-ame:_ (print) C‘WIDz; Honor Pledge: I promise or affirm that I will not at any time be involved with cheating, plagiarism, fabrication, or misrepresentation while enrolled as a student at The University of Alabama. I have read the Academic Honor Code, which explains disciplinary procedures that will result from the aforementioned. I understand that Violation of this code will result in WWW suspension from the University. (Wu/Va You will have 1 hour and 30 minutes to complete this exam. When time is called please stop all work and turn in your exam. Show all work. Partial credit will be given where appropriate. This exam has 10 pages. Make sure you have all 10 pages, and that they are correctly copied, before starting the exam. The last page is a periodic table. You may use molecular models to help you answer questions on this exam. You will not need a calculator or any other electronic device to complete this exam. Please put all cell phones (turn off or to silent), ipods, calculators, or other electronic devices away in a book bag. Your book and all notes should be placed out of sight of yourself and your neighbors before the exam begins. Problem Score 5 (10) 6 3 (12) 7 (16) Total 2 (22 (104) The exam is worth 100 points. There are 4 bonus points built in DOCTOR FUN 1'3 NovZOOE Ffisficiwmwo! IT Twang ow“ H525 Elm/we on THE mama! nf3rl&[email protected]fio.org Th1: cartoon is made available on the Inxemex for personal viewing only, Opinions expnessed herein are solely those a! me author, Copyright© 200! David Farie ,d h[to:I'fibibiio.org!Davefddun.htmi Exciting developments in down NMRL research Have a happy Thanksgiving 1. For each problem below, circle the best answer. In each case, there is only one correct answer (12 points) a. Which nucleophile would be most reactive in an 8N2 reaction with methyl iodide? H20 ® H2804 c:— b. Which compound below would give a signal at highest chemical shift in its 13 C NMR spectrum? - . V ,, CH4 % CHsBr CH3F (7 OH}? x/ 0. Which alcohol below would be least likely to undergo elimination when treated with H2804? OH e. Which alkyl chloride could not be made by reaction of an alcohol with SOC {and pyridine? Cl CI V\Cl /\/K ©)\ CHSCI f. Which molecule would be most reactive in an 8N2 reaction? m M» Ma ®/ Mow U) 2. Provide the missing starting material(s), product(s), or reagent(s) for each reaction below. Where appropriate, draw the correct stereochemistry of the product or starting material. If a mixture of enantiomers would be formed, you only need to draw one enantiomer. It is not necessary to draw the inorganic byproducts of reactions. (20 points) '- NaOCHQCH3 a. . 'rH HOCH20H3 \_ e. O/OH H2304 3. For each reaction below, indicate whether the major product would be formed by an SNl, 8N2, E1, or E2 reaction and draw the major product(s) that would be formed. In a few words, explain why the reaction you chose would be favored. (18 points) Nao+ E; 5" /\/\/' ———*—> W Her 1? (a TM El would he lat/Meal bum. Jh «mm mahoflflz I} 0‘ hz‘mlmd base, Br CH3OH D 0 + 7/ b. (j _.__..___. L ' ”W 5H1 Would humeral because «W; [W] i 1917) (gr ‘ 0 Com ML, and 4M nucleaphlc is m m 5M 3/ 0 CH 3 O Y OTos A c NaO CH3 C C. DMF TM Snl rgaclfm Wld baht/mg! Lem/use W 30M”? 1‘s Ina/qr we, the “WW“! a: 47M Lew/1'7 7MP (losylak’x fun) is a good we . {—6 //_ 6 /€ 4. For each reaction below, draw the chair conformation that would be required for an E2 reaction and draw the product(s) that would be formed from that conformation. If more than one product can be formed, draw each product. If no product can be formed, write “no reaction”. (16 points) \/ KO Which reaction above would be the fastest? Which would be the slowest. Briefly support your answer in each case. WWW A would {KS’W 56641156 W ”W ho eabsHv/Wnb molly? m (0” way . Rzachen B would glow/V because illz Mini [50 lml) alloyllll/Z’l’lmItkeS Pl’lWL Ola l‘O/Y K19“ +0 04le 4M allzl lillulfl RMCi’IM C clots mt MW beau/«13¢ lite axial we)? «9” lMIYl mtJtyl Prat/wt {Of/is ach 6 5. 13C NMR spectroscopy (10 points) a. For each structure, indicate how many carbon peaks you would expect to observe in a 13C NMR spectrum of the compound. WOH V 6 3 b. Circle the structure above that is most consistent with the 13 C NMR spectrum. Briefly explain your choice. ‘ 200 180 160 140 120 100 80 cos—04453 ppm The WW 3V0” F m Urdflli Sir 0 {6 5881115 40 be a good (amatdcrifi, WWW @th M Hm. 6. In the substitution reaction below, one of the major products isolated is a rearranged product. Draw a step-by-step mechanism showing how this product is formed. Draw each intermediate formed in this reaction and use arrows to show the movement of electrons (12 points). , , ' + HBr , o [W H3C0H fr'Q H .. :9 " \ UN 3 ; r, 259 «a We a? M tv ’7» 7. For each problem below, propose a way to synthesize the desired product starting from the indicated starting material. You may use any necessary reagent to complete the synthesis. Each step of your synthesis should provide the desired product as the major product. (16 points) ...
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