EXAM01b - Chemistry 2262 Section 1 Name 7%7 get/54"...

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Unformatted text preview: Chemistry 2262, Section 1 Name: 7%7 get/54" Exam 1 (last) first) September 23, 2010 The exam has 9 printed pages of questions and 1 page of tables. Check now to make sure you have all 12 questions and 10 total pages. Make sure to write your name on the first page and on the page 9 in the provided space, and put your initials in the designated boxes at the top right corner of all the other pages. Put your name, initials, and all answers on these sheets with an ink pen. The exam is worth a total of 100 points. IMPORTANT: If you decided to use your exam clicker score instead of the Section 1 score, mark the corresponding box on the page 9, and proceed to Section 2. In such a case, Section 1 will not be graded, and your exam clicker score (maximum 40 points) will be used instead. If the box on the page 9 is not marked, the Section 1 will be graded and used to calculate the exam total score. SECTION 1 40 oints total Multiple Choice (5 points each, 30 points total). Circle the one BEST answer for each problem. 1. Which of the following compounds is likely to have produced the 1H NMR spectrum shown below? (Only the aromatic region is shown.) 6.5 ppm 2. Which compound cannot be obtained by Friedel-Crafts alkylation of the corresponding mono-substituted benzene? p-methylphenol 3-bromotoluene p-tert-butylchlorobenzene 1-ethoxy-2-ethylbenzene A G) c o Your Initials 3. Which acid — base equilibrium will be most shifted to the right? OH O' Na+ (a) A + NaOH A + H20 OH O“Na+ (m [:E] -+ NaOH [:E] + rho OH o-Na+ r: + E: + CF3 CF3 OH o~Na+ (d) [f:] + NaOH =:======2= [f:] + H20 OH O" Na+ (e) + NaOH =;======== [::j +- Hgo CI CI 4. Which of the following resonance structures is/are particularly responsible for the increased facility towards alkaline hydrolysis of ortho-chloronitrobenzene relative to chlorobenzene? e e e e \e $9, 39,0 0\ ,0 O\N O O IN (9 e N OQN,O Cl CI Cl C! A C all four 9 OH 90H O OH OH ' 3’ structures A B c ‘III’ E F 5. Which of the amines shown below is the least basic? NH2 NH2 NH2 NH2 NH2 CF CL A N02 N02 N02 N02 NO A B c D < E ‘) | Yourlnitials 6. Which of the following aromatic compounds yields the highest ortho : para ratio in the product upon electrophilic chlorination? toluene ethylbenzene propylbenzene isopropylbenzene tert-butylbenzene ® B c D E Short Answers (5 points each, 10 points total). 7. Provide systematic IUPAC name for the mouth—washing antiseptic thymol: OH 2’ /®/r0fl%~5* 8. Explain the observed increase of reactivity of the following secondary alkyl halides in an SNl reaction: :H CH Gel Increasing reactivity flfl’ rage ‘“ w‘ y W Lil/V fZQGfl/boz \ Lg fl‘mdé’zfiww VAC? a, Wflaawvghormie, /WZ¢4¢¢CJW f «7L 6&@ My, [MW vice, We? M £69) SECTION 2 60 oints total 9. Draw a structure for the ma'or or anic roduct s of each of the following reactions, or write NR. for no reaction, if applicable. Place only one appropriate structure in each of the 9 boxes and assume only monoadditions 0r monosubstitutions (3 points each, 27 points total): 0 g“ CI F30 Zn/Hg, HCI M ———————--—-——————-> AlC's (>1 9%) heat i A|C|3 N114, 0 1) A|C|3(>1 eq.) Wm ~—W* 2) H2NNH2, 'OH heat Your Initials © 1) Gig, Fe (cat) ————~—-————————-> 2) fuming H2804 HNO3 CH3ONa 1) Sn, HCI 2) NaNOz, HCI, O 0C ———————————————-—n~——————————>- Your Initials ‘ 10. (5 points) Draw a stepwise detailed arrow-pushing mechanism for the following reaction: ©/Br HNOa Br WW?- H2804 OzN (a) Formation of the electrophile (1 point) A 4/ f] . p M (3 @ Mb'NMOZ ‘ifl MOM—NO; 5 AM); (b) Electrophilic attack to form the arenium ion (1 point) W W @W M N02, [/z/bea Wa / Your Initials Qx/za/ Lu} 1/ fie; bub/7 GAO/woe! ( 29M? , y 11. (18 points) Do two of the following three syntheses starting from benzene or toluene, any other monotunctional organic compounds [our carbons or less and any other needed inorganic reagents. ONLY TWO OF THE SYNTHESES WILL BE GRADED, so CLEARLY LABEL WHICH ONES YOU WANT GRADED. Wm 6% W W3 3 (A) COOH £943? L Q Li; FW; \7/ N02 7% Mgr? B 1991:" r W W W05 a H ‘/ i fife—M? I“: IN \ vaf \i/ M0% i W W Na L it rwwwwvwm~ {/0 QM (B) [QT] ‘ My?) 7 lg} ' new I / F we tie W {c} MOZ/ \/\ M02, / Wig I , M / Maw/0g #62 d m Lt?" My; 0°C; Q/~rt/Lc@ y 4w”: a 0 mes fro) f / l -—~—--—-—-‘-r / l (a ((3) OH _—\7 EQ/ 4: y realm: IQ/ k E:(No2 ‘ ‘Wwwywflww, CF?” «£16wafiL/Dwi / ,(1 ~—~> a f—e 1.4 _—> V flea} Q/ 2;” W05 “7/ - W (QM / Hogs , erg/<0 , / M02, “la/0+ W W 'V~—’ "if; ’p’ we to 3M 1;] 3M “ML R/ 12. (10 points total) Compound A of molecular formula C10H120 was subjected to electrophilic chlorination to form compound B. The 1H NMR spectrum of compound A and IR spectrum of compound B are shown below (tables of IR and NMR data are attached on the back of the exam). (i) Determine the (7: + r) for the compound A. Show your work. (1 point). I r, __L- C XI 0 "f’ "' J 2 ‘5’ @ «r r) 2 2 2, I 2/ S (ii) Clearly label on the IR spectrum key stretching frequencies with the functional group they represent (1 point). (iii) Draw the structures of compounds A and B in the boxes at the bottom of the page (6 points). (iv) Clearly label each type of protons a — c on the proposed structure of compound B (3 points). Compound A IUD mmsncrmncm :u S I {L fire“ I I 'r---—v—I—r— ‘ v . . I . 20m] 15m] 1000 EDD KHVENUNH ERI -1| Compound B a \ Ixytu 3000 . compound B ...
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This note was uploaded on 09/12/2011 for the course CHEM 2262 taught by Professor Smith during the Fall '08 term at LSU.

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EXAM01b - Chemistry 2262 Section 1 Name 7%7 get/54"...

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