Exam1_10_AnswerKey

Exam1_10_AnswerKey - Chemistry 2262, Section 1 Name: k 9...

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Unformatted text preview: Chemistry 2262, Section 1 Name: k 9 Exam 1 (last) first) February 25, 2010 The exam has 8 printed pages of questions and 1 page of tables. Check now to make sure you have all 12 questions and 9 total pages. Make sure to write your name on the first page and on the page 8 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 8, 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 8 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 was likely to produce the IR spectrum shown below? 100 6 0 “JWLWWWLMWIWMIWWLWWIW SD TRANSMHTANCE ["16] £19 20 EFWIWWWWWWWIW1W"W!WWMWWTWWM“WK%WWMWWWW‘WIWWMNWVW 4000 3500 3003 2500 2000 1500 1000 500 WAVENUMBER [cm~l] ed“ ed Hog; B C 2. Which compound would result in an electrophilic aromatic substitution product upon reaction with isopropyl bromide in the presence of A1C13 ’2 aniline 3-brooluene nitrobenzene m-chlorobenzenesulfonic acid 2,4-dinitrobenzene A ol c D E ‘ Your Initials 3. What is the correct sequence that places the following compounds in order of increasing chemical"; stability? A B C (a)A<B<C (b)B<C<A (d)C<B<A (e)A<C<B 4. Which nitrogen atom in the heterocyclic compound imidazole is more basic? 3\LN /\ (a) atom 1 tom 3 (c) all have the same basicity ((1) depends on the reaction conditions 5. Which of the following compounds reacts most rapidly with HN03 in concentrated H2804 ? A B c E 6. Which of the phenyl ethers below can be cleaved with concentrated HI ? O O O 0 G (3 (3 Y 0 i (j V< Short Answers (5 points each, 10 points total). 7. Provide systematic IUPAC name for the food antioxidant additive BHA (E320): OH 0\ 2-11va Wbcit awe/{flaxfi/tmoé #Isflflfx/L af’é'vé’é’ “'35? Caé’mwfl SECTION 2 160 points total) 9. Draw a structure for the major organic productgsl of each of the following reactions, or write N.R. for no reaction, if applicable. Place only one appropriate structure in each of the 9 boxes and assume only monoadditions or monosubstitutions (3 points each, 27 points total): / OH /\/ E Br.2 —————~————--———-> \ ——-———-———> H 80 Fe cat. 2 4 \ ( ) NaNH2 —-——~—-——> liquid NH3 Your Initials )VCI HNO3 *—w#-—> ——-———————-——-——-—-———-> AICI3 (cat) H2504 1)Sn/HO 2)NaN02/HC| 0°C "WW—9 3) H20. CU2O, Cu(N03)2 1) NaOH 2) CHgCHZBr 1)KMnO¢'OH 2) H30“ M——> O 1) MCI AICI3 (>1 eq.) . . 2) Zn(Hg), HCI heat 10. (6 points) Draw a stepwise detailed arrow—pushing mechanism for the following reaction: (a) Formation of the electrophile (1 point) AICI3 —--———--———-> “’ l /0 ‘3 M C) b.3c8'AlC/{73 (e) Regeneration of the catalyst and formation of HCl (1 point) 0%,» {ya/M «(gem/5M We fates”me our nitials 6224' a" 5!" Ci Cwflf: Y I 11. (18 points) Do two of the following three syntheses starting from benzene or toluene, any other i* 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. O I 12. (9 points total) Compound A of molecular formula C10H120 was brominated with NBS to to m H r ‘\ ‘ compound B. The IR spectrum of compound A and 1H NMR spectra of compound B are shown below (tables of IR and NMR data are attached on the back of the exam). (i) Determine the (1t + r) for the compound A. Show your work. (1 point). @410: 74/0 +2 “IZJ 3“ g (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 (4 points). (iv) Clearly label each type of protons a — e on the grogosed structure of compound B (3 points). Wth‘j Wrww~~mw~ ‘\ §—i 80 TRANSMITTANCE [Va] 60 40 ML» 20 Compound A n .MWMWMWWWIWWW'WW W 4000 3500 3000 2500 2000 1500 1000 500 WAVENUMBER [cm‘l] Compound B compound A 7 ...
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Exam1_10_AnswerKey - Chemistry 2262, Section 1 Name: k 9...

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