10 Questions for Exam 3 - Organic Chemistry Lecture | CHE 275, Exams of Organic Chemistry

Download 10 Questions for Exam 3 - Organic Chemistry Lecture | CHE 275 and more Exams Organic Chemistry in PDF only on Docsity! 1 _______________________________________ CHE 275 Exam 3 key Print Name Fall 2010 ________________________________________ SU ID number Please Note: • the exam is closed book (no book or notes or models are allowed) • no calculators are allowed • listening to music during the exam is prohibited • you may not refer to your cellular phone or pager (please turn them off) • write in permanent black or blue ink (exams in pencil will not be regraded) • all answers should be written on the exam • clearly indicate your answers in the spaces provided • if we have to guess what or where your answer is, it’s wrong • be sure to outline the logic behind your answer (you may get partial credit) • work pages are at the end of the exam Your signature below is your assurance you have worked independantly within the bounds of the Syracuse University Compact on Academic Honesty: ______________________________ Signature (1) 12 pts...................................... __________ (2) 5 pts....................................... __________ (3) 18 pts..................................... __________ (4) 15 pts..................................... __________ (5) 6 pts..................................... __________ (6) 5 pts..................................... __________ (7) 6 pts...................................... __________ (8) 6 pts..................................... __________ (9) 16 pts..................................... __________ (10) 11 pts...................................... __________ __________________________________ TOTAL 100 pts................................ __________ PERIODIC TABLE OF THE ELEMENTS enor TA | A mA WA] VA] YEA] VIA vu 1B} oma jms{ive| vs |visivis] ¢ -# +30 -2 +1 WALENCES +2 9 +2 VARIABLE +343 4s 36 a ? pemao] 1 2 t H He 4.008 4.003 “3 4 s 6 7 z 9 10 2 Li | Be Bic ]NIO F | Ne 6.941 | 9.012 10.81 | t2.08 | 14.01 | 16.00 | 19.00 | 20.18 1 12 wot fois [ 1% fo ] is 3) | Na | M Al | Si Pp Ss a] ar 22.99 | 24.51 26.98 | 28.09 | 30.97 | 32.06 | 35.45 | 39.95 19 [ 20 [3 22 f 23 | 24 | 2] 36 | 27 [ 28 | 23 7] sof ot f oe] 32 [ 3a fT 3s [36 4 K | Ca | Se ri Vv | Cr | Mn] Fe | Co |-Ni_} Cu | Zn | Ga | Ge | As | Se | Br | Kr 39.10 | 40.08 | 44.96 47.88 | 50.94 | 52.00 | 54.94 | 55.85 | 58.93 | 58.69 | 63.55 | 65.38 | 69.72 | 72.59 | 74.92 | 78.96 | 79.90 | 83.80 37 7 38 7 39 ao 7 43] 42 | a3 | aa [ as [ 46 [ a7 [aa | 49 | so | st [sz] sa fs 3s Rb |] Sr ¥ Zr | Nb | Mo | Te | Ru [ Rh | Pd Ag. Cd § In j Sn { Sb | Te 1 Xe 85,47 | 87.62 | 88.91 9t.22 | 92.91 | 95.94} 198) | 101.1 | 103.9 | 106.4 | 107-9 | 192.4 | bts.s f te8.7 | 128-8 | 127.6 | 126.9 f 13t3 ssf sé fF os7 -n{ 72 | 3 | 74 [| 7s | 76 | 7 | 7s | 79 | 80 | a1 | a2 | 83 | 8 | as f a5 6 Cs | Ba [La paste} He t Ta | W } Re |] Os | Ir Pt | Au | He | Tl | Pb Bi | Po | At j Rn 132.9 | £37.3 | 138.9 AWES| 178.5 | 180.9 | 183.9 | 186.2 | 190.2 | 192.2 | 195.1 | $97.0 | 200.6 ] 204.4 | 207.2 | 209.0 | (209) | id) jC] 37 as | 89 (o0-103/ tos | as | i06 7 Fr Ra | Ac facre| Ku | Ha . (223) | 26.0 | 277.0; SE | 261) | C62) { 6d) 38] 59 T oo fT a | ez fo joe: Tos [ ce [ or | oa | 69 | 70 Tm wee G6, | ft] Na] Pm | Sm] Es | Ga | Th | Dy | Ho | Br) Tm | vb | te 440.1 | 140.9 { 154.2 | (145) | 150.4 | 152.0 | 157.3 | 158.9 | 162.5 | 164.9 | 167.3 | 168.9 | 173.0 | 175.0 om oo 7 9 f of 99 [oe [os foe | 97 [9a f 99 fF oo | tor | toz { 103 abeires Th | Pa U Np Pu {Am | Cm j Bk | Cf | Es | Fm | Md | No | Lr 232.0 § 231.0 j 234.9 | 297.0 | eae | Gay | 2sr | Gan | asi [asa | sr | ese | 25% | enor 5 Problem 3: (18 points) Indicate the proper reagents needed to complete each transformation. a) HBr b) Br2, H2O c)OsO4 or 1)MCPBA, then 2) H2SO4, H2O d) CHCl3, KOH e) MCPBA or X2, H2O followed by NaOH (halohydrin followed by elimination) f) NBS, hv or NBS, peroxide, or Br2, hv, or Br2, peroxide OH Br OH OH Cl Cl O Br Br (a) (b) (c) (d) (e) (f) 6 Problem 4. (15 points) Supply the structure of the major product expected from each of the reactions shown below. (a) (elimination product also acceptable) (b) (c) (d) (e) CN Br Br Br Br 1) Hg(OAc)2, H2O/THF 2) NaBH4 OH 7 Problem 5. Draw an appropriate diene and dieneophile that you could use to synthesize each structure using the Diels-Alder reaction. (6 points) (a) (b) (c) 10 Problem 8. (6 points) Using reaction coordinate/energy diagrams and a minimum of words explain why tertiary alkyl halides react faster than primary alkyl halides under SN1 conditions. Please label all intermediates, all activation energies (Ea) and the coordinate axes. 11 Problem 9. Treatment of the alkene shown below with sulfuric acid in water does not lead to the desired hydration product. (a) (3 points) What product will result from the reaction above? (b) (7 points) Provide a mechanism for the formation of the correct product for part (a). (NOTE: if your structure is incorrect for part (a), you will receive no credit for this portion the question). (c) (6 points) What conditions should avoid these problems and provide the desired product on this substrate? What is it about these conditions that avoid the problems seen in the acidic hydration reaction? BH3, THF followed by H2O2, it doesn't go through a cationic intermediate Oxymercuration also works, as it doesn't go through a discreet carbocation H2SO4 H2O X OH OH OHH+ + + H O H H + OH 12 Problem 10. Show how you would prepare the molecule below from the indicated starting material (more than one step is required). Include reagents and the structure of any intermediate compounds. A mechanism for each step is not required. (11 pts) Br2 Br Br NaNH2 NaNH2, then BuBr H2, Lindlar catalyst