1 Chem 2320 Exam 1 January 26, 2006 Name: (Please print) (first) (last) Last 4 digits of I.D. ___ ___ ___ ___ Score I. Multiple Choice ( /20) /60 II /15 III /25 Total score /1002 I. Multiple choice questions. (3 points each). Please put your answers on Scantron sheet. Your score will be graded based only on your answers from Scantron sheet. 1. Which molecular formula has molecular ions ration as: M+/[M+2]+=1/3? (a) C7H18Cl2 (b) C9H10Cl (c) C10H16Br2 (d) C11H14Br (e) None of the above 2. Based on the IR below, what is the corresponding compound? OHClOIIIIIIIV (a) I (b) II (c) III (d) IV (e) None of the above3 3. Based on the IR below, what is the corresponding compound? OHCO2HOIIIIIIIVO2N (a) I (b) II (c) III (d) IV (e) None of the above Answer Q.4 to Q.7 base on the following four 1H NMR spectra (A-D). From the compounds listed below, assign the compound to its corresponding spectrum. Note: Splitting patterns were designed as s: singlet, d: doublet, t: triplet, q: quartet, m: multiplet IIIIIIIVClClClCl4 Spectrum A Spectrum B d d m 2 H 1 H 6 H t m m t 3 H 2 H 2 H 2 H5 Spectrum C Spectrum D s 9 H 3 H t d m m 3 H 2 H 1 H6 4. What should be the correct compound responsible for spectrum A? (a) I (b) II (c) III (d) IV (e) None of the above 5. What should be the correct compound responsible for spectrum B? (a) I (b) II (c) III (d) IV (e) None of the above 6. What should be the correct compound responsible for spectrum C? (a) I (b) II (c) III (d) IV (e) None of the above 7. What should be the correct compound responsible for spectrum D? (a) I (b) II (c) III (d) IV (e) None of the above How many types of peaks (signals) would you expect to see in the 1H or 13C NMR spectrum for the following compounds from questions 8 to 15? 8. (a) 2 (b) 3 (c) 4 (d) 5 (e) None of the above H ClHHHHHHFrom 1H NMR7 9. (a) 3 (b) 4 (c) 5 (d) 6 (e) None of the above 10. From 1H NMRBr (a) 2 (b) 3 (c) 4 (d) 5 (e) None of the above 11. From 1H NMRBr (a) 2 (b) 3 (c) 4 (d) 5 (e) None of the above 12. (a) 3 (b) 4 (c) 5 (d) 6 (e) None of the above 13. (a) 4 (b) 5 (c) 6 (d) 7 (e) None of the above From 1H NMRClCl From 13C NMRClNO2 H HHHHHHClFrom 1H NMR8 14. (a) 4 (b) 5 (c) 6 (d) 7 (e) None of the above 15. (a) 3 (b) 4 (c) 5 (d) 6 (e) None of the above Answer questions 16 to 20 according to the 1H NMR of the following compound. From 1H NMRBr From 13C NMRBr HaHdHbHcHeH2NOOHHHHHHHHH HHHbHcHe9 16. From the 1H NMR, what proton dose the signal at 7.8 ppm (doublet) correspond to? (a) Ha (b) Hb (c) Hc (d) Hd (e) He 17. From the 1H NMR, what proton dose the signal around 6.6 ppm (doublet) correspond to? (a) Ha (b) Hb (c) Hc (d) Hd (e) He 18. From the 1H NMR, what proton dose the signal around 5.2 ppm (multiple or septet) correspond to? (a) Ha (b) Hb (c) Hc (d) Hd (e) He 19. From the 1H NMR, what proton dose the signal around 4.0 ppm (broad) correspond to? (a) Ha (b) Hb (c) Hc (d) Hd (e) He 20. From the 1H NMR, what proton dose the signal around 1.3 ppm (doublet) correspond to? (a) Ha (b) Hb (c) Hc (d) Hd (e) He Continue to the Next Page10 II. Assign compounds I, II and III to their corresponding spectra (9 points). Briefly explain how you make the assignments. (6 points) Place your answer on the next page. NH2BrNH2NH2BrBrIIIIII Continue to the Next Page Spectrum A Spectrum B Spectrum C11 Continue to the Next Page12 III. Provide your analysis and answers for the following questions (p14-15) based on the given spectroscopic information. You may get partial credits even your proposed structure is incorrect. (25 points) *From Mass Spec: M+ = 103 *From elemental analysis: C: 46.5%; H: 8.7%; N: 13.6%. Continue to the Next Page m/z Relative Intensity 15.0 1.1 26.0 4.3 27.0 31.1 28.0 10.6 29.0 100.0 30.0 9.6 31.0 1.8 38.0 2.5 39.0 22.8 40.0 2.9 41.0 90.9 42.0 5.4 43.0 4.3 44.0 1.6 45.0 5.0 46.0 2.9 50.0 1.6 51.0 1.8 53.0 2.7 54.0 1.1 55.0 23.3 56.0 16.9 57.0 87.6 58.0 4.1 62.0 4.513 Continue to the Next Page s s s s14 1. What is the molecular formula? (3 points) 2. From the IR spectrum, is there a carbonyl group (C=O)? (2 points) 3. Your analysis from 1H NMR. Please write clearly how you interpret the chemical shifts and splitting diagrams. (10 points) Continue to the Next Page15 4. Your analysis from 13C NMR. (5 points) 5. Your proposed structure (5