CHE321_ExamFinal_22

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Form 1 CHE 321 Final Exam December 9, 2022 The first 21 questions are multiple choice questions, worth 5 points each, and should be answered by filling in the appropriate bubble for each question. Questions 22-31 are short answer questions with points indicated on the question. These questions should be answered in the space provided on the front and back of the answer form. Exact masses and isotopic abundance of selected isotopes Element Isotope Exact mass Abundance, % Hydrogen 1 H 1.007825 99.985 2 H 2.0140 0.015 Carbon 12 C 12.00000 98.90 13 C 13.00335 1.10 Nitrogen 14 N 14.00307 99.63 15 N 15.00011 0.37 Oxygen 16 O 15.99491 99.759 17 O 16.99913 0.037 18 O 17.99916 0.204 Fluorine 19 F 18.99840 100 Chlorine 35 Cl 34.96885 75.77 37 Cl 36.96590 24.23 Bromine 79 Br 78.91834 50.69 81 Br 80.91629 49.31
Form 1 CHE 321 Final Exam December 9, 2022 Page 2 Common IR Absorptions Alcohol: O-H (stretching) 3200-3650 cm -1 Nitrile: C≡N (stretching) 2200 -2260 cm -1 Amine: N-H (stretching) 3000-3500 cm -1 Alkynyl: C≡C (stretching) 2100 -2200 cm -1 Alkynyl: ≡C -H (stretching) ~3300 cm -1 Carbonyl: C=O (stretching) 1680-1750 cm -1 Alkenyl: =C-H (stretching) 3010-3095 cm -1 Alkenyl: C=C (stretching) 1620-1680 cm -1 Alkyl: -C-H (stretching) 2853-2962 cm -1 Aromatic: C=C (stretching) 1600, 1475 cm -1 Aldehyde: C-H (stretching) 2700-2770 cm -1 Alcohol/Ether: C-O (stretching) 1020-1275 cm -1 Approximate chemical shift ranges (in ppm) in 1 H-NMR
Form 1 CHE 321 Final Exam December 9, 2022 Page 3 1. Which structure is consistent with the mass spec shown? The molecular ion peak is at m/z 156 and isotope peak at m/z 158. 2. Which isomer(s) of trimethylcyclohexane drawn below have a conformation in which all three methyl groups are equatorial? A. 1 only B. 2 only C. 3 only D. 1 and 2 E. 1 and 3 F. 2 and 3
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Form 1 CHE 321 Final Exam December 9, 2022 Page 4 3. Which two reactions will form the same major product? A. 1 and 2 B. 1 and 3 C. 1 and 4 D. 2 and 3 E. 2 and 4 F. 3 and 4 4. How many signals would you expect in the following compound’s 1 H-NMR spectrum and 13 C-NMR spectrum? A. 1 H-NMR = 4 signals, 13 C-NMR = 4 signals B. 1 H-NMR = 4 signals, 13 C-NMR = 5 signals C. 1 H-NMR = 4 signals, 13 C-NMR = 6 signals D. 1 H-NMR = 5 signals, 13 C-NMR = 4 signals E. 1 H-NMR = 5 signals, 13 C-NMR = 5 signals F. 1 H-NMR = 5 signals, 13 C-NMR = 6 signals 5. Which structure(s) contain(s) an atom with a pyramidal molecular geometry? Note: all lone pairs are shown. A. 1 only B. 2 only C. 3 only D. 1 and 2 E. 1 and 3 F. 2 and 3
Form 1 CHE 321 Final Exam December 9, 2022 Page 5 6. Select the line-and-wedge structure that shows the same molecule as that shown by the Newman projection . 7. Arrange the conformations of R -2,3-dimethypentane shown in order of increasing stability (least stable to most stable). 8. Choose the major product(s) of the following reaction. A. 1 only B. 2 only C. 3 only D. 1 and 2 E. 1 and 3 F. 2 and 3
Form 1 CHE 321 Final Exam December 9, 2022 Page 6 9. Which structure is consistent with the IR spectrum shown? 10. Five of the structures shown are resonances structures of X . Which is not a resonance structure of X ? 11. Rank the compounds shown in order of increasing acidity (weakest acid to strongest acid). A. 1<2<3 B. 1<3<2 C. 2<1<3 D. 2<3<1 E. 3<1<2 F. 3<2<1
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Form 1 CHE 321 Final Exam December 9, 2022 Page 7 12. Choose the enantiomer of compound X . 13. Which of the following molecules is/are chiral? A. 1 only B. 2 only C. 3 only D. 1 and 2 E. 1 and 3 F. 2 and 3 14. Select the best description of the major product(s) formed from the following reaction. A. a single achiral compound B. a pair of enantiomers C. a pair of diastereomers D. only the (1 R,2R ) diastereomer E. only the (1 S ,2 S ) diastereomer F. a meso compound
Form 1 CHE 321 Final Exam December 9, 2022 Page 8 15. Which of the following signal types is the 1 H NMR spectrum of the following compound expected to show? A. singlet and doublet B. singlet, doublet, and triplet C. singlet and triplet D. singlet, triplet, and quartet E. doublet and quartet F. doublet, triplet and quartet 16. Which structure is consistent with the 1 H NMR spectrum shown?
Form 1 CHE 321 Final Exam December 9, 2022 Page 9 17. Select the structure(s) that represent the conjugate acid from the following acid-base reaction. A. 1 only B. 2 only C. 3 only D. 4 only E. 1 and 2 F. 3 and 4 18. Choose the structure that is a conformational isomer of X .
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Form 1 CHE 321 Final Exam December 9, 2022 Page 10 19. Which alkene reactant(s) would give the product shown as the only major product of the following reaction? A. 1 only B. 2 only C. 3 only D. 1 and 2 E. 1 and 3 F. 2 and 3 20. A solution of the three compounds shown dissolved in ether is extracted with a solution of aq. NaOH. Which compound(s) will remain primarily in the ether layer? A. 1 only B. 2 only C. 3 only D. 1 and 2 E. 1 and 3 F. 2 and 3 21. Choose the major product of the following reaction.
Form 1 CHE 321 Final Exam December 9, 2022 Page 11 22. The following reaction is a rearrangement that has been taught in CHE 322. Follow the curved arrows and draw the other product structure formed from this mechanistic step. (5 points) 23. Draw the reactant that would give the product shown as the major one of the following reaction sequence. (5 points) 24. The mass spectrum of 3-pentanol has a weak parent peak at 88, but it has a very strong base peak at 59. Draw a structure for the very stable cation corresponding to the base peak at 59. (5 points)
Form 1 CHE 321 Final Exam December 9, 2022 Page 12 25. The 1 H NMR spectrum of an unknown compound with formula C 4 H 10 O is shown below. The spectrum contains three signals: doublet with an integration of 6, singlet with an integration of 3, and a multiplet with an integration of 1. Determine and draw the structure of the unknown compound. (5 points) 26. Based on the following reactions, draw the structure of compound X . (5 points)
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Form 1 CHE 321 Final Exam December 9, 2022 Page 13 27. Determine and draw the structures of compounds A and B . Draw wedged and dashed bonds where appropriate. (10 points) 28. Propose a curved arrow mechanism of the following reaction. Show all intermediate structures. HINT: start with protonating the epoxide. (10 points)
Form 1 CHE 321 Final Exam December 9, 2022 Page 14 29. Draw a curved arrow mechanism of the following reaction, showing all bond breaking and bond making steps. Show all intermediate structures. (10 points) 30. Propose a synthesis of the following compound starting from compounds containing four carbon atoms or less. (10 points)
Form 1 CHE 321 Final Exam December 9, 2022 Page 15 31. Propose a synthesis of the following compound starting from compounds containing four carbon atoms or less. HINT: you should probably use a TMS protecting group in your synthesis. (10 points)
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Form 1 CHE 321 Final Exam December 9, 2022 Page 16
Form 1 CHE 321 Final Exam December 9, 2022 Page 17
Form 1 CHE 321 Final Exam December 9, 2022 Page 18
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Form 1 CHE 321 Final Exam December 9, 2022 Page 19

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