CHEM 2324 Exam 4 Version A Name: May 14, 2013 UTEP ID #: The Exam 4 retake homework is due Friday, May 17, before 5 p.m., no excuses or exceptions! 1. How many chiral centers with (R)-absolute configuration are in the following compound? (Hint: One of the nitrogens is a chiral center with lone pair of electrons pointing away from you in the provided structure. The arrow is pointing to overlapping lines, not a carbon. This compound is tetracyclic and a legal drug found in some sodas.) a. 1 e. not a.-d. b. 2 c. 3 N HO O H H H d. 4 N OH 2. The diol on the right is? a. chiral b. meso c. achiral but not meso d. not a.-c. OH 3. What is the relation between the following wedge and Fischer structures? a. constitutional isomers d. equivalent b. diastereomers e. not a.-d. Cl Cl H c. enantiomers H Br Br 4. Given that a 1:5 mixture of enantiomers has an observed specific rotation of 40°, what would be the specific optical rotation of pure (+)-enantiomer? a. 50° b. 60° c. 70° d. 80° e. not a.-d. O 5. The compound on the right is? a. L b. D c. both D and L H HO d. not a.-c. NH2 H 6. Considering only carbon chiral centers, how many stereoisomers are in the family of the Amoxicillin antibiotic that you probably took as a kid? a. 2 e. not a.-d. b. 4 c. 8 OH H OH N d. 16 O HO S N O HO 7. The following compounds should have the same 13C NMR? a. true b. false H H 8. The following compounds should have the same effect on runny noses? OH a. true b. false OH H Ph H N H Ph N H O 9.-13. Match each pair of hydrogens on the left (referring to the labeled hydrogens in the 3,4-dimethylhexane isomer structures to the far right) to a topicity relationship. Answers HH H HH H may be repeated. H1 9. 10. 11. 12. 13. H1 and H2 H3 and H4 H5 and H6 H7 and H8 H5 and H8 a. constitutional heterotopic b. diastereotopic c. enantiotopic d. equivalent e. not a.-d. H4 H H H H3 H H H H5 H2 H H HHH H8 H H7 H H H6 H HHH 14.-18. Match each hexane isomer to the number of 13C NMR signals that it should have. Answers may be repeated. 14. 15. 16. 17. 18. a. 2 b. 3 c. 4 d. 5. e. not a.-d. 19.-23. Match the each 1H NMR listings to a structure on the right. 19. 3.189 (3H, s), 3.171 (2H, d) , 1.828 (1H, non), 0.912 (6H, d) a. 20. 3.296 (2H, t), 3.183 (3H, s), 1.644 (2H, quin), 1.391 (2H, sex), 0.876 (3H, t) b. 21. 3.367 (2H, q), 3.334 (2H, t), 1.675 (2H, sex), 1.202 (3H, t), 0.929 (3H, t) c. O O O O 22. 3.575 (1H, sex), 3.215 (3H, s), 1.558 (2H, quin), 1.123 (3H, d), 0.933 (3H, t) d. 23. 3.703 (1H, sep), 3.414 (2H, q), 1.222 (3H, t), 1.123 (6H, d) e. O 24. Match the following infrared spectrum to a compound below. An infrared table is attached. OH a. b. O c. O d. O e. not a.-d.