Faculté des sciences Faculty of Science Département de chimie et science biomoléculaire Department of Chemistry and Biomolecular Sciences Pavillon d Iorio Hall 10 Marie-Curie Ottawa ON Canada K1N 6N5 ' 613-562-5728 7 613-562-5170 chminfo@uottawa.ca Final Exam CHM1321-B Date: April 19 Length: 3 hrs Last Name: Professor Sandro Gambarotta Name: Seat # First Student # - Instructions: ( all information that will be useful) Examples: - Calculator permitted (Faculty approved or any other kind) - Open or closed book - Indicate number of pages Cellular phones, unauthorized electronic devices or course notes (unless an open-book exam) are allowed during this exam. Phones and devices must be turned off and put away in your bag. Do keep them in your possession, such as in your pockets. If caught with such a device or document, following may occur: you will be asked to leave immediately the exam, academic fraud allegat will be filed which may result in you obtaining a 0 (zero) for the exam. Read carefully: By signing below, you acknowledge that you have read and ensured that you are complying with the above statement. Signature: Please put your INITIALS IN THE BOX when you have verified that there are # pages in this exam.
1. What is the IUPAC name of the following compound? 1-isopropyl-2,4-dimethylcyclohexane 2. Which of the following Newman projections represents 2,4-dimethylpentane? 1 3. Which of the following is the most stable conformation of cis-1-isopropyl-3- methylcyclohexane? 2
3 4. Provide a Newman projection of the most stable conformation of 3-methylpentane, CH 3 CH 2 CH(CH 3 )CH 2 CH 3 looking along the C2-C3 bond. 5. Which of the following compounds is/are chiral? only 1 6. Which of the following have the S configuration? 3
1 and 2 7. Which of the following compounds is a meso compound? (2R,3R)-dibromobutane (2R,3S)-dibromobutane (2R,3S)-3-bromo-2-butanol (2R,3R)-3-bromo-2-butanol (2R,3S)-dibromobutane 8. What is the relationship between the following pair of structures? a. They are enantiomers b. They are diastereomers c. The are constitutional isomers d. They are identical B 9. Draw the Fisher formula of (2R,3S)-3 bromo-2-butanol 4
10. Which of the following terms describes the role of ethanol in the acid-base reaction shown? a. Brønsted-Lowry acid b. Brønsted-Lowry base c. Lewis acid d. Lewis base B 5
11. Use curved arrows to show the movement of pairs of electrons in the following reaction between a Lewis acid and a Lewis base, and show the structure of the product. 12. What is the IUPAC name of the following compound? (E)-4-methyl-2-hexene 13. Which of the following alkenes is most likely to undergo skeletal rearrangement upon acidcatalyzed hydration (treatment with aqueous H 2 SO 4 )? 2 6
14. What is the major organic product obtained from the following reaction? 2 15. What is the major organic product obtained from the following reaction? 3 16. What is the major organic product obtained from the following reaction? 7
2 17. What is the major organic product obtained from the following reaction? 1 18. What is the major organic product obtained from the following reaction? 4 8
19. What is the major organic product obtained from the following reaction? 20. Provide a neatly drawn mechanism for the following reaction, including curved arrows to show the movement of pairs of electrons and the structure of reactive intermediates. 9
21. Provide a detailed mechanism for the reaction below showing the movement of pairs of electrons and the structure of reactive intermediates. 10
22. What is the major organic product obtained from the following reaction? 3 23. What is the major organic product obtained from the following reaction? 1 24. What is the best choice of reagent(s) to perform the following transformation? 11
a. CH 3 MgBr; followed by H 3 O + b. H 2 O, NaOH c. LiAlH 4 followed by H 3 O + d. KMnO4 C 25. What is the major organic product obtained from the following sequence of reactions? 2-methylbutane 26. What is the major organic product obtained from the following reaction? 4 12
27. What is the major organic product obtained from the following sequence of reactions? 1 28. What is the major organic product obtained from the following reaction? 4 29. What is the major organic product obtained from the following reaction? 13
3 30. What is the major organic product obtained from the following reaction? 3 31. What is the major organic product obtained from the following reaction? 2-pentanol 14
32. What is the major organic product obtained from the following reaction? 1 33. What is the major organic product obtained from the following reaction? 1 34. Which of the following ions is aromatic? 15
2 35. What is the major organic product obtained from the following reaction? 2 36. What is the major organic product obtained from the following reaction? 16
2 37. Which of the following undergoes the most rapid nitration upon treatment with HNO 3 /H 2 SO 4? a. toluene b. benzene c. bromobenzene d. nitrobenzene A 38. What is the major organic product obtained from the following reaction? 1 17