Final Exam CHM1321-B. Date: July 4th Length: 3 hrs Last Name:

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1 Pavillon d Iorio all Final Exam CM1321-B Date: July 4th Length: 3 hrs Last Name: Professor Sandro Gambarotta Name: First Student # Seat # - Instructions: ( all information that will be useful) Examples: - Calculator permitted (Faculty approved or any other kind) - pen or closed book - Indicate number of pages Cellular phones, unauthorized electronic devices or course notes (unless an open-book exam) are not allowed during this exam. Phones and devices must be turned off and put away in your bag. Do not keep them in your possession, such as in your pockets. If caught with such a device or document, the following may occur: you will be asked to leave immediately the exam, academic fraud allegations 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 TE BX when you have verified that there are # pages in this exam. Pag 1

2 Pavillon d Iorio all 1. A correct IUPAC name for the following compound is: A) 4-propyl-5-chloro-3-heptanol B) 4-propyl-3-chloro-5-heptanol C) 4-(1-chloropropyl)-3-heptanol D) 5-chloro-4-propyl-3-heptanol E) 3-hydroxy-4-propyl-5-chloroheptane Ans: D 2. Which cycloalkane would you expect to have the smallest heat of combustion? iefly and schematically explain your reasoning. Ans: cyclohexane Pag 2

3 Pavillon d Iorio all 3. Draw and name all the constitutional isomers for the formula C 5 12 Answ: n-pentane isopentane neopentane 4. Which of the following molecules is achiral? C 2 3 C C C C C 3 2 C I II III F C 2 C 2 C 3 C 2 C 3 V Ans: II Pag 3

4 Pavillon d Iorio all 5. Can you identify any enantiomeric pair in the list below?: C 3 C 3 3 C C 3 3 C C 2 C 2 C 3 I C 2 C 2 C 3 II C 2 C 2 C 3 III C 2 C 2 C 3 C 2 3 C C 2 C 2 C 3 V Ans: III, 6. The structures C 3 C 3 C 3 represent: C 3 A) a single compound. B) enantiomers. C) meso forms. D) diastereomers. E) conformational isomers. Ans: A Pag 4

5 Pavillon d Iorio all 7. Which structure(s) represent(s) diastereomer(s) of I? C 3 C 3 C 3 C 3 C 3 C 3 C 3 C 3 C 3 C 3 I II III V Ans: II and III 8. Give the proper name to the molecule below (including R,S labels if applicable) C 2 C 3 C 3 C 3 : Ans: (2S,3R,4S)-2,4-Dichloro-3-methylhexane Pag 5

6 Pavillon d Iorio all 9. An alkene adds hydrogen in the presence of a catalyst to give 3,4-dimethylhexane. zonolysis of the alkene followed by treatment with zinc and acetic acid gives a single organic product. Give the structure of the alkene : Answ: C 3 C 3 C 2 C=CC 3 C 2 C 3 (cis or trans) 10. Which of the following reagents might serve as the basis for a simple chemical test that would distinguish between pure 1-pentene and pure pentane? A) omine in carbon tetrachloride B) Dilute aqueous potassium permanganate C) Concentrated sulfuric acid D) All of the above E) Answers A) and B) only Ans: D Pag 6

7 Pavillon d Iorio all 11. What would be the major product of the following reaction? I II III V Ans: II 12. Which compound(s) will be formed by the reaction of 2 /C 4 with cyclohexene? I II III Ans: II and III Pag 7

8 Pavillon d Iorio all 13. What would be the major product of the following reaction? 2, C 4? C 3 C 3 C 3 C 3 7 C 3 7 C 3 C 3 7 C 3 7 I II III A) Equal amounts of I and II B) Equal amounts of II and III C) Equal amounts of III and D) I and II as major products, III and as minor products E) All of the above in equal amounts Ans: A 14. Which alkene would react with cold dilute alkaline permanganate solution to form an optically inactive and irresolvable product? A) B) C) D) E) Ans: C Pag 8

9 Pavillon d Iorio all 15. Select the structure of the major product formed from the following reaction. C 3 1. g(cc 3 ) 2 TF, 2 2. NaB 4, Na? C 3 C 3 C 2 C 3 C 3 I II III V Ans: 16. The hydroboration-oxidation procedure can be successfully employed for synthesis of deuterated derivatives, by using BD 3 instead of B 3. What product would you expect from the following reaction? C 3 1. (BD 3 ) /Na? D D BD 2 D D BD 2 C 3 C 3 C 3 C 3 D C 3 + enantiomer I + enantiomer II + enantiomer III + enantiomer + enantiomer V Ans: I Pag 9

10 17. What would be the final product? Faculté des sciences Faculty of Science Pavillon d Iorio all C 3 3 CC C 2 RC product C 3, A final product Ans: (C 3 ) 2 CC 2 C3 18. Which would be the best method for converting 3,3-dimethyl-1-pentene into 3,3- dimethyl-2-pentanol? A) 3 +, heat B) B 3 :TF; then 2 2, - C) concd. 2 S 4 ; then 2, heat D) g(ac) 2 /TF- 2 ; then NaB 4, - E) ; then Na/ 2 Ans: D Pag 10

11 Pavillon d Iorio all 19. What is the product, A, that would be obtained from the following reaction sequence? C 2 C 2 C 3 C 2 Mg 3 + C C A C CC 2 C 3 C CC 2 C 2 C 2 C 3 C 3 C 2 C CC 2 C 2 I II III C 3 C CC 2 C 2 C 3 C CCC 2 C 3 A) I B) II C) III D) E) V Ans: C V Pag 11

12 Pavillon d Iorio all 20. Which of the following structures would be aromatic? K -2 2K K I II III V A) I B) II C) III D) E) V Ans: B Pag 12

13 Pavillon d Iorio all 21. What would be the major product(s) of the following reaction? 2 S 4? N 2 S 3 3 S N 2 N 2 S 3 3 S N 2 N 2 I II III A) I B) II C) III D) Equal amounts of E) Equal amounts of II and Ans: C 22. Which compound is an acetal? C 3 I II III Ans: II 23. Draw the structure of the compound formed when is added to a solution of pentanal in methanol? Ans: Pag 13

14 Pavillon d Iorio all 24. Draw the mechanism of 1-hexene bromination. See slide show Pag 14