Exam 4. Name CHEM 210. PBr 3. HBr. 1) NaH 2) Br H 2 SO 4. 1) NaOCH 3 2) dil. H 3 O + O CH 3 OH, H 2 SO 4. 1) LDA, -78 o C.
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1 Exam 4 Name CEM (48 pts) Complete the equations for the following reactions. Show all organic products if two or more products form, indicate the major product. Indicate proper stereochemistry where necessary. a. P 3 1) Na 2 S 4 b. 1) NaC 3 2) dil. 3 C 3, 2 S 4 c. 1) LDA, -78 o C 1) LDA, 25 o C d. 1) B 3 2) 2 2, K S 4 C 2 N 2 peracid
2 2. (8 pts) Mechanism conversion of R to R with P 3 with stereochemical inversion. In the space below show how this conversion occurs using 2-butanol as the starting material with curved arrows for the movement of electrons, proper Lewis structures and formal charges. Be sure to show how the stereochemistry is inverted. P 3 3. (6 pts) When the following cyclic ether is treated with methanol with a catalytic amount of 2 S 4, one of the two products shown is formed quantitatively with only a trace of the other. Which one is the major product? Propose a reaction mechanism to illustrate why. C 3, 2 S 4 C 3 C 3 4. What is the most likely product of the following reaction? b. II e. A racemic mixture of I and II
3 5. What is the most likely product of the following reaction? 6. What reagent(s) would be the best choice to complete the following reaction? a. 1. Na; 2. 3 d. 1. Na; 2. - b. 2 e. c. P 3 7. What is the most likely product of the following reaction?
4 8. What is the most likely product of the following reaction? 9. Which of the following compounds would not produce the same major product as the others when treated with Cl? a. A d. D b. B e. E c. C 10. What will be the major product of the reaction below? (Tf is like Ts or 2 S 4 ) a. d. b. e. c.
5 Exam 4 - KEY Name CEM (48 pts) Complete the equations for the following reactions. Show all organic products if two or more products form, indicate the major product. Indicate proper stereochemistry where necessary. a. P 3 1) Na 2 S 4 major b. 3 C 1) NaC 3 2) dil. 3 C 3, 2 S 4 C 3 c. 1) LDA, -78 o C 1) LDA, 25 o C major d. 1) B 3 2) 2 2, K 2 2 S 4 2 C 2 N 2 peracid
6 12. (8 pts) Mechanism conversion of R to R with P 3 with stereochemical inversion. In the space below show how this conversion occurs using 2-butanol as the starting material with curved arrows for the movement of electrons, proper Lewis structures and formal charges. Be sure to show how the stereochemistry is inverted. P P P P 13. (6 pts) When the following cyclic ether is treated with methanol with a catalytic amount of 2 S 4, one of the two products shown is formed quantitatively with only a trace of the other. Which one is the major product? Propose a reaction mechanism to illustrate why. S 3 S 3 C 3 C 3 - C 3 2 o cation not resonance stabilized S 3 S 3 C 3 C 3 - C 3 2 o cation resonance stabilized lowers E A for this path 14. What is the most likely product of the following reaction? b. II e. A racemic mixture of I and II
7 15. What is the most likely product of the following reaction? 16. What reagent(s) would be the best choice to complete the following reaction? a. 1. Na; 2. 3 d. 1. Na; 2. - b. 2 e. c. P What is the most likely product of the following reaction?
8 18. What is the most likely product of the following reaction? 19. Which of the following compounds would not produce the same major product as the others when treated with Cl? a. A d. D b. B e. E c. C 20. What will be the major product of the reaction below? (Tf is like Ts or 2 S 4 ) a. d. b. e. c.
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+ HBr ΔH = OH CH CH 2. HgOAc
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NAME (Print): SIGNATURE: hemistry 320M/328M Dr. ent Iverson 3rd Midterm November 15, 2012 Please print the first three letters of your last name in the three boxes Please Note: This test may be a bit long,