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Name: ______________________ Class: _________________ Date: _________ ID: A
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CHEM 222 ASSIGNMENT #1 (due OCTOBER 14th, 2010, by END of class)
Multiple Choice
Identify the choice that best completes the statement or answers the question.
____ 1. Predict the product of the following reaction:
a. d.
b. e. No reaction occurs between the starting
material and reagents shown.
c.
____ 2. Which of the following statements about organolithium reagents is false?
a. They are strongly basic.
b. They are strongly acidic.
c. They are formed from the reaction of an alkyl halide and lithium metal.
d. They react with water to produce alkanes.
e. They are formed in a radical (one electron transfer) reaction.
Name: ______________________ ID: A
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____ 3. Which of the structures shown below is not a possible starting material for this reaction sequence?
a. d.
b. e. Any of these choices is an appropriate
starting material for the transformation
shown.
c.
____ 4. Which of the following can protonate ethanol? The pKa of CH3CH2OH2+ is –2.2.
a. H2O, pKa = 15.7 d. HCl, pKa = –7
b. CH3CH2OH, pKa = 15.9 e. Propanoic acid, pKa = 4.9
c. NH3, pKa = 36
____ 5. Which of the following is the weakest acid in solution?
a. A d. D
b. B e. All have the same acidity.
c. C
Name: ______________________ ID: A
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____ 6. Which of the following solvents is/are protic?
a. I and II d. I, II, and IV
b. I and III e. I, II, III, and IV
c. I, II, and III
____ 7. Which of the following compounds could result from the reaction conditions shown here?
a. d.
b. e.
c.
Name: ______________________ ID: A
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____ 8. Which of these molecules is the product of the reaction shown here?
a. d.
b. e.
c.
____ 9. Which reagent would you use to accomplish the transformation shown here?
a. H2/Wilkinson’s catalyst d. Br2/H2O
b. BH3•THF, then H2O2, H2O, NaOH e. O3, then (CH3)2S
c. Hg(OAc)2 and H2O, then NaBH4
Name: ______________________ ID: A
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____ 10. Which reagent would you use to accomplish the transformation shown here?
a. Br2/H2O d. CF3CO3H
b. Hg(OAc)2 and H2O, then NaBH4 e. H3O+/H2O
c. HO–/H2O
____ 11. Which of these molecules is the product of the reaction shown here?
a. d.
b. e.
c.
Name: ______________________ ID: A
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____ 12. What was the starting material used to produce the diol shown under the conditions given?
a. d.
b. e.
c.
____ 13. Which reagent would you use to accomplish the transformation shown here?
a. H2/Pd on C d. LiAlH4, then H2O or H3O+
b. H3O+ e. (CH3)2Cu(CN)Li2
c. CF3CO3H
Name: ______________________ ID: A
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____ 14. Which reagent would you use to accomplish the transformation shown here?
a. BH3•THF, then H2O2, H2O, NaOH d. CF3CO3H
b. Hg(OAc)2 and H2O, then NaBH4 e. KMnO4, CH3OH/H2O, HO–
c. O3, then H2O2
Name: ______________________ ID: A
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____ 15. Which of the following conditions and reagents were used to make this compound?
a.
b.
c.
d.
e.
Name: ______________________ ID: A
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____ 16. Which of the following conditions will result in the formation of the molecule shown here?
a.
b.
c.
d.
e. Both b or c will work.
Name: ______________________ ID: A
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____ 17. Which of these structures is a conjugated diene?
a. I and III
b. I, III, V
c. II and IV
d. II, IV, V
e. All of these structures are conjugated dienes
Name: ______________________ ID: A
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____ 18. Which of the structures shown is in the s-cis conformation?
a. I d. IV
b. II e. V
c. III
____ 19. Which of the following structures is the product of 1,2 addition of HCl to the molecule shown here?
a. 4-chloro-2-methyl-1-hexene d. 5-chloro-3-methyl-2-hexene
b. 4-chloro-3-methyl-2-hexene e. None of these
c. 3-chloro-3-methyl-1-hexene
Name: ______________________ ID: A
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____ 20. Which pairing of diene and dienophile would lead to the product shown here?
a. d.
b. e.
c.
Name: ______________________ ID: A
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____ 21. Which of the following structures is the dienophile used to make the molecule shown here?
Name: ______________________ ID: A
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a. d.
b. e.
c.
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____ 22. Which of these structures is aromatic?
a. I d. I, II, and III
b. II e. I, II, and IV
c. I and II
____ 23. Which of these ions is aromatic?
a. I d. II and III
b. II e. I and IV
c. III
Name: ______________________ ID: A
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____ 24. Which of the following ions is not aromatic? Assume all structures are planar.
a. d.
b. e.
c.
Name: ______________________ ID: A
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____ 25. Which of the following structures is the product of the reaction shown here?
a. d.
b. e.
c.
Name: ______________________ ID: A
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____ 26. Which of the following structures is the product of the reaction shown here?
a. d.
b. e.
c.
____ 27. Which is the correct sequence of reactions required to transform the starting material into the product
shown?
a. Na/NH3, then KMnO4 d. KMnO4, NBS, then Na/NH3
b. KMnO4, then Na/NH3 e. Na/NH3, then NBS
c. NBS, then KMnO4
Name: ______________________ ID: A
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____ 28. Which of the following will not react with KMnO4?
a. d.
b. e.
c.
Name: ______________________ ID: A
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____ 29. Which of these structures is the major product of the reaction shown?
a. d.
b. e.
c.
Name: ______________________ ID: A
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____ 30. Which of these compounds is the product of the reaction conditions shown?
a. d.
b. e.
c.
Name: ______________________ ID: A
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____ 31. Which reagent would you use to accomplish the transformation shown?
a. Br2 d. Br2/AlBr3
b. Br2/FeBr3 e. HBr
c. CuBr
____ 32. Which conditions would you use to accomplish the following transformation?
a. HNO3/H2SO4 d. HNO3/H2SO4, then H2O
b. KOH, H2NNH2, ethylene glycol e. Na, NH3
c. HNO3/H2SO4, then H2/Pd/C
Name: ______________________ ID: A
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____ 33. Which of the following compounds is the major product of this reaction?
a. d.
b. e.
c.
Name: ______________________ ID: A
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____ 34. Which of the following compounds is the major product of this reaction?
a. d.
b. e.
c.
Name: ______________________ ID: A
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____ 35. Which of the following compounds will undergo nucleophilic aromatic substitution with methoxide ion at
the fastest rate?
a. d.
b. e.
c.
Name: ______________________ ID: A
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Short Answer
36. Provide an arrow-pushing mechanism for the formation of the product shown. Your mechanism should
include stereochemistry and should result in the specific stereoisomer shown as the product. Include all
lone pairs, curved arrows, and nonzero formal charges.
37. Predict the product and draw a mechanism for its formation in the following reaction. Show all lone
pairs, curved arrows, and nonzero formal charges.
38. Draw a mechanism for the transformation shown here. Include all lone pairs of electrons, curved arrows,
and formal charges.
39. Devise a multistep synthesis for the following transformation.You may use any organic or inorganic
reagents of your choice. Show the reagents necessary for each step and the product of each step.
Name: ______________________ ID: A
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40. Draw a mechanism for the transformation shown here. Include all lone pairs, curved arrows, and nonzero
formal charges.
41. Design a multistep synthesis for the transformation shown using a Friedel–Crafts acylation as one of the
steps. You may use any organic or inorganic reagents. Show the reagents needed for each step and the
product of each step.
