Organic Chemistry 4th Edition

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Chapter 7: Alkyl Halides and Nucleophilic Substitution

1. Which of the following alkyl halides is a primary alkyl halide?

A) I B) II C) III D) IV

2. Which of the following alkyl halides is a secondary alkyl halide?

A) I B) II C) III D) IV

3. Which of the following alkyl halides is a tertiary alkyl halide?

A) I B) II C) III D) IV

4. Which of the following alkyl halides is a vinyl alkyl halide?

A) I B) II C) III D) IV

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 Chapter 7: Alkyl Halides and Nucleophilic Substitution

5. Which of the following structures have the correct common name?

A) I and II B) II and IV C) II and III D) III and IV

6. Which of the following structures have the correct common name?

A) I and II B) II and III C) I and III D) III and IV

7. Which of the following structures have the correct common name?

A) I and II B) II and III C) II and IV D) III and IV

8. What is the IUPAC name of the following compound?

A) 2-Methyl-4-chloropentane C) 2-Chloro-1-isopropylpropane
B) 2-Chloro-4-methylpentane D) 2-Chloro-2-methylpentane

9. What is the IUPAC name of the following compound?

A) 2-Bromo-5-methyloctane C) 2-Bromo-5-methylheptane
B) 2-Bromo-3-methylheptane D) 6-Bromo-3-methylheptane

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 Chapter 7: Alkyl Halides and Nucleophilic Substitution

10. What is the IUPAC name of the following compound?

A) 2-Bromo-5,5-dimethylheptane C) 6-Bromo-3,3-dimethylheptane
B) 3,3-Dimethyl-6-bromoheptane D) 2-Bromo-5,5-dimethyloctane

11. What is the IUPAC name of the following compound?

A) 2-Chloro-4-isopropyl-2,6-dimethyloctane
B) 2-Chloro-4-isopropyl-2,7-dimethylnonane
C) 2,6-Dimethyl-2-chloro-4-isopropyloctane
D) 7-Chloro-5-isopropyl-3,7-dimethyloctane

12. What is the IUPAC name of the following compound?

A) (R)-3-Chloro-6-ethyloctane C) (S)-6-Chloro-3-ethyloctane
B) (S)-3-Chloro-6-ethyloctane D) (R)-6-Chloro-3-ethyloctane

13. What is the IUPAC name of the following compound?

A) trans-4-Methylcyclohexyl chloride C) trans-4-Methyl-1-chlorocyclohexane

B) trans-p-Chloromethylcyclohexane D) trans-1-Chloro-4-methylcyclohexane

14. What is the IUPAC name of the following compound?

A) (R)-3-Bromo-1-methylcyclohexene C) (S)-1-Bromo-3-methyl-2-cyclohexene
B) (S)-3-Bromo-1-methylcyclohexene D) (R)-1-Bromo-3-methyl-2-cyclohexene

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 Chapter 7: Alkyl Halides and Nucleophilic Substitution

15. What is the IUPAC name of the following compound?

A) (E)-2-Bromo-3,4-dimethyl-2-pentene
B) (Z)-1-Bromo-1,2,3-trimethyl-1-butene
C) (Z)-2-Bromo-3,4-dimethyl-2-pentene
D) (E)-1-Bromo-1,2,3-trimethyl-1-butene

16. Rank the following halides in order of decreasing polarity, putting the most polar first.

A) II > IV > I > III C) I > II > III > IV

B) IV > II > I > III D) IV > III > II > I

17. Rank the following molecules in order of increasing polarity, putting the least polar
first.

A) IV < III < II < I C) I < II < III < IV

B) I < IV < III < II D) II < I < III < IV

18. Which of the following statements about the reactions of alkyl halides is true?
A) The characteristic reactions of alkyl halides are addition and elimination.
B) The characteristic reactions of alkyl halides are addition and substitution.
C) The characteristic reactions of alkyl halides are elimination and substitution.
D) The characteristic reactions of alkyl halides are oxidation and reduction.

19. Which of the following statements is true?

A) All good leaving groups are strong bases with weak conjugate acids.
B) Left-to-right across a row of the periodic table, leaving group ability decreases.
C) Down a column of the periodic table, leaving group ability decreases.
D) The conjugate bases of strong acids are good leaving groups.

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 Chapter 7: Alkyl Halides and Nucleophilic Substitution

20. Rank the following in order of decreasing leaving group ability, putting the best first.

A) III > II > IV > I C) IV > I > II > III

B) III > II > I > IV D) II > III > I > IV

21. Which of the following statements is not true?

A) All good leaving groups are weak bases with strong conjugate acids.
B) Left-to-right across a row of the periodic table, leaving group ability increases.
C) Down a column of the periodic table, leaving group ability increases.
D) Equilibrium favors the products of the nucleophilic substitution when the leaving
group is a stronger base than the nucleophile.

22. Rank the following in order of increasing leaving group ability, putting the worst
leaving group first.

A) IV < II < III < I C) II < IV < I < III

B) III < IV < I < II D) I < III < II < IV

23. Which of the following statements is not true?

A) Sodium ethoxide is a better nucleophile than sodium tert-butoxide.
B) Sodium tert-butoxide and sodium ethoxide have similar strengths as bases.
C) Sterically hindered bases are also called nonnucleophilic bases.
D) Steric hindrance decreases basicity but not nucleophilicity.

24. Which of the following statements is not true?

A) In polar protic solvents, nucleophilicity decreases down a column of the periodic
table as the size of the anion increases.
B) Nucleophilicity is affected by the solvent used in a substitution reaction.
C) Polar protic solvents are capable of intermolecular hydrogen bonding.
D) Polar protic solvents solvate both cations and anions.

25. Which of the following solvents is not a polar protic solvent?

A) I B) II C) III D) IV

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 Chapter 7: Alkyl Halides and Nucleophilic Substitution

26. Rank the following ions in order of increasing nucleophlicity in polar protic solvents,
starting with the least nucleophilic ion.

A) I < II < III < IV C) I < II < IV < III

B) IV < III < II < I D) IV < III < I < II

27. Which of the following anions is the most nucleophilic in polar aprotic solvents?
A) F- B) Cl- C) Br- D) I-

28. Rank the following in order of decreasing nucleophilicity, putting the most nucleophilic
first.

A) II > III > I > IV C) II > III > IV > I

B) III > II > IV > I D) III > II > I > IV

29. Which of the following is the most nucleophilic?

A) CH4 B) H2O C) NH3 D) HF

30. Rank the following in order of increasing nucleophilicity, putting the least nucleophilic
first.

A) II < IV < I < III C) III < IV < I < II

B) IV < III < II < I D) II < I < IV < III

31. The reaction of bromoethane with sodium acetate affords the substitution product
methyl acetate. What is the effect of doubling the concentration of sodium acetate on
the rate of the reaction?
A) The rate remains the same. C) The rate increases by a factor of 2.
B) The rate decreases by a factor of 2. D) The rate increases by a factor of 4.

32. The reaction of 1-bromobutane with sodium hydroxide affords the substitution product
1-butanol. What would happen to the rate of the reaction if the concentration of both 1-
bromobutane and sodium hydroxide were doubled?
A) The rate remains the same. C) The rate increases by a factor of 2.
B) The rate decreases by a factor of 2. D) The rate increases by a factor of 4.

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 Chapter 7: Alkyl Halides and Nucleophilic Substitution

33. The reaction of tert-butyl bromide, (CH3)3CBr, with ethanol affords the substitution
product tert-butyl ethyl ether, (CH3)3COCH2CH3, in acidic conditions. What would
happen to the rate of the reaction if the concentration of ethanol was doubled?
A) The rate remains the same. C) The rate increases by a factor of 2.
B) The rate decreases by a factor of 2. D) The rate increases by a factor of 4.

34. Which of the following statements about SN2 reactions is true?

A) The rate of reaction is dependent on just the substrate.
B) The fastest reaction will occur with a tertiary alkyl halide.
C) The mechanism is a two-step process.
D) Displacement occurs with inversion of configuration.

35. Which of the following statements about the SN2 mechanism for nucleophilic
substitution reactions is true?
A) Involves one step and occurs with retention of configuration.
B) Involves two steps and occurs with inversion of configuration.
C) Involves one step and occurs with inversion of configuration.
D) Involves one step and occurs with racemization.

36. Which compound is most likely to follow second-order kinetics in a substitution

reaction?
A) CH3Br B) (CH3)3CCH2Br C) CH3CH2Br D) (CH3)2CHBr

37. Which of the following alkyl halides undergoes the fastest SN2 reaction with sodium
hydroxide?
A) 1-Iodobutane
B) 1-Chlorobutane
C) 1-Fluorobutane
D) 1-Bromobutane

38. Rank the alkyl halides in order of decreasing SN2 reactivity, putting the most reactive
first.

A) I > II > III B) II > I > III C) III > I > II D) I > III > II

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 Chapter 7: Alkyl Halides and Nucleophilic Substitution

39. Given the following substitution reaction, what would the effect be of changing the
solvent from CH3OH to (CH3)2S=O?

CH3(CH2)5Br + NaOH → CH3(CH2)5OH + Br-

A) The rate would decrease because SN1 reactions are favored by polar protic solvents.
B) The rate would increase because SN2 reactions are favored by polar aprotic
solvents.
C) The rate would increase because SN1 reactions are favored by polar protic solvents.
D) The rate would decrease because SN2 reactions are favored by polar aprotic
solvents.

40. Which of the following is a polar aprotic solvent?

A) I B) II C) III D) IV

41. Which of the following statements about an SN1 reaction mechanism is true?
A) The reaction is fastest with primary alkyl halide.
B) The reaction exhibits a one-step mechanism.
C) The reaction rate increases as the leaving group ability increases.
D) The reaction rate increases as the strength of the nucleophile increases.

42. Which of the following statements about an SN1 reaction mechanism is true?
A) The reaction involves two steps and occurs fastest with primary alkyl halides.
B) The reaction involves one step and occurs fastest with primary alkyl halides.
C) The reaction involves one step and occurs fastest with tertiary alkyl halides.
D) The reaction involves two steps and occurs fastest with tertiary alkyl halides.

43. Which of the following alkyl halides will react fastest with CH3OH in an SN1
mechanism?

A) I B) II C) III D) IV

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 Chapter 7: Alkyl Halides and Nucleophilic Substitution

44. What is the rate-determining step of an SN1 reaction mechanism?

A) Reaction of the nucleophile with the carbocation to form the product.
B) Breaking the bond between the carbon and the leaving group to generate a
carbocation.
C) Attack of the nucleophile on the substrate to generate a pentavalent carbon.
D) None of the above.

45. Which of the following rate laws describes the kinetics of an SN1 reaction?
A) Rate = k[alkyl halide] C) Rate = k[nucleophile]
B) Rate = k[alkyl halide][nucleophile] D) Rate = k[solvent]

46. Which of the following carbocations is the most stable?

A) I B) II C) III D) IV

47. Rank the following carbocations in order of decreasing stability, putting the most stable
first.

A) I > II > III B) II > I > III C) III > I > II D) III > II > I

48. Which of the following is not a characteristic of an SN1 reaction?

A) The rate is proportional to the concentration of substrate.
B) The reaction is favored in polar protic solvents.
C) The rate is independent of the concentration of the nucleophile.
D) The electrophilic carbon undergoes inversion of stereochemistry.

49. Which of the following statements about carbocation stability is true?

A) Carbocations are stabilized by electron-withdrawing inductive effects only.
B) Carbocations are stabilized by electron-withdrawing inductive effects and
hyperconjugation.
C) Carbocations are stabilized by electron-donating inductive effects only.
D) Carbocations are stabilized by electro-donating inductive effects and
hyperconjugation.

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 Chapter 7: Alkyl Halides and Nucleophilic Substitution

50. Which of the following statements about the Hammond postulate is not true?
A) The Hammond postulate provides a quantitative estimate of the energy of a
transition state.
B) In endothermic reactions, the transition state is closer in energy to the products.
C) In exothermic reactions, the transition state is closer in energy to the reactants.
D) The Hammond postulate provides a qualitative estimate of the energy of a
transition state.

51. Which of the following statements about the Hammond postulate is true?
A) In an exothermic reaction, lowering the energy of the transition state increases the
activation energy, Ea.
B) In an endothermic reaction, the more stable product forms faster.
C) In an endothermic reaction, the less stable product forms faster.
D) In an endothermic reaction, the activation energy, Ea, is similar for both products.

52. The reaction of what nucleophile and substrate is represented by the following transition
state?

A) Methanol with 2-bromopropane C) Methoxide with 1-bromopropane

B) Methoxide with 2-bromopropane D) Methanol with 1-bromopropane

53. For the following reaction, use the identity of the alkyl halide and nucleophile to
determine which substitution mechanism occurs. Then determine which solvent affords
the faster reaction.

A) SN1, CH3OH B) SN1, DMSO C) SN2, CH3OH D) SN2, DMSO

54. For the following reaction, use the identity of the alkyl halide and nucleophile to
determine which substitution mechanism occurs. Then determine which solvent affords
the faster reaction.

A) SN1, H2O B) SN1, DMF C) SN2, H2O D) SN2, DMF

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 Chapter 7: Alkyl Halides and Nucleophilic Substitution

55. For the following reaction, use the identity of the alkyl halide and nucleophile to
determine which substitution mechanism occurs. Then determine which solvent affords
the faster reaction.

A) SN1, CH3OH B) SN1, HMPA C) SN2, CH3OH D) SN2, HMPA

56. What is the product of the nucleophilic substitution reaction shown below?

A) Only I B) Only II C) I and II D) None

57. What is the product of the nucleophilic substitution reaction shown below?

A) Only I B) Only II C) I and II D) None

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 Chapter 7: Alkyl Halides and Nucleophilic Substitution

58. What is the product of the nucleophilic substitution reaction shown below?

A) Only I B) Only II C) I and II D) None

59. What is the product of the nucleophilic substitution reaction shown below?

A) Only I B) Only II C) I and II D) None

60. What is the product of the nucleophilic substitution reaction shown below?

A) Only I B) Only II C) I and II D) None

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 Chapter 7: Alkyl Halides and Nucleophilic Substitution

61. What is the product of the nucleophilic substitution reaction shown below?

A) Only I B) Only II C) I and II D) None

62. What is the starting material in the reaction shown below?

A) I B) II C) III D) IV

63. What is the starting material in the reaction shown below?

A) I B) II C) III D) IV

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 Chapter 7: Alkyl Halides and Nucleophilic Substitution

64. Which of the following statements explain why aryl halides and vinyl halides do not
undergo nucleophilic substitution by either the SN1 or SN2 mechanism?
A) They don't undergo SN1 reactions because a higher percent s-character makes the
bond longer and stronger.
B) They don't undergo SN2 reactions because a higher percent s-character makes the
bond shorter and stronger.
C) They don't undergo SN2 reactions because heterolysis of the C-X bond forms a
highly unstable carbocation.
D) They don't undergo SN1 reactions because the carbocation is highly
electronegative.

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 Chapter 7: Alkyl Halides and Nucleophilic Substitution

Answer Key
1. A
2. C
3. B
4. D
5. C
6. B
7. D
8. B
9. C
10. A
11. A
12. B
13. D
14. B
15. C
16. D
17. B
18. C
19. D
20. B
21. D
22. A
23. D
24. A
25. B
26. A
27. A
28. B
29. C
30. C
31. C
32. D
33. A
34. D
35. C
36. A
37. A
38. B
39. B
40. B
41. C
42. D
43. D
44. B

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 Chapter 7: Alkyl Halides and Nucleophilic Substitution

45. A
46. B
47. A
48. D
49. D
50. A
51. B
52. B
53. A
54. D
55. D
56. B
57. A
58. C
59. D
60. C
61. B
62. D
63. D
64. B

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