1.

II- Which of the following is not an ambident nucleophile?

2. SN1 – By analyzing the starting material and the products

3. It would double the rate – Consider the reaction of 2-Chloro-2-

methylpentane with sodium iodide. Assuming no other charges. How

would it affect the rate if one simultaneously doubled the concentration of

2-Chloro-2-methylpentane and sodium iodide.

4. None of the choices - By analyzing the starting material and the

product(s), the following reaction is possibly an example of what type of

mechanism?

5. III > II > I > IV Rank the following in order of decreasing leaving group

ability, by putting the best first.

6. EQUILIBRIUM FAVORS THE PRODUCTS OF THE NUCLEOPHILIC

SUBSTITUTION WHEN THE LEAVING GROUP IS A STRONGER BASE THAN

THE NUCLEOPHILE. – Which of the following statements is not true

7. I and II – what is the product of the nucleophilic substitution reaction

below?

8. IV – what is the starting material in the reaction shown below?

9. II & III – Which of the following structures have the correct common

name?

10. Methoxide with 2-bromopropane – the reaction of what nucleophile and

substrate is represented by the following transition state?

11.(S)-3-bromo-1-methylcyclohexene – what is the IUPAC name of the

following compound?

12. Breaking the bond between the carbon and the leaving group to

generate a carbocation – What is the rate-determining step of an Sn1

mechanism?

13. The reaction involves two steps and occurs fastest with tertiary alkyl

halides. – Which of the following statements about SN1 reaction

mechanism is true?

14. Displacement occurs with inversion of configuration. – Which of the

following statements about SN2 reactions is true?

15.None – what is the product of the nucleophilic substitution reaction shown

below?

16. IV – What is the starting material in the reaction shown below?

17. IV – Which of the following alkyl halides is a vinyl alkyl halide?

18. the characteristic reactions of alkyl halides are elimination and

substitution – Which of the following statements about the reactions of

alkyl halides is true?

19. IV – which of the following alkyl halides will react fastest with CH3OH in an

SN1 mechanism?

20. The electrophilic carbon undergoes inversion of stereochemistry. –

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

21. 2-bromo-5,5-dimethylheptane – what is the IUPAC name of the following

compound?

22. only II – what is the product of the nucleophilic substitution reaction

shown below?

23. F- -- which of the following anions is the most nucleophilic in polar aprotic

solvents?

24. Carbocations are stabilized by electro-donating inductive effects and

hyperconjugation - Which of the following statements about carbocation

stability is true?

25. II – which of the following is carbocations is the most stable?

26. CH3Br – Which compound is the most likely to follow second-order kinetics

in a substitution reaction?
27. II & III – Which of the following structures have the correct common

name?

28. The rate decreases by a factor of 2 -- 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?

29. 2-chloro-4-isopropyl-2,6-dimethyloctane – what is the IUPAC name of the

following compound?

30. III < IV < I < II – Rank the following in the order of increasing

nucleophilicity, putting the least nucleophilic first.

31. The reaction rate increases as the leaving group ability increases – which

of the following statements about an SN1 reaction mechanism is true?

32. III > II > I > IV Rank the following compounds in order of increasing SN1

reactivity.

33. Only I – what is the product of the nucleophilic substitution reaction

shown below?

34.SN1, CH3OH – For the following reaction, use the identity of the alkyl halide

and nucleophile to determine which substitution mechanism occurs. Then

determine what solvent affords the faster reaction.\

35. (S)-3-Chloro-6-ethyloctane

36. only II – what is the product of the nucleophilic substitution reaction

shown below?

37. CH3CH2I – Which of the following alkyl halides would react the fastest with
–
OH in SN2 reaction?

38. IV > III > II > I – rank the following halides in order of decreasing polarity,

putting the most polar first.

39. Steric hindrance decreases basicity but not nucleophilicity – Which of the

following statements is not true?

40. They don’t undergo SN2 reactions because a higher percentage of s-

character makes the bond shorter and stronger. – which of the following

statements explains why aryl halides and vinyl halides do not undergo

nucleophilic substitution by either the Sn1 or Sn2 mechanism?

41.2-bromo-5-methyloctane –what is the IUPAC name of the following

compound.

42. IV > I > II > III - Rank the following compounds in order of increasing SN2

reactivity?

43. In polar protic solvents, nucleophilicity decreases down a column of the

periodic table as the size of the atom increases. – Which of the following

statements is not true.

44. IV < II< III <I – rank the following in order of increasing leaving group

ability

45. rate = k[alkyl halide]-- Which of the following rate laws describes the

kinetics of an SN1 reaction?

putting the most reactive first.

47. 2-chloro-4-methylpentane – what is the IUPAC name of the following

compound.

48. involves one step and occurs with inversion of configuration – Which of

the following statements about SN2 mechanism for nucleophilic

substitution reactions is true?

49. I & II – what is the product of the nucleophilic substitution reaction shown

below?

50. The rate would increase because SN2 reactions are favored by polar

aprotic solvents. – given the following substitution reaction, what would

be the effect of changing the solvent from CH3OH to (CH3)2SO?

51. 1-iodobutane – which of the following alkyl halides undergoes the fastest

SN2 reaction with sodium hydroxide?

52. SN2, DMF -- 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.

53. III -- Which of the following alkyl halides is a secondary halide?

54. II - Which of the following solvents is not a polar protic solvent?

55. In an endothermic reaction, the more stable product forms faster. –

which of the following statements about the Hammond Postulate is true?

56. NH3 – most nucleophilic

57. DMSO – pick the solvent that gives the fastest SN2 reaction between

CH2CH2Br and OCH3

58. I < II < III < IV -- rank the following ions in order of increasing

nucleophilicity in polar protic solvents starting with the least nucleophilic

ions.

59. The rate remains the same. – The reaction of tert-butyl bromide with

ethanol zffords the substitution product tertbutyl ethyl ether in acidic

conditions. What would happen to the rate of the reaction if the

concentration of ethanol was doubled.

60. I - which of the following alkyl halides is a primary alkyl halide.

61. (Z)-2-bromo-3,4-dimethyl-2-pentene -- what is the IUPAC name of the

following compound?

62. The rate increases by a factor of 4. The reaction of 1-bromobitane 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?

63. The Hammond postulate provides a quantitative estimate of the energy

of a transition state. – Which of the following statements about the

Hammond postulates is not true?

64. I > II > III -- Rank the following carbocations in order of decreasong

stability, putting the most stable first.

65. none of these choices. – by analyzing the starting material and the

product(s), the following reaction is possibly an example of what type of

mechanism?

66. More than one of the above. – By analyzing the starting material and the

product, the following reaction is probably an example of what type of

mechanism?

67. It would increase the rate four times. – consider the sn2 reaction of butyl

bromide with OH ion. Assuming no other changes, what effect on the rate

would result from simultaneously doubling the concentrations of both

butly bromide and OH ions

68.SN2 -- – by analyzing the starting material and the product(s), the following

reaction is possibly an example of what type of mechanism?

69. An increase in the kinetic energy of the reacting molecules results in an

increase in the reaction rate

70. E2 -- by analyzing the starting material and the product(s), the following

reaction is possibly an example of what type of mechanism?

71. The reaction would take place with racemization. – Consider the

substitution reaction that takes place when (R )-3-bromo-3-methylhexane

is treated with methanol.

72.It would increase the rate four times. – Consider the SN2 reaction of 2-

iodopentane with CH3CO2- ion. Assuming no other changes, what effect on

the rate would result from simultaneously doubling the concentrations of

both 2-iodopentane and acetate?

73. III & IV -- which of the following structures have the correct common

name?

74. SN2, HMPA -- 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.

75. III > II > IV > I - Rank the following in order of decreasing nucleophilicity,

putting the most nucleophilic first.

76. The conjugate bases of strong acids are good leaving groups. – Which of

the following statements is true?

77. II - which of the following is a polar aprotic solvent?

78. trans-1-chloro-4-methylcyclohexane – what is the IUPAC name of the

following compound?

79. II -- which of the following alkyl halides is a tertiary alkyl halide?

 80. (CH3)3CBr – Which of the following alkyl halides would react the fastest

with H2O in SN1 reaction?