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Which of the following anions is the most nucleophilic in polar aprotic solvents?


A) F-
B) Cl-
C) Br-
D) I-

E) A) and B)
F) B) and C)

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Rank the following ions in order of increasing nucleophilicity in polar protic solvents,starting with the least nucleophilic ion. Rank the following ions in order of increasing nucleophilicity in polar protic solvents,starting with the least nucleophilic ion. A) I < II < III < IV B) IV < III < II < I C) I < II < IV < III D) IV < III < I < II


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

E) None of the above
F) A) and C)

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Which alkyl halide will form the most stable carbocation? Which alkyl halide will form the most stable carbocation? A) I B) II C) III D) IV


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

E) B) and D)
F) B) and C)

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A

Rank the following compounds in order of increasing SN1 reactivity? Rank the following compounds in order of increasing S<sub>N</sub>1 reactivity? A) I > II > III > IV B) IV > I > II > III C) IV > III > II > I D) III > II > I > IV


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

E) None of the above
F) A) and B)

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What is the IUPAC name of the following compound? What is the IUPAC name of the following compound? A) (3R,4R) -3-chloro-4-methylhexane B) (3R,4S) -3-chloro-4-methylhexane C) (3S,4R) -3-chloro-4-methylhexane D) (3S,4S) -3-chloro-4-methylhexane


A) (3R,4R) -3-chloro-4-methylhexane
B) (3R,4S) -3-chloro-4-methylhexane
C) (3S,4R) -3-chloro-4-methylhexane
D) (3S,4S) -3-chloro-4-methylhexane

E) None of the above
F) All of the above

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Rank the following in order of decreasing leaving group ability,putting the best first. Rank the following in order of decreasing leaving group ability,putting the best first. A) III > II > IV > I B) III > II > I > IV C) IV > I > II > III D) II > III > I > IV


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

E) All of the above
F) C) and D)

Correct Answer

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Rank the following in order of decreasing nucleophilicity,putting the most nucleophilic first. Rank the following in order of decreasing nucleophilicity,putting the most nucleophilic first. A) II > III > I > IV B) III > II > IV > I C) II > III > IV > I D) III > II > I > IV


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

E) B) and D)
F) A) and B)

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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.

E) All of the above
F) C) and D)

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What is the starting material in the reaction shown below? What is the starting material in the reaction shown below? A) I B) II C) III D) IV


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

E) B) and D)
F) A) and D)

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Rank the alkyl halides in order of decreasing SN2 reactivity,putting the most reactive first. Rank the alkyl halides in order of decreasing S<sub>N</sub>2 reactivity,putting the most reactive first. A) I > II > III B) II > I > III C) III > I > II D) I > III > II


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

E) None of the above
F) A) and C)

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B

Identify the nucleophile and type of substitution reaction in the following: Identify the nucleophile and type of substitution reaction in the following: A) CN<sup>-</sup>,S<sub>n</sub>1 B) CN<sup>-</sup>,S<sub>n</sub>2 C) Br<sup>-</sup>,S<sub>n</sub>1 D) Br<sup>-</sup>,S<sub>n</sub>2


A) CN-,Sn1
B) CN-,Sn2
C) Br-,Sn1
D) Br-,Sn2

E) None of the above
F) A) and C)

Correct Answer

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What is the IUPAC name of the following compound? What is the IUPAC name of the following compound? A) (R) -3-Bromo-1-methylcyclohexene B) (S) -3-Bromo-1-methylcyclohexene C) (S) -1-Bromo-3-methyl-2-cyclohexene D) (R) -1-Bromo-3-methyl-2-cyclohexene


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

E) A) and B)
F) A) and C)

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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.

E) None of the above
F) All of the above

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What is the product of the nucleophilic substitution reaction shown below? What is the product of the nucleophilic substitution reaction shown below? A) Only I B) Only II C) I and II D) None


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

E) C) and D)
F) None of the above

Correct Answer

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Which of the following alkyl halides will react fastest with CH3OH in an SN1 mechanism? Which of the following alkyl halides will react fastest with CH<sub>3</sub>OH in an S<sub>N</sub>1 mechanism? A) I B) II C) III D) IV


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

E) B) and C)
F) All of the above

Correct Answer

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Which of the following structures have the correct common name? 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


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

E) A) and B)
F) C) and D)

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Rank the following molecules in order of increasing polarity,putting the least polar first. Rank the following molecules in order of increasing polarity,putting the least polar first. A) IV < III < II < I B) I < IV < III < II C) I < II < III < IV D) II < I < III < IV


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

E) A) and C)
F) B) and D)

Correct Answer

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What is the product of the nucleophilic substitution reaction shown below? What is the product of the nucleophilic substitution reaction shown below? A) Only I B) Only II C) I and II D) None


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

E) A) and B)
F) All of the above

Correct Answer

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Which compound is most likely to follow second-order kinetics in a substitution reaction?


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

E) B) and D)
F) All of the above

Correct Answer

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A

What is the starting material in the reaction shown below? What is the starting material in the reaction shown below? A) I B) II C) III D) IV


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

E) A) and B)
F) C) and D)

Correct Answer

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