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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.

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

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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. <sup> </sup>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) S<sub>N</sub>1, CH<sub>3</sub>OH B) S<sub>N</sub>1, DMSO C) S<sub>N</sub>2, CH<sub>3</sub>OH D) S<sub>N</sub>2, DMSO


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

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

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Which of the following carbocations is the most stable? Which of the following carbocations is the most stable? A) I B) II C) III D) IV


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

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

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Which of the following alkyl halides is a tertiary alkyl halide? Which of the following alkyl halides is a tertiary alkyl halide? A) I B) II C) III D) IV


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

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

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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.

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

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

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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) B) and C)

Correct Answer

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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. <sup> </sup>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) S<sub>N</sub>1, CH<sub>3</sub>OH B) S<sub>N</sub>1, HMPA C) S<sub>N</sub>2, CH<sub>3</sub>OH D) S<sub>N</sub>2, HMPA


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

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

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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) All of the above

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Rank the following in order of increasing leaving group ability, putting the worst leaving group first. Rank the following in order of increasing leaving group ability, putting the worst leaving group first. A) IV < II < III < I B) III < IV < I < II C) II < IV < I < III D) I < III < II < IV


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

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

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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.

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

Correct Answer

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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 these.

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

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What is the IUPAC name of the following compound? What is the IUPAC name of the following compound? A) 2-Bromo-5,5-dimethylheptane B) 3,3-Dimethyl-6-bromoheptane C) 6-Bromo-3,3-dimethylheptane D) 2-Bromo-5,5-dimethyloctane


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

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

Correct Answer

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Rank the following compounds in order of increasing SN2 reactivity? Rank the following compounds in order of increasing S<sub>N</sub>2 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) A) and C)
F) A) and B)

Correct Answer

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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.

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

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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.

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

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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 C)
F) A) and B)

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) None of the above

Correct Answer

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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 B)
F) A) and C)

Correct Answer

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

Correct Answer

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