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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. 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) C) and D)
F) B) and D)

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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) None of the above
F) B) and D)

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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. 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) A) and D)
F) A) and C)

Correct Answer

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


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

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

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Which of the following alkyl halides would react the fastest with -OH in SN2 reaction? CH3CH2Br,CH3CH2Cl,CH3CH2F,CH3CH2I


A) CH3CH2Br
B) CH3CH2Cl
C) CH3CH2F
D) CH3CH2I

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

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


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

E) A) and B)
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) (1R,3R) -1-bromo-3-isopropylcyclopentane B) (1R,3S) -1-bromo-3-isopropylcyclopentane C) (1S,3R) -1-bromo-3-isopropylcyclopentane D) (1S,3S) -1-bromo-3-isopropylcyclopentane


A) (1R,3R) -1-bromo-3-isopropylcyclopentane
B) (1R,3S) -1-bromo-3-isopropylcyclopentane
C) (1S,3R) -1-bromo-3-isopropylcyclopentane
D) (1S,3S) -1-bromo-3-isopropylcyclopentane

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

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) C) and D)

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 B)
F) None of the above

Correct Answer

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

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

Correct Answer

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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.

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

Correct Answer

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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.

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

Correct Answer

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