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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 B)
F) A) and C)

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


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

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

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C

Pick the solvent that gives the fastest SN2 reaction between CH2CH2Br and -OCH3.


A) CH2CH2OH
B) CH3OH
C) DMSO
D) H2O

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

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C

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


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

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

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What is the IUPAC name of the following compound? 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


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

E) B) and D)
F) C) 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,H<sub>2</sub>O B) S<sub>N</sub>1,DMF C) S<sub>N</sub>2,H<sub>2</sub>O D) S<sub>N</sub>2,DMF


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

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

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

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The reaction of what nucleophile and substrate is represented by the following transition state? The reaction of what nucleophile and substrate is represented by the following transition state? A) Methanol with 2-bromopropane B) Methoxide with 2-bromopropane C) Methoxide with 1-bromopropane D) Methanol with 1-bromopropane


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

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

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Which of the following is a polar aprotic solvent? Which of the following is a polar aprotic solvent? 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)

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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 III C) I and III D) III and IV


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

E) B) and D)
F) None 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) B) and D)

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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) All of the above
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) (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 D)
F) A) 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) trans-4-Methylcyclohexyl chloride B) trans-p-Chloromethylcyclohexane C) trans-4-Methyl-1-chlorocyclohexane D) trans-1-Chloro-4-methylcyclohexane


A) trans-4-Methylcyclohexyl chloride
B) trans-p-Chloromethylcyclohexane
C) trans-4-Methyl-1-chlorocyclohexane
D) trans-1-Chloro-4-methylcyclohexane

E) None of the above
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-methyloctane B) 2-Bromo-3-methylheptane C) 2-Bromo-5-methylheptane D) 6-Bromo-3-methylheptane


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

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

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

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Which of the following alkyl halides would react the fastest with H2O in SN1 reaction? CH3CH2CH2CH2Br,(CH3) 2CHCH2Br,CH3CH2CH(CH3) Br,(CH3) 3CBr


A) CH3CH2CH2CH2Br
B) (CH3) 2CHCH2Br
C) CH3CH2CH(CH3) Br
D) (CH3) 3CBr

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

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What is the IUPAC name of the following compound? 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


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

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

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A

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