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

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D

Rank the following carbocations in order of decreasing stability, putting the most stable first. Rank the following carbocations in order of decreasing stability, putting the most stable first. A) I > II > III B) II > I > III C) III > I > II D) III > II > I


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

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

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

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A

Which of the following solvents is not a polar protic solvent? CH3OHCH3CNCH3COOHH2O I  II  III  IV \begin{array} { c c c c } \mathrm { CH } _ { 3 } \mathrm { OH } & \mathrm { CH } _ { 3 } \mathrm { CN } & \mathrm { CH } _ { 3 } \mathrm { COOH } & \mathrm { H } _ { 2 } \mathrm { O } \\\text { I } & \text { II } & \text { III } & \text { IV }\end{array}


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

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

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Which of the following is the most nucleophilic?


A) CH4
B) H2O
C) NH3
D) HF

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

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Given the following substitution reaction, what would the effect be of changing the solvent from CH3OH to (CH3) 2S=O? CH3(CH2) 5Br + NaOH CH3(CH2) 5OH + Br-


A) The rate would decrease because SN1 reactions are favored by polar protic solvents.
B) The rate would increase because SN2 reactions are favored by polar aprotic solvents.
C) The rate would increase because SN1 reactions are favored by polar protic solvents.
D) The rate would decrease because SN2 reactions are favored by polar aprotic solvents.

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

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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?


A) The rate remains the same.
B) The rate decreases by a factor of 2.
C) The rate increases by a factor of 2.
D) The rate increases by a factor of 4.

E) A) and B)
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-Methyl-4-chloropentane B) 2-Chloro-4-methylpentane C) 2-Chloro-1-isopropylpropane D) 2-Chloro-2-methylpentane


A) 2-Methyl-4-chloropentane
B) 2-Chloro-4-methylpentane
C) 2-Chloro-1-isopropylpropane
D) 2-Chloro-2-methylpentane

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

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

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

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

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Which of the following statements about SN2 reactions is true?


A) The rate of reaction is dependent on just the substrate.
B) The fastest reaction will occur with a tertiary alkyl halide.
C) The mechanism is a two-step process.
D) Displacement occurs with inversion of configuration.

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

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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 C)
F) A) and B)

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D

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

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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) B) 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) 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) All of the above

Correct Answer

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