Question 1

Which of the following carbocations is the most stable?

Accepted Answer

A)   I
B)   II
C)   III
D)   IVE) None of the above
F) B) and C)

Question 2

Which of the following statements is not true?

Accepted Answer

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) A) and B)

Question 3

Which of the following statements about an SN1 reaction mechanism is true?

Accepted Answer

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) None of the above
F) All of the above

Question 4

Which of the following statements is not true?

Accepted Answer

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 C)
F) None of the above

Question 5

The reaction of tert-butyl bromide, (CH3) 3CBr, with ethanol affords the substitution product tert-butyl ethyl ether, (CH3) 3COCH2CH3, in acidic conditions. What would happen to the rate of the reaction if the concentration of ethanol was doubled?

Accepted Answer

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

Question 6

Rank the following ions in order of increasing nucleophlicity in polar protic solvents, starting with the least nucleophilic ion.  F∗Cl−Br−I−I  II  III  IV \begin{array} { c c c c } \mathrm { F } ^ { * } & \mathrm { Cl } ^ { - } & \mathrm { Br } ^ { - } & \mathrm { I } ^ { - } \	ext {I } & 	ext { II } & 	ext { III } & 	ext { IV }\end{array}F∗I ​Cl− II ​Br− III ​I− IV ​

Accepted Answer

A)   I 
B)   IV 
C)   I 
D)   IV < III < I < II E) A) and D)
F) B) and C)

Question 7

What is the IUPAC name of the following compound?

Accepted Answer

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

Question 8

Which of the following statements about the reactions of alkyl halides is true?

Accepted Answer

A)   The characteristic reactions of alkyl halides are addition and elimination.
B)   The characteristic reactions of alkyl halides are addition and substitution.
C)   The characteristic reactions of alkyl halides are elimination and substitution.
D)   The characteristic reactions of alkyl halides are oxidation and reduction.E) B) and C)
F) B) and D)

Question 9

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

Accepted Answer

A)   F-
B)   Cl-
C)   Br-
D)   I-E) None of the above
F) A) and B)

Question 10

What is the IUPAC name of the following compound?

Accepted Answer

A)   (R) -3-Chloro-6-ethyloctane
B)   (S) -3-Chloro-6-ethyloctane
C)   (S) -6-Chloro-3-ethyloctane
D)   (R) -6-Chloro-3-ethyloctaneE) A) and C)
F) A) and B)

Question 11

Rank the following in order of decreasing leaving group ability, putting the best first.  Cl−Br−I−H2O I  II  III  IV \begin{array} { l c c c } \mathrm { Cl } ^ { - } & \mathrm { Br } ^ { - } & \mathrm { I } ^ { - } & \mathrm { H } _ { 2 } \mathrm { O } \	ext { I } & 	ext { II } & 	ext { III } & 	ext { IV }\end{array}Cl− I ​Br− II ​I− III ​H2​O IV ​

Accepted Answer

A)   III > II > IV > I
B)   III > II > I > IV
C)   IV > I > II > III
D)   II > III > I > IV E) A) and C)
F) B) and C)

Question 12

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. N1, CH3OH B)  SN1, HMPA C)  SN2, CH3OH D)  SN2, HMPA" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)   SN1, CH3OH
B)   SN1, HMPA
C)   SN2, CH3OH
D)   SN2, HMPAE) C) and D)
F) A) and B)

Question 13

What is the product of the nucleophilic substitution reaction shown below?

Accepted Answer

A)   Only I
B)   Only II
C)   I and II
D)   NoneE) B) and D)
F) A) and B)

Question 14

Which of the following statements about the SN2 mechanism for nucleophilic substitution reactions is true?

Accepted Answer

A)   Involves one step and occurs with retention of configuration.
B)   Involves two steps and occurs with inversion of configuration.
C)   Involves one step and occurs with inversion of configuration.
D)   Involves one step and occurs with racemization.E) All of the above
F) B) and C)

Question 15

What is the IUPAC name of the following compound?

Accepted Answer

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

Question 16

Which of the following alkyl halides is a vinyl alkyl halide?

Accepted Answer

A)   I
B)   II
C)   III
D)   IVE) A) and B)
F) A) and C)

Question 17

Which of the following statements about the Hammond postulate is true?

Accepted Answer

A)   In an exothermic reaction, lowering the energy of the transition state increases the activation energy, Ea.
B)   In an endothermic reaction, the more stable product forms faster.
C)   In an endothermic reaction, the less stable product forms faster.
D)   In an endothermic reaction, the activation energy, Ea, is similar for both products.E) A) and B)
F) None of the above

Question 18

What is the starting material in the reaction shown below?

Accepted Answer

A)   I
B)   II
C)   III
D)   IVE) All of the above
F) A) and D)

Question 19

What is the IUPAC name of the following compound?

Accepted Answer

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

Question 20

What is the product of the nucleophilic substitution reaction shown below?

Accepted Answer

A)   Only I
B)   Only II
C)   I and II
D)   NoneE) C) and D)
F) All of the above

Exam 7: Alkyl Halides and Nucleophilic Substitution

Rank the following in order of decreasing leaving group ability, putting the best first. $\begin{array} { l c c c } \mathrm { Cl } ^ { - } & \mathrm { Br } ^ { - } & \mathrm { I } ^ { - } & \mathrm { H } _ { 2 } \mathrm { O } \\\text { I } & \text { II } & \text { III } & \text { IV }\end{array}$

Correct Answer
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What is the product of the nucleophilic substitution reaction shown below?

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.

Correct Answer
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Which of the following statements is not true?

Correct Answer
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Which of the following statements about the Hammond postulate is true?

Correct Answer
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What is the starting material in the reaction shown below?

Correct Answer
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Which of the following statements is not true?

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Which of the following statements about the S_N2 mechanism for nucleophilic substitution reactions is true?

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What is the IUPAC name of the following compound?

Correct Answer
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Which of the following statements about the reactions of alkyl halides is true?

Correct Answer
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What is the IUPAC name of the following compound?

Correct Answer
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Which of the following carbocations is the most stable?

Correct Answer
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What is the product of the nucleophilic substitution reaction shown below?

Correct Answer
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What is the IUPAC name of the following compound?

Correct Answer
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Which of the following alkyl halides is a vinyl alkyl halide?

Correct Answer
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The reaction of tert-butyl bromide, (CH₃) ₃CBr, with ethanol affords the substitution product tert-butyl ethyl ether, (CH₃) ₃COCH₂CH₃, in acidic conditions. What would happen to the rate of the reaction if the concentration of ethanol was doubled?

Correct Answer
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What is the IUPAC name of the following compound?

Correct Answer
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Which of the following statements about an S_N1 reaction mechanism is true?

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

Correct Answer
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Exam 7: Alkyl Halides and Nucleophilic Substitution

Correct AnswerverifiedShow Answer

What is the product of the nucleophilic substitution reaction shown below?

Correct AnswerverifiedShow Answer

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.

Correct AnswerverifiedShow Answer

Which of the following statements is not true?

Correct AnswerverifiedShow Answer

Correct AnswerverifiedShow Answer

Which of the following statements about the Hammond postulate is true?

Correct AnswerverifiedShow Answer

What is the starting material in the reaction shown below?

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Which of the following statements is not true?

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Which of the following statements about the SN2 mechanism for nucleophilic substitution reactions is true?

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What is the IUPAC name of the following compound?

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Which of the following statements about the reactions of alkyl halides is true?

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What is the IUPAC name of the following compound?

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Which of the following carbocations is the most stable?

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What is the product of the nucleophilic substitution reaction shown below?

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What is the IUPAC name of the following compound?

Correct AnswerverifiedShow Answer

Which of the following alkyl halides is a vinyl alkyl halide?

Correct AnswerverifiedShow Answer

The reaction of tert-butyl bromide, (CH3) 3CBr, with ethanol affords the substitution product tert-butyl ethyl ether, (CH3) 3COCH2CH3, in acidic conditions. What would happen to the rate of the reaction if the concentration of ethanol was doubled?

Correct AnswerverifiedShow Answer

What is the IUPAC name of the following compound?

Correct AnswerverifiedShow Answer

Which of the following statements about an SN1 reaction mechanism is true?

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

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Which of the following statements about the S_N2 mechanism for nucleophilic substitution reactions is true?

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The reaction of tert-butyl bromide, (CH₃) ₃CBr, with ethanol affords the substitution product tert-butyl ethyl ether, (CH₃) ₃COCH₂CH₃, in acidic conditions. What would happen to the rate of the reaction if the concentration of ethanol was doubled?

Correct Answer
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Correct Answer
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Which of the following statements about an S_N1 reaction mechanism is true?

Correct Answer
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Correct Answer
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