Question 1

Rank the following in order of increasing leaving group ability, putting the worst leaving group first.  H2OHO−NH3H2 N−I  II  III  IV \begin{array} { c c c c } \mathrm { H } _ { 2 } \mathrm { O } & \mathrm { HO } ^ { - } & \mathrm { NH } _ { 3 } & \mathrm { H } _ { 2 } \mathrm {~N} ^ { - } \	ext {I } & 	ext { II } & 	ext { III } & 	ext { IV }\end{array}H2​OI ​HO− II ​NH3​ III ​H2​ N− IV ​

Accepted Answer

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

Question 2

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

Accepted Answer

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

Question 3

Which of the following rate laws describes the kinetics of an SN1 reaction?

Accepted Answer

A)   Rate = k[alkyl halide]
B)   Rate = k[alkyl halide][nucleophile]
C)   Rate = k[nucleophile]
D)   Rate = k[solvent]E) B) and C)
F) None of the above

Question 4

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, DMSO C)  SN2, CH3OH D)  SN2, DMSO" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)   SN1, CH3OH
B)   SN1, DMSO
C)   SN2, CH3OH
D)   SN2, DMSOE) A) and C)
F) A) and B)

Question 5

Which of the following statements is not true?

Accepted Answer

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) All of the above
F) None of the above

Question 6

Rank the following halides in order of decreasing polarity, putting the most polar first.  CCl4CHCl3CH2Cl2CH3Cl I  II  III  IV \begin{array} { c c c c } \mathrm { CCl } _ { 4 } & \mathrm { CHCl } _ { 3 } & \mathrm { CH } _ { 2 } \mathrm { Cl } _ { 2 } & \mathrm { CH } _ { 3 } \mathrm { Cl } \	ext { I } & 	ext { II } & 	ext { III } & 	ext { IV }\end{array}CCl4​ I ​CHCl3​ II ​CH2​Cl2​ III ​CH3​Cl IV ​

Accepted Answer

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

Question 7

Rank the following in order of increasing nucleophilicity, putting the least nucleophilic first.  CH3CH2O−CH3CH2 S−CH3CH2OHCH3CH2SH I  II  III  IV \begin{array} { c c c c } \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { O } ^ { - } & \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm {~S} ^ { - } & \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { OH } & \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { SH } \	ext { I } & 	ext { II } & 	ext { III } & 	ext { IV }\end{array}CH3​CH2​O− I ​CH3​CH2​ S− II ​CH3​CH2​OH III ​CH3​CH2​SH IV ​

Accepted Answer

A)   II 
B)   IV 
C)   III 
D)   II < I < IV < III E) None of the above
F) B) and D)

Question 8

Which of the following statements explain why aryl halides and vinyl halides do not undergo nucleophilic substitution by either the SN1 or SN2 mechanism?

Accepted Answer

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

Question 9

Which of the following alkyl halides undergoes the fastest SN2 reaction with sodium hydroxide?

Accepted Answer

A)   1-Iodobutane
B)   1-Chlorobutane
C)   1-Fluorobutane
D)   1-BromobutaneE) C) and D)
F) B) and C)

Question 10

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

Accepted Answer

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

Question 11

What is the rate-determining step of an SN1 reaction mechanism?

Accepted Answer

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 the above.E) B) and D)
F) A) and B)

Question 12

Which of the following is not a characteristic of an SN1 reaction?

Accepted Answer

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 D)
F) C) and D)

Question 13

Rank the following in order of decreasing nucleophilicity, putting the most nucleophilic first.  CH3OHCH3O−CH3 S−CH3SH I  II  III  IV \begin{array} { c c c c } \mathrm { CH } _ { 3 } \mathrm { OH } & \mathrm { CH } _ { 3 } \mathrm { O } ^ { - } & \mathrm { CH } _ { 3 } \mathrm {~S} ^ { - } & \mathrm { CH } _ { 3 } \mathrm { SH } \	ext { I } & 	ext { II } & 	ext { III } & 	ext { IV }\end{array}CH3​OH I ​CH3​O− II ​CH3​ S− III ​CH3​SH IV ​

Accepted Answer

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

Question 14

What is the starting material in the reaction shown below?

Accepted Answer

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

Question 15

Which of the following structures have the correct common name?

Accepted Answer

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

Question 16

The reaction of what nucleophile and substrate is represented by the following transition state?

Accepted Answer

A)   Methanol with 2-bromopropane
B)   Methoxide with 2-bromopropane
C)   Methoxide with 1-bromopropane
D)   Methanol with 1-bromopropaneE) All of the above
F) C) and D)

Question 17

Rank the following molecules in order of increasing polarity, putting the least polar first.  CH4CH3ClCH3BrCH3I I  II  III  IV \begin{array} { c c c c } \mathrm { CH } _ { 4 } & \mathrm { CH } _ { 3 } \mathrm { Cl } & \mathrm { CH } _ { 3 } \mathrm { Br } & \mathrm { CH } _ { 3 } \mathrm { I } \	ext { I } & 	ext { II } & 	ext { III } & 	ext { IV }\end{array}CH4​ I ​CH3​Cl II ​CH3​Br III ​CH3​I IV ​

Accepted Answer

A)   IV 
B)   I 
C)   I 
D)   II < I < III < IV E) B) and D)
F) All of the above

Question 18

Which of the following statements is true?

Accepted Answer

A)   All good leaving groups are strong bases with weak conjugate acids.
B)   Left-to-right across a row of the periodic table, leaving group ability decreases.
C)   Down a column of the periodic table, leaving group ability decreases.
D)   The conjugate bases of strong acids are good leaving groups.E) A) and B)
F) A) and C)

Question 19

Rank the alkyl halides in order of decreasing SN2 reactivity, putting the most reactive first. N2 reactivity, putting the most reactive first.   A)  I > II > III B)  II > I > III C)  III > I > II D)  I > III > II" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

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

Question 20

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

Accepted Answer

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

Exam 7: Alkyl Halides and Nucleophilic Substitution

Correct Answer
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Which of the following structures have the correct common name?

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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.

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

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The reaction of what nucleophile and substrate is represented by the following transition state?

Correct Answer
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Rank the alkyl halides in order of decreasing S_N2 reactivity, putting the most reactive first.

Correct Answer
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Which of the following statements is not true?

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

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What is the rate-determining step of an S_N1 reaction mechanism?

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Which of the following is not a characteristic of an S_N1 reaction?

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Which of the following statements is true?

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Which of the following statements explain why aryl halides and vinyl halides do not undergo nucleophilic substitution by either the S_N1 or S_N2 mechanism?

Correct Answer
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Which of the following alkyl halides undergoes the fastest S_N2 reaction with sodium hydroxide?

Correct Answer
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Which of the following rate laws describes the kinetics of an S_N1 reaction?

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 alkyl halides is a tertiary alkyl halide?

Correct Answer
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Exam 7: Alkyl Halides and Nucleophilic Substitution

Correct AnswerverifiedShow Answer

Which of the following structures have the correct common name?

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 alkyl halides is a secondary alkyl halide?

Correct AnswerverifiedShow Answer

The reaction of what nucleophile and substrate is represented by the following transition state?

Correct AnswerverifiedShow Answer

Rank the alkyl halides in order of decreasing SN2 reactivity, putting the most reactive first.

Correct AnswerverifiedShow Answer

Which of the following statements is not true?

Correct AnswerverifiedShow Answer

Correct AnswerverifiedShow Answer

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

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What is the rate-determining step of an SN1 reaction mechanism?

Correct AnswerverifiedShow Answer

Correct AnswerverifiedShow Answer

Which of the following is not a characteristic of an SN1 reaction?

Correct AnswerverifiedShow Answer

Correct AnswerverifiedShow Answer

Which of the following statements is true?

Correct AnswerverifiedShow Answer

Which of the following statements explain why aryl halides and vinyl halides do not undergo nucleophilic substitution by either the SN1 or SN2 mechanism?

Correct AnswerverifiedShow Answer

Which of the following alkyl halides undergoes the fastest SN2 reaction with sodium hydroxide?

Correct AnswerverifiedShow Answer

Correct AnswerverifiedShow Answer

Which of the following rate laws describes the kinetics of an SN1 reaction?

Correct AnswerverifiedShow Answer

What is the starting material in the reaction shown below?

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

Correct AnswerverifiedShow Answer

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Correct Answer
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Rank the alkyl halides in order of decreasing S_N2 reactivity, putting the most reactive first.

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What is the rate-determining step of an S_N1 reaction mechanism?

Correct Answer
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Which of the following is not a characteristic of an S_N1 reaction?

Correct Answer
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Which of the following statements explain why aryl halides and vinyl halides do not undergo nucleophilic substitution by either the S_N1 or S_N2 mechanism?

Correct Answer
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Which of the following alkyl halides undergoes the fastest S_N2 reaction with sodium hydroxide?

Correct Answer
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Correct Answer
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Which of the following rate laws describes the kinetics of an S_N1 reaction?

Correct Answer
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Correct Answer
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Correct Answer
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