Question 1

Rank the following compounds in order of increasing SN1 reactivity? N1 reactivity?   A) I > II > III > IV B) IV > I > II > III C) IV > III > II > I D) III > II > I > IV" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

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

Question 2

Rank the following ions in order of increasing nucleophilicity in polar protic solvents,starting with the least nucleophilic ion.

Accepted Answer

A)  I 
B)  IV 
C)  I 
D)  IV < III < I < IIE) A) and D)
F) A) and C)

Question 3

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

Accepted Answer

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

Question 4

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

Question 5

What is the IUPAC name of the following compound?

Accepted Answer

A)  (3R,4R) -3-chloro-4-methylhexane
B)  (3R,4S) -3-chloro-4-methylhexane
C)  (3S,4R) -3-chloro-4-methylhexane
D)  (3S,4S) -3-chloro-4-methylhexaneE) B) and D)
F) None of the above

Question 6

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

Question 7

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 C)
F) A) and C)

Question 8

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

Question 9

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

Accepted Answer

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

Question 10

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 11

What is the starting material in the reaction shown below?

Accepted Answer

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

Question 12

Which of the following statements about SN2 reactions is true?

Accepted Answer

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) None of the above

Question 13

Rank the following in order of decreasing nucleophilicity,putting the most nucleophilic first.  III > I > IV B) III > II > IV > I C) II > III > IV > I D) III > II > I > IV" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

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

Question 14

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) None of the above
F) All of the above

Question 15

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) None of the above

Question 16

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

Question 17

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

Question 18

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

Question 19

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

Accepted Answer

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

Question 20

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) A) and C)

Exam 7: Alkyl Halides and Nucleophilic Substitution

What is the starting material in the reaction shown below?

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

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

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

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

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What is the IUPAC name of the following compound?

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

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Rank the following in order of decreasing nucleophilicity,putting the most nucleophilic first.

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

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

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Which of the following statements about SN2 reactions is true?

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

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Rank the following compounds in order of increasing SN1 reactivity?

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

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What is the IUPAC name of the following compound?

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Which of the following structures have the correct common name?

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Rank the following ions in order of increasing nucleophilicity in polar protic solvents,starting with the least nucleophilic ion.

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

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

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Which of the following statements is not true?

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

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

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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?

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Which of the following statements about S_N2 reactions is true?

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Rank the following compounds in order of increasing S_N1 reactivity?

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

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