Question 1

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 D)
F) A) and C)

Question 2

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

Accepted Answer

A)  CH2CH2OH
B)  CH3OH
C)  DMSO
D)  H2OE) A) and C)
F) B) and D)

Question 3

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

Question 4

What is the IUPAC name of the following compound?

Accepted Answer

A)  (1R,3R) -1-bromo-3-isopropylcyclopentane
B)  (1R,3S) -1-bromo-3-isopropylcyclopentane
C)  (1S,3R) -1-bromo-3-isopropylcyclopentane
D)  (1S,3S) -1-bromo-3-isopropylcyclopentaneE) A) and D)
F) All of the above

Question 5

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

Question 6

What is the IUPAC name of the following compound?

Accepted Answer

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-buteneE) C) and D)
F) A) and C)

Question 7

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

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

Question 9

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

Accepted Answer

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

Question 10

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

Question 11

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

Accepted Answer

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

Question 12

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 D)
F) A) and C)

Question 13

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 B)
F) B) and D)

Question 14

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

Question 15

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?

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 B)

Question 16

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 17

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

Accepted Answer

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

Question 18

Rank the following in order of increasing nucleophilicity,putting the least nucleophilic first.

Accepted Answer

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

Question 19

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

Accepted Answer

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

Question 20

Which of the following solvents is not a polar protic solvent?

Accepted Answer

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

Exam 7: Alkyl Halides and Nucleophilic Substitution

What is the IUPAC name of the following compound?

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Rank the following halides in order of decreasing polarity,putting the most polar first.

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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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Which of the following statements about the SN2 mechanism for nucleophilic substitution reactions 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 SN1 or SN2 mechanism?

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

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

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Which of the following statements is not true?

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Which of the following solvents is not a polar protic solvent?

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Rank the following carbocations in order of decreasing stability,putting the most stable first.

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What is the IUPAC name of the following compound?

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What is the IUPAC name of the following compound?

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

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

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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?

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

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Which of the following statements is not true?

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Rank the following in order of increasing nucleophilicity,putting the least nucleophilic first.

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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 statements about the S_N2 mechanism for nucleophilic substitution reactions 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?

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

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Pick the solvent that gives the fastest S_N2 reaction between CH₂CH₂Br and ^-OCH₃.

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