Question 1

What is the IUPAC name of the following compound?

Accepted Answer

A)   2-Chloro-4-methylpentane
B)   2-Chloro-1-isopropylpropane
C)   2-Chloro-2-methylpentane
D)   2-Methyl-4-chloropentaneE) A) and C)
F) C) and D) A

Question 2

The reaction oftert-butyl bromide, (CH3) 3CBr, with ethanol affords the substitution producttert-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 increases by a factor of 4.
B)   The rate increases by a factor of 2.
C)   The rate remains the same.
D)   The rate decreases by a factor of 2.E) B) and C)
F) A) and B)

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 as it goes to CH3(CH2) 5OH + Br?

Accepted Answer

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

Question 4

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

Accepted Answer

A)   In endothermic reactions, the transition state is closer in energy to the products.
B)   The Hammond postulate provides a qualitative estimate of the energy of a transition state.
C)   The Hammond postulate provides a quantitative estimate of the energy of a transition state.
D)   In exothermic reactions, the transition state is closer in energy to the reactants.E) A) and D)
F) B) and C)

Question 5

Which of the following statements is true?

Accepted Answer

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

Question 6

Which is the best reagent to carry out the following organic synthesis? 2O B)  H2S C)  HCl D)  MeOH" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)   H2O
B)   H2S
C)   HCl
D)   MeOHE) A) and B)
F) A) and C)

Question 7

Which of the following statements isnot true?

Accepted Answer

A)   Equilibrium favors the products of the nucleophilic substitution when the leaving group is a stronger base than the nucleophile.
B)   All good leaving groups are weak bases with strong conjugate acids.
C)   Left-to-right across a row of the periodic table, leaving group ability increases.
D)   Down a column of the periodic table, leaving group ability increases.E) A) and C)
F) A) and D)

Question 8

Which of the following statements about SN2 reactions is true?

Accepted Answer

A)   The mechanism is a two-step process.
B)   The rate of reaction is dependent on just the substrate.
C)   Displacement occurs with inversion of configuration.
D)   The fastest reaction will occur with a tertiary alkyl halide.E) None of the above
F) B) and C) C

Question 9

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

Accepted Answer

A)   In an endothermic reaction, the more stable product forms faster.
B)   In an endothermic reaction, the less stable product forms faster.
C)   In an endothermic reaction, the activation energy, Ea, is similar for both products.
D)   In an exothermic reaction, lowering the energy of the transition state increases the activation energy, Ea.E) All of the above
F) C) and D) A

Question 10

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

Accepted Answer

A)   They don't undergo SN1 reactions because a higher percents-character makes the bond longer and stronger.
B)   They don't undergo SN1 reactions because the carbocation is highly electronegative.
C)   They don't undergo SN2 reactions because a higher percents-character makes the bond shorter and stronger.
D)   They don't undergo SN2 reactions because heterolysis of the C-X bond forms a highly unstable carbocation.E) B) and C)
F) A) and B)

Question 11

Which is the best reagent to carry out the following organic synthesis? 2O D)  MeOH" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)   NaOH, DMSO
B)   NaOMe, DMSO
C)   H2O
D)   MeOHE) B) and C)
F) A) and D)

Exam 6: Alkyl Halides and Nucleophilic Substitution

What is the IUPAC name of the following compound?

Correct Answer
verified
A

The reaction oftert-butyl bromide, (CH₃) ₃CBr, with ethanol affords the substitution producttert-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
verified

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

Correct Answer
verified

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

Correct Answer
verified

Which of the following statements is true?

Correct Answer
verified

Which is the best reagent to carry out the following organic synthesis?

Correct Answer
verified

Which of the following statements isnot true?

Correct Answer
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Which of the following statements about S_N2 reactions is true?

Correct Answer
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C

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

Correct Answer
verified
A

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

Correct Answer
verified

Which is the best reagent to carry out the following organic synthesis?

Correct Answer
verified

Exam 6: Alkyl Halides and Nucleophilic Substitution

What is the IUPAC name of the following compound?

Correct AnswerverifiedA

The reaction oftert-butyl bromide, (CH3) 3CBr, with ethanol affords the substitution producttert-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

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

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedShow Answer

Which of the following statements is true?

Correct AnswerverifiedShow Answer

Which is the best reagent to carry out the following organic synthesis?

Correct AnswerverifiedShow Answer

Which of the following statements isnot true?

Correct AnswerverifiedShow Answer

Which of the following statements about SN2 reactions is true?

Correct AnswerverifiedC

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

Correct AnswerverifiedA

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

Correct AnswerverifiedShow Answer

Which is the best reagent to carry out the following organic synthesis?

Correct AnswerverifiedShow Answer

Correct Answer
verified
A

The reaction oftert-butyl bromide, (CH₃) ₃CBr, with ethanol affords the substitution producttert-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
verified

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

Correct Answer
verified

Correct Answer
verified

Correct Answer
verified

Correct Answer
verified

Correct Answer
verified

Which of the following statements about S_N2 reactions is true?

Correct Answer
verified
C

Correct Answer
verified
A

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

Correct Answer
verified

Correct Answer
verified