Question 1

What is the major organic product obtained from the following reaction?

Accepted Answer

A)  1
B)  2
C)  3
D)  4E) B) and C)
F) C) and D)

Question 2

What is(are)  the major organic product(s)  obtained from the following substitution reaction?

Accepted Answer

A)  only 1
B)  only 2
C)  only 3
D)  a mixture of 1 and 2E) B) and D)
F) A) and C)

Question 3

What is the equation for the rate of formation of 1-iodobutane from the reaction of 1-chlorobutane (BuCl)  with NaI by an SN2 mechanism?

Accepted Answer

A)  Rate = k [BuCl]
B)  Rate = k [BuCl][NaI]
C)  Rate = k [NaI]
D)  Rate = k [BuCl]2E) C) and D)
F) B) and C)

Question 4

Consider the reaction below to answer the following question:  This reaction proceeds by an E1 mechanism.

Accepted Answer

A) True 
 B)False

Question 5

What is the major organic product obtained from the following reaction?

Accepted Answer

A)  1
B)  2
C)  3
D)  4E) A) and B)
F) C) and D)

Question 6

HCl is the electrophile in the following reaction.

Accepted Answer

A) True 
 B)False

Question 7

What is(are)  the major organic product(s)  obtained from the following substitution reaction?

Accepted Answer

A)  only 1
B)  only 2
C)  only 1 and 2
D)  1, 2 and 3E) B) and C)
F) A) and B)

Question 8

What is the major product formed upon treatment of (R)  1-bromo-4-methylhexane with sodium cyanide?

Accepted Answer

A)  (R)  1-cyano-4-methylhexane
B)  (S)  1-cyano-4-methylhexane
C)  (R)  4-methyl-1-hexene
D)  (S)  4-methyl-1-hexeneE) A) and B)
F) A) and C)

Question 9

What is the major organic product obtained from the following reaction?

Accepted Answer

The answer of What is the major organic product obtained...

Question 10

What is the major organic product obtained from the following reaction?

Accepted Answer

A)  1
B)  2
C)  3
D)  4E) A) and B)
F) A) and C)

Question 11

The following energy diagram could represent an SN2 reaction.

Accepted Answer

A) True 
 B)False

Question 12

What is the equation for the rate of formation of 2-methoxypropane, CH3CH(OCH3) CH3, from the reaction of 2-bromopropane (i-PrBr)  with methanol?

Accepted Answer

A)  Rate = k [i-PrBr]
B)  Rate = k [i-PrBr]2
C)  Rate = k [CH3OH]
D)  Rate = k [i-PrBr][CH3OH]E) All of the above
F) B) and C)

Question 13

Which of the following sets consists of only polar aprotic solvents?

Accepted Answer

A)  water, hexane, methanol
B)  acetic acid, DMF, toluene
C)  DMSO, ethanol, acetonitrile
D)  DMF, acetonitrile, DMSOE) None of the above
F) B) and C)

Question 14

Consider the pair of reactions below to answer the following question(s).
a.  
or
b. 
-The mechanism for these reactions is _______.

Accepted Answer

The answer of Consider the pair of reactions below to...

Question 15

Which of the following statements related to SN1 reactions is not true?

Accepted Answer

A)  The heterolysis of a bond between atoms which do not bear formal charges always produces a cation and an anion
B)  The charged carbon atom of a carbocation has a complete octet of valence shell electrons
C)  Carbocations are Lewis acids
D)  Nucleophiles seek centers of low electron densityE) C) and D)
F) A) and C)

Question 16

Which of the following represents the transition state of the rate-determining step in the reaction between 2-chloropropane and sodium amide leading to elimination?

Accepted Answer

A)  1
B)  2
C)  3
D)  4E) B) and C)
F) A) and D)

Question 17

What is the role of tetrabutylammonium chloride as a phase transfer catalyst in the reaction of 1-chlorooctane and sodium cyanide in a mixture of water and CH2Cl2?

Accepted Answer

A)  it transfers 1-chlorooctane into the aqueous phase
B)  it transfers cyanide anion into the organic phase
C)  it makes water and dichloromethane miscible
D)  it transfers the sodium cation into the organic phaseE) None of the above
F) C) and D)

Question 18

Which of the following statements is not true regarding SN2 reactions?

Accepted Answer

A)  A carbocation intermediate is formed.
B)  The mechanism has only one step.
C)  Aprotic solvents are good choices for SN1 reactions.
D)  The stereochemical outcome is inversion at the carbon bearing the leaving group.E) A) and C)
F) B) and C)

Question 19

Which of the following alkyl halides undergoes the fastest SN2 reaction with sodium azide, NaN3?

Accepted Answer

A)  1-fluorohexane
B)  1-chlorohexane
C)  1-bromohexane
D)  1-iodohexaneE) A) and C)
F) B) and D)

Question 20

Which of the following represents the transition state of the rate-determining step in the SN1 reaction between tert-butyl chloride and water? N1 reaction between tert-butyl chloride and water?   A) 1 B) 2 C) 3 D) 4" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)  1
B)  2
C)  3
D)  4E) All of the above
F) C) and D)

Exam 9: Nucleophilic Substitution and Beta-Elimination

HCl is the electrophile in the following reaction.

Correct AnswerverifiedShow Answer

What is the equation for the rate of formation of 1-iodobutane from the reaction of 1-chlorobutane (BuCl) with NaI by an SN2 mechanism?

Correct AnswerverifiedShow Answer

Consider the pair of reactions below to answer the following question(s). a. or b. -The mechanism for these reactions is _______.

Correct AnswerverifiedShow Answer

What is(are) the major organic product(s) obtained from the following substitution reaction?

Correct AnswerverifiedShow Answer

What is the major organic product obtained from the following reaction?

Correct AnswerverifiedShow Answer

Which of the following represents the transition state of the rate-determining step in the SN1 reaction between tert-butyl chloride and water?

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Which of the following statements related to SN1 reactions is not true?

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Which of the following statements is not true regarding SN2 reactions?

Correct AnswerverifiedShow Answer

What is(are) the major organic product(s) obtained from the following substitution reaction?

Correct AnswerverifiedShow Answer

Which of the following alkyl halides undergoes the fastest SN2 reaction with sodium azide, NaN3?

Correct AnswerverifiedShow Answer

The following energy diagram could represent an SN2 reaction.

Correct AnswerverifiedShow Answer

What is the major organic product obtained from the following reaction?

Correct AnswerverifiedShow Answer

Which of the following represents the transition state of the rate-determining step in the reaction between 2-chloropropane and sodium amide leading to elimination?

Correct AnswerverifiedShow Answer

Which of the following sets consists of only polar aprotic solvents?

Correct AnswerverifiedShow Answer

What is the equation for the rate of formation of 2-methoxypropane, CH3CH(OCH3) CH3, from the reaction of 2-bromopropane (i-PrBr) with methanol?

Correct AnswerverifiedShow Answer

What is the role of tetrabutylammonium chloride as a phase transfer catalyst in the reaction of 1-chlorooctane and sodium cyanide in a mixture of water and CH2Cl2?

Correct AnswerverifiedShow Answer

What is the major product formed upon treatment of (R) 1-bromo-4-methylhexane with sodium cyanide?

Correct AnswerverifiedShow Answer

Consider the reaction below to answer the following question: This reaction proceeds by an E1 mechanism.

Correct AnswerverifiedShow Answer

What is the major organic product obtained from the following reaction?

Correct AnswerverifiedShow Answer

What is the major organic product obtained from the following reaction?

Correct AnswerverifiedShow Answer

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What is the equation for the rate of formation of 1-iodobutane from the reaction of 1-chlorobutane (BuCl) with NaI by an S_N2 mechanism?

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Which of the following represents the transition state of the rate-determining step in the S_N1 reaction between tert-butyl chloride and water?

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Which of the following statements related to S_N1 reactions is not true?

Correct Answer
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Which of the following statements is not true regarding S_N2 reactions?

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Which of the following alkyl halides undergoes the fastest S_N2 reaction with sodium azide, NaN₃?

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The following energy diagram could represent an S_N2 reaction.

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What is the equation for the rate of formation of 2-methoxypropane, CH₃CH(OCH₃) CH₃, from the reaction of 2-bromopropane (i-PrBr) with methanol?

Correct Answer
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What is the role of tetrabutylammonium chloride as a phase transfer catalyst in the reaction of 1-chlorooctane and sodium cyanide in a mixture of water and CH₂Cl₂?

Correct Answer
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