Question 1

What is the major product formed upon treatment of (R)  2-bromohexane with sodium cyanide?

Accepted Answer

A)   (R)  2-cyanohexane
B)   (S)  2-cyanohexane
C)   1-hexene
D)   2-hexeneE) None of the above
F) B) and D)

Question 2

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

Question 3

The reaction of tert-butyl bromide, (CH3) 3CBr, with methanol in an inert solvent proceeds by an SN1 mechanism to give tert-butyl methyl ether, (CH3) 3COCH3. What is the effect of doubling the concentration of methanol 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 4E) B) and C)
F) A) and B)

Question 4

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

Accepted Answer

A)   The SN1 reaction can be described as a heterolytic bond cleavage followed by nucleophilic attack
B)   Carbocations are electrophilic
C)   The charged carbon atom of a carbocation has an unfilled valence shell
D)   Nucleophiles are Lewis acidsE) A) and C)
F) All of the above

Question 5

Which of the following alkyl halides undergoes the fastest solvolysis reaction with methanol, CH3OH?

Accepted Answer

A)   methyl chloride
B)   ethyl chloride
C)   2-chloropropane
D)   tert-butyl chlorideE) A) and B)
F) B) and D)

Question 6

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

Question 7

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

Question 8

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

Question 9

Draw all of the chloroalkanes that undergo base-promoted dehydrochlorination to form the following alkene?

Accepted Answer

The answer of Draw all of the chloroalkanes that undergo...

Question 10

Draw all of the chloroalkanes that undergo base-promoted dehydrochlorination to form the following alkene?

Accepted Answer

The answer of Draw all of the chloroalkanes that undergo...

Question 11

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

Question 12

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

Accepted Answer

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

Question 13

Which of the following reactions corresponds to a substitution?

Accepted Answer

A)   tert-butanol tert-butyl chloride
B)   tert-butanol 2-methylpropene
C)   3,3-dimethyl-2-butanol 2,3-dimethyl-2-butene
D)   cyclohexene 1,2-dichlorocyclohexaneE) A) and C)
F) B) and D)

Question 14

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

Question 15

Which of the following represents the transition state of the rate-determining step in the reaction between tert-butyl bromide and methanol?

Accepted Answer

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

Question 16

Which of the following alkyl bromides reacts the slowest with NaSCH3 in DMF? 3 in DMF?   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) A) and D)
F) All of the above

Question 17

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

Question 18

Which of the following solvents is the best choice for the reaction of 1-chlorohexane with sodium bromide?

Accepted Answer

A)   water
B)   N,N-dimethylformamide
C)   hexane
D)   toluene, PhCH3E) A) and B)
F) B) and D)

Question 19

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

Accepted Answer

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

Question 20

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

Exam 9: Nucleophilic Substitution and Beta-Elimination

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

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

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

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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?

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Draw all of the chloroalkanes that undergo base-promoted dehydrochlorination to form the following alkene?

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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 SN2 mechanism?

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Which of the following reactions corresponds to a substitution?

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

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The reaction of tert-butyl bromide, (CH3) 3CBr, with methanol in an inert solvent proceeds by an SN1 mechanism to give tert-butyl methyl ether, (CH3) 3COCH3. What is the effect of doubling the concentration of methanol on the rate of the reaction?

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?

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

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Which of the following alkyl halides undergoes the fastest solvolysis reaction with methanol, CH3OH?

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Which of the following alkyl bromides reacts the slowest with NaSCH3 in DMF?

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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?

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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?

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Which of the following represents the transition state of the rate-determining step in the reaction between tert-butyl bromide and methanol?

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Draw all of the chloroalkanes that undergo base-promoted dehydrochlorination to form the following alkene?

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What is the major product formed upon treatment of (R) 2-bromohexane with sodium cyanide?

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Which of the following solvents is the best choice for the reaction of 1-chlorohexane with sodium bromide?

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

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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?

Correct Answer
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The reaction of tert-butyl bromide, (CH₃) ₃CBr, with methanol in an inert solvent proceeds by an S_N1 mechanism to give tert-butyl methyl ether, (CH₃) ₃COCH₃. What is the effect of doubling the concentration of methanol on the rate of the reaction?

Correct Answer
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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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Which of the following alkyl halides undergoes the fastest solvolysis reaction with methanol, CH₃OH?

Correct Answer
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Which of the following alkyl bromides reacts the slowest with NaSCH₃ in DMF?

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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?

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

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

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