Question 1

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 acids 
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 acids

Question 2

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)  4 
A)  1 
B)  2 
C)  3 
D)  4

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

Question 4

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

Accepted Answer

A)  1 
B)  2 
C)  3 
D)  4 
A)  1 
B)  2 
C)  3 
D)  4

Question 5

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, DMSO 
A)  water, hexane, methanol 
B)  acetic acid, DMF, toluene 
C)  DMSO, ethanol, acetonitrile 
D)  DMF, acetonitrile, DMSO

Question 6

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 4 
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

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 phase 
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 phase

Question 8

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] 
A)  Rate = k [i-PrBr] 
B)  Rate = k [i-PrBr]2 
C)  Rate = k [CH3OH] 
D)  Rate = k [i-PrBr][CH3OH]

Question 9

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-dichlorocyclohexane 
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-dichlorocyclohexane

Question 10

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

Question 11

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 12

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

Accepted Answer

A)  1 
B)  2 
C)  3 
D)  4 
A)  1 
B)  2 
C)  3 
D)  4

Question 13

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

Question 14

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-hexene 
A)  (R) 2-cyanohexane 
B)  (S) 2-cyanohexane 
C)  1-hexene 
D)  2-hexene

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)  4 
A)  1 
B)  2 
C)  3 
D)  4

Question 16

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 17

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

Accepted Answer

A)  1 
B)  2 
C)  3 
D)  4 
A)  1 
B)  2 
C)  3 
D)  4

Question 18

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 density 
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 density

Question 19

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, PhCH3 
A)  water 
B)  N,N-dimethylformamide 
C)  hexane 
D)  toluene, PhCH3

Question 20

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. 
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.

Exam 9: Nucleophilic Substitution and Beta-Elimination

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

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?

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?

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

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

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?

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?

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?

Which of the following reactions corresponds to a substitution?

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

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

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

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

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

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

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

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

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

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

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

Covalent Bonding and Shapes of Molecules

Alkanes and Cycloalkanes

Stereoisomerism and Chirality

Acids and Bases

Alkenes: Bonding, Nomenclature, and Properties

Reactions of Alkenes

Alkynes

Haloalkanes, Halogenation, and Radical Reactions

Alcohols

Ethers, Epoxides, and Sulfides

Infrared Spectroscopy

Nuclear Magnetic Resonance Spectroscopy

Mass Spectrometry

An Introduction to Organometallic Compounds

Aldehydes and Ketones

Carboxylic Acids

Functional Derivatives of Carboxylic Acids

Enolate Anions and Enamines

Dienes, Conjugated Systems, and Pericyclic Reactions

Benzene and the Concept of Aromaticity

Reactions of Benzene and Its Derivatives

Filters

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

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?

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

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?

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?

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?

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

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

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