Question 1

Which of the following alkyl halides undergoes the fastest solvolysis reaction with ethanol, CH3CH2OH?

Accepted Answer

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

Question 2

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 3

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 4

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 5

Which of the following energy diagrams represents the course of an exothermic SN1 reaction?

Accepted Answer

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

Question 6

Which of the following statements is not true regarding the SN2 reaction of (R)-2-bromobutane with sodium cyanide?

Accepted Answer

A)  the reaction proceeds with inversion of configuration 
B)  the rate is proportional to the concentration of sodium cyanide 
C)  the rate is proportional to the concentration of (R)-2-bromobutane 
D)  the rate of the reaction is independent of the identity of the solvent 
A)  the reaction proceeds with inversion of configuration 
B)  the rate is proportional to the concentration of sodium cyanide 
C)  the rate is proportional to the concentration of (R)-2-bromobutane 
D)  the rate of the reaction is independent of the identity of the solvent

Question 7

Which of the following is not a characteristic of SN1 reactions?

Accepted Answer

A)  the electrophilic carbon undergoes inversion of stereochemistry 
B)  the rate is proportional to the concentration of substrate 
C)  the reaction proceeds faster in a more polar solvent 
D)  the rate is independent of the concentration of nucleophile 
A)  the electrophilic carbon undergoes inversion of stereochemistry 
B)  the rate is proportional to the concentration of substrate 
C)  the reaction proceeds faster in a more polar solvent 
D)  the rate is independent of the concentration of nucleophile

Question 8

Which of the following alkyl halides undergoes the fastest solvolysis reaction with formic acid, HCOOH?

Accepted Answer

A)  tert-butyl fluoride 
B)  tert-butyl chloride 
C)  tert-butyl bromide 
D)  tert-butyl iodide 
A)  tert-butyl fluoride 
B)  tert-butyl chloride 
C)  tert-butyl bromide 
D)  tert-butyl iodide

Question 9

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-iodohexane 
A)  1-fluorohexane 
B)  1-chlorohexane 
C)  1-bromohexane 
D)  1-iodohexane

Question 10

In which of the following solvents would the reaction of 1-bromobutane with sodium azide, NaN3, proceed the fastest?

Accepted Answer

A)  acetic acid 
B)  ethanol 
C)  water 
D)  acetonitrile 
A)  acetic acid 
B)  ethanol 
C)  water 
D)  acetonitrile

Question 11

What is the major elimination 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 12

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

Accepted Answer

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

Question 13

In the case of a unimolecular nucleophilic substitution reaction, the reaction rate completely depends on the concentration of the _____.

Accepted Answer

The answer of In the case of a unimolecular nucleophilic...

Question 14

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

Question 15

The reaction of 1-bromopropane with sodium iodide gives 1-iodopropane. What is the effect of doubling the concentration of NaI 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 16

Which of the following most favors elimination rather substitution in a reaction with sodium methoxide?

Accepted Answer

A)  bromomethane 
B)  bromoethane 
C)  1-bromopropane 
D)  2-bromopropane 
A)  bromomethane 
B)  bromoethane 
C)  1-bromopropane 
D)  2-bromopropane

Question 17

Which of the following compounds is the most nucleophilic in polar protic solvents?

Accepted Answer

A)  H2O 
B)  NH3 
C)  H2S 
D)  PH3 
A)  H2O 
B)  NH3 
C)  H2S 
D)  PH3

Question 18

Consider the reaction below to answer the following question:   The product of this reaction is

Accepted Answer

A) True 
 B)False

Question 19

The following reaction would be classified as an elimination.

Accepted Answer

A) True 
 B)False

Question 20

Which of the following is the best leaving group in an SN2 reaction?

Accepted Answer

A)  F− 
B)  H3C− 
C)  CH3O2SO− 
D)  HO− 
A)  F− 
B)  H3C− 
C)  CH3O2SO− 
D)  HO−

Exam 9: Nucleophilic Substitution and Beta-Elimination

Which of the following alkyl halides undergoes the fastest solvolysis reaction with ethanol, CH3CH2OH?

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

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

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

Which of the following energy diagrams represents the course of an exothermic SN1 reaction?

Which of the following statements is not true regarding the SN2 reaction of (R)-2-bromobutane with sodium cyanide?

Which of the following is not a characteristic of SN1 reactions?

Which of the following alkyl halides undergoes the fastest solvolysis reaction with formic acid, HCOOH?

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

In which of the following solvents would the reaction of 1-bromobutane with sodium azide, NaN3, proceed the fastest?

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

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

In the case of a unimolecular nucleophilic substitution reaction, the reaction rate completely depends on the concentration of the _____.

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

The reaction of 1-bromopropane with sodium iodide gives 1-iodopropane. What is the effect of doubling the concentration of NaI on the rate of the reaction?

Which of the following most favors elimination rather substitution in a reaction with sodium methoxide?

Which of the following compounds is the most nucleophilic in polar protic solvents?

Consider the reaction below to answer the following question: The product of this reaction is

The following reaction would be classified as an elimination.

Which of the following is the best leaving group in an SN2 reaction?

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

Amines

Catalytic Carbon-Carbon Bond Formation

Carbohydrates

Lipids

Amino Acids and Proteins

Nucleic Acids

Organic Polymer Chemistry

Filters

Which of the following alkyl halides undergoes the fastest solvolysis reaction with ethanol, CH₃CH₂OH?

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

Which of the following energy diagrams represents the course of an exothermic S_N1 reaction?

Which of the following statements is not true regarding the S_N2 reaction of (R)-2-bromobutane with sodium cyanide?

Which of the following is not a characteristic of S_N1 reactions?

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

In which of the following solvents would the reaction of 1-bromobutane with sodium azide, NaN₃, proceed the fastest?

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

Which of the following is the best leaving group in an S_N2 reaction?