Question 1

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 2

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 3

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 4

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

Accepted Answer

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

Question 5

Provide a neatly drawn mechanism for the following reaction, including curved arrows to show the movement of pairs of electrons and the structure of reactive intermediates.

Accepted Answer

The reaction proceeds in a sin

Question 6

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

Question 8

Which of the following is the most nucleophilic?

Accepted Answer

A)  sodium ethoxide 
B)  acetic acid 
C)  methanol 
D)  water 
A)  sodium ethoxide 
B)  acetic acid 
C)  methanol 
D)  water

Question 9

Which of the following statements is true regarding the reaction of tert-butyl bromide with water?

Accepted Answer

A)  the rate is proportional to the concentration of tert-butyl bromide 
B)  the rate is proportional to the concentration of water 
C)  the rate is independent of the identity of the solvent 
D)  the rate of the reaction is independent of the temperature 
A)  the rate is proportional to the concentration of tert-butyl bromide 
B)  the rate is proportional to the concentration of water 
C)  the rate is independent of the identity of the solvent 
D)  the rate of the reaction is independent of the temperature

Question 10

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

Accepted Answer

A)  dimethylsulfoxide 
B)  water 
C)  hexane 
D)  toluene, PhCH3 
A)  dimethylsulfoxide 
B)  water 
C)  hexane 
D)  toluene, PhCH3

Question 11

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

Accepted Answer

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

Question 12

Which of the following energy diagrams represents the course of an exothermic SN2 reaction?

Accepted Answer

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

Question 13

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

Accepted Answer

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

Question 14

Identify the major product of the following reaction. ​

Accepted Answer

A) 
  
B) 
  
C) 
  
D) 
  
A) 
  
B) 
  
C) 
  
D)

Question 15

Which of the following anions is the best leaving group in an SN1 reaction?

Accepted Answer

A)  F− 
B)  HO− 
C)  NH2− 
D)  Cl− 
A)  F− 
B)  HO− 
C)  NH2− 
D)  Cl−

Question 16

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 17

Which of the following alkyl halides undergoes the fastest SN2 reaction with sodium methylthiolate, NaSMe?

Accepted Answer

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

Question 18

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 19

Identify the major product of the following reaction. ​

Accepted Answer

A) 
  
B) 
  
C) 
  
D) 
  
A) 
  
B) 
  
C) 
  
D)

Question 20

Arrange the following in decreasing order of their nucleophilicity. CH3CH2CH2Li, CF3CH2CH2O−, CH3CH2CH2O−, CH3CH2CH2S−

Accepted Answer

A)  CH3CH2CH2Li > CH3CH2CH2S− > CH3CH2CH2O− > CF3CH2CH2O− 
B)  CH3CH2CH2S− > CH3CH2CH2O− > CF3CH2CH2O− > CH3CH2CH2Li 
C)  CH3CH2CH2Li > CF3CH2CH2O− > CH3CH2CH2O− > CH3CH2CH2S− 
D)  CF3CH2CH2O− > CH3CH2CH2O− > CH3CH2CH2S− > CH3CH2CH2Li 
A)  CH3CH2CH2Li > CH3CH2CH2S− > CH3CH2CH2O− > CF3CH2CH2O− 
B)  CH3CH2CH2S− > CH3CH2CH2O− > CF3CH2CH2O− > CH3CH2CH2Li 
C)  CH3CH2CH2Li > CF3CH2CH2O− > CH3CH2CH2O− > CH3CH2CH2S− 
D)  CF3CH2CH2O− > CH3CH2CH2O− > CH3CH2CH2S− > CH3CH2CH2Li

Exam 9: Nucleophilic Substitution and Beta-Elimination

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

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 organic product obtained from the following reaction?

Provide a neatly drawn mechanism for the following reaction, including curved arrows to show the movement of pairs of electrons and the structure of reactive intermediates.

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

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

Which of the following is the most nucleophilic?

Which of the following statements is true regarding the reaction of tert-butyl bromide with water?

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

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

Which of the following energy diagrams represents the course of an exothermic SN2 reaction?

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

Identify the major product of the following reaction. ​

Which of the following anions is the best leaving group in an SN1 reaction?

Which of the following reactions corresponds to a substitution?

Which of the following alkyl halides undergoes the fastest SN2 reaction with sodium methylthiolate, NaSMe?

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

Identify the major product of the following reaction. ​

Arrange the following in decreasing order of their nucleophilicity. CH3CH2CH2Li, CF3CH2CH2O−, CH3CH2CH2O−, CH3CH2CH2S−

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 bromides reacts the slowest with NaSCH₃ in DMF?

Which of the following energy diagrams represents the course of an exothermic S_N2 reaction?

Identify the major product of the following reaction.

Which of the following anions is the best leaving group in an S_N1 reaction?

Which of the following alkyl halides undergoes the fastest S_N2 reaction with sodium methylthiolate, NaSMe?

Identify the major product of the following reaction.

Arrange the following in decreasing order of their nucleophilicity. CH₃CH₂CH₂Li, CF₃CH₂CH₂O−, CH₃CH₂CH₂O−, CH₃CH₂CH₂S−