Question 1

The following energy diagram could represent an SN2 reaction.

Accepted Answer

A) True 
 B)False

Question 2

The reaction of methyl iodide with sodium azide, NaN3, proceeds by an SN2 mechanism. What is the effect of doubling the concentration of NaN3 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 3

Why is cyclohexylamine more reactive than aniline when the former reacts with methyl bromide?

Accepted Answer

-NH₂ is a poor leaving group, but it is a

Question 4

Which of the following statements is true regarding the reactivity of 1 and 2 with potassium tert-butoxide?

Accepted Answer

A)  1 reacts faster than 2 
B)  1 and 2 give different dehydrochlorinated products 
C)  2 reacts by elimination whereas 1 reacts by substitution 
D)  1 reacts by elimination whereas 2 reacts by substitution 
A)  1 reacts faster than 2 
B)  1 and 2 give different dehydrochlorinated products 
C)  2 reacts by elimination whereas 1 reacts by substitution 
D)  1 reacts by elimination whereas 2 reacts by substitution

Question 5

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 6

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 7

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 8

What is the equation for the rate of formation of tert-butyl alcohol from the reaction of tert-butyl bromide (t-BuBr) with water by an SN1 mechanism?

Accepted Answer

A)  Rate = k [t-BuBr] 
B)  Rate = k [t-BuBr][H2O] 
C)  Rate = k [H2O] 
D)  Rate = k [t-BuBr]2 
A)  Rate = k [t-BuBr] 
B)  Rate = k [t-BuBr][H2O] 
C)  Rate = k [H2O] 
D)  Rate = k [t-BuBr]2

Question 9

The reaction of tert-butyl chloride, (CH3)3CCl, with water in an inert solvent gives tert-butyl alcohol, (CH3)3COH. What is the effect of doubling the concentration of water 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 10

Which of the following alkyl halides undergoes the fastest SN2 reaction with sodium cyanide, NaCN?

Accepted Answer

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

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 is the best set of conditions for the preparation of tert-butyl methyl ether?

Accepted Answer

A)  tert-butyl fluoride and NaOCH3 in CH3OH 
B)  methanol and sodium tert-butoxide in tert-butanol 
C)  fluoromethane and sodium tert-butoxide in tert-butanol 
D)  tert-butyl bromide and CH3OH 
A)  tert-butyl fluoride and NaOCH3 in CH3OH 
B)  methanol and sodium tert-butoxide in tert-butanol 
C)  fluoromethane and sodium tert-butoxide in tert-butanol 
D)  tert-butyl bromide and CH3OH

Question 13

Which of the following energy diagrams represents the course of an exothermic E2 reaction?

Accepted Answer

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

Question 14

Explain Walden inversion.

Accepted Answer

During an aliphatic nucleophilic substit

Question 15

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 three steps:
1.

Question 16

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

Accepted Answer

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

Question 17

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 18

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

Accepted Answer

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

Question 19

Which of the following reactions corresponds to a substitution?

Accepted Answer

A)  propene → 1,2-dibromopropane 
B)  1-iodopropane → propene 
C)  propene → propane 
D)  1-iodopropane → 1-bromopropane 
A)  propene → 1,2-dibromopropane 
B)  1-iodopropane → propene 
C)  propene → propane 
D)  1-iodopropane → 1-bromopropane

Question 20

The following reaction would have a faster rate in a higher polarity solvent than one of low polarity.

Accepted Answer

A) True 
 B)False

Exam 9: Nucleophilic Substitution and Beta-Elimination

The following energy diagram could represent an SN2 reaction.

The reaction of methyl iodide with sodium azide, NaN3, proceeds by an SN2 mechanism. What is the effect of doubling the concentration of NaN3 on the rate of the reaction?

Why is cyclohexylamine more reactive than aniline when the former reacts with methyl bromide?

Which of the following statements is true regarding the reactivity of 1 and 2 with potassium tert-butoxide?

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

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

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

What is the equation for the rate of formation of tert-butyl alcohol from the reaction of tert-butyl bromide (t-BuBr) with water by an SN1 mechanism?

The reaction of tert-butyl chloride, (CH3)3CCl, with water in an inert solvent gives tert-butyl alcohol, (CH3)3COH. What is the effect of doubling the concentration of water on the rate of the reaction?

Which of the following alkyl halides undergoes the fastest SN2 reaction with sodium cyanide, NaCN?

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

Which of the following is the best set of conditions for the preparation of tert-butyl methyl ether?

Which of the following energy diagrams represents the course of an exothermic E2 reaction?

Explain Walden inversion.

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.

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

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 reactions corresponds to a substitution?

The following reaction would have a faster rate in a higher polarity solvent than one of low polarity.

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

The following energy diagram could represent an S_N2 reaction.

The reaction of methyl iodide with sodium azide, NaN₃, proceeds by an S_N2 mechanism. What is the effect of doubling the concentration of NaN₃ on the rate of the reaction?

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

What is the equation for the rate of formation of tert-butyl alcohol from the reaction of tert-butyl bromide (t-BuBr) with water by an S_N1 mechanism?

The reaction of tert-butyl chloride, (CH₃)₃CCl, with water in an inert solvent gives tert-butyl alcohol, (CH₃)₃COH. What is the effect of doubling the concentration of water on the rate of the reaction?

Which of the following alkyl halides undergoes the fastest S_N2 reaction with sodium cyanide, NaCN?