Question 1

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 B

Question 2

Consider the pair of reactions below to answer the following question(s).
a.   
or
b.  
-Reaction ____ will be faster.

Accepted Answer

A)   
or 
B)   
A)   
or 
B)   B

Question 3

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- C

Question 4

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 5

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

Accepted Answer

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

Question 6

Consider the pair of reactions below to answer the following question(s).
-Reaction ____ is faster.

Accepted Answer

A)   
or 
B)   
A)   
or 
B)

Question 7

Which of the following reactions corresponds to a substitution?

Accepted Answer

A) tert-butanol $\rarr$ tert-butyl chloride 
B) tert-butanol $\rarr$ 2-methylpropene 
C) 3,3-dimethyl-2-butanol $\rarr$2,3-dimethyl-2-butene 
D) cyclohexene $\rarr$1,2-dichlorocyclohexane 
A) tert-butanol $\rarr$ tert-butyl chloride 
B) tert-butanol $\rarr$ 2-methylpropene 
C) 3,3-dimethyl-2-butanol $\rarr$2,3-dimethyl-2-butene 
D) cyclohexene $\rarr$1,2-dichlorocyclohexane

Question 8

Which of the following is most likely to undergo rearrangement during reaction with methanol?

Accepted Answer

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

Question 9

For each substrate below, choose which reaction type is favored. Place the letter of the reaction type in the blank to the left of the substrate.
-_____

Accepted Answer

A) SN1 
B) SN2 
C) E1 
D) E2 
A) SN1 
B) SN2 
C) E1 
D) E2

Question 10

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 11

Consider the reaction below to answer the following question(s).  
-Compound C is formed by an _____ mechanism.

Accepted Answer

The answer of Consider the reaction below to answer the...

Question 12

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 13

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

Accepted Answer

A) True 
 B)False

Question 14

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 15

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 16

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 17

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 18

Consider the pair of reactions below to answer the following question(s).
-The nucleophile is these reactions is________.

Accepted Answer

The answer of Consider the pair of reactions below to...

Question 19

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 20

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

Accepted Answer

A) 1-hexyne 
B) 2-hexyne 
C) propene + propyne 
D) propane + propyne 
A) 1-hexyne 
B) 2-hexyne 
C) propene + propyne 
D) propane + propyne

Exam 9: Nucleophilic Substitution and Beta-Elimination

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

Consider the pair of reactions below to answer the following question(s). a. or b. -Reaction ____ will be faster.

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

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

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

Consider the pair of reactions below to answer the following question(s). -Reaction ____ is faster.

Which of the following reactions corresponds to a substitution?

Which of the following is most likely to undergo rearrangement during reaction with methanol?

For each substrate below, choose which reaction type is favored. Place the letter of the reaction type in the blank to the left of the substrate. -_____

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

Consider the reaction below to answer the following question(s). -Compound C is formed by an _____ 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?

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

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

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

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

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

Consider the pair of reactions below to answer the following question(s). -The nucleophile is these reactions is________.

Which of the following is the most nucleophilic?

What is the major organic product(s) obtained from the following 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 is the best leaving group in an S_N2 reaction?

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

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?

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