Question 1

The following reaction will occur via which mechanism?

Accepted Answer

A)  elimination-addition 
B)  nucleophilic aromatic substitution 
C)  electrophilic aromatic substitution 
D)  addition-elimination 
E)  both B and C 
A)  elimination-addition 
B)  nucleophilic aromatic substitution 
C)  electrophilic aromatic substitution 
D)  addition-elimination 
E)  both B and C

Question 2

The following reaction will occur via which mechanism?

Accepted Answer

A)  elimination-addition 
B)  nucleophilic aromatic substitution 
C)  electrophilic aromatic substitution 
D)  both B and C 
A)  elimination-addition 
B)  nucleophilic aromatic substitution 
C)  electrophilic aromatic substitution 
D)  both B and C

Question 3

Propose a stepwise synthesis for the following compound from benzene.

Accepted Answer

@#IMG-DLM&_TB4454_00

Question 4

Predict the product for the following reaction.

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  V 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  V

Question 5

Predict the major product for the following reaction.

Accepted Answer

The answer of Predict the major product for the following...

Question 6

Predict the structure of the product for the following reaction.

Accepted Answer

The answer of Predict the structure of the product for...

Question 7

Which of the following criteria is necessary for a nucleophilic aromatic substitution reaction?

Accepted Answer

A)  the ring must contain a very strong electron withdrawing group 
B)  the ring must contain a leaving group 
C)  the leaving group must be ortho or para to the electron withdrawing group 
D)  the leaving group must be meta to the electron withdrawing group 
E)  A, B and C 
A)  the ring must contain a very strong electron withdrawing group 
B)  the ring must contain a leaving group 
C)  the leaving group must be ortho or para to the electron withdrawing group 
D)  the leaving group must be meta to the electron withdrawing group 
E)  A, B and C

Question 8

Predict the product for the following reaction.

Accepted Answer

The answer of Predict the product for the following reaction....

Question 9

Provide the reagents necessary to carry out the following conversion.

Accepted Answer

1. CH₃CH₂Cl/AlCl₃ 2. HN

Question 10

Predict the structure of the major product for the following reaction.

Accepted Answer

The answer of Predict the structure of the major product...

Question 11

Predict the product for the following reaction.

Accepted Answer

The answer of Predict the product for the following reaction....

Question 12

Provide the reagents necessary to carry out the following conversion.

Accepted Answer

1. Cl₂/ FeC

Question 13

Draw all of the resonance structures of the sigma complex which is formed when benzene reacts with an electrophile (E+).

Accepted Answer

Question 14

Identify the electrophile in the iodination of benzene.

Accepted Answer

A)  I2 
B)    
C)  CuI3 
D)  CuI2 
E)    
A)  I2 
B)    
C)  CuI3 
D)  CuI2 
E)

Question 15

Predict the major product for the reaction between benzene and 2-chlorobutane in the presence of AlCl3.

Accepted Answer

A)  chlorobenzene 
B)  sec-butylbenzene 
C)  ethylbenzene 
D)  isopropylbenzene 
E)  t-butylbenzene 
A)  chlorobenzene 
B)  sec-butylbenzene 
C)  ethylbenzene 
D)  isopropylbenzene 
E)  t-butylbenzene

Question 16

Predict the major product for the following reaction.

Accepted Answer

The answer of Predict the major product for the following...

Question 17

The following reaction will occur via which mechanism?

Accepted Answer

A)  elimination-addition 
B)  nucleophilic aromatic substitution 
C)  electrophilic aromatic substitution 
D)  addition-elimination 
E)  both B and C 
A)  elimination-addition 
B)  nucleophilic aromatic substitution 
C)  electrophilic aromatic substitution 
D)  addition-elimination 
E)  both B and C

Question 18

Identify the electrophile in the nitration of benzene.

Accepted Answer

A)  NO2+ 
B)  HNO3 
C)  NO3+ 
D)  H2SO4 
E)  NO2 
A)  NO2+ 
B)  HNO3 
C)  NO3+ 
D)  H2SO4 
E)  NO2

Question 19

Provide the reagents necessary to carry out the following conversion.

Accepted Answer

1. Cl₂/FeCl

Question 20

Which of the following compounds will yield the ortho substituted compound as the major product for a nitration reaction?

Accepted Answer

A)  toluene 
B)  ethylbenzene 
C)  cumene 
D)  t-butylbenzene 
E)  none of these 
A)  toluene 
B)  ethylbenzene 
C)  cumene 
D)  t-butylbenzene 
E)  none of these

Exam 18: Aromatic Substitution Reactions

The following reaction will occur via which mechanism?

The following reaction will occur via which mechanism?

Propose a stepwise synthesis for the following compound from benzene.

Predict the product for the following reaction.

Predict the major product for the following reaction.

Predict the structure of the product for the following reaction.

Which of the following criteria is necessary for a nucleophilic aromatic substitution reaction?

Predict the product for the following reaction.

Provide the reagents necessary to carry out the following conversion.

Predict the structure of the major product for the following reaction.

Predict the product for the following reaction.

Provide the reagents necessary to carry out the following conversion.

Draw all of the resonance structures of the sigma complex which is formed when benzene reacts with an electrophile (E+).

Identify the electrophile in the iodination of benzene.

Predict the major product for the reaction between benzene and 2-chlorobutane in the presence of AlCl3.

Predict the major product for the following reaction.

The following reaction will occur via which mechanism?

Identify the electrophile in the nitration of benzene.

Provide the reagents necessary to carry out the following conversion.

Which of the following compounds will yield the ortho substituted compound as the major product for a nitration reaction?

A Review of General Chemistry: Electrons, Bonds, and Molecular Properties

Molecular Representations

Acids and Bases

Alkanes and Cycloalkanes

Stereoisomerism

Chemical Reactivity and Mechanisms

Alkyl Halides: Nucleophilic Substitution and Elimination Reactions

Addition Reactions of Alkenes

Alkynes

Radical Reactions

Synthesis

Alcohols and Phenols

Ethers and Epoxides; Thiols and Sulfides

Infrared Spectroscopy and Mass Spectrometry

Nuclear Magnetic Resonance Spectroscopy

Conjugated Pi Systems and Pericyclic Reactions

Aromatic Compounds

Aldehydes and Ketones

Carboxylic Acids and Their Derivatives

Alpha Carbon Chemistry: Enols and Enolates

Amines

Introduction to Organometallic Compounds

Carbohydrates

Amino Acids, Peptides, and Proteins

Lipids

Synthetic Polymers

Filters

Draw all of the resonance structures of the sigma complex which is formed when benzene reacts with an electrophile (E⁺).

Predict the major product for the reaction between benzene and 2-chlorobutane in the presence of AlCl₃.