Question 1

Which would be the product of the following reaction sequence?

Accepted Answer

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

Question 2

The reaction of benzene with   in the presence of anhydrous aluminum chloride produces principally which of these?

Accepted Answer

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

Question 3

How might the following synthesis be carried out:

Accepted Answer

A)    
B)    
C)    
D)    
E) None of these syntheses is satisfactory. 
A)    
B)    
C)    
D)    
E) None of these syntheses is satisfactory.

Question 4

What would you expect to be the major product obtained from 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

Which alkyl halide would be most reactive in an SN2 reaction?

Accepted Answer

A) C6H5CH2CH2CH2Br 
B)    
C)    
D)    
E)    
A) C6H5CH2CH2CH2Br 
B)    
C)    
D)    
E)

Question 6

Which of the following compounds would be most reactive toward ring nitration?

Accepted Answer

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

Question 7

In electrophilic aromatic substitution,the attacking species (the electrophile)necessarily is a:

Accepted Answer

A) neutral species. 
B) positively charged species. 
C) lewis acid. 
D) proton. 
E) carbocation. 
A) neutral species. 
B) positively charged species. 
C) lewis acid. 
D) proton. 
E) carbocation.

Question 8

Consider the resonance forms shown for the arenium ionformed from the bromination of acetanilide.Which resonance form contributes most to the overall resonance hybrid?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
E) All contribute equally. 
A) I 
B) II 
C) III 
D) IV 
E) All contribute equally.

Question 9

Which would be a good synthesis of m-nitrobenzoic acid?

Accepted Answer

A)    
B)    
C)    
D) More than one of these choices. 
E) None of these choices. 
A)    
B)    
C)    
D) More than one of these choices. 
E) None of these choices.

Question 10

Which of the following reactions would yield isopropylbenzene as the major product?

Accepted Answer

A)    
B)    
C)    
D)    
E) All of these choices. 
A)    
B)    
C)    
D)    
E) All of these choices.

Question 11

Which would be the product of the following reaction sequence?

Accepted Answer

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

Question 12

Electron-donating groups increase the electron density on the aromatic ring,causing it to be more reactive than benzene itself towards EAS.These types of groups are called ___ groups.

Accepted Answer

The answer of Electron-donating groups increase the electron density on...

Question 13

When toluene reacts with Cl2,the identity of the major product(s)obtained depends on whether the reaction is carried out in the presence of catalytic amounts of FeCl3,or without catalyst,at high temp.Explain clearly.

Accepted Answer

Reaction with Cl₂/FeCl₃ results in electro

Question 14

Which of the following compounds would you expect to be most reactive toward ring nitration?

Accepted Answer

A) Benzene 
B) Toluene 
C) m-Xylene 
D) p-Xylene 
E) Benzoic acid 
A) Benzene 
B) Toluene 
C) m-Xylene 
D) p-Xylene 
E) Benzoic acid

Question 15

Which reagent(s)would you use to carry out the following transformation? cumene $\to$ 2- and 4-chlorocumene

Accepted Answer

A) Cl2,light,and heat 
B) Cl2,FeCl3 
C) SOCl2 
D) C2H5Cl,AlCl3 
E) HCl,peroxides 
A) Cl2,light,and heat 
B) Cl2,FeCl3 
C) SOCl2 
D) C2H5Cl,AlCl3 
E) HCl,peroxides

Question 16

Which of the following structures contribute(s)to the resonance hybrid of the intermediate formed when bromobenzene undergoes para-chlorination?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
E) All of these choices. 
A) I 
B) II 
C) III 
D) IV 
E) All of these choices.

Question 17

Starting with benzene,the best method for preparing m-nitrobenzoic acid is:

Accepted Answer

A) HNO3/H2SO4; then CH3Cl/AlCl3; then separation of isomers; then KMnO4/ -OH/heat,followed by H3O+. 
B) CH3Cl/AlCl3; then HNO3/H2SO4; then separation of isomers; then KMnO4/ -OH/heat,followed by H3O+. 
C) CH3Cl/AlCl3; then KMnO4/-OH/heat,followed by H3O+; then HNO3/H2SO4. 
D) HNO3/H2SO4; then KMnO4/-OH/heat,followed by H3O+; then CH3Cl/AlCl3. 
E) HNO3/H2SO4; then CO2,followed by H3O+. 
A) HNO3/H2SO4; then CH3Cl/AlCl3; then separation of isomers; then KMnO4/ -OH/heat,followed by H3O+. 
B) CH3Cl/AlCl3; then HNO3/H2SO4; then separation of isomers; then KMnO4/ -OH/heat,followed by H3O+. 
C) CH3Cl/AlCl3; then KMnO4/-OH/heat,followed by H3O+; then HNO3/H2SO4. 
D) HNO3/H2SO4; then KMnO4/-OH/heat,followed by H3O+; then CH3Cl/AlCl3. 
E) HNO3/H2SO4; then CO2,followed by H3O+.

Question 18

Electron-withdrawing groups decrease the electron density on the aromatic ring,causing it to be less reactive than benzene itself towards EAS.These types of groups are called ___ groups.

Accepted Answer

The answer of Electron-withdrawing groups decrease the electron density on...

Question 19

Benzoic acid can be prepared by the oxidation of all of the following compounds except this one:

Accepted Answer

A) C6H5CH=CH2 
B) C6H5C$\equiv$CH 
C) C6H5COCH3 
D) C6H5CH2CH2CH3 
E) C6H5C(CH3)3 
A) C6H5CH=CH2 
B) C6H5C$\equiv$CH 
C) C6H5COCH3 
D) C6H5CH2CH2CH3 
E) C6H5C(CH3)3

Question 20

Which of the following compounds would be least reactive toward electrophilic substitution?

Accepted Answer

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

Exam 15: Reactions of Aromatic Compounds

Which would be the product of the following reaction sequence?

The reaction of benzene with in the presence of anhydrous aluminum chloride produces principally which of these?

How might the following synthesis be carried out:

What would you expect to be the major product obtained from the following reaction?

Which alkyl halide would be most reactive in an SN2 reaction?

Which of the following compounds would be most reactive toward ring nitration?

In electrophilic aromatic substitution,the attacking species (the electrophile)necessarily is a:

Consider the resonance forms shown for the arenium ionformed from the bromination of acetanilide.Which resonance form contributes most to the overall resonance hybrid?

Which would be a good synthesis of m-nitrobenzoic acid?

Which of the following reactions would yield isopropylbenzene as the major product?

Which would be the product of the following reaction sequence?

Electron-donating groups increase the electron density on the aromatic ring,causing it to be more reactive than benzene itself towards EAS.These types of groups are called ___ groups.

When toluene reacts with Cl2,the identity of the major product(s)obtained depends on whether the reaction is carried out in the presence of catalytic amounts of FeCl3,or without catalyst,at high temp.Explain clearly.

Which of the following compounds would you expect to be most reactive toward ring nitration?

Which reagent(s)would you use to carry out the following transformation? cumene →\to→ 2- and 4-chlorocumene

Which of the following structures contribute(s)to the resonance hybrid of the intermediate formed when bromobenzene undergoes para-chlorination?

Starting with benzene,the best method for preparing m-nitrobenzoic acid is:

Electron-withdrawing groups decrease the electron density on the aromatic ring,causing it to be less reactive than benzene itself towards EAS.These types of groups are called ___ groups.

Benzoic acid can be prepared by the oxidation of all of the following compounds except this one:

Which of the following compounds would be least reactive toward electrophilic substitution?

The Basics

Families of Carbon

Acids and Bases

Nomenclature and Conformations of Alkanes and Cycloalkanes

Stereochemistry

Nucleophilic Reactions

Alkenes and Alkynes I

Alkenes and Alkynes II

Nuclear Magnetic Resonance and Mass Spectrometry

Radical Reactions

Alcohols and Ethers

Alcohols From Carbonyl Compounds

Conjugated Unsaturated Systems

Aromatic Compounds

Aldehydes and Ketones

Carboxylic Acids and Their Derivatives

Reactions at the Α Carbon of Carbonyl Compounds

Condensation and Conjugate Addition Reactions of Carbonyl Compounds

Amines

Transition Metal Complexes

Carbohydrates

Lipids

Amino Acids and Proteins

Nucleic Acids and Protein Synthesis

Filters

Which alkyl halide would be most reactive in an S_N2 reaction?

When toluene reacts with Cl₂,the identity of the major product(s)obtained depends on whether the reaction is carried out in the presence of catalytic amounts of FeCl₃,or without catalyst,at high temp.Explain clearly.

Which reagent(s)would you use to carry out the following transformation? cumene $\to$ 2- and 4-chlorocumene